View Details

95: The biggest concern many would-be retirees have, at least in the US, is the cost of healthcare.

Not only is healthcare more expensive in the US than in every other industrialized country. There’s also no national health insurance system to control costs or standardize care quality…unless you’re a senior or very poor (or both).

In fact, were it not for worries about healthcare, there would undoubtedly be way more US retirees out there today. The average retirement age would drop noticeably.

Because no less than your retirement security is at stake, healthcare financial planning is retirement planning.

That’s why I invited Bo Bowen to the podcast today to share his unique perspective on healthcare financial planning in retirement. Bo is both a healthcare practitioner (pharmacist) and a certified financial advisor who has specialized in advising on healthcare financial planning and retirement health insurance. His dual background gives him unique insight into the way healthcare financial planning is crucial for retirement security.

We discuss:

• The biggest challenges retirees face when it comes to healthcare planning
• What retirees should think carefully about when it comes to health insurance in retirement
• How those considerations change depending on your retirement age
• Checklist for choosing the right health insurance plan if you’re retiring soon
• Common mistakes retirees make when planning for post-retirement healthcare
• When self-insuring might be your best choice in retirement
• How medical tourism can play an important role in retirement healthcare
• What retirees should know about buying health insurance on ACA marketplace exchanges

Check it out here:

https://hackyourwealth.com/health-insurance-retirement-planning

If you’ve already retired, what do you do for health insurance? Knowing what you know now, what (if anything) would you do differently in terms of healthcare planning in the years before retiring?

If you have NOT retired yet, how big of a factor is healthcare and health insurance to your decision of when to retire?

Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Related links:

• https://www.healthinsurance.org
• https://www.healthcarebluebook.com
• https://www.medibid.com
• https://www.linkedin.com/in/bo-bowen-1b64341a6
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

94: Real estate investing changed a lot the last couple years, but one asset class consistently punched above its weight: short-term rentals, a.k.a., STRs, e.g., Airbnbs.

In 2020, when people couldn’t go on vacation by hopping on a plane to Europe, South America, or Asia, they got in their cars and drove to national parks and mountain / beach / lake towns. Short-term rentals, often seen as safer than hotels, were on 🔥.

In 2021, this trend exploded. 🔥🔥

In 2022, when flying became a thing again, so did “revenge travel.” STRs accelerated even more. 🔥🔥🔥

With average daily rates skyrocketing the last couple years, hordes of real estate investors snapped up homes to turn them into Airbnbs, trying to chase yield.

Now the market is super saturated, with daily rates even contracting in places, and there’s tons of new short-term rental inventory (over half of Airbnb listings added since 2020).

So how can you stand out as an STR real estate investor in the current climate?

In this episode, I interview Diya Liu, a seasoned short-term rental investor who scaled from zero to 9 STRs in one year, netting $100k annual profit, and then quit her BigLaw job to do short-term rental real estate investing full-time. She currently owns three hotels and a dozen STRs.

We discuss:

• Diya’s RE portfolio breakdown - STRs vs. hotels
• Her step-by-step analysis process for screening potential STR vs. hotel deals
• How she analyzes local STR regulations in a market
• Key interior design principles she implements for her STRs
• Marketing strategies to help your STR stand out
• Automation strategies for your STRs - using VAs, messaging guests, etc
• How she met her investment partners and how they split up work

​Check it out here:

​https://hackyourwealth.com/short-term-rental-hotel-investing​

​Are you an STR investor? If so, how have bookings changed in the last 1-2 years? Do you see over-saturation in listings inventory in your area? Are you trying out any different strategies this year? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Related links:

• https://www.instagram.com/diyaesq
• https://www.facebook.com/groups/AirbnbProfessional
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

93: Early retirees often fill their early years in retirement with lots of travel. There is even a vibrant community of nomadic early retirees who travel long-term.

But what do you do about health insurance, especially if you’re American? Unlike in most other industrialized countries that have universal health insurance, American health insurance is generally tied to your employer, at least before you’re old enough to qualify for Medicare. That means if you don’t have a job, you generally don’t have health insurance. For early retirees, that’s a problem.

**What are the health insurance options for early retirees, especially those who plan to travel significantly in retirement?

This week, I chat about early retirement health insurance options with Tracy Winters**, Director of Individual Insurance at Good Neighbor Insurance, an Arizona-based health insurance brokerage that specializes in health insurance consulting for long-term travelers, expats, and traveling early retirees.

We discuss:

• The big picture for how traveling early retirees should think about their health insurance options
• When it makes sense to simply self-insure
• Tracy’s observations on which countries offer both high-quality and affordable healthcare
• Tracy’s health insurance recommendations for early retirees who wish to travel abroad 100% vs. 90% vs. 50% vs. 25% of the time
• ACA marketplace health insurance options to consider for early retirees
• How Medicare coverage is impacted when you travel long-term
• When it’s worth repatriating to the US vs. staying in-country to get medical care, plus what kind of insurance plans provide repatriation services

Check it out here:

https://hackyourwealth.com/health-insurance-retirement-travelIf you’re early retired, what do you do for health insurance?

How do you handle health insurance when traveling as an early retiree?

If you’re planning to early retire in the future, how important is health insurance coverage to your decision of timing when to early retiree?

Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Related links:

• About Tracy Winters
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

92: Most FIRE stories are of men. A lot seem to be of ex-software engineers (on blogs anyway). It’s rare to see profiles of early retired women, especially single women who retired early from ambitious careers.

Also, most FIRE stories focus on strategies for things like accumulating enough assets to FIRE. Investment selection. Portfolio allocation. Safe withdrawal rates. Sequence risk.

These are important topics for sure. I’ve covered many of them on HYW. But they are also very much about the mechanics.

It’s rare to hear how early retirees grapple with stuff like: loss of professional identity, building a new non-career identity, finding purpose, fulfillment, and community as an early retiree; or dating and companionship in early retirement.

This week, I chat with Kim (last name withheld at her request) about her journey from MBA to corporate career to early retirement at 39 and her life and identity now 5 years post-FIRE. We discuss some of these rarely mentioned topics, as well as what it’s been like so far in early retirement as a single woman.

We talk about:

• Kim’s career path before early retirement
• How she came up with her FIRE number
• Her numbers: earning/income trajectory from MBA graduation to early retirement, spending level during her career & now in retirement
• Her asset allocation + tactics she uses for managing, rebalancing, risk mitigation, and withdrawing from her portfolio
• Factors she considered in terms of spouse/family vs. early retirement
• Advice on dating and companionship in early retirement
• What she learned about finding a new non-career identity, purpose, and fulfillment in early retirement
• How Kim spends her days now & how she’s found community as an early retiree
• Her advice for other young women who are interested in FIRE

Check it out here:

https://hackyourwealth.com/retire-early-women-business-career-professional

Know any other interesting unmarried women who are pursuing or achieved FIRE? I’d be interested in potentially interviewing them for the podcast. Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Related links:

• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

91: It’s no secret that many healthcare professionals earn lots of money. So, you might think it’s relatively easy for them to achieve financial independence and retire early (or at least step back from demanding clinical hours).

Aaaand….you’d be right about that!

Sure, earning healthcare money is not a requirement for FIRE. But if you do, you certainly have more options…even if you also have large expenses (like kids).

This week, I talk with Dr. G (anonymized, his request), a dentist with two kids in the midwest who built a $7 million nest egg before stepping back from clinical practice. He explains the actions he took to build his wealth…and what he’s doing now.

We discuss:

• His career path as a dentist
• Net worth after finishing dental school
• Age when he broke even and when he reached FI
• How much he earned right out of dental school, when he broke even, when he reached FI, plus how much he earns passively now
• Spending level over the years, plus how much he spends post-FI
• Asset allocation breakdown
• Main actions he took that had the biggest impact on net worth
• His thought process on stepping back from clinical work with two young kids still in tow
• FIRE tips for people with kids

Check it out here:

https://hackyourwealth.com/dentist-financial-independence-retire-early

What type of FIRE profiles (career path, earning level, family/kid status, etc) do you want to hear more about? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Related links:

• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

90: It’s back to school season, and that means it’s also the time of year for high school seniors to start agonizing over college applications.

Applying to college is an anxiety-filled rite of passage for high school seniors, but it’s often just as anxiety-inducing for parents who bang their heads on how to pay for it.

That’s because paying for college is, for many families, the biggest single expense they’ll have for their child. It’s also often the second biggest life expense a family will incur, right behind buying a home. Paying for college is like buying a Tesla Model Y and giving it away. Every year, for four years.

So this week, I chat with my friend Ann Garcia about how to pay for college. She just wrote a new book on this topic, which we discuss in detail, along with important new updates to the federal financial aid process (FAFSA) + key things to know about 529 plan rules.

We discuss:

• Why Ann decided to write this book now, what makes it different
• The mind-boggling cost of college today; forecasted cost in 15 years
• Why college costs so much now, what’s driven up the cost in recent decades
• Goals that colleges are trying to accomplish with their financial aid awards
• Things parents should do to prepare their child and finances for the cost of college from birth to high school
• Why it’s important for your child to do the official campus tour for colleges they’re interested in
• Recent key changes and updates to the FAFSA process
• Difference between 529 savings plans vs. pre-paid tuition plans vs. Private College 529
• Mechanics of 529s: roll-over-ability, qualified expenses, taxes & penalties for non-qualified expenses, how scholarships are handled, changing beneficiaries

Check it out here:

https://hackyourwealth.com/how-to-pay-for-college

Have you been through (or will soon go through) the college financial aid process? What’s been the most confusing or frustrating aspect? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Related links:

• Book: How to Pay for College: A complete financial plan for funding your child's education
• Online course: The College Financial Plan Masterclass - 20% discount exclusively for HYW subscribers (use code: HYW20)
• TheCollegeFinancialLady.com
• 529 college savings plans: rules, tax benefits, & qualified expenses (HYW026)
• College financial aid tips and strategies, with Ann Garcia (HYW053)
• College student financial aid changes coming to the FAFSA application (HYW079)
• Schedule a private 1:1 consult with me
• HYW private FB community

Intro/Outro: Old Bossa by Twin Mus

View Details

89: Summer is fast approaching, and that’s traditionally when home-buying season ramps up.

This week, I share insights on how to conduct due diligence when you’re looking to buy a home. Whether you’re buying a primary residence or investing in rental real estate, rigorous due diligence is critical to ensuring you get a good property at a reasonable price. In this episode, I explain my entire process for thoroughly analyzing a property before writing an offer.

You learn:

• 10 key things to look for when doing pre-tour due diligence
• The 4 big things to look for in disclosure packets
• How to evaluate the history of previous remodels, structural changes, or additions to the house done by prior owners
• Special tips for buying a condo – how to analyze HOA records, financials, rules, and CC&Rs
• My 12-point checklist on what to look for when touring a home in person

Check it out here:

https://hackyourwealth.com/real-estate-due-diligence

If you’ve bought a home before, what are the most important due diligence items you look for? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Related links:

• Battle-tested home remodeling tips for saving serious money and getting the most from your contractors
• How to find and vet good home remodeling contractors like a boss
• How to write an offer to purchase a house (that stands out and wins)
• How to do a residential property inspection step by step: What smart real estate investors look for
• How to research real estate markets: The single best resource you need
• Avoiding capital gains tax on real estate: how the home sale exclusion works
• The True Benefit of Homeownership (why buying has paid off over renting, even in a million dollar market)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

88: Have you maxed out your backdoor + mega backdoor Roth conversions yet?

For high earners, direct contributions to a Roth IRA, and tax-deductible contributions to a traditional IRA, are limited by income thresholds.

But ALL taxpayers – even high earners – can still invest money into a Roth via backdoor Roth conversion. And if your employer’s 401k has the right plan features, you can turbo-charge your Roth conversions another 7x by doing the “mega backdoor” Roth conversion.

What the heck do these mean? And how exactly do you do them?

This week, I share what these concepts are, tips for how to execute them successfully, and what you need to know about your employer 401k to turbo-charge your Roth conversions.

I explain:

• The difference between a backdoor Roth vs. mega backdoor Roth
• How to execute each one + tips to ensure no tax liability when you convert
• What plan features your employer 401k must have to do a mega backdoor Roth
• Workaround if your employer 401k does NOT allow in-plan Roth conversions, but DOES allow after-tax contributions (yes, you can still move that money into Roth)
• How recent proposed legislative changes would curtail the backdoor Roth strategy, and whether you need to worry about it
• A note about doing mega backdoor Roth conversions via Solo 401k.

Check it out here:

https://hackyourwealth.com/mega-backdoor-roth

Have you done a backdoor or mega backdoor Roth conversion before? If you’ve decided not to, what dissuaded you? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Related links:

• Traditional vs. Roth? How to double-dip on the tax benefits of BOTH
• What is a Solo 401k? And Why It Beats All Other Retirement Accounts
• Everything you need to know about 401Ks (HYW003)
• IRAs, Roth IRAs, and how to get the tax benefits of BOTH (HYW004)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

87: Remote work and digital nomadism have always been of particular interest to folks in the FIRE community.

After the pandemic, remote work was suddenly thrust upon the entire knowledge workforce. And after two long pandemic years, the possibility that remote work for many professions will persist and become long-term viable options is tantalizingly close.

What is the state of remote work right now? Where is the future of remote work headed? What jobs are most in-demand for remote work, and how much can you get paid for them?

This week, I deep dive on these questions with Sharon Koifman, founder of DistantJob, a remote-only recruiting agency that helps companies find full-time remote employees around the world.

We discuss:

• How Sharon became an advocate for remote work and got into remote recruiting
• How the pandemic changed norms around remote work
• What types of jobs are most in-demand for remote work right now
• What types of jobs still have not embraced remote work
• Skills and qualities employers look for when hiring remote employees (profile of an ideal candidate)
• Compensation: what remote employees can earn for certain roles (including pay range - min and max)
• How companies adjust compensation for remote employees
• How companies can promote strong, healthy remote work cultures

Check it out here:

https://hackyourwealth.com/future-of-remote-work

And now, I’m super curious…. Are you a remote worker or digital nomad? Trying to be? Wish to be? If so, what type of work do you do?

If you work remotely for a company, was your compensation adjusted when you switched to remote?

What’s the biggest benefit vs. challenge you have experienced as a remote worker? How do you build (and keep) strong connections to people in your company/organization?

Does being able to be remote change your FIRE plans, timeline, or philosophy at all?

Let me know by leaving a comment!

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Related links:

• DistantJob
• Surviving Remote Work: How to Thrive as a Leader and Entrepreneur in the Remote Age
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

86: Pretty much everyone in the FIRE community has heard of the 4% rule.

It is the starting safe withdrawal rate number for a 30-year retirement horizon that was proposed a few decades ago by retirement researchers.

And it has attained near pop culture status in the FIRE community because it’s such a simple mental shortcut to answer the question: “how much can I safely withdraw from my portfolio each year in retirement and have high confidence that I’ll be financially secure for the rest of my life?”

This is easily the most important question for ANY retiree, and especially early retirees. So, it’s no wonder this topic is so intensely discussed in the FIRE community.

More than a few early retirees and FIRE bloggers swear by the 4% rule and have plunged into their own retirement using this withdrawal rate expecting that it will carry them through for the rest of their lives.

But when you ask the quants – the economists with the PhDs – there is broad agreement that the 4% rule no longer works most of the time.

But why not?

This week, I invited the renowned retirement economist Wade Pfau, PhD/CFA, who is Co-Director of the American College Center for Retirement Income, to share insight on why the 4% rule no longer works in today’s environment. He suggests an alternate safe withdrawal rate number that may be better suited for today’s retirees.

