Check Your Balances: Recent Episodes

Ross Anderson, CFP® and Daniel Messeca, CFP®

Check Your Balances explores the world of personal finance, investing, and business through the lens of two financial planners that help people navigate some of life's most impactful financial decisions.

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Most people spend the vast majority of their financial lives hyper-focused on the resources side of the equation: maximizing investment returns, optimizing tax strategies, cutting expenses, and watching net worth numbers grow. But accumulation without direction is just dynamic asset management in a vacuum. Resources are simply the engine; your goals are the steering wheel.

Without clearly defined targets, it is impossible to know if you actually have "enough," what level of risk you genuinely need to take, or whether your daily trade-offs align with the life you actually want to live.

In this episode, we break down why defining your actual life outcomes must happen before you start crunching numbers, how to unearth what you actually care about funding, and why the best financial plan is always built backward from your values rather than forward from your bank account.

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Most people who seem to have incredible financial discipline don’t actually possess superhuman willpower. Instead, they’ve just built environment-driven systems that eliminate temptation altogether. In this episode, Ross and Dan break down why relying on self-control is a losing strategy and how to engineer financial systems that make smart money moves effortless.

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Financial decisions are really just a series of trade-offs—some straightforward, others a little unhinged.

This week on Check Your Balances, Ross Anderson, CFP® and Daniel Messeca, CFP® turn financial planning into a game of "Would You Rather?"

We start with the everyday dilemmas that you might be considering in your life, finances, and career and let the conversation devolve from there. Would you make the same choices we would or go a completely different path?

Got a question or your own "Would You Rather" scenario?

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podcast #wouldyourather #personalfinance #CFP

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Your 401(k) is likely your largest retirement asset, but are you managing it with a blind spot? This week, we cover the spectrum of 401(k) mistakes, starting with the heaviest hitter: Net Unrealized Appreciation (NUA). We explain how this specific IRS rule allows you to move company stock out of your 401(k) and pay lower capital gains rates instead of ordinary income tax.

From there, we scale down to the everyday mistakes. Tune in to ensure your retirement strategy is actually optimized.

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For decades, standard capital markets assumptions have relied on a predictable, cyclical conveyor belt of capital: workers save, institutions invest, markets rise. But we might be staring down a massive, structural wrench in the gears. Between the Great Retirement of the Boomer generation and the cultural explosion of Coast FIRE—where millions of younger investors stop contributing to retirement entirely to coast on part-time work—we are looking at an unprecedented slowdown in fresh capital flows. Join us as we play out a "slightly out there" macroeconomic thought experiment: is the collective pursuit of financial independence actually toxic to the systemic liquidity that makes independence possible?

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In this week's mailbag episode, we are diving straight into the listener inbox to tackle the financial questions on your mind.

First up, we break down a fundamental investing trap: Portfolio Overlap. A listener asks how to actually tell if adding a new ETF to their portfolio provides true, independent diversification, or if they are just buying the same exact stocks under a different wrapper. We discuss how to look "under the hood" of your funds, the difference between asset class diversification vs. fund diversification, and tools you can use to check your exposure.

Check out https://www.etfrc.com/funds/overlap.php to learn more about your ETFs!

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Corporate America isn't the only path to building wealth, but starting a business from scratch can feel like jumping without a parachute. This week, we sit down with top non-food franchise consultant and investor Jon Ostenson to explore a powerful alternative. If you think franchising is limited to fast-food burgers, think again. Jon breaks down why some of the best opportunities actually lie in "boring" boutique industries like home services, insulation, and health and wellness.

We pull back the curtain on who is the right candidate for franchise ownership, and who should stay away. Whether you are looking to diversify your portfolio or plan a total corporate escape, tune in to learn how to measure the risks, rewards, and royalties of buying into an established brand.

Get a copy of the ebook here: https://franbridgeconsulting.com/

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Happy Birthday, Dan! In this special episode, we’re celebrating another trip around the sun by taking a deep dive into Dan’s personal finances over the last 12 months. It’s been a whirlwind of a year defined by two of life’s biggest milestones: packing up and moving to a new home, and welcoming a beautiful new baby to the family.

Join us as Dan opens up his own playbook to share the real-life financial strategies, unexpected expenses, and budget adjustments that come with major life transitions. From navigating the housing market to prepping the nursery (and the bank account) for a newborn, we break down how to keep your financial plan on track when everything is changing. Whether you're expecting a major life shift of your own or just want a look at how financial advisors manage their own money through major milestones, you'll want to tune in!

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SpaceX is days away from the largest IPO in history, and the ripple effects are going to hit every single investor. With a massive projected market cap, this launch could force index funds to aggressively dump shares of other tech giants just to make room for Elon Musk's aerospace behemoth.

How do major indices protect portfolios from that kind of sudden systemic risk? When will SpaceX actually qualify for the S&P 500? And should you be rushing to buy shares on day one, or watching from a safe distance?

We break down the mechanics of a landmark market event and share our personal game plans for the biggest IPO in history.

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We’ve all been told that skipping your daily latte is the secret to building wealth. But is sacrificing small joys actually moving the needle, or is it just a distraction from the real culprits?

In this episode of Check Your Balances, we unpack a recent Business Insider article on "Wealth Traps" to reveal what’s really holding people back from financial freedom. Spoiler alert: It’s almost never your morning caffeine fix.

Tune in to find out if we can find a more thoughtful way to teach young investors the impact of a creating financial discipline.

Link to Article: What Wealth Managers Teach About Avoiding Spending Traps via Business Insider (https://www.businessinsider.com/teach-wealth-management-avoid-these-spending-traps-save-money-invest-2026-5)

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For decades, Warren Buffett’s annual letter to Berkshire Hathaway shareholders was the ultimate textbook for value investing. Packed with folksy wisdom, sharp market critiques, and fundamental business truths, it was considered mandatory reading for anyone serious about finance.

But with Greg Abel officially taking the helm as CEO, the landscape has shifted. Is the letter still worth your time?

This week Ross and Dan break down Greg Abel's first letter and whether it still deserves a spot on your reading pile.

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It’s time to open up the mailbag! In this episode, Ross and Dan dive into your financial questions, tackling everything from early retirement strategies to the interpersonal dynamics of shared household finances.

First up, we break down the Rule of 55. If you’re looking to retire or step away from your job early, this IRS provision sounds like a dream—allowing you to tap into your current 401(k) penalty-free before the magical age of 59½. But is it actually as simple as it sounds? We look at the fine print, the common traps people fall into, and why your employer’s specific plan documents hold all the power.

We later transition from tax code to relationship dynamics. How much can you or your spouse spend without asking for permission? We discuss how to establish "no-questions-asked" spending limits, and whether a wheel of cheese could actually be a good investment.

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In this episode of Check Your Balances, we dive deep into the haunting parallels between the modern financial landscape and the most infamous market collapse in history. We explore Andrew Ross Sorkin’s thoughtful insights and historical analysis surrounding the Great Crash of 1929.

Is a century of economic "progress" enough to save us from ourselves, or are we just 1929 investors with faster internet? Let's get into it.

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In financial planning, we often talk about "the numbers," but behind every projection lies a set of assumptions. Whether it’s an estimated rate of return, a projected inflation figure, or even how long you expect to live, these inputs are the foundation of your entire strategy. But what happens when you pull on a single thread?

This week on Check Your Balances, we dive into the sensitivity of financial plans. We discuss how making an assumption that feels conservative in one way can have completely unintended consequences, and vice versa. In a world where more people are turning to AI to ask their financial questions - can the wrong assumptions have a major impact for you?

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In this week's episode, Ross and Dan review the businesses that have wronged them. Whether that grudge is for the most petty thing ever, that's for you to decide. Do you have businesses that you simply won't work with again because they have wronged you in some way?

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In this episode, we’re digging into Vanguard’s 2025 BETR (Break-Even Tax Rate) Framework to see if it’s a legitimate breakthrough or just a fancy new acronym for the same old math. We explore whether this methodology actually simplifies the Roth conversion debate or if it just adds another layer of "analysis paralysis" for investors trying to outrun the IRS. Is pinpointing a break-even rate actually realistic, over-engineered, or not going far enough?

We’re breaking down the mechanics to see if Vanguard’s "gold standard" is a must-use tool. Tune in as we question whether this framework is truly better, or just better marketing.

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This week we re-examine our favorite strategy for making the transition into retirement, the "Carve Out." When transitioning into retirement, the safe asset bucket or "Carve Out" is often touted as the ultimate psychological safety net. But how much cash is actually enough to weather a prolonged market downturn without selling equities at a loss?

In this episode, we revisit the mechanics of the retirement carve out. Is 5 years the magic number? Whether you are five years out or already enjoying your golden years, we explore the strategies needed to ensure your liquidity matches your needs.

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As the seasons shift and the weather clears, it is the perfect time to open the windows, clear out the dust, and take a fresh look at your financial life. This week on Check Your Balances, we are diving into a comprehensive "Spring Cleaning" checklist for your money. Whether you are looking to simplify your accounts or maximize your savings rate, a little seasonal maintenance goes a long way toward long-term clarity.

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March madness isn't just for the court—sometimes, life throws a full-court press at your financial plan that you never saw coming. In this episode, we take a look at the "bracket busters" of personal finance: those unexpected or overlooked situations that can derail even the most carefully constructed strategy for financial independence.

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In this March mailbag episode, we’re diving into the listener inbox to tackle the psychological hurdle of oversaving and how to transition from a lifetime of hoarding to intentional spending. We also clear up the "sloppy" discourse surrounding Roth conversions, cutting through the noise to discuss the tax nuances and math that actually matter. Whether you're struggling to give yourself permission to spend or weighing a big tax move, we’re bringing some much-needed clarity to your financial plan.

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If you feel like the ground is shifting under your feet as a tech investor, you aren’t alone. Early 2026 has introduced a new term to the financial lexicon: the SAASpocalypse. With AI agents beginning to perform tasks that used to require a $50-per-seat software subscription, the traditional "moats" of the software-as-a-service world are being tested like never before.

This week, we are joined by Simon Erickson, founder of 7Investing and one of the most forward-looking minds in growth investing. Simon helps us break down whether the recent $1 trillion sell-off in software stocks is a permanent structural shift or the ultimate "buy the dip" opportunity.

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If you've got mutual funds in your portfolio you might be familiar with that uncomfortable feeling at tax-time when your CPA sends you a bill even when you didn't sell anything. We talk about how to anticipate and navigate capital gains distributions on a mutual fund, and also weigh in on whether its the right time to refinance a high rate mortgage.

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It’s hard to believe it’s been half a decade since we first hit "record" to talk shop about markets, financial planning, and the psychology of money. To celebrate our 5th Anniversary, we’re stepping out from behind the microphones and into the room with the people who made it all possible: You.

Join Ross and Dan for a special live taping of the Check Your Balances podcast! This isn't just another episode; it’s an interactive event dedicated to the community that has grown alongside us.

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In mailbag episode of Check Your Balances, we break down the financial reality of choosing between 1099 and W2 employment. Do the additional deductions actually make this a way better deal? We also tackle the Roth IRA debate of whether you should swing for the fences with high-growth stocks or play the long game with broad-market index funds. Finally, we tackle tax season head-on by evaluating if premium tax software offers genuine value or if you're better off with a less expensive option - and how to evaluate them. Whether you're weighing a new job offer or optimizing your retirement bucket, this episode provides the framework for making smarter money moves this spring.

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If you could borrow money for a century, should you? This episode explores the strategy behind Alphabet's 100-year bond and why one of the world's wealthiest companies chooses to stay in debt until the next century.

We bridge the gap between corporate finance and your front door, breaking down how inflation acts as a "discount" on long-term debt like mortgages. By analyzing the math of eroding buying power, we reveal why time is the ultimate lever for the borrower—and how you can use a fixed-rate mindset to short the dollar and build long-term wealth.

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It’s the ultimate "break glass in case of emergency" move: tapping into your 401(k) or IRA before you hit age 59½. Usually, the advice is a resounding "don't do it," thanks to that stinging 10% early withdrawal penalty plus ordinary income taxes.

But life rarely follows a linear spreadsheet. In this episode, we tackle the nuance of the "forbidden" withdrawal. We’re diving into the specific scenarios where paying the penalty might actually be the most logical—or least destructive—financial move available to you.

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Staring at a driveway buried by a snowstorm is a lot like looking at a massive financial goal—overwhelming until you start chipping away. This episode of Check Your Balances explores how small, "baby steps" eventually lead to a critical inflection point where momentum takes over. We discuss the transition from the "grind" of active saving to the moment your portfolio’s growth begins to outpace your contributions. By staying consistent through the heavy lifting, you allow your wealth to transform from a stationary pile into a self-sustaining engine.

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Tax season is a different beast under the One Big Beautiful Bill (OBBB), and it’s time to see if your strategy holds up. This week, we’re joined by Ryan Flanigan, CPA, to break down the legislative shifts and what they mean for your bottom line. From permanent bonus depreciation to the new incentive structures, we’re cutting through the noise to make sure you’re prepared for the "Big Beautiful Bill" you’ll face in April.

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Finding overstated benefits in real estate and annuities might just be our favorite pastime. This week on Check Your Balances, Ross and Dan are putting on the gloves to take down the myths and math of these two common financial tropes.

The rant gets specific as we highlight the absurdity of pitching annuities to investors who already enjoy the security of a strong pension—essentially solving a problem that doesn't exist. Whether it’s the over-glamorized world of property management or the fear-based selling of insurance products, we’re here to help you spot the red flags before you sign a contract. Tune in for a dose of much-needed skepticism and a reality check on our favorite financial punching bags.

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The K-shaped economy is a jarring reality right now. On the "upward" arm, you have households with significant exposure to assets like stocks and real estate—which have reached record highs—alongside industries like AI and tech that are booming. On the "downward" arm, you have those feeling the squeeze of high interest rates, stagnant wages relative to costs, and the "disappearance" of affordable housing.

In an environment where the "market" and the "economy" are moving in different directions, how should you be positioning your portfolio?

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Is there a "magic bullet" for generating tax-free income in retirement? This week, Ross and Dan dive back into the mailbag to tackle a question that sounds almost too good to be true: The Tax-Free Dividend Roth Strategy. We’ve all heard that Roth IRAs are powerful, but a listener asks if specifically loading a Roth with high-yield dividend stocks is the ultimate "cheat code" for retirement cash flow. That and more on this week's episode!

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As we close out 2025, Ross and Dan look back at a year that defied the scripts, from "sure-thing" predictions that fizzled to the market moves that caught even the pros off guard. Join us for a final look at the lessons of 2025 and a clear-eyed strategy for your money as we head into 2026.

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Which holiday icon would be a financial advisor’s worst nightmare? This week, we’re putting Christmas characters under the microscope. We debate whether the Grinch or Scrooge is the tougher client to manage and dive into the 'North Pole Economics' of how Santa actually funds his global operation.

Beyond the festive fun, we explore what these fictional portfolios teach us about behavioral finance, cash flow, and legacy planning. Join us for a holiday-themed deep dive on this week’s Check Your Balances!

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Could a $100 million career income actually be insufficient for true, lasting generational wealth? This week, Ross and Dan dive deep into the ultimate financial paradox: the hidden, massive costs of being ultra-wealthy.