We discuss:

• Why Dr. Pfau thinks the 4% rule is flawed today + how the world has changed since the 4% rule was first proposed
• Pfau’s recommended safe withdrawal rate number for the current environment (including assumed asset allocation)
• How Pfau thinks safe withdrawal rate planning will differ for early retirees
• Pfau’s thoughts on asset allocation in the current environment of rising interest rates, high inflation, and high asset valuations
• What Pfau personally projects as his assumed real rate of return on stocks for his own portfolio
• How annuities can play a crucial role in your retirement portfolio depending on your investor risk profile and desired stock allocation
• Pfau’s framework of 4 retirement styles + optimal asset allocation for each

Check it out here:

https://hackyourwealth.com/4-percent-rule

What do you think your safe withdrawal rate number is? And what asset allocation do you assume for that? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast

I need your help, please leave a listener review :)

If you liked this episode, would you leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Wade Pfau
• Retirement Planning Guidebook
• Safety-First Retirement Planning: An Integrated Approach for a Worry-Free Retirement
• How Much Can I Spend in Retirement?
• Reverse Mortgages: How to Use Reverse Mortgages to Secure Your Retirement
• Schedule a 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

85: Recently I’ve really started to notice the impact of inflation on daily spending. Have you?

At first, it was just 1-2 things. Then it was a handful. Now it seems like everything is noticeably more expensive. (Assuming it’s even in stock in the first place.)

Gas. Groceries. Takeout. Toiletries. Utilities. Car maintenance. Healthcare/supplies. Pre-school. Appliances.

Everything seems to cost more and you just can’t buy as much with the same budget anymore.

This got me wondering about how recent macroeconomic changes over the last 6 months might impact retirement safe withdrawal rates and asset allocations.

The macro changes I’m referring to are: Inflation at a 40-year high. Stock valuations doubling since their pandemic lows. Interest rates that are scheduled to increase a minimum of 3 times this year.

In these times, what should investors and retirees be doing to defend their portfolio values and retirement security?

This week, I asked my friend Karsten Jeske (aka “Big ERN”) to help us make sense of all that is going on right now in terms of macro trends…and what it all means for safe withdrawal rates and asset allocation. We had a wide-ranging, nearly 2-hour(!) discussion full of insights and tips that you won’t want to miss.

We discuss:

• Major recent macroeconomic changes that (early) retirees may want to factor into their retirement planning
• What new safe withdrawal rate % retirees should consider right now
• Whether investors should potentially update their asset allocation given current macro trends
• Whether he believes asset prices are overvalued right now
• Alternative assets (like cryptocurrencies) and their merits / concerns
• How much cash he believes is advisable to hold right now

Do you plan to make changes to your asset allocation or safe withdrawal rate in light of recent macroeconomic changes? Let me know by leaving a comment!

Don't miss an episode, hit that subscribe button...

If you liked this episode, subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify

I need your help, please leave a listener review :)

If you liked this episode, would you leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Karsten's Safe Withdrawal Rate Series
• Karsten's Google Sheet DIY Withdrawal Rate Toolbox
• Karsten's post on Preferred Stocks
• The shockingly un-simple math behind safe withdrawal rates (HYW035)
• How to use a bond tent to reduce sequence of returns risk (HYW068)
• Does the “yield shield” protect against sequence risk? (HYW069)
• Is rental real estate a safer type of “yield shield”? (HYW070)
• Schedule a 1:1 consult with me
• HYW Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

84: Today's episode is about an important end-of-year planning topic: asset allocation and portfolio rebalancing.

Many otherwise smart investors set their portfolio once, but then fail to rigorously monitor their asset allocation and rebalance regularly.

Whether due to inertia or hassle, this inaction is costly. It results in lower returns and greater risk as your asset allocation drifts…bad for wealth-building.

How do you set your target asset allocation optimally and rigorously? And how do you rebalance tax-efficiently?

This week, I show you how to set your target asset allocation to match your risk profile and investment goals. I share how to track your asset allocation to see how much it has drifted from your target allocation. And I explain step-by-step how to tax-efficiently rebalance.

If asset allocation and rebalancing feel like a mystery or chore, then don’t miss today’s episode. I’ll show you how to do it systematically, efficiently, and rigorously…all in 1 hour or less per year.

What you’ll learn:

• Why it’s prudent to sell your winning investments and rebalance toward your underdogs
• How to create and define your target asset allocation starting from first principles
• How to determine your investment style and risk tolerance in an intellectually honest way
• How to track your current allocation and analyze drift from your target
• How to rebalance your portfolio tax-efficiently step-by-step
• How often you should rebalance

Check it out here:

https://hackyourwealth.com/asset-allocation-rebalance-portfolio-replay

How often do you rebalance your portfolio? Let me know by leaving a comment!

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Download my FREE spreadsheet to track your current vs. target asset allocation
• My 4×4 FIRE framework for creating and protecting wealth (HYW002)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

83: You’ve worked hard all your life. At retirement, it’s time to kick back and relax, right?

Not so fast.

You still have to get THROUGH retirement.

That means knowing how to draw down your portfolio to:

1. meet all your monthly cash flow needs
2. cushion against unexpected expenses
3. minimize tax liability
4. ideally help your kids / grandkids, give to charity, or leave a legacy
5. ensure your retirement nut doesn’t run out before you do

This is very challenging because you have to forecast things you simply can’t know with certainty. Inflation rates. Market returns. Sequence risk. Tax rates. Your health condition and anticipated healthcare needs.

So, how can retirees plan their retirement portfolio withdrawals to actually enjoy retirement and not worry about running out of money?

This week, I sit down with Steve Parrish, Co-Director of the Center for Retirement Income at The American College of Financial Services, to talk about tax-efficient portfolio withdrawal strategies in retirement.

We discuss:

• Key principles retirees should understand when deciding which assets to draw down and in what sequence
• How those principles change when you have alternate monthly income sources (like rental real estate, pension, etc)
• Why your wealth bracket determines what is the most tax-efficient sequence of portfolio withdrawals
• How soon-to-be and current retirees can protect themselves against sequence of returns risk
• When it makes sense to use legal tools like tax-free gifts, GRATs, etc, to reduce tax liability on retirement assets
• Why you might want to pay taxes now to do annual Roth conversions to ratchet down your IRA/401ks and the ticking tax time bomb attached to them
• Portfolio withdrawal advice for early retirees (FIRE)

Check it out here:

https://hackyourwealth.com/retirement-withdrawal-strategies

Do you worry about running out of money in retirement? If so, what is the biggest reason why – not saving enough, spending too fast, market tanks during retirement, something else? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify

I need your help, please leave a listener review :)

If you liked this episode, would you leave a quick review on Apple Podcasts? It’d mean the world to me and your review helps others find my podcast, too!

Links mentioned in this episode:

• Steve Parrish
• The shockingly un-simple math behind safe withdrawal rates (HYW035)
• How to FIRE with confidence, step by step (HYW060)
• How to use a bond tent to reduce sequence risk (HYW068)
• How long will your retirement savings last?
• Schedule a private 1:1 consultation
• HYW Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

82: Are annuities a good investment for retirement?

With $250 billion in sales each year, and $2.5 trillion in retirement annuity assets under contract, annuities comprise a huge slice of US retirement assets.

Understanding annuities – whether annuities are right for you, and how annuities fit into your retirement strategy – can get complicated given all the annuity options out there and the extreme uncertainty in today’s markets.

So this week, I sat down with Stan Haithcock, aka “Stan The Annuity Man,” to deep dive on annuities. We chat about how annuities work, why annuities are not investments (in the portfolio sense), and why there is no such thing as “best annuities.”

We discuss:

• What annuities are and what purpose they serve
• The different types of annuity options (immediate annuity, deferred annuity, fixed annuity, variable annuity, indexed annuity, multi-year guaranteed annuity, life annuity)
• How annuities account for inflation
• The mechanics of how to buy an annuity
• How insurance companies that sell annuities make money
• The different type of annuity fees you can expect, and typical all-in costs for different annuity types
• How to vet the insurance companies that sell annuities
• How to vet an agent and questions to ask before buying an annuity from them
• How agents who sell annuities are compensated
• Annuity taxes and the tax profile of annuities
• Basic protections your annuity gets if the insurance company you bought it from goes bankrupt
• Who annuities are best suited for, and whether annuities are a good idea for early retirees (FIRE)

Check it out here:

https://hackyourwealth.com/annuities

Have you purchased any annuities before, either for yourself or a family member? What kind of annuity did you buy, and why? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• The Annuity Man
• National Organization of Life & Health Insurance Guaranty Associations
• Social Security: How it works and optimal claiming strategies (HYW050)
• How Medicare works: eligibility, enrollment, cost, and coverage options (HYW048)
• How Social Security Works: The Ultimate Guide For Laypersons
• Retirement withdrawal calculator: How long will your savings last in retirement?
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

81: With the market rallying like crazy this past year, you might have significant capital gains on stocks right now.

Now might be a good time for some of you investors to harvest some capital gains. Maybe you’re looking to buy a house. Or maybe you just want to rebalance your investments.

But when you sell stock, you pay taxes on the sale.

And capital gains taxes can get complex because the effective tax rate you pay when you sell stock depends on whether there are long-term vs. short-term capital gains, whether there are any long-term vs. short-term losses, what your marginal tax rate is, and even whether you are required to pay the Medicare Surcharge Tax.

That’s why this week I invited CFA Scott Stratton to explain the intricacies of how capital gains taxes work. We discuss key rules and strategies you need to know to do thoughtful capital gains tax planning. If you want to learn how to minimize capital gains taxes, then don’t miss this episode.

You’ll learn:

• What types of assets capital gains taxes apply to
• Difference between short-term vs. long-term capital gains tax treatment
• How capital gains and losses work in tandem come tax filing time
• How to harvest capital losses and harvest capital gains
• Current proposed legislative changes to capital gains tax rates
• What investors may want to consider doing now before potential changes take effect

Check it out here:

https://hackyourwealth.com/capital-gains-tax-on-stocks

What other tax planning questions do you have about capital gains taxes? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Good Life Wealth Management
• Tax Loss Harvesting: Rules and Strategies with Bob Dockendorff (HYW022)
• How to take a year off, earn 6 figures, harvest capital gains, do Roth conversions…and pay zero taxes on it all
• How to earn 6 figures and legally pay zero taxes (updated for 2020) (HYW021)
• Avoiding capital gains tax on real estate: how the home sale exclusion works
• How the Home Sale Capital Gains Tax Exclusion Works (HYW033)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

80: Teaching kids about money isn’t easy, but it’s crucial if you want to boot them off your payroll after they graduate from school.

But while financial literacy is good, helping your kids build the mindset and momentum to achieve financial independence is even better.

It requires that they internalize (and value) aggressive saving, investing, and compounding…not just living within their means.

That’s why I was so excited to chat this week with Doug Nordman and Carol Pittner, father and daughter co-authors of a new book on how to teach next-generation financial independence.

We discuss:

• Why it’s important to let kids make their own financial choices (and mistakes) when the stakes are low
• Why letting your kids buy “One Special Thing” per shopping trip is an effective teaching strategy
• Why you might want to pay your kids for jobs, but not chores…and the difference between the two
• Why it might not be a good idea to pay your kids for getting good grades, and what you can do instead
• Why “profit sharing” is an especially powerful strategy to teach kids about savings and frugality
• How to create a “kid 401k” to teach your kid lasting lessons about compounding and long-term investing
• How to incentivize your kid to contribute to a Roth IRA early on
• How to handle the question of “how rich are we?”

Check it out here:

https://hackyourwealth.com/teaching-kids-about-money-financial-independence

What strategies do you use to teach your kids about saving, investing, and compounding? How are you helping them learn about financial independence, if at all? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Raising Your Money-Savvy Family For Next Generation Financial Independence
• The Military Guide
• childFIRE
• Financial literacy for kids: how to teach your kids about money (HYW077)
• 9 Crucial Money Lessons Your Kids Must Learn to Succeed as Adults (HYW027)
• How to financially prepare for starting a family with Kevin Mahoney (HYW038)
• The best parenting guidance I’ve learned for raising successful children
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

79: This one’s for you parents who have kids in college or soon going to college…

In the COVID relief stimulus bill that passed at the end of 2020, there was a big chunk about federal student financial aid.

New rules are bringing significant changes to college financial aid. This week, I deep dive with my friend Ann Garcia, aka The College Financial Lady, on what these changes are and how they will impact you and your family.

We discuss:

• Overview of the federal student financial aid application process, including key dates
• Important changes coming to the federal financial aid process: for the FAFSA application, families with multiple college-aged kids, grandparent 529 plans, divorced parents, and more
• Timeline and phasing of these changes coming in 2021, 2022, 2023 and beyond

Check it out here:

https://hackyourwealth.com/fafsa-federal-student-financial-aid-changes

Will you be applying for college financial aid over the next few years? What one thing brings you the biggest worry when it comes to college financial aid? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• The College Financial Lady
• College financial aid tips and strategies, with Ann Garcia (HYW053)
• 529 college savings plans: rules, tax benefits, & qualified expenses (HYW026)
• College financial aid strategies to optimize your assets, income & EFC (HYW025)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

78: For this episode, I polled other influencers in the personal finance community to ask for their best tip on teaching money lessons to kids.

I had four different personal finance influencers weigh in – a range of bloggers, podcasters, authors, and community admins. All of them are parents themselves.

I asked each person to answer one simple question:

“When it comes to teaching your kids about money, what single method or strategy have you personally found to be most effective?”

Check out their collective tips here:

https://hackyourwealth.com/money-lessons-for-kids-tips-from-personal-finance-influencers

What strategy have YOU found to be most effective when it comes to teaching your kids about money? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Couple Money Podcast, Thriving Families FB group
• Raising Your Money-Savvy Family For Next Generation Financial Independence
• KateHorrell.com
• Personal Finance for U.S. Military Service Members and Families FB group
• Her Dinero Matters podcast
• Financial literacy for kids: how to teach your kids about money (HYW077)
• 9 Crucial Money Lessons Your Kids Must Learn to Succeed as Adults (HYW027)
• How to financially prepare for starting a family with Kevin Mahoney (HYW038)
• Hey, rich people. Wealth management includes telling your kids how rich you are.
• The best parenting guidance I’ve learned for raising successful children
• How to motivate your kid to win the national spelling bee (and excel in life)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

77: Teaching financial literacy for kids may seem like a tall order…when considering that financial literacy even for adults is a national deficiency.

But teaching kids about money is crucial if you want your kids to grow up financially responsible and independent.

As a parent, you will have a strong vested interest in it, because if you fail at it you’ll eventually pay the consequences (literally), e.g., if your adult kid can’t support themselves and move out of the house.

And early retirement? You can probably kiss that goodbye if your kid is financially reckless.

So, instilling good financial education for your kids is a wise investment…maybe even the wisest investment.

This week, I spoke with Robin Taub, author of the book “The Wisest Investment,” about how to instill financial literacy for children. We discuss strategies, role modeling, and techniques for teaching personal finance and money lessons to your kids.