We unpack the eye-opening comments from NFL star Odell Beckham Jr. about how quickly a pro athlete's money evaporates. At this level, do standard retirement rules still apply, or are you just running faster on a much bigger treadmill?

Tune in to find out!

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In a world where cash is yielding around 4% and the bond index has lost 0.35% over the last 5 years*... why would you buy bonds instead of sitting on cash? This week we dive into that question and several others from our Mailbag.

  • Data as of 11/30/2025 via Vanguard

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We've always championed the long-term view of budgeting, but what if thinking about your money daily is the real secret to financial control? This week, we explore the idea of micro-timeframe spending: Is hyper-focusing on every 24 hours empowering and key to hitting your goals, or is it a recipe for driving yourself completely nuts? We'll reveal how we came to this counter-intuitive idea and deliver our verdict on whether a daily approach could finally be the breakthrough your budget needs. Tune in this week for our take!

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We celebrate Thanksgiving with some light hearted banter, and exploring the question of whether "High Watermarking" can lead to disappointment (even if it's hypothetical). We hope you're enjoying time with your family and friends this week, but if you want your weekly dose of personal finance content, we're here for you!

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Could a half-century loan be the answer to the housing crisis, or is it a financial nightmare waiting to happen? We break down the pros, cons, and the brutal amortization schedules of 50-year mortgages to see who actually benefits. Plus, we’re emptying the mailbag to cover the specific financial hurdles you are facing right now. Tune in to this week's mailbag episode!

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This week, Ross and Dan tackle a fun question... If you had to invest $100,000 without using the stock market, what would you do? Would you become a landlord and try to buy real estate? Would you try to start a business or invest in something truly "passive?"

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Does the average financial plan have "retirement tunnel vision," with a focus on pouring every spare dollar into your retirement accounts. We're all told to save for the future, but what happens when that focus makes us 'house poor' or 'life poor' today? Big goals like buying a home, funding college, or starting a business can't always wait until you're 65. Is it possible to be too focused on saving for your golden years?

retirement #financialplanning #balance

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First up: A listener challenges our take on Dollar Cost Averaging out.

Then, we confront the fear: How spooky is this market? Ross and Dan bust the financial ghouls and tell you what’s truly frightening for your portfolio (and what’s just noise).

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The October Mailbag is here! Ross and Dan open up the mailbag to answer your pressing financial questions, tackling everything from navigating the costs of college to whether you can Dollar Cost Averaging (DCA) out of a position as you approach retirement. Plus, they dive into the latest listener stories and tips on spotting and avoiding financial scams. Tune in for practical advice and a breakdown of the things you need to know right now!

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Is the grueling pace of your job fueling your desire for FIRE (Financial Independence, Retire Early)? This week on Check Your Balances, Ross and Dan tackle the reality that for many, burnout is the primary driver of the movement, not just aspiration. We discuss how to re-evaluate your aggressive savings strategy, explore more balanced options like Coast FIRE, and ensure your pursuit of freedom doesn't cost you your current well-being. Stop letting the corporate grind dictate your financial plan—it's time to find a path to independence that's sustainable.

#FIREMovement #Burnout #FinancialIndependence #CheckYourBalances #CoastFIRE

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When it's time to sell your personal home, do you treat it like a purely emotional move or a smart financial transaction? This week, our resident real estate expert, Dan, is under contract on selling his personal home.

Join us as Dan breaks down the process, from pre-listing prep and pricing strategy to staging secrets and negotiation tactics. Whether you're moving next month or just planning for the future, this episode is packed with must-hear, actionable lessons on maximizing your home's sale price and minimizing costly mistakes.

RealEstate #personalfinance #Investing #HomeSale #PropertyInvestment #WealthBuilding

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Your Catch-Up Contributions Are Changing! This week, Ross and Dan dive into the new guidance from the Treasury Department that will redefine how high earners over age 50 make their 401(k) catch-up contributions. The new rule mandates Roth contributions for certain savers, forcing many to lose a key pre-tax deduction. We break down who is affected, when this starts, and what you need to do to prepare. Plus, we open the mailbag to answer listener questions on all things Roth.

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30 Year Fixed Mortgage rates decline down to 6.26%, is it too early to consider a re-finance from a high rate loan? This week Ross and Dan unpack some of the trickery that can make you think you're saving more money than you really are when you look at refi numbers and how to make sure you don't get fooled.

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This week, Ross and Dan read and discuss The Millionaire Next Door. Does a finance book from 1996 still have precious lessons for us to learn about becoming Prodigious Accumulators of Wealth (PAWs) and avoiding the dreaded Under-Accumulator of Wealth (UAW) title? Tune in this week to see if this still deserves a spot on your shelf almost 30 years later.

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As a follow up to last week's episode with David Gardner, we dive deeper into whether the Rule Breaker Investing philosophy is suited for an investor that is approaching retirement. Ross and Dan spent 6 years almost exclusively trying to answer that question for many many investors. Here's what they think about that concept today!

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This week we are honored to have the Co-Founder and Chief Rule Breaker of The Motley Fool, David Gardner, join the show. David has an unbelievable investing track record, and his new book Rule Breaker Investing is his formula for success. We know many of our listeners are excited to hear David's thoughts!

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Got extra cash and wondering if you should throw it at your mortgage? 🤔 This week, we dive into the age-old debate: when does it actually make sense to overpay your mortgage? What are you using if you still mourn the loss of Mint.com? That and more in this week's mailbag episode.

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When it comes to talking about finance, not all of the theories you hear out there are going to be winners. What are some of the dumbest theories that we've come across, and why are they wrong? Tune in to find out.

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Are you one of the many people who've inherited a retirement account and are now wondering, "What's an RMD and how do I manage it?" The rules around inherited IRAs and required minimum distributions have changed, and it can be confusing.

In this episode of Check Your Balances, we're tackling the complex topic of managing Required Minimum Distributions (RMDs) on an inherited IRA. We'll break down the key rules, including the 10-year rule, and discuss how to create a strategy that works for you.

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Scott Galloway recently announced he’s dropped all of his insurance—but is he an anomaly or onto something? Dan and Ross break down his controversial stance and discuss whether most people are actually over-insuring themselves against small risks. Tune in to find out if you're a Scott Galloway, or if you're just paying too much.

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The highly anticipated "One Big Beautiful Bill" has officially been signed into law, sparking intense debate and speculation. This week on Check Your Balances, we're cutting through the noise to deliver a crucial breakdown of its sweeping changes. From tax tweaks and investment implications to critical shifts in financial planning, we'll equip you with the essential insights you need to understand exactly how this legislation impacts your individual finances.

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In this episode of Check Your Balances, we're joined by Callum Thomas to tackle a crucial question for your portfolio: Do you own enough emerging markets? Callum shares his expert insights on the current landscape, potential, and risks of investing in these dynamic economies. Tune in to understand if your asset allocation is truly optimized for global growth.

Learn more about Callum at Top Down Charts and The Weekly ChartStorm

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This week, NerdWallet's Sara Rathner makes a second appearance on the show to talk about the changes to the Chase Sapphire Reserve card. As one of the most prominent travel cards and the market, and one that Ross happens to personally use... this was of particular interest.

Sara Rathner is a NerdWallet travel and credit cards expert. She has appeared on the “Today” show and CNBC’s “Nightly Business Report,” and has been quoted in The New York Times, The Washington Post, The Wall Street Journal, Yahoo Finance, Time, Reuters, NBC News, Business Insider and MarketWatch.

Learn more about her work here: https://www.nerdwallet.com/author/sara-rathner

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On this week's episode of Check Your Balances, a mailbag episode! Does Chat GPT know how each of your retirement account taxes actually works? How do the fees in mutual funds and ETFs actually get deducted? These questions and more as we dive into what our listeners want to hear us talk about.

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What can the hit Apple TV show Severance teach the fellas about saving for financial independence? Join us this week as Ross and Dan explore the idea that you might be "severed" from the version of yourself that you're supposed to be saving money for.

Wishing everyone a safe and happy 4th of July!

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How do you you get your money to line up with being available when you actually need it? Designing a portfolio with this strategy in mind is called "Liability Matching" and it's a concept that Ross and Dan believe in and teach regularly. While rules of thumb like "The 4% Rule" get all the buzz, this is how to think about actually connecting your money with its purpose.

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Think you know the average American? Ross and Dan are about to find out if they do! Welcome to "Over Under," the brand new game on Check Your Balances where our hosts put their statistical savvy to the test. They'll compete in a lighthearted game to see how well they know the wealth and financial habits of the typical American.

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A surge in homes for sale relative to the number of buyers leads Ross to question whether his purchase of a home 6 months ago might have been poorly timed. Is he the worlds worst real estate investor? Only time will tell, but you can hear the boys discuss it on this weeks episode of Check Your Balances.

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This week on Check Your Balances, we tackle a listener question: Should your Roth IRA double as an emergency fund? We'll explore the pros and cons. We'll also demystify the critical difference between correlation and causation in personal finance. Understanding this distinction is key to making sound financial decisions, ensuring you build a robust financial plan based on true cause-and-effect, not just coincidental relationships.

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This week we're diving into the big questions we think you should be asking. We break down the latest rumblings around SALT deduction changes and what they could mean for your tax bill. Then, we pivot to the ever-shifting housing market, and whether you should bite off a bigger purchase for better schools. And finally, is a recession really on the horizon? We analyze the economic tea leaves and offer insights to help you prepare.

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What do you do when the numbers tell a different story than your gut? This episode tackles a common planner's dilemma: how to help clients truly believe their financial plan when the data clearly shows they'll be okay. We'll explore if it's about our planning approach, or the deeper issue of trusting the data itself.

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Want a fun and engaging way to talk about money with your partner? This episode of Check Your Balances explores how "Would You Rather...?" style finance questions can be a fantastic tool for uncovering each other's financial values and perspectives. We'll show you how these playful scenarios can lead to richer, more meaningful conversations and ultimately strengthen your financial understanding as a couple.

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On this episode of Check Your Balances, we're putting replacement ratios in the hot seat! Is this financial fortune-telling or just lazy math? We'll ask the tough questions: Are they the ultimate shortcut to a comfy retirement, or a recipe for financial disaster served up with a side of wishful thinking? Get ready for a lively debate as we uncover the truth behind these so-called rules of thumb and explore whether they're genius or just plain... well, sloppy. Tune in for a dose of financial reality with a twist of fun – because planning your future shouldn't be a snooze fest!

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Stop wondering what to do with that extra paycheck, bonus, or side hustle income! "Save vs. Splurge" empowers you to make confident financial decisions that align with your values and goals. We explore the art of balancing saving for a secure future with enjoying the present moment. Learn how to make your extra cash work harder for you, whether it's paying down debt, investing wisely, or indulging in something you truly value.

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Have you ever wondered why you'd use a money market or a CD instead of a high yield savings account? Are you concerned about battling it out with a sibling over an inheritance? If so, this week's mailbag episode is for you!

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Should you even try to hedge a single position inside an index fund? What happens when you spot a single stock within your broad market index that looks seriously overvalued? We'll weigh the costs, complexities, and potential benefits against simpler, more effective risk management approaches for index fund investors.

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The headlines are screaming about tariffs and trade wars, but what does it all mean for your wallet? In this episode of Check Your Balances, we break down the "Tariff Tantrum" and explore how these international trade spats could impact business and ultimately your portfolio.

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It's March Madness, but make it money! This week, we're pitting the biggest personal finance debates against each other in a head-to-head bracket showdown. From "Debt Snowball vs. Avalanche" to "Roth vs. Traditional IRA," which financial strategies will reign supreme? Tune in for the ultimate financial face-off and level up your money game!

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What if you had access to capital, but it cost you some of the upside value of your home? This week Ross and Dan explore a product that they were recently introduced to and look at what situations it makes sense for. Like most exotic lending options, this one can be really dangerous if not used correctly!

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Ever wonder if all those market buzzwords—overvalued, undervalued, fear, greed—are just dressed-up ways to say "time the market"? In a world where it's easy to get spooked by the news and want to sit on the sidelines, let's get real about market timing. Let's break down the concept of market timing and discuss how to navigate the market with clarity.

This episode is on YouTube: https://youtu.be/ZV-tF62eB_Q

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Warren Buffett's annual letter is a must-read for investors. Join us as we break down the key takeaways from his 2024 missive, exploring his insights on the economy, Berkshire Hathaway's performance, and of course, his enduring love for equities. Is his wisdom still relevant in today's market? We'll discuss that and more on this episode.

Find us on YouTube: https://youtu.be/VVCCeGuH5RA

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This week's Mailbag episode has great listener questions about whether rolling money back into a 401(K) is worth it for backdoor Roth IRA contributions, how to withhold taxes for a small business, and whether you can actually have too much money in your 401(K) plan.

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Are your RSUs a golden ticket to financial freedom or just a confusing piece of your compensation package? This week, we demystify Restricted Stock Units and show you how to turn them into a powerful wealth-building tool. Learn how to navigate vesting schedules, understand the tax implications, and develop a smart strategy for managing your RSUs. Don't leave money on the table – tune in and unlock the potential of your equity compensation.

This episode is on YouTube: https://youtu.be/KfX1rEcPwGs

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In a world where everyone from the car finance office to an insurance salesperson calls themselves a "Financial Advisor" what can advisors actually provide? Do you have to have your money managed, or can they simply act as a consultant? Tune int his week for Ross and Dan's take on a listener question about what advisors can actually offer.

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Your money personality plays a bigger role in your financial success than you might think. In this episode, Ross and Dan introduce a framework of four distinct money personalities. Learn how to identify your own archetype and understand how it impacts your saving, investing, and overall financial well-being. We'll also discuss strategies for leveraging your strengths and mitigating your weaknesses to achieve your financial goals.

This episode is on YouTube: https://youtu.be/94wRwj_f1RM

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This week Jesse Cramer of the Best Interest Blog and Podcast joins the show to talk about how different advisors can approach the same decision of getting to where we need to go. Join us for a fun conversation about Jesse's journey and how we all approach the vehicle decisions.

This episode is on YouTube: https://youtu.be/pShIUwiYJTM

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We kick off 2025 with an update on a few of the key things you might want to update heading into the new year and then move into a discussion about asset location. Are your growth assets in the right buckets? Are your safe assets in the right buckets? We give our current thoughts on how to think about it.

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If you had the money to buy a home outright, would you still take a mortgage at our current rates? This week's episode dives into the pros and cons of whether it makes sense to borrow money or invest based on the current landscape.

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This time of year we think a lot about gift giving. But what about the gifts you truly don't want? We don't mean a bad neck tie or macaroni art, but maybe one that costs you thousands of dollars just to maintain... tune in this week for our discussion about how to avoid inheriting a timeshare.

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This month's mailbag episode is a super-sized catch-up! We're diving deep into your burning questions about personal finance. From the ins and outs of taxes on gifts to strategies for supercharging your retirement savings, we've got you covered. Tune in to hear our expert insights and practical advice.

This episode is on YouTube: https://youtu.be/Atb7blHB7wY

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Confused about capital gains tax and whether you should be selling stocks before the end of the year? In this episode, we break down the basics of capital gains tax and discuss the factors to consider when deciding whether to sell your stocks before year end.

This episode is on YouTube: https://youtu.be/c5ME5uG-Ny0

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This week Ross and Dan celebrate their 200th episode of Check Your Balances with a lighthearted reflective episode of the journey up to this point. We appreciate each and every one of you, whether you've listened to a single segment or every single episode of the show up to this point. Happy Thanksgiving!