What you’ll learn:

• Why teaching kids about money is hard
• What financially well-educated kids have in common
• The right age to start teaching kids about money in earnest
• The crucial money lessons kids at each maturity level should know to have healthy skills, habits, and mindsets about money
• Robin’s core framework for teaching kids about money
• Common mistakes parents make when teaching their kids about money, and the most effective role modeling parents can do to successfully teach their kids about money
• How to get kids to become self-motivated to learn about money, saving, investing, and budgeting
• How parents can create teachable moments in daily life and turn them into money lessons for their kids
• How to answer awkward questions like “how rich are we” and “how much money does our family make”
• How parents can help teach their kids to embrace impulse control and delayed gratification when it comes to money
• Guidelines for paying kids an allowance or paying kids to do chores
• How to teach kids about budgeting (and when it’s age appropriate)
• For affluent families: how to make sure your kids don’t take money for granted or become spoiled entitled brats

What methods have you found to be effective when it comes to teaching your kids about money? If your kids are self-motivated to learn about personal finance – earning, budgeting, saving, investing – how did you get them to be self-motivated? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Related links:

• The Wisest Investment: Teaching Your Kids to Be Responsible, Independent and Money-Smart for Life
• Robin Taub
• 9 Crucial Money Lessons Your Kids Must Learn to Succeed as Adults (HYW027)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

76: Retiring early to travel the world is a common goal for FIRE aspirants.

But full-time travel can lose appeal quickly. Churches and temples quickly start to look the same. Gardens and palaces quickly look the same.

When you’re responsible for creating all the structure to your day – every day for weeks and months on end – it gets exhausting and can feel purposeless.

But what if you could design early retirement travel around language learning?

By enrolling in language immersion courses at local language schools in countries you travel to, you not only learn how to communicate conversationally with locals. You also get structured and even vibrant exposure to local culture, food, people, and activities because being situated in a school or university environment creates that exposure and structure for you naturally.

This week, I invited Ingrid, a software engineer turned early retiree and successful travel blogger, to share about her early retirement experience pursuing language learning through travel immersion courses. Making language learning the focus of early retirement has brought joy and purpose and structure to her travel experiences.

We discuss:

• How Ingrid came up with and built strong confidence in her FIRE number
• Her asset allocation and withdrawal rate
• Her blog’s revenue contribution (and what helped her blog get traction)
• How Ingrid plans travel around language immersion courses
• How she meets and connects with locals when she travels, plus her advice for solo female travelers
• How she handles health insurance and healthcare costs as an early retiree and when she’s traveling
• How she believes one’s emotional well being and personality change in early retirement
• How she contemplated family and children alongside her early retirement plan, why she decided against having a family, and her thoughts on loneliness, dating, and companionship as an early retiree
• What Ingrid would have done differently if she could do it over again

Check it out here:

https://hackyourwealth.com/language-learning-courses-retirement-travel-immersion

Have you ever studied abroad or taken a language immersion course in another country? What do you think about the notion of pursuing language learning through travel immersion courses in early retirement? Let me know by leaving a comment!

Don't miss an episode, hit that subscribe button...

If you liked this episode, subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Second-Half Travels
• Firecalc
• Couchsurfing
• Squaremouth
• Nomad Cruise
• Remote Year
• WiFi Tribe
• Schedule a 1:1 consult with me
• HYW FB community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

75: Real estate investing might seem like something only wealthy people can do.

It’s expensive, down payments can be high, and you may feel you don’t have enough income to afford it.

Maybe you think: “I can’t even afford a house to LIVE in…how would I afford a house to invest in?”

But the plain truth is: there are lots of average Joes who do it…and who build a lot of wealth from it!

Today’s podcast guest is one such (inspiring) example.

John and Rosalina Steiner reached out to me (after following the podcast!) to share their real estate investing story. I found it compelling and wanted to share their insights and wisdom with you, too. Hope you enjoy listening to their story as much as I did!

We chat about:

• How and why the Steiners started investing in real estate in the first place
• Their 25-door real estate portfolio breakdown – what type of units, where they’re located, how many have mortgages
• How they financed the down payments and loans for each property
• Why they chose the neighborhoods they invest in
• Why they self-manage, and their best tips for managing tenants effectively
• Their views on Section 8 and how they manage Section 8 tenants
• Why they never plan to stop investing…even though they’re 65!

Check it out here:

https://hackyourwealth.com/real-estate-investing-with-middle-class-income

Do you wish to invest in real estate but feel like you don’t know how to get started? What’s the biggest factor you think holding you back? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• John & Rosalina Steiner
• Multifamily real estate investing: how to build a $175M portfolio in 7 years with Andrew Campbell (HYW029)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

74: This week, I chat with Caroline Ceniza-Levine, a career coach now early retired, whose own spouse wasn’t on board with early retirement for many years before she finally convinced him to get on the FIRE train.

We talk about tips and advice for how to convince your spouse about early retirement – and all it entails...

We discuss:

• Caroline’s own path to FIRE – from music, to strategy consulting, to corporate, to coaching, to FIRE
• Her spouse’s main concerns when it came to early retirement
• How she got her spouse on board, what she would have done differently, and her advice for others who are struggling to convince their partner about early retirement
• Plus: how Caroline handles healthcare / insurance as an early (pre-Medicare) retiree, her passive rental real estate portfolio breakdown and how she manages her rentals remotely

Check it out here:

https://hackyourwealth.com/retire-early-with-spouse-working

Have you ever been at odds with your spouse about early retirement? What were their main concerns? Were you able to change their mind – how? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Costa Rica FIRE
• Money issues in marriage: why spouses fight about money, how to fight with empathy, and how to convince your spouse to FIRE (HYW065)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

73: One big reason the tech industry attracts a lot of talent: you get partly compensated in stock, and if you’re early enough at a company that IPOs, your stock options or RSUs can make you a millionaire multiple times over when the company goes public.

Google created >1000 millionaires at IPO. Facebook too. Microsoft has created >10k millionaires. Amazon probably even more.

But with stock compensation, your taxes can quickly get complicated. You need thoughtful tax planning to make sure you don’t pay more in taxes than needed. As with other types of income, what matters isn’t what you earn – it’s what you keep.

So this week, I spoke with Shane Mason, whose CPA firm specializes in advising entrepreneurs and tech workers, to share tips and strategies on stock option and RSU tax planning.

We discuss:

• The different types of stock-based compensation and tax regime applicable to each
• Deep dive on Incentive Stock Options + AMT + AMT “refund” rules
• How an 83(b) election works, and pros/cons of doing it
• Key tax planning strategies applicable to stock compensation (e.g. timing strategies, optimizing tax buckets)

Check it out here:

https://hackyourwealth.com/stock-option-rsu-tax-planning

Do you earn stock-based compensation? What tax planning best practices have you followed? What do you want to know more about when it comes to stock tax planning? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Brooklyn FI
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

72: This week, I invited Bill Exeter to teach us about 1031 exchanges. He is the CEO of Exeter 1031 Exchange Services and has been doing 1031s for nearly four decades.

You might know at a high level that a 1031 exchange means deferring real estate capital gains taxes. But the details are important to avoid dumb mistakes that will disqualify you.

We discuss:

• Different types of 1031 exchanges
• Key criteria and deadlines + step-by-step process for executing a 1031
• How to optimize timing your buy/sell transactions
• Like-kind replacement property rules
• Domestic vs. foreign property exchanges
• What constitutes “Qualified Use” + holding period requirements
• State tax consequences
• Why investors can’t do 1031s themselves
• The role of a Qualified Intermediary, how to vet one, and how much they cost
• Tax impact of converting a 1031 property into owner-occupied housing, and vice versa
• Common mistakes that disqualify you from a 1031
• Proposed Biden administration changes to 1031s: likelihood of passage + actions you can take now to mitigate adverse tax impact

Check it out here:

https://hackyourwealth.com/1031-exchange

Ever done a 1031 transaction? What was your experience? Anything you would do differently next time? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Exeter Group
• 1031taxreform.com
• How to avoid capital gains taxes when selling your house
• How the Home Sale Capital Gains Tax Exclusion Works (HYW033)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

71: Tax deed auctions provide an opportunity to buy tax-delinquent properties at a discount, wipe away existing liens and mortgages, and earn sizable profits in the process.

This week, I invited my friend Phil Kessler back to the podcast to teach us how this unique type of real estate investing works.

If you’ve ever wondered how tax deed auctions work, how to win them, and how to due diligence this type of real estate, then don’t miss this insight-packed episode.

What you’ll learn:

• How tax deed investing differs from tax lien investing
• How tax deed auctions work, how they differ from other foreclosure auctions
• The most important things to due diligence when it comes to tax deed properties, and how to due diligence them
• The most helpful online tools for property due diligence
• How to buy tax delinquent properties BEFORE they go to auction (and avoid competing against scores of other bidders)
• How redemption periods work, and which states have them
• How a quiet title lawsuit works, how much it costs, and what happens if a title dispute arises
• How tax deed auctions affect existing mortgages and liens, and how to verify the rules in your state

Check it out here:

https://hackyourwealth.com/tax-deed-investing

Have you ever bid in a real estate auction? What was your experience? What other questions do you have about tax deed investing that weren’t covered here? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• propertyonion.com
• The Deed Feed
• Velocity REOs
• RealAuction.com
• Grant Street Group
• CivicSource
• AAR Auction
• GovEase
• How tax lien investing works and how to buy tax lien certificates (HYW066)
• Real estate investing through house auctions and hard money lending with Ethan Gao (HYW032)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

70: Last time, we talked about the pros and cons of the “yield shield” and the impassioned views on both sides of that debate.

But what if you sidestep that entirely and generate your dividend yield through rental real estate instead?

Unlike stock dividends, which can be cut by company management, rents are arguably way more stable. Plus, real estate can be leveraged with a mortgage to juice a higher capital return.

Separately, regardless of which strategy you use, how should retirees think about the “crossover” point beyond which sequence risk effectively disappears?

This week, in the final part of our 3-part series on asset allocation, we talk again with Karsten Jeske, CFA, about both these topics.

We discuss:

• How rental real estate can change your optimal asset allocation
• Whether a bond tent strategy is still relevant if you have rental real estate
• How to analyze the sequence risk crossover point after which you are guaranteed to outlive your savings
• How to visualize the relationship between “how much nest egg is left” vs. “how much retirement is left,” and how to know when you’re really “out of the woods”

Check it out here:

https://hackyourwealth.com/sequence-risk-analysis

Do you think rental real estate is a more effective “yield shield” vs. dividend stocks? Would you change your asset allocation with rental real estate? How will you know when you’ve crossed the sequence risk “crossover” point?

Let me know by leaving a comment!

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• ERN's "When Can We Stop Worrying about Sequence Risk?"
• Asset allocation: Does the “yield shield” really protect against sequence of returns risk? (HYW069)
• Asset allocation: How to use a bond tent to reduce sequence of returns risk (HYW068)
• The shockingly un-simple math behind retirement safe withdrawal rates (Part 1) (HYW035)
• The shockingly un-simple math behind retirement safe withdrawal rates (Part 2) (HYW036)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

69: Last time we talked about using a “bond tent” strategy to reduce sequence risk in the years just before and just after retirement.

In FIRE communities, an alternate strategy that has become popular is the “yield shield.”

A yield shield strategy involves holding primarily investments that pay a high dividend yield.

The theory is: if the investment pays a dividend yield of 3-4% that might be all you need to cover your safe withdrawal rate. If you don’t ever have to touch the principal, sequence risk might disappear entirely.

But is it really that simple?

This week, in part 2 of our 3-part series on asset allocation, we continue our discussion with Karsten Jeske, CFA, about the pros and cons of a yield shield strategy. We start by wrapping up our glide path discussion from last week, then dive into a critique of the yield shield.

We discuss:

• How early retirees with kids should plan for key expense milestones during retirement that traditional retirees have already dealt with (college, buying a home, etc)
• Pros and cons of a yield shield strategy
• Whether investing in dividend kings or dividend aristocrats helps to address the cons
• The importance of looking at total return when analyzing the yield shield, and why a high dividend doesn’t translate into higher total return
• Reasons why the yield shield can fall short (and examples where it did)
• The right way to define success of a yield shield strategy
• Why Karsten doesn’t fundamentally believe the yield shield does better than a plain vanilla stock index

Check it out here:

https://hackyourwealth.com/yield-shield-critique

This yield shield critique has been very controversial in FIRE communities. Are you persuaded by it? Or do you believe the yield shield performs better? Why or why not? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Dividend ETFs: VYM, NOBL, SDY, DVY
• ERN's Yield Shield critique
• ERN's critique of the dividends-only approach
• Asset allocation: How to use a bond tent to reduce sequence of returns risk (HYW068)
• The shockingly un-simple math behind retirement safe withdrawal rates (Part 1) (HYW035)
• The shockingly un-simple math behind retirement safe withdrawal rates (Part 2) (HYW036)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

68: This week, in part 1 of a 3-part series on asset allocation, I talk with Karsten Jeske, CFA, about how to implement bond/equity glide paths, both leading into retirement and in the initial years after retirement.

Getting your asset allocation right, and shrewdly changing its composition in the years just before and just after retirement is one of the most impactful things you can do to offset sequence of returns risk.

If you want to understand how to do this effectively, don’t miss today’s episode!

We discuss:

• The intuition behind bond tents and equity glide paths
• Pros and cons of a bond tent strategy (what you gain, what you lose)
• How to determine the optimal % peak allocation of bonds
• How long you should optimally stretch each glide path over (and why each side probably should be different durations)
• When is a longer vs. shorter glide path better in terms of returns and risk
• When is a bond tent NOT worth it and you should just stick with 100% equities

Check it out here:

https://hackyourwealth.com/asset-allocation

What do you think about the bond tent strategy? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• ERN's cashflow modeling spreadsheet
• ERN's posts on glidepaths: part 1, part 2
• The shockingly un-simple math behind retirement safe withdrawal rates (Part 1) (HYW035)
• The shockingly un-simple math behind retirement safe withdrawal rates (Part 2) (HYW036)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

67: Given how big of a shock the events of 2020 were for just about everyone on the planet, what changes to the tax rules happened as a result?

This week I invited Katelynn Minott, CPA and managing partner at Bright!Tax, to share key tax filing updates to be aware of when you file your tax returns this year.

What you’ll learn:

• Tax treatment of CARES Act stimulus checks
• Healthcare related tax updates (e.g., qualified medical expense deductions)
• Updates to retirement plan rules (e.g., contributions, withdrawals, inherited IRAs)
• Tips for reducing investment income taxes
• Education related changes (e.g., student loan payments)
• Charitable donation changes
• Commonly missed business deductions for self-employed / sole proprietors
• Tax issues and updates applicable to remote workers (e.g., state tax residency rules, foreign earned income exclusion for expats)

Check it out here:

https://hackyourwealth.com/2020-tax-filing

What other 2020 tax filing questions do you have? Let me know by leaving a comment and, if there are enough, I’ll send them to Katelynn for feedback!

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Bright!Tax
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

66: Investing in tax liens may sound scary and complicated. But as you’ll see from today’s podcast interview, with a little bit of research upfront, it can be as easy as buying toilet paper on Amazon. And the capital required to invest can be as little as a couple hundred bucks, making it a low-risk way (compared to buy-and-hold real estate) to try a new investing strategy.

This week, I deep dive on tax lien investing with Phil Kessler, a prolific tax lien investor who has extensively researched the tax lien investing laws of multiple states. He also creates a lot of educational content about tax lien and tax deed investing online.