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When financial decisions matter most, you need strong arguments to consider. This week episode brings you a lighthearted debate on 5 financial topics:

  • How relevant is net worth as a metric?
  • Should I just invest in the S&P 500 and stop overthinking it?
  • Do you really need an emergency fund before investing?
  • Is the FIRE movement good for personal finance?
  • Should you have a side hustle to accelerate your progress?

Tune in this week to hear us battle it out!

This episode is on YouTube: https://youtu.be/W5_yW6JimE0

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As we celebrate our Veterans this week, we got a great listener questions about what unique benefits our Veterans have access to. We also answer questions about whether high earners should consider a 529 for themselves to gain access to a Roth IRA.

Our apologies for the late post, we were having technical difficulties!

This episode is on YouTube: https://youtu.be/IP_b-5Ea5VY

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Elections can be a rollercoaster of emotions, and it's easy to get caught up in the hype and fear-mongering. But as investors, it's crucial to stay calm and focused on our long-term financial goals. In this episode, we'll discuss how to avoid making big mistakes with your investing regardless of the election outcome.

This episode is on YouTube: https://youtu.be/-YTCVeVV_70

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In this episode, we dissect the iconic personal finance book, "Rich Dad, Poor Dad" at the request of our listeners. We'll delve into the core principles, analyze their effectiveness, and challenge some of the controversial claims. While acknowledging the book's influence on millions, we'll explore its limitations and discuss why a more nuanced approach to wealth building is often necessary. Join us as we separate fact from fiction and provide practical advice to help you achieve your financial goals.

This episode is on YouTube: https://youtu.be/hpc-FNweaJ0

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Ever wondered how the couples on Love is Blind discuss their finances? Join us for a look into the financial decisions made by the contestants, and how we might treat the same questions. We'll analyze their choices through a financial lens and discuss how their financial literacy (or lack thereof) could impact their relationships and future. Will their love stand the test of money?

This episode is on YouTube: https://youtu.be/xeYk37KxFYc

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Ever wondered how your taxes change after you retire? In this episode, we'll break down the key tax implications of retirement, and what sources you can still have withholding versus the ones where you'll have to take care of it yourself.

Find this episode on YouTube: https://youtu.be/WFBaNImVUpM

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Join us for the October edition of our personal finance mailbag podcast. In this episode, we dive deep into listener questions and provide insights on:

  • Safe Withdrawal Rate: How much can you safely withdraw from your retirement savings without depleting your funds? Can you safely adjust up after a good year?
  • Investing $500K: Do your portfolio options need to change as your capital grows?

Find this episode on YouTube: https://youtu.be/SqAtc11kLswWe're

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The final chapter (we hope) in the Ross' house saga. Drew McKenzie from Long and Foster joins the show to talk about what it's like trying to give advice to a guy that gives advice for a living.

Find this episode on YouTube (to see the inside of the actual home): https://youtu.be/GpjBZlu_r68
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It finally happened, the Fed has cut rates... so now what? We talk about the impact of the new interest rate environment and what it means for you.

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Prominent financial pundits and, like Robert Kiyosaki, will tell you the 401(k) is a 'Horrible' retirement plan. Why is that the case, and are they really right? Tune in this week for our take.

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Mortgage rates have already have already dropped more than a full percent from their recent highs. Is it too soon to talk about refinancing your mortgage? Why don't financial podcasters talk about the real costs associated with a refinance? Tune in this week to hear our take.

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Perhaps not the most romantic reason, but does it make sense to get married for the tax benfits? Also how do you invest if you've got a windfall of cash to deal with? That and more in this week's mailbag episode.

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This episode is on YouTube: https://youtu.be/-Iy271i2XY8

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We commonly talk with people that underestimate the impact of Social Security (and pensions) and how big of a deal it can for building their retirement plan. This week we have a philosophical question about how to think about it and how it relates to your own plans.

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How do the taxes actually work on a non-Roth IRA? Should you prioritize Long-Term Care Insurance or Disability Insurance? If you're like our listeners, these questions may be on your mind too.

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This episode is on YouTube: https://youtu.be/vXb4sU4R1lM

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The past couple of weeks have shown an interruption in what has otherwise been a very comfy ride in the markets so far in 2024. With some major investors unloading big chunks of stock we look at the recent volatility and talk about whether it should affect positioning moving forward.

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This week we are joined by Meredith Hill, the founder and principal attorney, of the Hill Law Group. Meredith joins the show to discuss who needs estate plans and the pitfalls that families can fall into without having the proper documents in place.

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This week we celebrate that the IRS has finally clarified guidance for Inherited IRA Required Minimum Distribution (RMD) rules. And also an update on the ongoing housing drama for Ross.

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This week Ross and Dan welcome tax attorney and expert, Jasmine DiLucci to the show to talk about how you can use the tax code to your advantage, and avoid silly scams that originate online.

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This week Ross and Dan break down what they look for when evaluating a clients' 401(k) plan and whether it's actually any good. Some a great, and some not be the best home for your funds. Tune in this week to find out!

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This week Ross and Dan dive into the mailbag to find what books they missed, whether recasting a mortgage is worth it (debate style) and how to calculate an RMD.

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What has been on the recent reading list for Ross and Dan, and should you considering adding it to your beach reads? We'll give you our take so you can decide if you should give it your time.

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This week Ross and Dan dive into a deal that Bobby Bonilla made in 1999 that will continue to pay him a reported $1.19 million per year until 2035. Why would the Mets make that deal, and who was the big winner? Tune in to find out!

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This week Ross and Dan unleash the fury on unnecessary products being sold to people that simply don't need them. Tune in to make sure you think about the right considerations when an annuity salesman turns their sights on you.

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This week Ross and Dan tackle listener questions about how Inherited IRAs are taxed, who needs a trust and why, as well as whether financial planning could be a part time venture. All that, and Dan's pool getting opened in this week's mailbag!

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Ranging from where the market goes from here to radical Bitcoinization of the monetary system, this week's show is dedicated to Ross and Dan weighing in on a series of reckless predictions.

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This week we welcome financial content creator and author, Brian Feroldi, back to the show. Learn why the P/E ratio is a sloppy metric at face value. What metrics should you use depending on what stage of life a business is in? Tune in to find out.

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Could being an authorized user on a business credit card really affect your credit, even if you're not on the hook for the debt? This week Ross and Dan dive into the mailbag to give genuine reactions and advice to listener questions.

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This week Ross and Dan explore a common term that is being used increasingly liberally. What does "Paycheck to Paycheck" really mean, and are American's really in as much trouble as a Forbe's article suggests?

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This week, Ross and Dan discuss a (frothy) way that you can access a private company through a public market investment. Whether you should or not is totally up to you. There is also some additional can kicking on IRS guidance around RMDs.

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Check Your Balances typically tries to be a "200 level class," but we often get asked for how to present these topics to novice investors. We do our best to get the content we love into its simplest form without getting too lost in the weeds.

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This week, Ryan Hutchins, from Peak Business Valuation joins the show to talk about valuing companies of all types, private and public. Join us as we talk about what small business opportunities might present the juiciest opportunities to be an owner.

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If commissions are all free, why wouldn't you take every bonus offer a broker sends your way? And if trading is free, how are the brokers still making money? All that and more on this week's episode.

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This week Ross and Dan ponder whether clients at any level actually feel rich? With a second helping of our typical tax season complaining about business owner problems.

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This week, The Realtress, Adrienne Messeca joins us to talk about the big news in real estate. From lawsuits to how much you'll pay your agent while buying, there is a lot changing right now. Tune in for our update this week, and check out her blog: https://adriennemesseca.substack.com/

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This week we dive into the mailbag to hear what you, our listeners, are interested in learning more about. This week we try to tackle covered calls (despite them being super hard in an audio format), whether you need to actually retitle accounts into trusts, and whether your 401(k) contributions affect your Roth eligibility.

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This week Ross and Dan explore the observance of people who feel shame about their finances. From those in relatively great situations to those in very challenging situations, the best path forward is simply to start today in tackling it.

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This week Ross and Dan explore concepts that seemingly should be illegal, but fascinatingly aren't. From regulators trading stocks in companies they influence to credit monitors selling ways to improve your score.

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This week Ross and Dan unpack how The Lindy Effect could be considered as part of your investing journey. Check out the Market Sentiment post that inspired the show for a great study on how investing in the old guard might be your best bet.

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Is leverage the wealth building tool that you've been missing this whole time? An article from The Economist sparks an old idea. Why can we use long-term fixed leverage to buy a house but not a portfolio?

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This week Ross and Dan dive into the listener mailbag and come up with questions around Cash Balance Plans, the tax benefits of I-Bonds and 529 funding strategies.

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This week we share our system for how many savings accounts to use so that you can accurately track your savings and spending guilt-free at the same time. If you've had trouble keeping your savings organized, this episode is for you!

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If you gave us a magic wand and let us change the tax code, what would we do to it? Hear our take as well as the advice from several tax experts on this week's show!

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Longtime listener and cute dog owner, Tyler, sends us a clip of Ron Baron talking about bonds. Does this billionaire's advice apply to your life? Probably not, but we had fun discussing it anyway.

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This week's mailbag episode features questions on backdoor Roth conversions gone wrong, how attractive are I-Bonds today, and how a dog photo will ensure your question makes it to our air!

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This week Adam Nash joins the show to talk about his newest business, Daffy, which is broadening access to a Donor Advised Fund (DAF) platform.

He's a Silicon Valley veteran and the former CEO of Wealthfront. His resume includes experience at Dropbox, LinkedIn, eBay, and many others... and he even teaches a personal finance class at Stanford.

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The author of A Simple Path to Wealth, JL Collins, is back with a new book called Pathfinders. JL Joins us this week to talk about his views on building wealth and investing in an easy to follow plan.

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Ross and Dan Reveal Their Most Ridiculous (and Relatable) 2023 Purchases and how the markets did. We've all been there: splurging on something we definitely didn't need. Ross and Dan take you on a lighthearted journey through their own hilariously questionable spending habits of 2023. You'll laugh, you'll cringe, you'll realize you're not alone in your financial oddities.

Email your questions for the show to checkyourbalances@outlook.com to have them featured on an upcoming mailbag.

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This week, Kelly Phillips Erb (AKA Taxgirl), joins the show again to explain a meaningful tax case that is currently being argued in the Supreme Court. How could Moore vs. United States impact us in the future? Tune in to find out.

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With the announcement that Mark Cuban is leaving Shark Tank, Ross and Dan reflect on the show's accomplishments and places where it can be misleading for entrepreneurs and investors. What's really a "flyer" when you have a reported $6.2 Billion net worth?

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This week Ross and Dan dip into the listener questions and talk about Securities Based Lending, Noncontrolling Interest on a balance sheet, and the role of gold in a portfolio.

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This week Ross and Dan raise a glass in memory of investing legend Charlie Munger. From his thoughts on business incentives to simply winning by not being stupid... we owe Charlie a lot.

Add your questions to the comments section on YouTube or email us at checkyourbalances@outlook.com to be featured on the show!

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This week, US Tax Attorney and Expat Entrepreneur, Stewart Patton joins the show to talk about some of the methods and pitfalls you should consider if you're planning to live or work outside of the United States. This is a complex topic area, so as always, we recommend consulting with a tax advisor personally. But we hope this episode gives you a few ideas on where to start your international living journey!

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This week is the first repeat guest in show history! Chris Hill joins Ross & Dan for a lighthearted discussion about investing and the best dishes to bring to Thanksgiving dinner!

Email checkyourbalances@outlook.com to send your questions to the show!
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This week, Ross and Dan react to a portfolio proposal called "The Cockroach Portfolio" from Market Sentiment. Should our goal be to just survive? Tune in this week to find out.

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Before getting to your questions, Ross and Dan stop to see who can win the most money with a biased coin. Play the simulator for yourself here.

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As we celebrate the end of "Spooky Season," Ross and Dan pull back the curtain on a few transactions in finance that may seem scary, but really shouldn't be. Hopefully understanding how they work gives you more confidence the next time you have a scary transaction to handle.

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Money regrets aren't limited to mere mortals. Magic Johnson spoke recently about his regrets about what could have been if he had taken Nike's offer of stock in the company versus a higher cash offer from Converse. We break down his comments and offer our own thoughts.

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Famed author, Michael Lewis, is taking a lot of heat for his portrayal of Sam Bankman-Fried in his new book, Going Infinite: The Rise and Fall of a New Tycoon. Dan's take on the book and a discussion of how much you need to be offered to switch banks on this week's show.

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This week Ross and Dan unpack how a charitable deduction really works to reduce your taxes as well as some other unique areas of the tax code that you might consider (only with the help of your CPA or tax professional).

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It's October, so we pay a visit to our email queue to address your questions.

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We spend a lot of time talking about how to retire, but not a lot talking about where. This week we unpack some of the main considerations we hear from clients, and help you look for pitfalls to avoid.

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Check this episode out on our YouTube Channel if you'd rather see us do this same show!

This week Ross and Dan revisit a popular topic in their practice which is how to approach portfolio income. Should you be switching to a dividend-focused approach, or would a "Carve Out" strategy give you better access to the funds you'll need to live on in retirement?

Email your questions for the show to checkyourbalances@outlook.com to be featured on upcoming mailbag episodes!

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This week Ross and Dan rant about some of the headlines commonly seen in the personal finance space. Why we hate them, and you should too!

Email questions for the show to checkyourbalances@outlook.com.

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This week's show gets into how a Backdoor Roth actually works (and whether it's actually legal), the mechanics of a target date fund, and a notable stock spin-off.

To have your question featured on the next mailbag episode, email us at checkyourbalances@outlook.com.

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The real estate landscape has changed meaningfully since Ross and Dan recorded the "Rent, Buy and PMI" episode in late 2021.  This week, they discuss how this new environment is impacting the way people approach housing.

The Check Your Balances crew also wants to give a very special shout out to our partner Matt for welcoming a new baby girl to his family.  Congratulations!

Have thoughts or questions for the show?  Email us at checkyourbalances@outlook.com or shoot us a note on Instagram!

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This week, Ross and Dan take on two topics that felt important but didn't quite need a full show on their own.  Should you take money out of your retirement accounts in an emergency situation? How do you avoid tax penalties for under-withholding? Tune in this week to find out.

Send your questions for the show to checkyourbalances@outlook.com or slide in our DMs on Instagram!

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Serving as a Trustee comes with a laundry list of responsibilities.  This week, Ross and Dan go over what is required of someone serving in that role, and introduce how a Corporate Trustee might be able to help.

Give us a follow on Instagram, and send your questions to checkyourbalances@outlook.com!

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A good idea taken to its most extreme place can lead to trouble. This week, Ross and Dan unpack what might have seemed like a good idea to the programmers at a prominent "Robo-advisor," but might not be the best in practical application...

Give us a follow on Instagram, and send your questions to checkyourbalances@outlook.com!

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July came and went without us diving into the mailbag, so we kick off August with a few listener questions!  Ross and Dan respond to a Money With Katie episode that suggests Roth contributions are rarely more favorable than pre-tax savings, and we share why using a direct indexing strategy is still...indexing.

Send your questions for the show to checkyourbalances@outlook.com! 