We discuss:

• How tax lien investing works + how to make money from it
• Differences between tax lien vs. tax deed investing
• How tax lien interest rates are set + realistic rates you can expect
• What makes an ideal tax lien investment
• Due diligence checklist for analyzing tax lien deals (and how it differs from typical real estate investing due diligence)
• Tips and tricks for evaluating physical property condition, environmental risks, etc, when you can’t access the house
• How tax lien auctions work + winning bid strategies
• How tax lien investment funds work + tradeoffs of investing in a fund

Check it out here:

https://hackyourwealth.com/tax-lien-investing

Have you ever invested in tax liens? What’s been your experience? What other questions do you have about it? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Nationwide Environmental Title Research (directory of public records websites)
• Velocity REOs (drive to any property, take 10-15 photos for you)
• National Association of Counties (find tax sale info on county treasurer site)
• National Tax Lien Association
• RealAuction.com
• Grant Street Group
• propertyonion.com
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

65: Last time we talked about money issues when dating.

But dating isn’t the end game (for most).

As the schoolyard song goes: “First comes love, then comes marriage…”

…And money matters, if anything, get amplified once you’re married.

It’s why money problems are the top or second leading cause of failed marriages (read: divorce) depending on which study you read…and it’s always a contributing factor even if it isn’t the straw that breaks the camel’s back.

So this week, I continue my conversation with Megan McCoy and Ed Coambs, two leading marriage therapists who specialize in financial therapy and conflict, to discuss how money matters get more complex after marriage…and what spouses can do about it to preserve and strengthen their relationship.

We discuss:

• The most common reasons and triggers why couples fight about money
• Whether keeping separate money accounts is a good idea
• How to fight about money productively, with empathy, to keep your relationship healthy and even strengthen it
• Where spouses should learn to compromise when it comes to money and finances
• Intentional money rituals that spouses can do to keep their relationship healthy
• How to get your spouse on board with early retirement (and the financial sacrifices required to do it)

Check it out here:

https://hackyourwealth.com/money-marriage

What is the most important thing young married couples should know about handling money issues together? Do you think keeping separate money accounts is a good idea? What’s your best advice for fighting about money with your spouse, with empathy? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Ed Coambs’ Healthy Love & Money
• Megan McCoy, Ph.D., LMFT
• Money Scripts article; Klontz Money Script Inventory
• Prepare Enrich workbook for couples
• Dew, J., & Dakin, J. (2011). Financial Disagreements and Marital Conflict Tactics. Journal of Financial Therapy, 2 (1) 7
• Love Sense: The Revolutionary New Science of Romantic Relationships
• Healing Your Attachment Wounds: How to Create Deep and Lasting Intimate Relationships
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

64: How do you have difficult conversations about money when you’re dating? What words should you use? What do you do if the conversations go south?

This week, I invited Megan McCoy and Ed Coambs, two leading couples therapists who specialize in financial therapy and conflict, to share insights about how to talk about money matters when you’re dating.

We discuss:

• Questions to ask (and behaviors to observe) early in a relationship to learn your partner’s financial values
• Tips for asking sensitive money-related questions that don’t rub your partner the wrong way
• How to handle it if your partner does get defensive or reacts the wrong way
• Tips for attracting a partner who shares your financial values
• What to do if you’ve met “the one” but have totally different mindsets and behaviors about money

Check it out here:

https://hackyourwealth.com/money-dating

How have you approached talking about money when dating? What tips and best practices have worked for you? What advice do you have for other couples? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Ed Coambs’ Healthy Love & Money
• Ed Coambs’ Charlotte Couples Counseling
• Megan McCoy, Ph.D., LMFT
• Money Scripts article; Klontz Money Script Inventory
• Brad Klontz’s How Clients’ Money Scripts Predict Their Financial Behaviors
• Prepare Enrich workbook for couples
• Dew, J., & Dakin, J. (2011). Financial Disagreements and Marital Conflict Tactics. Journal of Financial Therapy, 2 (1) 7
• Love Sense: The Revolutionary New Science of Romantic Relationships
• Healing Your Attachment Wounds: How to Create Deep and Lasting Intimate Relationships
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

63: Last time, we talked about general asset location principles, plus best practices for major asset classes like stocks, bonds, and real estate.

But what about non-traditional asset classes?

Also, if you’re planning to early retire, should your asset location considerations change at all…given that you generally cannot touch your tax-advantaged accounts until you’re nearly 60?

This week, we continue our discussion with Jonathan Duong, CFA, about both these topics as they relate to tax-efficient asset location.

We discuss:

• Commodities (gold, oil)
• Currencies
• Illiquid investments like LPs, private equity, private loans, etc
• Speculative holdings like Bitcoin, art, collectibles
• How asset location considerations might change for early retirees

Listen here:

https://hackyourwealth.com/asset-location-part-2

If you’re thinking about early retirement, what is your asset location plan? What are you holding in your taxable vs. tax-advantaged accounts? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Wealth Engineers
• Financial planning software: eMoney, Advyzon, Covisum
• Asset location: What assets should you hold in each account to minimize taxes? (HYW062)
• How to set your target asset allocation and rebalance your portfolio efficiently (HYW058)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

62: It might seem obvious that the best performing car isn’t just a function of the car itself…but also WHERE you’re driving it.

Ferraris vs. Hummers will perform best in very different environments.

When it comes to asset management, a similar thing is true.

A few episodes back, I did a 3-part series on asset allocation. However, asset allocation is only part of the puzzle to optimizing your portfolio.

To maximize total after-tax returns, WHERE you hold your assets is just as important as WHAT assets you hold.

Asset allocation is WHAT you hold.

Asset location is WHERE you hold it.

You have to make sure you drive the Ferrari vs. the Hummer on appropriate terrains.

Asset location strategy is about holding the right asset classes in the right accounts bearing the right tax profile.

The goal is to minimize taxes on the way in, minimize tax drag while you invest, and minimize tax liability upon withdrawal.

How do you do this?

This week, I talk with Jonathan Duong, CFA, about how to manage your asset location to be as tax-efficient as possible. (This is part 1 of a 2-part discussion.)

In addition to best practices and general principles, we discuss optimal asset location for:

• Stock holdings (both indexes and individual stocks, both dividend and non-dividend paying)
• Non-tax exempt bond holdings
• Tax-exempt bonds
• REITS
• Physical real estate

Check it out here:

https://hackyourwealth.com/asset-location-part-1

What asset location principles are most relevant to you? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Wealth Engineers
• Financial planning software: eMoney, Advyzon, Covisum
• How to set your target asset allocation and rebalance your portfolio efficiently (HYW058)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

61: All right champs – new year!

That means a fresh opportunity for goal setting to transform your financial situation this year.

To kick off the new year, I recorded a short episode this week about goal setting, mindset, and behaviors to help you make big strides toward your FIRE goals in 2021.

I also invited a couple other leaders in the FIRE community to share their best advice when it comes to financial goal setting for people who are serious about pursuing FIRE.

Check it out here:

https://hackyourwealth.com/new-year-goals-2021

Are you setting any FIRE related goals for 2021? What are they? Let me know by leaving a comment!

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• The exact spreadsheet I use to analyze income, expenses, and net wealth
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

60: Over the past year, I’ve done various podcast episodes about early retirement. I’ve also had numerous guests share their FIRE stories.

But what about the tactical steps for how to FIRE?

Many FIRE blogs talk a bit too high-level and not enough about the mechanics of how to do it, step by step.

So in today’s episode, I share tactics and best practices I’ve observed on how to retire early. With confidence and assurance. With hard numbers and analysis. With a proper weighing of risks and tradeoffs.

If FIRE is a goal for you, then be sure to listen closely for key insights on how to do it effectively.

What you’ll learn:

• How to project your early retirement cash flow needs / expenses with clarity and confidence
• How to project your retirement income cash flows with clarity and confidence to match those expenses
• How to build the investment assets needed to generate that retirement income
• The 4 main type of investment assets for funding early retirement (and their tradeoffs)
• How to withdraw your retirement spending needs while minimizing risk
• How certain life milestones will impact your income and expense projections
• Tax planning in early retirement

Check it out here:

https://hackyourwealth.com/early-retirement-fire

What tips from today’s episode do you agree with / not agree with? What questions of yours about FIRE did I not answer? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• The exact spreadsheet I use to analyze my income, expenses, and net wealth
• How to set your target asset allocation and rebalance your portfolio efficiently (HYW058)
• Download my FREE spreadsheet to track your current vs. target asset allocation
• Retirement withdrawal calculator: How long will your savings last in retirement?
• My 4×4 FIRE framework for creating and protecting wealth (HYW002)
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

59: It’s hard to consistently beat the market as an investor…but it takes zero effort to match the market.

Picking good index funds lets you match the market for near-zero cost.

And matching the market produces some pretty good results. If you had invested – and held – $100k (and not a dime more) in a plain vanilla S&P 500 index fund in January 1990, today it would be worth over $1M.

That’s 10x growth in 3 decades, or +7.7% annualized returns.

That’s despite a 1990 recession, 2000-2002 dot com bust, 2008 financial crisis, and 2020 coronavirus.

And all for zero effort.

I dunno about you, but index fund investing sounds richer and a lot more laid back than active stock picking (which almost uniformly results in lower returns anyway).

The key is picking good funds. What’s the best way to do this?

This week, I talk with Jonathan Duong, CFA, founder of Wealth Engineers, a wealth management consultancy, about how to pick the best index funds to invest in.

We discuss:

• Key differences between mutual funds vs. ETFs; between tracking, passive, and active funds
• Step-by-step tips for evaluating an index fund: attributes, criteria, performance indicators
• Recommended online tools to search for and filter indexes and fund options
• How fund expense ratios work
• Specific names (and ticker symbols) of popular index funds for: total stock market, total bond market, government bonds, real estate, all-weather portfolio

Check it out here:

https://hackyourwealth.com/best-index-funds

What are your favorite index funds, and why? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Resources mentioned in this episode:

• Wealth Engineers
• ETF.com
• Morningstar
• ETFdb
• ETF Replay
• MSCI
• The CRSP Indexes
• US total stock market:
• International stocks:
• Dividend-focused stocks:
• US investment grade bonds:
• US government and municipal bonds:
• International investment grade bonds:
• Real estate:
• Total market / all weather portfolio:
• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

58: How to set your target asset allocation can feel like a mystery. How do you do it rigorously? How do you know what’s optimal?

Rebalancing can also feel like a chore. Where do you start? How do you make sure you’re doing it rigorously and tax-efficiently?

This week, I show you how to set your target asset allocation tailored to your investment and risk profile. I share how to track your allocation over time and analyze drift from your target allocation. And I explain how to tax-efficiently rebalance back to your target allocation step-by-step.

If asset allocation and portfolio rebalancing feels like a mystery, chore, or headache, then don’t miss this episode because it will teach you how to do it rigorously and with no guesswork.

What you’ll learn:

• Why it’s prudent to sell your winning investments and rebalance toward your underdogs
• How to create and define your target asset allocation starting from first principles
• How to determine your investment style and risk tolerance in an intellectually honest way
• How to track your current allocation and analyze drift from your target
• How to rebalance your portfolio tax-efficiently step-by-step
• How often you should rebalance

If you really learn the principles taught in today’s episode, you’ll be able to rebalance your portfolio and ensure your asset allocation stays closely aligned with your investment goals (yielding higher returns and lower risk).

…And you can do it in 1 hour or less per year.

Check it out here:

https://hackyourwealth.com/asset-allocation-rebalance-portfolio

What is YOUR target asset allocation? How often do you rebalance? Any rebalancing strategies you use that I didn’t cover? What questions do you have about asset allocation and rebalancing? Let me know by leaving a comment!

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Download my FREE spreadsheet to track your current vs. target asset allocation
• My 4×4 FIRE framework for creating and protecting wealth (HYW002)
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

57: When it comes to investment management, it is crucial to write down your investing goals/plan in order to stay disciplined as an investor and get the returns you need with the least amount of risk possible.

The way to do this is by writing an investment policy statement.

This week, I explain about investment policy statements: what they are, why they’re important, and how to write a good one.

What you’ll learn:

• What an investment policy statement is and why it’s important to your financial future
• Why a thoughtfully written IPS will turn you into a better investor and yield higher returns
• How to write a good IPS
• The 3 crucial components all good investment policy statements have
• How often you should update your IPS
• When to reference your IPS on a day-to-day basis

Check it out here:

https://hackyourwealth.com/investment-policy-statement

If you have an IPS, what are the key sections in it? When and how often do you reference your IPS? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Schedule a private 1:1 consultation with me
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

56: This week, I invited CPA Steve Nelson, whose tax blog I’ve followed for years, to chat with us about the details of how Section 199A works and the restrictions around it.199A created a huge new tax break for small business owners, partnerships, real estate investors, and contractors. But there was a lot of uncertainty initially due to seeming ambiguities and loopholes in 199A without clear guidance/regulations to address them.

Now, two years later, a lot has become clearer.

We discuss:

• Section 199A overview
• What counts as Qualified Business Income
• Key rules and restrictions of 199A
• Strategies for maximizing the 199A deduction
• How 199A might alter your retirement contribution strategy
• Special considerations for real estate investors (including why a 1031 exchange may no longer make sense with 199A)
• Special considerations for professional service partnerships (law, medicine, accounting, etc)
• Special considerations for freelancers and online business owners
• What happens to 199A after 2025

Check it out here:

https://hackyourwealth.com/section-199a

Are you currently able to avail Section 199A? If so, how has it changed your business operations and/or financial planning considerations, if at all? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Evergreen Small Business blog
• How the final Trump tax bill affects you: analysis for early retirees
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

55: This week, I explain 6 key areas where there may be significant tax code changes under a Biden administration – including how these changes may impact your personal financial planning and what actions you can take to prepare for them.

What you’ll learn:

• How Biden’s proposal would impact income tax rates, deductions, and Section 199A
• How it could impact capital gains and qualified dividends tax rates
• How estate taxes and the step-up in basis at death could change
• Important changes that would affect retirement account contribution deductions
• How 1031 exchanges for real estate investors might be impacted
• Expected changes to the corporate tax rate

Check it out here:

https://hackyourwealth.com/biden-tax-proposal

Do you plan to make changes to your portfolio or personal finances in anticipation of tax law changes under a new administration? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• How the final Trump tax bill affects you: analysis for early retirees
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

54: In all my prior jobs except the current one, I can now say in hindsight that my 401k sucked.

It only offered 10-15 fund options…which is like being forced to shop for weekly groceries in a gas station mini-mart when you know that Kroger is on the other side of the street.

Their fund expense ratios were mediocre, even for the passive funds. You couldn’t beef up pre-tax money with additional after-tax money. There was no mega-backdoor Roth conversion option.

These are really easy ways for companies to create value for employees via 401k plans. Why they are so often deficient when it comes to these things, I’m sure I don’t know.

Luckily, there is a way you can take greater control over your 401k money (or IRA for that matter) to invest more freely and build wealth.

It’s called a self-directed retirement account.

This week, I chat with Dmitriy Fomichenko, a financial planner who specializes in using self-directed retirement accounts “with checkbook control” to beef up your investing and retirement planning strategy.

What you’ll learn:

• What is a self-directed retirement account, the different types that exist, key risks, and how they differ from traditional retirement accounts
• The process for setting up a self-directed retirement account, and how to fund it
• Maintenance costs associated with self-directed accounts
• The role of the custodian / trustee / administrator for self-directed accounts
• How to access your self-directed account funds to invest (and key differences here between 401k vs. IRA versions)
• What kind of assets you can invest in with a self-directed account, and how income and expenses generated by those investments are treated
• Why mixing outside funds with self-directed account funds is such a big no-no, and the consequences if you do

Check it out here:

https://hackyourwealth.com/self-directed-retirement-account-401k-IRA

Are you satisfied with your 401k? Why or why not? Does a self-directed account sound appealing? Why or why not? Let me know by leaving a comment when you’re done.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Sense Financial free consultation
• List of non-recourse lenders
• Everything you need to know about 401Ks (HYW003)
• IRAs, Roth IRAs, and how to get the tax benefits of BOTH (HYW004)
• 18 real estate investors share what they wish they knew at college graduation
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

53: No matter how you cut it, the cost of college these days is pretty crushing.