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What are the critical discussions you should be having with your parents about money? As you transition from your formative first impressions of money to trying to "lead up" - how do you even start to bring it up?

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Index funds have become a popular tool for investors when building a portfolio.  This week, we talk about the origins of the earliest indexes, their rise to popularity, and how direct indexing could change the way we think about index investing.

Send your questions and feedback to checkyourbalances@outlook.com, or connect with us on Instagram!

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This week Ross and Dan ponder a range of "Would you rather?" style questions from the practical to the absurd. We hope you enjoy the hot takes on a wide range of topics.

Send your questions and feedback to checkyourbalances@outlook.com, or connect with us on Instagram!

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This week Ross and Dan use two listener questions to reflect on the current state of the mortgage market.

Check your own math with this handy Free Amortization Calculator.

Send questions to the show to checkyourbalanaces@outlook.com.

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This week we open the mailbag to see what you, our listeners, want to hear about. Should you let AI help with your stock picking? Does the Social Security trust fund running low change your strategy around filing? Tune in to find out.

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As more Americans seem to be struggling with "Tip fatigue" we wanted to talk about tipping from an academic lens. This week we are joined by Dr. Michael Lynn from Cornell who has studied the service industry and written extensively on tipping practices.

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Does beach season have you thinking about how nice a second home would be? This week Ross and Dan unpack some of the considerations, pitfalls, and a simple way to test if your theory is really right.

Send your questions for an upcoming mailbag episode to checkyourbalances@outlook.com to have them featured!

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How worried should we be about the increase in consumer debt?  What does a persistently low Expecations Index mean?  What is the Expectations Index anyway?  That and more on this week's show.

If you have any questions for the show send them to checkyourbalances@outlook.com!

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A veteran of the car dealership and finance world, Chris Johnson joins the show to talk about the places where the dealership really makes their money. Do you really need that warranty they offer in the finance office? Tune in this week or check out Chris' e-books to learn more.

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Non-Profit hospitals in the United States are required to offer Charity Care programs to help reduce or eliminate medical bills for low to midddle income patients.  Why don't more of us know about this?

Today we are joined by Jared Walker, founder of the charity Dollar For.  His organization is dedicated to increasing awareness of these programs, and advocating for patients to help eliminate medical debt.  

To seek assistance, or to support Dollar For, visit: https://dollarfor.org/

Have any questions for the show?  Email us at checkyourbalances@outlook.com!

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While most of our loyal listeners are very comfortable in the language of personal finance, we know not everyone feels the same. This week Adam Koren of Adam Koren Coaching joins the show to talk about his approach.

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Does it make sense to adjust your net worth for the taxes that are embedded in your portfolio? This week Ross and Dan open up the mailbag to dive into your feedback and questions. 

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The internet was abuzz with a story about how under new mortgage rules, borrowers with better credit will pay more for mortgages than borrowers with poor credit.  Could that be true?  We dive into that story, as well as a potential tax reduction strategy for owners of pass through entities.

Do you have any questions for the show?  Email us at checkyourbalances@outlook.com!

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Matt Trogdon, CFP joins us for this week's episode to talk about the ways a financial plan can give you permission to spend more of your money rather than saving it. Whether you want permission for the little things or the big things, knowing where you stand can make those choices more comfortable.

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This week Ross and Dan look at all of the parallels between the game of golf and the game of investing. From temperament to where you focus your time, there are a lot of ways they can be compared.

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As the 2023 tax deadline looms, Ross and Dan talk through a number of situations that seem to come up frequently.

Dial in your withholding with the IRS Withholding Estimator.

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How safe is your money with SIPC, and what does it even protect? We answer that and more on this week's mailbag episode.

Send your questions to checkyourbalances@outlook.com to have Ross and Dan weigh in on your finance questions!

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While researching a complex loan situation for a client, Dan stumbled upon The Institute of Student Loan Advisors (TISLA). Betsy Mayotte was kind enough to join us for an interview to talk about the landscape of student loans and all of the great work that she and her team at TISLA are doing FOR FREE!

Send your questions for the show to checkyourbalances@outlook.com to be featured on an upcoming mailbag!

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In the wake of multiple bank failures, Ross and Dan talk about the implications of the Silicon Valley Bank failure and the cloudy nature of the current banking environment. Where might you be exposed to the problems, and what should you be doing about it? Tune in to hear.

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Matt Malkus, Partner and Director of Analytics at Institutional Life, joins the show to talk about what is going on behind the scenes in the insurance world.

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It's the most wonderful time of the year... no, not that one. The annual Berkshire Hathaway report with Warren Buffett's letter to shareholders is out, and we give you our 10 takeaways.

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This week Ross and Dan ask Chat GPT to craft answers to financial planning questions and evaluate how safe their jobs are from the AI sensation.

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Are you converting a rental into your primary residence, or thinking about how many different accounts you should have? This week's mailbag episode could be for you.

Send your questions for the CYB Podcast to checkyourbalances@outlook.com to be featured on an upcoming show!

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This week, Ross and Dan celebrate Valentine's day with a Love and Money episode. From gift-giving to challenging conversations around estate planning, there are endless ways that your money and relationships ultimately intersect.

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This week Ross and Dan unpack five "tax traps" that can sneak up on you if you're not paying attention to them. Tune in for what to look for and possibly how to mitigate the impact.

As always, know that Ross & Dan are not CPAs or Tax Preparers. Any tax discussion is strategic in nature, and should always be discussed with your personal tax advisor prior to implementing!

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Ross and Dan spend this week trying to react to some of the advice found on TikTok and other social media platforms. With videos about Stock Splits, Roth IRAs,  529s, and even Whole Life Insurance - there is something here for everyone!

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Inspired by a listener email, Ross and Dan dive into a brief history of retirement. From some common misconceptions to how recent some of our most beloved tools are, we hope you find this timeline entertaining.

The majority of the data for this show was sourced from this Georgetown Law Timeline.

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On this month's mailbag episode, Ross and Dan talk through questions on Qualified Charitable Distributions (QCDs), how to understand your index funds better, and how we personally look at shopping habits.

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SECURE Act 2.0 introduces a massive number of changes for American taxpayers. In this week's episode, we outline the updates we think have the biggest impacts on you and your planning.

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Is tech investing dead? Is a recession already happening? Is the Dow even relevant anymore? This week Ross and Dan take a quick look at closing the books on 2022 and what they're looking at heading into the new year.

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We made it! Check Your Balances has produced its first 100 episodes. We are exceptionally grateful to everyone who has tuned in and listened. Whether this is your first time hearing us, or you've listened to every show, we hope you have found our show valuable and entertaining.

This week we are honored to have one of our biggest supporters, Chris Hill, join us for the celebration of making it to 100 shows.

Send your questions for Ross and Dan to checkyourbalances@outlook.com to have them featured in the next 100.

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Dan sits down for a 1:1 interview with his childhood friend and sports writer Mike Prada to talk about his new book Spaced Out: The Tactical Evolution of the Modern NBA.

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As 2022 comes to a close, Ross and Dan kick around planning ideas you may want to consider before we kick off 2023. Should you be thinking about tax loss harvesting or tax gain harvesting? The answers lie ahead in this weeks episode.

Send your questions for our January mailbag episode to checkyourbalances@outlook.com to have them featured on the show!

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This week Ross and Dan tackle questions from listeners on topics ranging from the 5-year rule for Roth IRAs to books to learn more about bond investing.

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Many high profile tech companies have already announced largescale layoffs, and it is likely we will see more to come in the future.  In this episode, Ross and Dan address what you should be thinking about if you or someone you know is facing job loss.

...and do you know your blood type?

E-mail your questions for the show to checkyourbalance@outlook.com for a chance to be featured on our December mailbag episode!