And getting into your top choice college is well and good and all, but it doesn’t matter much unless you can afford to attend!

How can parents and families afford college (potentially for multiple kids) without ravaging their retirement savings?

This week, I invited my friend Ann Garcia, aka the “College Financial Lady,” back to the podcast to explain the intricacies of how college financial aid works. She shares insights and wisdom on how to plan for the cost of college, the different types of aid available, and strategies for maximizing financial aid.

We discuss:

• A big picture framework thinking about college financial aid
• The overall financial aid process, timeline, and key dates
• The role each type of aid (need-based, merit, government, and college aid) plays in a family’s financial aid strategy
• How FAFSA works, the 4 buckets of money that must be reported, what money can be excluded
• What federal EFC is, how it’s calculated, and how it’s used
• What the CSS Profile is, key differences vs. FAFSA, and what money must be reported on it
• How CSS Profile schools calculate EFC and differences vs. FAFSA methodology
• When it might be useful to leverage a grandparent-funded 529 plan + tradeoffs
• Student loan options and key types of loans available to students
• Tips for negotiating / appealing your financial aid package
• Financial strategies related to the “prior-prior” year once January of sophomore year arrives
• Financial strategies in the years BEFORE your child applies for college financial aid to maximize aid

Check it out here:

https://hackyourwealth.com/college-financial-aid

Has your child (or children) attended college with financial aid? What surprised you about the financial aid process? What do you wish you had known that you know now? What other questions do you have about financial aid? Let me know by leaving a comment when you’re done.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• The College Financial Lady
• College Data
• Federal housing multiplier index for financial aid
• 529 college savings plans: rules, tax benefits, & qualified expenses (HYW026)
• College financial aid strategies to optimize your assets, income & EFC (HYW025)
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

52: The competition for admissions to the most elite colleges in America (think Ivy League, US News top 10) is fiercer than ever.

That’s because top colleges provide the best academic opportunities. Resources. Career opportunities. Pathways to elite grad schools. Student and alumni communities (where you’ll forge lifelong connections, friendships, potentially even meet your spouse). Not to mention, you’ll have a powerful brand associated with you for life.

How can students and parents without special connections distinguish themselves amidst a sea of qualified applicants?

This week, I chat again with my friend Shirag Shemmassian, a college admissions expert who has coached thousands of students to successful admission at elite colleges, about the mindsets and accomplishments you really need to win admission to the most elite colleges.

We discuss:

• Biggest myths and misconceptions when it comes to getting into elite colleges
• What elite college admissions committees are looking for, and how to differentiate yourself
• What level/degree of accomplishment you need to get in
• What students (and parents) can do well ahead of the application year to distinguish themselves, and how far in advance to do it
• How lower / middle income / rural / etc students with access to fewer opportunities can still differentiate themselves compellingly
• Why your “message” and the way you deliver it is just as important as your actual accomplishments
• The mindset students should have when writing their college essays
• How to pick an essay topic and write it compellingly (even if you’re not a great writer)
• Who should write your recommendation letters, and how to build genuine relationships with recommenders that blossom into great letters
• The qualities that make a stand-out recommendation letter

Check it out here:

https://hackyourwealth.com/college-admissions

Did you attend (or send your kid to) an elite college? What do you think principally contributed to your / their admissions success? What would you have done differently if you could do it over? Let me know by leaving a comment when you’re done.

NOTE: Apologies in advance we had some audio problems in the second half of the interview, so some parts may sound choppy. However, all key points should still be clear. I’ve also cleaned up the transcript (at the link above) to fill in missing words / phrases, so check that out if you’re struggling to understand any key points.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Shirag's guide to getting into top colleges
• Shirag's successful college essay examples
• Shirag's tips on writing the common app essay
• How to attend any college for free, with Shirag Shemmassian, PhD (HYW039)
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

51: Despite the pain (and cost) that not having an estate plan will cause your heirs, fully two-thirds of Americans don’t even have so much as a will if they got hit by a bus.

There are many reasons why people fail to create an estate plan. None are good.

So for this week’s podcast, I invited Spiro Verras, a Florida estate planning attorney, to share key things you need to know about creating a proper estate plan.

We discuss:

• Elements of a good estate plan
• How probate works step by step, how long it takes, and how much it costs
• At what point in your life you should write a will
• Differences between wills and trusts
• Legal formalities of wills and trusts
• How wills and trusts change the probate process
• What DIY-ers need to know before drafting their own estate planning docs
• Special considerations for real estate investors, family business owners, professional service practice owners, and high net-worth individuals

Check it out here:

https://hackyourwealth.com/estate-planning-basics

Do you have a will or trust? What about a medical directive or power of attorney agreement? Have you ever been through the probate process? What was it like for you? Let me know by leaving a comment!

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Verras Law
• How to write a will
• How to set up a revocable living trust (with sample trust document)
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

50: Social Security is crucial to American retirement. 1 in 5 Americans and 1 in 4 families depend on it. That’s 65M people who will collect $1 trillion in Social Security benefits in 2020.

I said, $1 trillion.

With this massive of an entitlement program, it serves you well to understand how it works in gory detail so you can maximize your benefits. Sound good?

(If you’re a youngster, don’t glaze your eyes over…you may think Social Security is not relevant to you anytime soon, but what you do now impacts how much you collect in the future. So listen up – your retired self will thank you….)

This week, I invited Jim Blair to come share the goods on how Social Security works. Jim is a Social Security expert who spent 35 years at the Social Security Administration advising on benefits and claims, so he knows a thing or two about it.

We discuss:

• How Social Security benefits are calculated
• Key factors to consider when deciding what age to claim
• Optimal claiming strategies and tradeoffs of claiming younger vs. older
• How spousal, divorced, and survivor benefits work (and how they impact your claiming strategy)
• When Social Security is subject to taxes (and how much)
• What is likely to happen to Social Security when its assets go to zero (in <20 years)
• Whether young people should count on Social Security being there in the future as they plan their retirement finances

Check it out here:

https://hackyourwealth.com/social-security-podcast

Do you factor in future expected Social Security benefits into your retirement planning? Or do you just assume it won’t exist by the time you retire? Do you think it’s better to claim younger or older? Why? Let me know by leaving a comment when you’re done.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Premier Social Security Consulting
• jblair at mypremierplan.com
• How Social Security Works: The Ultimate Guide For Laypersons
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

49: The Health Savings Account is an incredible tool to take greater control over your healthcare. It is the most tax-efficient investment account on the planet.

So, if you’re eligible for it and not at least considering how to take advantage of it, you’re missing out.

In this week’s podcast, I deep dive on HSAs with Roy Ramthun. Roy is a nationally-recognized HSA expert, because he led the Treasury Department’s implementation of HSAs when they were signed into law in 2003, and then he served as a White House healthcare policy advisor.

I thought I already knew a lot about HSAs, but I still learned new things from Roy.

We discuss:

• How Roy got the nickname “Mr. HSA”
• Why HSAs are so special and how they work
• Tax benefits of HSAs at both federal and state level
• The 3 main eligibility criteria for HSAs
• Ways to fund HSA contributions
• What health expenses are considered qualified
• HSA bank options and factors to consider when selecting a custodian bank
• Reimbursement rules, receipt saving tips
• Tips for maximizing the growth of your HSA
• What happens to your HSA when you retire or pass away

Do you have an HSA? What kind of health expenses have you been able to save on using an HSA? Any follow up questions for Roy? (He’s offered to help answer them.) Let me know by posting a comment on the show notes page.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• HSA Consulting Services
• Health Savings Accounts: Contribution Limits, Eligibility Rules, Benefits
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

48: Seniors often enter retirement (a) thinking Medicare is free, and (b) not at ALL clear how the details work – rules, restrictions, limitations, costs.

But it’s most certainly not free: your portion of costs could be unlimited and bankrupt you. And, like other healthcare matters in the US, “how it works” gets complicated fast!

How can seniors (and their loved ones, like you) make sense of it all?

This week, I talk with Danielle Kunkle Roberts, a nationally-recognized expert on Medicare insurance, about how to evaluate, navigate, calculate, and decide on the best configuration of Medicare coverage for you and your family. If health insurance “peace of mind” is important to you in your elder years, this is an action-packed episode you do not want to miss.

What you’ll learn:

• Medicare eligibility requirements
• Options for expats who haven’t paid into Medicare taxes
• What exactly Medicare covers, how each “part” works, and premium costs
• How to determine which doctors, hospitals, clinics, and pharmacies will accept your Medicare coverage
• How the premium surcharge (IRMAA) works if your income exceeds certain thresholds
• All-in costs you can expect to pay for Medicare coverage
• How the “initial enrollment period” works, including how the penalty works
• How Medicare Advantage works + when it’s a better choice than original Medicare (tradeoffs, considerations, cost differences, network differences)
• How Medigap works and tradeoffs and considerations
• How expat retirees should plan for Medicare, given it generally doesn’t cover them overseas

What other questions do you have about Medicare? If you’re looking into Medicare for yourself or a loved one, are you leaning toward original Medicare or Advantage? Why? Let me know by leaving a comment right now.

Don’t miss an episode, hit that subscribe button…

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Overcast
• Spotify
• Stitcher

I need your help, please leave a listener review

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Boomer Benefits website
• Boomer Benefits Book: 10 Costly Medicare Mistakes You Can’t Afford to Make
• Boomer Benefits private Facebook group
• Boomer Benefits YouTube video: Will Medicare Cover My Procedure?
• Medicare.gov: What Medicare Covers
• Medicare.gov: Find & compare doctors
• Medicare.gov: Medicare plan finder tool
• CPT codes & ICD 10 codes: How medical billing & insurance claims work (HYW020)
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

47: In this week’s podcast, I explain how to create a family emergency binder using 11 essential categories of info to make it easy for loved ones to understand your finances and figure out what you have, what you owe, and what you’re owed.

What you’ll learn:

• 11 essential types of info to include in your binder
• Tips on how to organize documents, PDFs, spreadsheets, and videos
• How often to update it + tips on staying organized
• Why it’s worth starting now, even if it takes a long time to finish

Do you have a family emergency binder? What other info do you think belongs in it? Let me know by leaving a comment when you’re done.

Don’t miss an episode, hit that subscribe button…

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Free downloadable checklist: 11 Essential Categories of Financial Info For Family Emergency Binders
• 16 essential estate planning checklist topics to protect your family and give you peace of mind (HYW009)
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

46: Most people know what life insurance is. But they tend to think of it as term life: fixed payments for 20-30 years that pay out a death benefit if you die before the term is up (while paying nothing if you outlive it).

There’s another type of life insurance called permanent life insurance. It never expires. The most common type is whole life insurance.

Whole life insurance can get very complicated, so I invited a financial planning veteran with extensive experience in it (not affiliated with any insurance company) to share insight on how it works.

This week, I talk with Eric Brotman, CEO of BFG Financial Advisors, a wealth management consultancy, about the intricacies of whole life insurance: who it’s best suited for, its tax and estate planning benefits, and how to use it for investing purposes.

What you’ll learn:

• How a policy his parents bought for him at 14 which he inherited at 24 got him hooked on whole life insurance
• The main tax advantages of whole life
• How whole life is used for estate planning
• The type of securities life insurance companies invest in
• How to choose a whole life insurance company
• How life insurance broker commissions work (and how much they are)
• What paid-up additions are and why they matter
• How to borrow against your whole life policy
• The tradeoffs of borrowing from vs. against your policy
• How whole life can supplement social security in retirement

If you have whole life insurance, are you satisfied with it? Why or why not? If you borrow against your life insurance to invest in other assets, what do you invest in? Let me know by **leaving a comment.

Don't miss an episode, hit that subscribe button...**

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Brotman Financial Group
• www.lowtaxbook.com
• Don't Retire...Graduate Podcast
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

45: Early retirement must be executed differently, and very intentionally, with kids. There are no easy, silver-bullet solutions.

I think about this topic often. And, ever since my kiddo popped out a few years ago, I’ve made real changes to my financial planning in response – from building larger, stronger passive income streams to doing very detailed financial analysis of kid costs that, in turn, have influenced our planning decisions.

This week, I invited to the podcast Michael Quan, an early retiree (now blogger) with 2 kids who founded and ran an IT services company for a decade before selling it (and not for “FU money” btw) and retiring. I ask about Michael’s mindset, actions, and challenges he faced when early retiring with kids.

We discuss:

• How the financial crisis motivated Michael to start his own company
• How much he had saved up on the day he retired vs. where his portfolio is at now
• When did kids enter the picture relative to his retirement date
• How kids impacted the family budget, including lifestyle trade-offs they made to accommodate
• Key areas where early retirement actually brought significant savings
• How Michael spends his days now
• How having kids has influenced the way he thinks about wealth building

What resonated with you from Michael’s story? What seemed less relevant to your own situation? Let me know by leaving a comment when you’re done.

Also: I want to bring on more guests who have FIRE’d with kids.

Michael’s is one story, and hopefully you got good nuggets of insight from it, but it’s not the only story. If you know a good potential guest (early retiree family with unique story), tell me about them. I’d love to reach out.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Financially Alert
• Breakthrough Millionaire Podcast
• The FIRE Planner book
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

44: One common trait of ordinary people who accomplish extraordinary things is their ability to turn personal struggle and tragedy into resilient energy channeled toward big goals.

And one of the most challenging tragedies ordinary people commonly face is the death of an immediate family member.

This week, I talk with Adam Fortuna, an engineer who turned his mother’s untimely death into motivation to achieve financial independence and retire early – which he did at age 36 with a portfolio >$2M.

We discuss:

• How Adam got into software development, then transitioned into product management
• How his mother’s premature death suddenly forced him to figure out how to manage and invest assets…and why it made him realize he wanted to retire early
• How he applied an estimation technique used in the software development industry to come up with his FIRE number
• Why moving states cost him 6 figures in taxes
• How his boss reacted when he pulled the trigger and gave notice
• How his portfolio crashed 30% when he quit his job…and why that didn’t faze him
• Why he scrutinizes trailing averages (rather than specific months) when analyzing his safe withdrawal rate
• How he uses the 4% rule as a heuristic, but doesn’t apply it strictly
• How he handles health insurance post-retirement
• The simple Google spreadsheet plugin he uses to import all his financial data into Google sheets for manual number crunching

What personal life events motivated YOU to get smart about your finances? How would a windfall impact your retirement plans? Let me know by leaving a comment when you’re done.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Minafi
• Tiller (automatically export personal finance data into Google spreadsheets)
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

43: People spend way too much time scrutinizing examples of early retirees who just recently FIRE’d and not nearly enough time on early retirees who actually made it through decades of retirement.

That’s why there’s a whole cottage industry of blogs and books by recent retirees dispensing advice (and downloadable spreadsheets) on how to save a million bucks, retire to Southeast Asia, and sip mango juice all day and get cheap massages.

But there’s nothing to actually scrutinize in these examples because no one really miscalculates their nest egg so badly that they have to go back to work within a few years.

We should spend more effort analyzing examples of people who actually successfully STAYED retired for decades. (And I don’t mean folks with $10s of millions.)

That’s because the shockingly simple math to get TO early retirement is different from the shockingly un-simple math to get THROUGH early retirement.

Yet there are few and far between examples of early retirees who actually made it through decades, weathered all the ups and downs intact, lived a good and fulfilling life, and are still in good physical and financial shape.

So you can imagine how excited I was to speak with today’s guests, a senior couple who achieved precisely this.

This week, I chat with Billy and Akaisha Kaderli, a husband wife couple who early retired 3 DECADES ago in 1991 and are still going strong. With one full 30-year retirement already behind them and a nest egg that is bigger than ever, Billy and Akaisha have traveled the world across decades, lived a great life, and have tons of stories and advice to share.

We discuss:

• Their varied career path before retirement (French chef, stock broker)
• Why they decided to retire early long before a FIRE community existed
• Why they decided not to tell anyone about their early retirement plans
• Why they defined their FIRE number based on only a subset of their expenses (and which expenses those were)
• What they invested in before there were ETFs, and how big their portfolio was on the day they retired
• How they planned their travels via a multi-year loop over the decades, and how they chose regional “home bases” around the world
• When they decide to travel together vs. solo
• How large their portfolio is now 3 decades later
• How they afforded healthcare over the decades (including emergency surgeries) with no health insurance…and without bankrupting themselves
• How they dealt with downturns and recessions over the decades…including the one time they briefly considered going back to get a j-o-b (and why they decided against it)
• What they would have done differently if they could do it all over again

Does Billy and Akaisha’s story change your view on what it takes to get to FIRE? What it takes to successfully live a good and full retirement life for decades? Does it influence any choices you might make in your retirement planning plans? Let me know by leaving a comment when you’re done.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Retire Early Lifestyle
• Retire Early Lifestyle bookstore
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

42: A big reason why I started HYW was to show how you can “hack systems” in large and small ways – whether related to taxes, travel, real estate, etc – to achieve FI and retire early…

…and to continue growing wealth even in retirement.

That’s probably why many readers are engineers: you likely know a thing or two about hacking / optimizing systems.

That’s also probably why there are many ex-engineers in the FIRE community.

Today’s guests, who were engineers before early retiring, were one of the first folks in the FIRE community I started following a few years ago.

So it’s a real treat to talk with Kristy Shen and Bryce Leung, millennial early retirees who quit well-paying engineering jobs to travel the world, initially, for one year…but decided – after analyzing their spend that year and realizing it cost less to travel than to live in their hometown – to do it for good. (Along the way, they also wrote a popular FIRE blog and best-selling book.)

Their story is about applying simple rules of thumb to saving and investing to build a 7-figure portfolio and retire early, then optimizing your investments efficiently to withdraw safely into perpetuity.

We discuss:

• What motivated them to leave well-paying engineering jobs
• How they came up with their FIRE number and what they invested in
• Why they rebelled against conventional wisdom to buy a home
• How they stayed focused as friends and colleagues upgraded their lifestyles…and how they eventually became the envy of peers back home
• Why their parents objected but eventually came around (and what convinced them)
• The moment they realized it was cheaper to travel than to stay at home
• How big their portfolio was on the day they retired and how big it is now (after traveling over the years)
• How they use a “yield shield” to structure their withdrawals so they never have to sell in a down-market (and how long their cash buffer will last)
• How their mindset shifted from “traveling to consume” to “traveling to learn”
• How they deal with loneliness when traveling for long stretches
• How they handle health insurance after losing their universal coverage
• How getting older and potentially starting a family may change their travel lifestyle in the future

Would you travel long-term – potentially forever – in early retirement? Do you agree with Kristy’s and Bryce’s views on homeownership? What are your reactions to their safe withdrawal strategy (yield shield)? Let me know by leaving a comment!

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Millennial Revolution
• FIRE explained in Mandarin
• Kristy's and Bryce's book: Quit Like a Millionaire
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

41: Is it crazy to quit a high-paying law firm job to take a lower-paying law job (not in a law firm)?

The majority of lawyers will say no. Because that’s what most lawyers who start their careers in law firms do! Whether it’s for better hours, better balance, less travel, whatever.

Now, is it crazy to quit being a lawyer to do something completely non-law related?

Again, most lawyers will say no – because tons of lawyers do exactly that.

But: is it crazy to quit the law to…deliver for DoorDash, shop for Instacart, be a dog walker, or recharge Lime scooters?

The first time I read today’s guest’s story, I admit I thought so. Why would you seemingly throw away a promising legal career to be a manual gig laborer, when there are plenty of folks who would dream about doing the opposite?

Then I realized two things.

1. I should be the last person to critique this because I myself “threw away” a legal career for a totally non-law path. Granted, I didn’t do it for manual labor, but it also wasn’t conventional by any means.
2. It’s not my place (or yours or anyone’s) to judge the career choices of others. What makes people happy is their personal decision alone, and no damn business of anyone else’s!

Interviewing today’s guest for the podcast just made that even clearer.

This week, I talk with Kevin Ha, a prolific side hustle expert, about why he quit the law to pursue a unique path to financial independence. He generates income both from his blog and through side hustles (which he often blogs about), each of which separately and independently replaced his full-time salary from his last job.

We discuss:

• Why Kevin quit the law without a traditional FIRE portfolio already in place
• How Kevin defines financial independence
• Why he doesn’t view gig economy side hustles as manual labor
• How he makes side hustles fit super efficiently around his schedule to minimize time spent
• How he structures his daytime hours now without a traditional job
• His technique for letting go of the “prestige trap” (notorious among lawyers), despite graduating with honors (and law review) from law school
• Whether Kevin would have gone to law school again knowing what he knows now

Do you agree with Kevin’s philosophy on FI? Even if you would not have made the same choice, do you see merit in this path? If not, why? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Financial Panther
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

40: Early retirement may seem glamorous when you’re dreaming about it….

Sleeping in every day. Going jogging mid-day. Picnicking on a random Tuesday. Flying off to vacation on a moment’s notice. Wandering abroad for months at a time.

But once early retirement is actually your life, it’ll feel different. You have to be intentional about it to make sure it lives up to your expectations.

This week, I invited Anita Dhake – a lawyer turned early retiree who’s retirement plan has shifted over time – to share her story about retiring from the law at 33 to travel the world, what she’s learned along the way, and why she no longer travels full-time.

We discuss:

• Why she walked away from a high-powered law firm career after graduating from an elite law school
• What motivated her to retire early, and how she came up with her FIRE number
• How she tackled student debt at the same time
• How much she had in the bank on the day she FIRE’d…and how much she has now
• How retiring early actually made health insurance easier
• How many countries she’s traveled to since retiring, and why long-term travel is so difficult compared to vacation travel
• Why she ultimately stopped long-term traveling and what she’s doing now instead

Did anything in Anita’s story surprise you? Do you agree with her view on long-term travel? Would you do anything differently? Let me know by leaving a comment when you’re done.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• The Power of Thrift
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

39: Everyone knows the cost of college is cray. 😖

It can create serious retirement speed bumps for parents…

…and it only gets worse with every passing year. 📈

But for students and parents who are super on top of their 💩, there is a real path – through scholarships and fellowships – to make the cost of college (and grad school) FREE.

Not only that, if you’re really good and write superb applications, you can even get PAID to attend.

They say, “There’s tons of free money out there for college; you just have to know where to look.”

Well, so…where’s all that free money? And how can you get it?

This week, I talk in-depth with Shirag Shemmassian, PhD, about the exact tips and tactics you need to win scholarships hand over fist, so that you can attend college and grad school for free…or even get paid to attend.

Shirag is a university admissions expert and founder of Shemmassian Academic Consulting, where he has helped students win admission to every elite college in the country.

As someone who himself won over $200k in scholarships, Shirag’s insights are pure gold, so for you neurotic parents out there, this is an episode you won’t want to miss.

What you’ll learn:

• The biggest myths and misconceptions when it comes to winning scholarships
• The 4 key places to find scholarships and the pros and cons of each
• How to write a superb scholarship application (and do it super efficiently again and again)
• How to ask for standout recommendation letters
• How the game up-levels (and differs) for the most prestigious and competitive scholarships in the world (Coca-Cola, Gates, Goldwater, Rhodes, Marshall, Soros, Fulbright, Truman)
• How to prepare for interviews with these scholarship selection committees

What tips / advice resonate most? If you’re a parent of a successful scholarship student, what other tips did you find effective for winning scholarships? Let me know by leaving a comment when you’re done.

Don’t miss an episode, hit that subscribe button…

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• The Ultimate Guide to Finding and Winning College Scholarships
• Shemmassian Academic Consulting
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

38: With all the ways your budget can explode after you start having kids, what can you do in advance to better prepare financially to reduce the financial stress that comes with starting a family? 👶

In this week’s podcast, I deep dive on this with Kevin Mahoney, founder of Illumint, a financial planning company focused on helping millennials in their 20s-30s navigate family finances.

We discuss:

• Why money so often causes marital strain and conflict
• The big money-related questions to ask that will help you understand your partner’s financial philosophy and values
• Why it’s important for both spouses to lean in equally when it comes to family finances
• The biggest ways your finances change after having a baby
• Concrete actions would-be parents can take to prepare financially for a family
• When and whether to buy life insurance

How did you prepare financially for starting a family? For getting married? What would you have done differently? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Illumint
• Lifehappens.org - for estimating life insurance coverage
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

37: It costs a pretty penny to raise a kid.

I knew my expenses would go up with a kid in tow, but looking back I underestimated exactly how much they would go up by.

Hmm. “Go up” isn’t quite the right word. “Blow up” is a bit more accurate.

That’s because kids are like vacuum cleaners: they clean your budget out.

In this week’s podcast, I share what I’ve learned, using direct examples from our own budget, about how our expenses blew up after starting a family.

What you’ll learn:

• 6 expenses that explode when your bouncing baby arrives
• How much you can roughly expect your costs to increase with a kid in tow
• Some practical tips on how to reduce those costs and save money

What’s been your experience with budgeting and expenses after having a kid? Any other expenses that ballooned after you had a kid? Did your costs increase by similar percentages as mine? Let me know by leaving a comment when you’re done.

Don’t miss an episode, hit that subscribe button…

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• House Hacking San Francisco Bay Area style
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

36: Last week, we dove headlong into the wonky but uber-crucial topic of retirement safe withdrawal rates.

My conversation with Karsten Jeske, PhD – a former professor, Fed economist, quantitative finance researcher, and early retiree – focused last week on sequence of returns risk and how to estimate your safe withdrawal rate in early retirement.

Our conversation was so action-packed that I had to break it up into two episodes, so this week we continue our discussion and focus on how to mitigate sequence of returns risk during early retirement.

We discuss:

• How to adjust your withdrawal rate and rebalance your portfolio in response to market conditions
• How to critique the common advice that the returns risk in the first 10 years of retirement determine success or failure in all retirement
• Why sequence of returns risk is a “zero sum game” between retirees vs. savers, and why investing strategies for these two groups should therefore inversely mirror each other
• Concrete actions investors can take, during their accumulation phase and during retirement, to reduce sequence of returns risk
• How early retirees can use rental real estate to reduce sequence of returns risk
• What is the lowest historical safe withdrawal rate that entirely eliminated sequence of returns risk
• How coronavirus might impact your safe withdrawal analysis and early retirement prospects

What actions do you plan to take to fortify your safe withdrawal rate? What other questions about safe withdrawal rates and sequence of returns risk do you have? Let me know by leaving a comment when you’re done.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Early Retirement Now Safe Withdrawal Rate Series
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

35: When it comes to early retirement the most important (and difficult) thing you have to grasp is your safe withdrawal rate.

FIRE bloggers rave about “the shockingly simple math behind early retirement,” but they almost never talk about the shockingly un-simple math behind safe withdrawal rates.

So this week, I invited Karsten Jeske, PhD – a former professor, Fed economist, quantitative finance researcher, and early retiree – to the podcast to share insight on how to estimate your safe withdrawal rate in retirement.

This is the most important financial planning concept early retirees must grasp to stay retired and guarantee they never have to go back to a j-o-b.

What you’ll learn:

• The fatal flaw of the “4% rule” and why you might easily run out of money in retirement if you follow it blindly
• The importance of analyzing the conditional probability of failure based on the actual year you retire
• Why sequence of returns risk and safe withdrawals rates are inextricably linked
• Why the business cycle in the year you retire is crucial to your safe withdrawal analysis, plus how to use the Shiller CAPE ratio to estimate your safe withdrawal rate
• How Social Security factors into your safe withdrawal analysis
• Why sequence of returns risk is front-loaded for early retirees but back-loaded for wage earners

Have you analyzed your safe withdrawal rate? Do you think it is more or less than 4%? 3%? Let me know by leaving a comment when you’re done.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Early Retirement Now Safe Withdrawal Rate Series
• Trinity Study (4% rule)
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

34: The extraordinary market volatility the last couple months has been enough to wrench the stomachs of even the most battle-hardened investors.

Right now, the markets are on a tear and have recovered most of their losses since the coronavirus sent us running for cover.

But the kind of top to bottom -35% freefall we saw in one single month earlier this year is exactly the kind of whiplash that destroys an early retiree’s confidence when it comes to retirement withdrawals.

That’s why it is so crucial for at least part of your portfolio to be stable cash-flowing assets. Stable cash flows that don’t go poof when the market tanks will help tide you over to the recovery, whether recovery takes 3 months or 3 years.

We’ve been talking a lot about real estate the last few episodes. One richly cash-flowing real estate asset class we haven’t talked about yet is mobile home park investing.

In this week’s podcast, I chat with mobile home park investor Andrew Keel about this unique real estate investing strategy.

Andrew owns and operates more than 1,000 mobile home lots across 17 parks in 7 states. He shares insight on how wealth is built with mobile home parks by owning the land and not the homes that sit on it.

We discuss:

• Structure of the mobile home park industry
• How mobile home park investing differs from traditional real estate investing + what makes it especially attractive vs. other niches
• Why supply and demand for parks increasingly favors investors
• How to find mobile home park deals
• How mortgage financing works for mobile home parks (what kind of banks lend to park investors, typical loan terms)
• How Andrew found, acquired, and turned around his first mobile home park deal
• What are the markers of an attractive mobile home park deal
• Typical value-add improvements to increase park value
• Why a park’s utilities can make or break the deal

Have you or anyone you know invested in mobile home parks before? If you’re intrigued but hesitant, what concerns do you have? Let me know by leaving a comment when you’re done.

Don’t miss an episode, hit that subscribe button…

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Keel Team
• Bestplaces.net – demographic data and stats about cities and zipcodes
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

33: Each summer, the real estate market turns into a zoo as buyers and sellers play a big game of musical chairs. Everyone’s trying to get a new seat before the school year starts up again.

Buyers who are also selling a home that has gone up in value will face capital gains taxes…

Or will they?

If you do things right, you can exclude from taxes up to $500k capital gain married filing joint (single filers divide by 2).

In this week’s podcast, I share how the home sale capital gains tax exclusion works, the rules you must follow, and common mistakes sellers make that cut into the tax benefit.

What you’ll learn:

• Basic rules of the home sale capital gains tax exclusion
• The 2009 change that made claiming your exclusion more difficult
• What qualified vs. non-qualified uses are…and how it impacts your tax liability
• The safe harbors that help you exclude more from taxes

Have you sold a home before and were able to get the exclusion? What’s the most confusing part of the rules to you? Let me know by leaving a comment when you’re done.

Don’t miss an episode, hit that subscribe button…If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener reviewIf you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• How to avoid capital gains taxes when selling your house
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

32: The last few podcast episodes have explored alternate real estate investing strategies like large-scale multifamily and fix & flipping.

But two more strategies worth deep-diving on are: private lending (i.e. hard money lending) + foreclosure auction investing/flipping.

So this week, I invited former BigLaw attorney turned real estate investor Ethan Gao to share about his experience as a hard money lender and foreclosure auction flipper.

Ethan has made over 120 hard money loans and flipped over 100 foreclosure auction properties, making serious double-digit returns in the process.

Bigger risk, bigger reward, right?

…Except Ethan would argue, the risk isn’t necessarily bigger. If you know what you’re doing, it’s actually smaller. It just requires more upfront cash.

Tune in to our interview to learn all about:

• Why Ethan pivoted from syndications and crowdfunding to hard money lending and foreclosure auction flipping
• How he finds and vets hard money borrowers, how much he typically lends, on what terms, and what happens when a hard money loan goes bad
• How foreclosure auctions work step by step (including bidding strategies, and why you need to bring tons of cash on top of cashier’s checks)
• How to get the list of auction properties in advance and how to diligence them before auction day

Have you invested in foreclosure auction properties or loaned hard money before? Did you earn higher returns? What key lessons did you learn? What other questions about lending / auctions do you want answered? Let me know by leaving a comment when you’re done.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• ethangao at gmail dot com
• Foreclose Houston
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

31: So, we’ve been talking real estate the last few podcast episodes.

So far, though, we’ve only talked about buying and rehabbing rental properties.

But buying/rehabbing isn’t enough.

You need tenants to actually make money – and build wealth – from real estate. Tenants pay the rent!

But how do you find great tenants? Manage them? And, importantly, keep them around?

In this week’s podcast, I talk with Mark Ainley in depth about how to manage rental properties effectively by attracting and retaining quality tenants.

Mark is a long-time real estate investor and co-founder of a Chicago-based property management company that currently manages ~1K residential doors + 2M square feet of commercial real estate.

We chat about:

• Best practices for attracting quality tenants to your listing (and screening applicants)
• Tips for managing tenants effectively – including key lease provisions, dealing with lease expirations, and regularly inspecting units
• How to retain good tenants and handle bad ones
• Key things to look for when hiring & reference-checking property management companies

If you own rental properties, what are your best practices for finding, managing, and retaining great tenants? Do you use a property management company? If so, how do you make sure you’re getting good service from them? Let me know by leaving a comment when you’re done!

Don’t miss an episode, hit that subscribe button…

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• GC Realty & Development
• Get Mark’s Tenant Scoring Matrix to help you screen tenants effectively
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

30: Juggling work and family is always hard.

Adding serious real estate investing to the mix is even harder.

But juggling toddler + newborn + investing in 19 doors your first year as a buy and hold real estate investor + rehabbing and flipping properties remotely from out of state + building an online real estate coaching/consulting business all at the same time is…insane.

Or crushing it.

And today’s guest has done just that. In this week’s podcast, I talk with Erin Helle, an army veteran turned “take-massive-action” real estate investor and house flipper.

We deep dive specifically on tips and strategies for rehabbing fixer-upper properties for maximum impact.

What you’ll learn:

• How to evaluate which upgrades will give the biggest bang for buck when you have a limited budget
• Erin’s step-by-step process for rehabbing, from first inspection to project complete
• How much $/time to budget for a rehab
• Tips for finding good contractors at reasonable rates
• How to manage contractors (dealing with poor communication, staying on schedule, etc)
• Simple rehab tasks that are worth learning yourself to save time and money

Have you rehabbed and flipped real estate before? What key lessons did you learn? What are your tips for finding and managing contractors effectively? Let me know by leaving a comment when you’re done.

Don’t miss an episode, hit that subscribe button…If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener reviewIf you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• BC Global Investments
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

29: How do 2 guys working on their own build a $175M multifamily real estate portfolio in 7 years spanning 1,700 apartment units?

That’s $25M of real estate acquired…every year.

In this week’s podcast, I talk with Andrew Campbell about large-scale multifamily real estate investing.

After building a personal portfolio of 76 doors ranging from single family homes to 4-plexes, Andrew switched to large-scale apartment complex investing – raising private capital to acquire 200+ unit complexes.

Since real estate is a powerful vehicle for building wealth, I wanted to learn from Andrew how he transitioned from small-scale to large-scale investing and lessons that other real estate investors can apply to their own real estate portfolios.

We talk about:

• How Andrew grew his personal portfolio to 76 doors in 3 years, including how he financed all the properties
• How he pivoted step by step to large scale multifamily investing
• How he found his first large multifamily apartment complex deal, the purchase price, the financing structure, and what post-purchase actions he took to increase its value
• His investment criteria for evaluating apartment complex deals today
• The key skills he believes you need to succeed at large-scale apartment complex investing

Do you invest in multifamily real estate? If you made the transition from single family to multifamily investing, what’s your story for how you did it? What other questions do you have about apartment complex investing that you want answered? Let me know by leaving a comment when you’re done.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Wildhorn Capital
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

28: Ever notice that wealthy people tend to own real estate, and real estate investors tend to be wealthy? #NotACoincidence

I’m not talking Forbes 400 kind of wealth (for that, um, please start a big successful company like Facebook)…but wealthy enough to FIRE comfortably.

In this week’s podcast, I share 7 powerful ways you can invest in real estate, from classic buy and hold to tax lien investing.

What you’ll learn:

• The 3 things that make real estate so attractive for building FI wealth
• 7 powerful ways to actually invest in real estate
• The 4 levers where wealth is actually created using real estate
• What I look for in investment properties and how I personally analyze them

Are there other powerful ways you invest in real estate? Any other factors you consider when analyzing a deal? Let me know by leaving a comment when you’re done.

Don’t miss an episode, hit that subscribe button…If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• My 4×4 FIRE framework for creating and protecting wealth (HYW002)
• House Hacking San Francisco Bay Area style
• How to do a residential property inspection step by step
• Real estate valuation spreadsheet to quickly compare properties side by side
• Free video tutorial: How to Analyze a Rental Property (What to Look For)
• RealtyMogul
• Fundrise
• Crowdstreet
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

27: Sometimes, you have to help loved ones learn a new skill, or else it actually becomes YOUR problem.

Teaching your kiddos about money is one of those skills.

You don’t want them to be clueless once they’re young adults and blow all their money…or make bad decisions and fall into debt.

If they fail at money, it becomes YOUR problem…just as you’re starting to enjoy more free time as an empty nester.

But the financial learning curve is long, so it’s important to start when they’re young and reinforce lessons consistently over the years.

That’s why in this week’s podcast, I share 9 crucial money lessons your kids must learn to succeed as adults.

Here’s what you’ll learn:

• The surprisingly young age when kids’ money mindsets/habits start to crystallize
• 9 crucial lessons to teach your kiddos from infant→toddler→tween→teen→young adult
• Tips for helping parents to actually make their kid internalize important money lessons
• Why giving kids decision-making control over their own budget early on will help them rapidly develop good financial judgment
• Why the most important lesson of all is to teach them how to find contentment in what they have, and how to know their self-worth is in who they are, not what they buy

What money lessons do YOU feel are most important to teach your kids? Let me know by leaving a comment when you’re done.

Don’t miss an episode, hit that subscribe button…If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• How to motivate your kid to win the national spelling bee (and excel in life)
• How to make sure the cost of college doesn’t ruin your kid’s future
• The best parenting guidance I’ve learned for raising successful children
• Why child care is so damn challenging (and what to do about it)
• Hey, rich people. Wealth management includes telling your kids how rich you are.
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

26: College affordability is tough but 529 college savings plans can help you boost college savings.

529s have similarities to Roth accounts. They are (mostly) taxed going in, but grow and get withdrawn tax-free (if spent on qualified things).

But 529s also have complexities, and the rules changed significantly with the Tax Cuts and Jobs Act and, more recently, the Secure Act.

So for this week’s podcast, I invited Ann Garcia, a CFP who specializes in (and blogs about) college financial planning, to deep dive on how 529 college savings plans work.

We talk about:

• Key rules, tax benefits, and pros & cons of 529s
• What are considered “qualified” educational expenses, how it’s enforced, and what happens if you fail to spend on qualified expenses
• When it makes sense to invest in a different state’s 529 plan vs. your own state’s
• Strategies and tradeoffs of grandparents funding 529s
• Important changes to 529s introduced by the Tax Cuts and Jobs Act and the Secure Act
• How the Private College 529 allows you to lock in future tuition using today’s prices

Do you have a 529 plan for your kiddos? Do you invest in an out-of-state 529 (if so, why)? Do you plan to roll into a Private College 529? What other 529 questions do you have? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• College Financial Lady
• Independent Progressive Advisors
• savingforcollege.com – for comparing different states’ 529s
• Private College 529
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

25: If you plan to pay for kiddo’s college education, then get ready to potentially nearly double what you spent from 0-18.

Right now, the average cost of public in-state 4-year university (tuition, room, board) is $21k per year. Private universities, $49k per year.

When I was in college, it was $12k/year public, $32k private (in today’s dollars)…

So, given how expensive college is (esp private), it’s natural for parents to feel anxious about how to afford college for their kids.

“Will we qualify for enough financial aid?”

“How much will we have to dip into our retirement nest egg?”

“Will we need to have a hard conversation with our kid that we can’t afford her dream school?”

These are common worries parents of college-bound kids grapple with.

Getting a handle on college expense and financial aid is crucial to ensuring you have enough saved to afford it. And it behooves you to start planning WAY in advance so you actually have enough time to optimize your assets, income, and financial situation for the best possible aid package.

So in this week’s podcast, I invited Paula Bishop, a college financial planning consultant and CPA who helps families strategize their college finances, to share tips and insights about college financial aid.

We talk about:

• How the financial aid process works (including timelines)
• What assets and income get reported on FAFSA vs. CSS Profile to compute EFC
• Key differences between FAFSA vs. Profile
• Special situations: rental properties, business owners, divorced parents
• How to appeal financial aid awards
• Why your funding strategy should shift after January of your kid’s sophomore year

Do you plan to pay your kid’s college expenses? What optimizations to family finances should parents be doing to make the cost of college more manageable? What other questions do you want answered about financial aid? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Paula Bishop, CPA​
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

24: Whether you retire early, take a sabbatical, or just take vacay, when you travel abroad there’s often multiple great opportunities to turbocharge your 4×4 FIRE framework “save” pillar.

One: overseas destinations often have lower cost of living compared to home, so you save on daily spend.

Two: when booking overseas flights, you can often arbitrage your miles & point redemptions for outsized value (we covered some juicy strategies in Episode 17).

Today, we deep dive on a third way: hacking your expat taxes.

In this week’s podcast, I talk with expat tax CPA (US) Grace Taylor about how to be strategic with tax optimization as an expat.

What you’ll learn:

• Key tax issues affecting expats – whether you’re a company employee, digital nomad, or early retiree
• How the foreign earned income exclusion works
• How state residency rules interact with expat tax strategies (and how to optimize)
• For digital nomads: strategies for using an LLC/S-Corp to optimize taxes
• Key rules re: foreign tax credits

Have you ever filed taxes as an expat? Was your tax bill lower vs. non-expat years? What other questions about expat taxes and FEIE do you want answered? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Gracefully Expat
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

23: Like learning how to optimize your taxes/wealth?

Then heads up, because Opportunity Zones may be really relevant to you.

In a nutshell: It’s a government investment program designed to spur economic development in certain geographic zones; in return, it provides a way to snag huge tax breaks and tax-free investment gains.

Think of it as a turbocharge for your 4x4 FIRE framework “save” & “invest” pillars.

But the O-Zone program is not well-understood or even well-known by most investors.

So this week, I invited David Sillaman, one of the pioneers in Opportunity Zone fund creation, to the podcast to explain key rules and benefits of the program.

We talk about:

• Goals of the program and tax benefits to investors
• Where Opportunity Zones are located and how to view an O-Zone map
• Rules on contributions, deferred capital gains tax, and tax-free investment gains
• What type of investments inside Opportunity Zones qualify for favorable tax treatment
• How to research Qualified Opportunity Funds

Is this program attractive to you as an investor? What questions do you still have about it that you want me to answer? Let me know by leaving a comment.

Don't miss an episode, hit that subscribe button...

If you liked this episode, be sure to subscribe so you don’t miss any upcoming episodes!

• Apple Podcasts
• Spotify
• Google Podcasts
• Stitcher

I need your help, please leave a listener review :)

If you liked this episode, would you please leave a quick review on Apple Podcasts? It’d mean the world to me and your review also helps others find my podcast, too!

Links mentioned in this episode:

• Ozfunds.com
• Eazy Do It
• Map of opportunity zones
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

22: Bob Dockendorff, a lawyer, tax expert, and financial planner who focuses on tax efficiency in his wealth management practice, talks shop with us about tax loss harvesting strategies.

What you’ll learn in this episode:

• Tips for maximizing tax “alpha” in your portfolio
• Common mistakes investors make when tax loss harvesting
• How wash sales work
• Why it’s so hard to execute tax loss harvesting even when the benefit is clear and you know you should

Links mentioned in this episode:

• Robert Dockendorff
• Tax loss harvesting and tax gain harvesting step by step
• Morningstar Tax Cost Ratio
• Tickers mentioned in this episode: SPY, FCNTX, VOO, VT
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

21: The US tax system vastly favors leisure over labor. It favors people who just own things and sit around and collect rents over people who actually do work for a living.

How is this so?

Because rents and returns on capital assets are taxed WAY more favorably than wages from labor. So favorably, in fact, that you can actually make 6 figures income and pay zero taxes.

Every year.

For the rest of your life.

This would never be possible with labor wages.

So in this week’s podcast episode, I’ll show you how our tax system is structured in a way that allows you to make over 6-figures in income with zero tax liability.

What you’ll learn in this episode:

• Why and how our tax system creates this opportunity
• What are the scenarios in your life where you can take advantage of this
• Exactly how it works step by step
• And the best way to optimize this loophole

Links mentioned in this episode:

• IRAs, Roth IRAs, and how to get the tax benefits of BOTH (HYW004)
• How to take a year off, earn 6 figures, harvest capital gains, do Roth conversions…and pay zero taxes on it all (updated for 2020)
• TurboTax TaxCaster
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

20: I recently went through a medical billing hassle that was such a PITA that I decided to do a special podcast episode about it because it has such direct impact on saving money on healthcare.

So in episode 20 this week, I talk about how medical billing and health insurance claims work.

Using my own experience as an example, I share tips on how to be vigilant about health insurance so you save yourself from unpleasant surprise costs.

What you’ll learn in this episode:

• Why it is so difficult to get transparent healthcare price information in the US
• How medical billing works and why it can lead to some very big unpleasant surprise costs
• What CPT codes and ICD 10 codes are, and exactly how they are used to determine how much you vs. insurance pays
• A 5-step checklist of actions to take so you never get stuck with surprise medical costs

Links mentioned in this episode:

• Health savings account rules
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

19: This week brings another solopreneur interview. In episode 19, I talk with Paul Stevens-Fulbrook, a high school science teacher in England whose side hustle is an education blog for teachers.

What you’ll learn in this episode:

• How his blog serves teachers at different stages of their teaching career
• How he got the idea
• How much he’s currently earning (and where the revenue is coming from)
• How he grew his traffic using Facebook (plus how he landed in “Facebook jail”)
• What his day currently looks like balancing side hustle vs. classroom job
• The importance of staying focused on a few important things to not spread yourself thin

Links mentioned in this episode:

• https://teacherofsci.com
• Ezoic (ad broker)
• Do You Even Blog Podcast (Pete McPherson)
• Brandon Gaille podcast (Blogging Millionaire)
• Income School YouTube channel
• Backlinko (Brian Dean)
• Neil Patel
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

18: I discuss how to get aligned with your significant other / fiancé / fiancée / or even spouse when it comes to money and finances.

Specifically, I share 17 questions to discuss with your partner to get aligned on money and finances.

This is important for any couple. But it’s absolutely critical once you start to seriously contemplate marriage.

Even if you are already married and haven’t gotten aligned on money yet, it’s better to do it now (especially before kids) rather than put it off.

It may be...not the most fun conversation. But it’s an investment in your relationship because finances are a leading cause of divorce: about a quarter of all divorces are because of money issues.

So, develop a curiosity mindset for the other person’s philosophy around money. It’ll be one of the best investments you can make in each other.

What you’ll learn in this episode:

• Why it's so hard to have completely transparent money conversations with your partner
• Why money and finances is not a single conversation...but a long series of them
• Why investing in this conversation stacks the marriage odds hugely in your favor
• How I have navigated money issues with my own spouse
• The 17 questions you should ask / get to know about your person, ideally before getting married, plus the rationale for each question

Links mentioned in this episode:

• 17 questions to ask your partner, ideally before getting married
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

17: Last week I talked about how I treat miles and points as a tax-free asset class in my portfolio.

That’s because they literally translate into thousands of bucks in savings. For every trip.

It’s one of the highest impact ways to boost your nest egg because those dollars stay compounding in your portfolio rather than getting spent.

That’s why for this week’s podcast, I invited Sarah Page Maxwell, a miles and points expert, to share strategies on how to maximize point redemptions specifically for free flights – especially international flights, since those have the biggest arbitrage opportunities for outsized redemption value.

Whether you’re booking long-haul economy or splurging for business class, today’s episode will train you to think strategically about award travel so you save big on your future trips…and boost your nest egg at the same time!

What you’ll learn in this episode:

• How the miles and points landscape has changed over the years and where the opportunities still are
• Strategies for maximizing your point redemptions
• What is considered a “good” redemption value (and why you shouldn’t just use the sticker price of a flight)
• How to pick the flexible point program that best matches your travel goals
• Tradeoffs for redeeming from an issuer’s own travel portal vs. transferring out to partners
• Tools for getting the latest scuttlebutt on redemption arbitrage opportunities/inefficiencies

Links mentioned in this episode:

• MileValue
• Milez.biz
• PointsBuzz
• Credit card churning subreddit
• FlyerTalk
• After our interview, Sarah also shared this resource: Where to credit. Tool to help you figure out where to best credit miles you earn when you fly. From Sarah: “Many don’t realize that just because you’re flying American doesn’t mean you have to credit the miles you earn to American. Credit them instead to a foreign frequent flyer program that hasn’t shifted to a revenue-based earning structure, but instead still awards miles based on distance flown. Simply put in what airline you’re flying and in what class, and it tells you how many miles you’d earning crediting to all the different partners.”
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

16: Anyone who likes traveling (by definition, FIRE adherents) should pay attention to how to optimize and maximize their travel rewards portfolio.

So in episode 16, I talk with Dave Grossman about how to do just that.

Dave is a travel loyalty program consultant and credit card rewards expert. He runs two travel rewards websites and has written a book on using miles and points to score free travel around the world.

Our discussion was chock full of tips, strategies, and insights, so this episode is definitely one you do NOT want to miss….

What you’ll learn in this episode:

• How travel rewards programs have evolved in recent years
• Key application strategies to think about for optimizing credit card travel rewards
• Optimal velocity for applying for new cards
• How the 5/24 rule is actually enforced
• Best practices for calling the reconsideration line
• Tips for meeting spend requirements
• How to incorporate business credit cards into your travel rewards strategy
• How to evaluate annual card fees
• Best practices for closing cards

Links mentioned in this episode:

• MilesTalk
• YourBestCreditCards.com
• AwardHacker
• FlyerTalk
• Plastiq
• Chase Ultimate Rewards
• American Express Membership Rewards
• Citi ThankYou Rewards
• Capital One rewards
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

15: I share some tangible ways that high earnings + a high credit score actually make life cheaper (with better service, to boot)…which in turn accelerates your FIRE goals.

What you’ll learn in this episode:

• Why banks, lenders, and credit card companies look for customers who don’t need them
• How you can use this to your advantage
• 5 major life expenses that get cheaper the higher your credit score / earnings are

Links mentioned in this episode:

• My 4×4 FIRE framework for creating and protecting wealth (HYW002)
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

14: The credit score is the metric for how borrower creditworthiness is judged.

In episode 14, I talk with Louis DeNicola a consumer credit expert and credit writer who works with clients including Experian, Credit Karma, LendingTree, and Nova Credit.

What you’ll learn in this episode:

• How credit scores are calculated and how each major component is weighted
• Why credit scores fluctuate constantly and how lenders and card companies often use proprietary credit scoring models internally
• How to increase and protect your credit score
• What to focus on when auditing your credit report
• The difference between soft vs. hard inquiries and how each impacts your credit
• The optimal “utilization” level (plus a hack for making your utilization appear low)

Links mentioned in this episode:

• Louis DeNicola
• FICO
• VantageScore
• AnnualCreditReport.com
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

13: Many folks dream of getting paid to travel. For Ernest Shahbazian, his side hustle as a travel content creator allows him to do just that.

In episode 13 of the podcast, I talk with Ernest, a management consultant who solopreneurs on the side as a YouTube travel influencer (>22k subscribers) providing travel tips, destination reviews, points and miles tutorials, and travel gear reviews.

With over 2B monthly users and crazy engagement, YouTube has become a “too big to ignore” platform for video influencers.

We talk with Ernest about how he got started, his content creation process, and how much he is currently earning.

What you’ll learn in this episode:

• How Ernest got the idea for starting a travel content channel
• Why he decided to focus on YouTube early on
• How he has grown his subscribership
• The diverse ways he is monetizing (not all ads and affiliates)
• Growing pains of scaling

Links mentioned in this episode:

• Trip Astute YouTube channel
• Trip Astute website
• TubeBuddy
• Yoast
• HARO
• CardRatings Affiliate program
• BlackBox
• Video Creators podcast (Tim Schmoyer)
• TubeBuddy Express podcast (Dusty Porter)
• Side Hustle School podcast
• Born for This: How to Find the Work You Were Meant to Do (Chris Guillebeau)
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

12: Ever wonder what type of solopreneur businesses are possible to help you build additional income streams?

A big part of the HYW podcast will be interviews with solopreneurs who are building lifestyle businesses that enable them to be completely time, location, and financially independent.

This week, I talk with Jeff Campbell, who spent more than 2 decades in the corporate world before starting an online side hustle with niche blogs. He plans to solopreneur full time starting in 2020.

We dive into the details of what he does, how he does it, and how he started.

What you’ll learn in this episode:

• What kind of niche blogs Jeff has started
• How he landed on the idea and got started
• How much he’s currently earning
• What his day looks like balancing side hustle and job at the moment
• How he taught himself the marketing and analytical skills needed to grow his traffic
• Jeff’s advice for other solopreneurs

Links mentioned in this episode:

• Pat Flynn’s podcast (Smart Passive Income)
• Tailwind
• Media Vine (ad broker)
• Income School podcast
• Brandon Gaille podcast (Blogging Millionaire)
• Authority Hacker podcast
• Simple Pin podcast
• Side Hustle School
• Side Hustle Nation
• Late Night Internet Marketing
• Help A Reporter Out (HARO)
• After we stopped the recording, Jeff also mentioned Lumen 5 for automated video creation using blog posts as the source material
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

11: I share some personal thoughts on FIRE and 8 key takeaways from a recent study of 150 millionaire interviews.

I share why there is no guaranteed path you can simply follow like an instruction manual to lead predictably to FI. FI must be achieved on your own terms, and we talk about lessons and mindsets to help you get clarity on your own pathway to FI.

What you’ll learn in this episode:

• Why, despite all the blogs/podcasts, no one can give you a golden formula checklist to follow that will lead you predictably to FI
• But how you can still draw critical lessons & insights from others to achieve FI on your own terms
• Some "things that I have done" that have worked to help me achieve FI
• 8 key takeaways drawn from 150 millionaire interviews
• Questions to think about to help you get clarity on your own pathway to FI

Links mentioned in this episode:

• List of questions to help you clarify your pathway to FIRE
• Lessons from 150 millionaires
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

10: We talk about the pros and cons of using a robo advisor. Are the advantages of automating your portfolio management worth the costs and downsides?

What you’ll learn in this episode:

• What are robo advisors
• Pros and cons
• How much robo advisors cost in fees
• What parts of your portfolio robo advisors don't work for
• How to think about robo advisors vs. human financial advisors
• Ultimately, should you use a robo advisor?

Links mentioned in this episode:

• Vanguard
• List of robo advisors
• Tax loss harvesting and tax gain harvesting step by step
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

9: We discuss the details of actually HOW to do estate planning, including the 16 essential estate planning checklist topics you need to prepare or update your estate plan.

We talk about: 

• The 16 essential checklist topics that should be part of any comprehensive estate plan
• The role of attorneys and CPAs in estate planning (and the distinction between what each does)
• How much an attorney will cost, how to find a good one, and things to think about if you’re considering to do parts of your estate plan yourself

Links mentioned in this episode:

• 16-point estate planning checklist
• How to set up a revocable living trust (with sample trust document)
• How to write a will
• Life insurance: How to calculate exactly how much you need in 4 simple steps
• Martindale-Hubbell
• Avvo
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom. 

View Details

8: I discuss why estate planning is so critical for wealth preservation. This episode is part 1 of 2 and covers big picture questions around the “who, what, when, why” of estate planning. In the next episode, we’ll cover the “how” part of estate planning.

What you’ll learn in this episode:

• What estate planning is
• Why it’s critical to think about it as part of your FIRE framework for wealth preservation
• Who needs it
• When you should do it
• What does it involve

Links mentioned in this episode:

• 16-point estate planning checklist
• How to set up a revocable living trust (with sample trust document)
• How to write a will
• Life insurance: How to calculate exactly how much you need in 4 simple steps
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

7: We talk about the importance of luck when it comes to FIRE.

How important is it for FIRE? Can you achieve FIRE even if you aren’t particularly lucky?

We’ll answer these questions and share some mindsets that’ll help you stay on track in making FIRE progress.

What you’ll learn in this episode:

• Why luck is hugely important in life to get to the very top
• How, even though you can't control luck, the factors you CAN control can get you to FIRE if you plan thoughtfully and work hard
• Plus, the simple strategy and mindset you need to do this

Links mentioned in this episode:

• My Top 5 Free Tools For Building Wealth And Minimizing Taxes
• HYW episode 2: My 4x4 FIRE framework for creating and protecting wealth
• Mobility Report Cards: The Role of Colleges in Intergenerational Mobility
• NYT: Extensive Data Shows Punishing Reach of Racism for Black Boys
• NYT: Income Mobility Charts for Girls, Asian-Americans and Other Groups. Or Make Your Own.
• NYT: What College Admissions Offices Really Want
• NYT: Getting Into Harvard Is Hard. Here Are 4 Ways Applicants Get an Edge.
• Robert Kiyosaki: Rich Dad, Poor Dad
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

6: I summarize the most important changes to the federal tax brackets and retirement contribution limits to be aware of in 2020.

What you’ll learn in this episode:

• Federal income tax rates for 2020
• Standard deduction changes
• Alternative Minimum Tax updates
• Capital gains tax rates for 2020
• Retirement & tax-advantaged account changes
• Roth IRA Income Limits
• IRA Deduction Phaseouts
• Misc updates: state & local taxes, mortgage interest deduction, Child Tax Credit, estate tax, foreign earned income exclusion, Section 199A

Links mentioned in this episode:

• How the final Trump tax bill affects you: analysis and charts
• Take a year off with the foreign earned income exclusion
• TurboTax TaxCaster
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

5: Roger Ma, an industry recognized CFP, talks with me about how high earners can optimize their retirement accounts and avoid common mistakes.

What you’ll learn in this episode:

• Roger’s path from investment banker to financial advisor
• The most common mistakes working professionals (even high earners) make when it comes to their retirement accounts
• What moments in life are there special opportunities to optimize your retirement accounts (plus, the concrete steps to take)
• Why early retirees should be thinking about their “why” more than their “how”
• Why Roger joined the AARP at 35

Links mentioned in this episode:

• Life Laid Out
• Bogleheads
• Donor-advised funds
• AARP
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom. 

View Details

4: We discuss IRAs and Roth IRAs – the "consumer retail" cousin of the 401k / Roth 401k. We also show you how the Roth laddering strategy works, why for early retirees this strategy means it's always better to contribute pre-tax upfront, and exactly how to implement the strategy.

What you’ll learn in this episode:

• IRA and Roth rules for contributions, tax deferral, withdrawals, RMDs, rollovers, loans, beneficiaries, creditors, inheritance
• How the Roth laddering strategy works and why it is the best method to avoid taxes entirely

Links mentioned in this episode:

• Traditional vs. Roth spreadsheet template to quickly see how much you’ll personally save with a tax-deferred upfront strategy
• HYW episode 3: Everything you need to know about 401Ks
• HYW blog post: Traditional vs. Roth?
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom. 

View Details

3: I discuss a comprehensive framework for understanding how 401ks work and how to use them strategically.

What you’ll learn in this episode:

• Origins of the 401k and some interesting stats
• Contributions
• Tax deferral
• Withdrawal age + tax at withdrawal
• RMDs
• Other: Rollovers, loans, beneficiaries, creditors, inheritance

Links mentioned in this episode:

• Download 401k reference checklist freebie (show notes)
• All about Solo 401ks
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom.

View Details

2: I discuss my 4x4 FIRE framework for methodically planning, building, and protecting financial wealth/independence. Centered around earning, saving, investing, and protecting, my framework is simple and manageable yet comprehensive.

What you’ll learn in this episode:

• Why an IKEA showroom illustrates how important it is to have a strong, clear FI framework
• My 4x4 framework for achieving and protecting financial independence
• Why my 4x4 framework is simple and manageable yet comprehensive in breadth
• How content I publish on HYW is connected to my 4x4 framework

Links mentioned in this episode:

• Download 4x4 FIRE framework freebie (show notes page)
• HYW private Facebook community

Intro/Outro: Old Bossa by Twin Musicom. 

View Details

1: I share why I started Hack Your Wealth, my personal story, how I once lost 1/3 of my savings, what change my thinking afterward, how that motivated me to became a financial expert, how much wealth that expertise has created for me today, what I now teach on HYW and what makes HYW different from other personal finance podcasts.

What you’ll learn in this episode:

• My origin story – the personal struggles/setbacks that motivated me to become a financial expert
• My credibility and credentials
• What motivated me to become a financial expert and how I did it
• Why financial literacy/proficiency is only half the story
• How my thinking changed after starting a family
• How my actions changed as a result
• Why I didn’t like about other personal finance sites
• What makes HYW different and worth following
• Why I’m starting this podcast

Links mentioned in this episode:

• My personal story
• HYW private Facebook community
• CFA program

Intro/Outro: Old Bossa by Twin Musicom.