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The Check Your Balances team wishes a happy and meaningful Thanksgiving to all our listeners.  We hope you enjoy the holidays and look forward to getting back to our regularly scheduled program next week.

E-mail checkyourbalance@outlook.com to weigh in on the best Thanksgiving side dishes!

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The collapse of a $32 billion dollar market cap exchange is a story that seems to just be getting started. Ross and Dan weigh in with a high level review of what's going on, and what it means moving forward.

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Matt Trogdon, CFP joins the show to talk about all things side hustle. From the aversions that people have when considering them to some simple ideas that can be pursued. The team shares their insight on what kind of impact a side business can have.

E-mail your questions for the team to checkyourbalances@outlook.com to be featured on the show and a chance to get one of the last remaining CYB coffee mugs!

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Kicking off November with a mailbag episode where we talk through your feedback and answer questions on wash sales and long-term care needs!

E-mail your questions for the show to checkyourbalances@outlook.com to get one of the few remaining CYB coffee mugs!

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At the risk of putting you to sleep, Ross and Dan try to take on bonds. As an incredibly large, meaningful, and often misunderstood asset class, the primer on how and why bonds might belong in your portfolio is hopefully helpful.

Ross talks briefly about this chart showing the 10 year treasury yield relative to the real yield, and we know you love a good chart.

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Ross and Dan talk through cost of living updates as they relate to Social Security as well as the cost of having children.

See the Washington Post's coverage of Brookings Institute data on costs of childcare: https://www.washingtonpost.com/business/interactive/2022/cost-raising-child-calculator/

Send your questions or what you a decluttering to checkyourbalances@outlook.com!

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This week Ross and Dan explore three possible strategies for the challenging environment we find ourselves in. Whether you're considering a home transaction or looking for cash, we just might have an idea that will help.

E-mail questions or topic suggestions to the show at checkyourbalances@outlook.com!

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A recent article from MarketWatch suggests that many young people should not be saving for retirement.  Ross and Dan react. 

You can read the article by clicking here.

We love hearing from you!  Send any comments or questions to checkyourbalances@outlook.com for the chance to be featured on the show.

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This week Ross and Dan dive into the mailbag to answer listener questions on tax withholding possibilities as well as why there aren't always as many Roth options available as there should be.

Send your questions for the show to checkyourbalances@outlook.com to have a question featured and get a CYB coffee mug if you want one!

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Forget beets, bears and Battlestar Galactica...this week it is all about burgers, buyouts, and bear markets!  Join Ross and Dan as they tackle some listener questions and address the bearish sentiments expressed last week.

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Ross and Dan reveal 6 different private companies that they wish they had the opportunity to learn more about and possibly invest in.

And we immediately have to retract our shade thrown at the Washington Commanders as apparently the mugs were not in the stadium.

Speaking of mugs... shoot your questions for the show to checkyourbalances@outlook.com and we will send you a Check Your Balances coffee mug for your contribution (while supplies last)!

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David Blanchett is the Managing Director and Head of Retirement Research with PGIM DC Solutions.  His work has been featured prominently in many industry publications as well as the Wall Street Journal.  This week, he shares some of his research with the Check Your Balances team. 

Keep up to date on David's research by visiting his website:
https://www.davidmblanchett.com/

Have questions or thoughts for the podcast?  Email us at checkyourbalances@outlook.com.

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A sad tale of the sandwich that never got eaten, Ross and Dan follow up on the $100 Million deli. They also discuss the student loan relief package and the food budget of a 20-something high-earner in DC.

E-mail us with questions at checkyourbalances@outlook.com with show topics, questions, or feedback!

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This week we are joined by Sharon Schneider, author of Handbook for an Integrated Life: A Practical Guide to Aligning Your Everyday Choices with Your Internal Compass.  Sharon has overseen the deployment of over $1.5 Billion in philanthropic capital for some of America's most prominent families, and has now written a guide on how to be more purposeful with the dollars flowing through your household budget.

Visit Sharon's website: https://www.theintegratedlife.com/
Click here to get your copy of Handbook for an Integrated Life

Have questions for Ross and Dan?  Email us at checkyourbalances@outlook.com.

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Ross and Dan clarify their position that they aren't (complete) bears when it comes to real estate investing, but they want to consider the range of options available. Check out this week's show to hear some of their favorite ways to access a lucrative asset class.

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Are you one of the many people who feel they got a late start saving for their future?  In this episode, we discuss how to approach your finances if you fall into that camp.  Ross also gets a rare message of support for one of his unpopular opinions.  

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Is it possible to boil your financial planning down to a single critical number? In this week's episode, Ross and Dan try to get to the bottom of that question.

Send your questions and thoughts on rice cakes to checkyourbalances@outlook.com.

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Ready for a financial planning throwdown? Ross and Dan go head to head as they debate heated topics in financial planning. Friend of the show Matt Trogdon joins as moderator.

In the episode Dan made reference to a book, but forgot the name. It was The Outsiders by William N. Thorndike, Jr., which tells the story of 8 unconventional CEOs and how their approach to capital allocation led to their success.

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Washington Post reporter Andrea Sachs joins the show to talk about what is going on in the travel market today, and where the deals still exist if you're looking. In an era where everybody seems to want travel built into their financial plan, we thought it was important to share.

Send your questions on personal finance, investing, or business to the show at checkyourbalances@outlook.com.

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On this week's episode we discuss our feelings for Jimmy Buffet's music and review our thoughts on App Economy Insight's article, How To Handle Big Losers.

Submit questions for the show to checkyourbalances@outlook.com to have Ross and Dan weigh in!

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We celebrate Independence Day with a breakdown of how we define 5 (or is it 6?) levels of financial freedom. Our simple to understand framework should apply to wherever you are in your financial life today and give you a target for how to get to the next step.

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How can approaching things with a "scout mindset" make us better investors? Ross and Dan discuss their takeaways from Julia Galef's book The Scout Mindset: Why Some People See Things Clearly and Others Don't.

Shoot a note to checkyourbalances@outlook.com with any questions, comments, or jokes for the team!

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It feels like just yesterday we were talking about what was in the first SECURE act, and now we get to talk about the sequel. Ross and Dan talk about what is expected (and stupid) in the current proposals.

Send your questions to checkyourbalances@outlook.com to have them answered on our air! 

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Ross and Dan recap their takeaways from last week's Financial Planning Association conference.  In particular they cover two strategies that can help avoid capital gains tax: upstream gifting, and the qualified small business stock exclusion.

E-mail your questions or thoughts for Ross and Dan to checkyourbalances@outlook.com!

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Do you share the same financial concerns as Cardi B? We think you might. This week's show addresses a 20:1 stock split and how negative the overall sentiment seems right now.

The chart Ross references in the show can be seen here.

E-mail your questions for Ross and Dan to checkyourbalances@outlook.com to have them weigh in!

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Ross and Dan dive into the mailbag for this episode.  They tackle a listener question on how to think about inherited assets as well as the strategies for saving money on behalf of your kids. 

E-mail your questions for the show to checkyourbalances@outlook.com.
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This week Dan and Ross consider whether life insurance could act as a safe haven in what we're calling the "Nowhere to hide" market. And we also answer a listener question about where to focus savings.

E-mail your questions for the show to checkyourbalances@outlook.com.

YouTube Channel coming soon... 

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This week, we are joined by our old friend Robert "Bro" Brokamp, from Motley Fool's Rule Your Retirement service.  Tune is as we talk financial calculators, financial therapy, and more! 

Test out CalcXML's retirement calculator by clicking here.

Join Robert Brokamp's Rule Your Retirement Service here.

Shoot us an email with your personal finance and investing questions at checkyourbalances@outlook.com.

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This week, Nick Maggiulli joins the podcast to talk about his new book Just Keep Buying: Proven Ways to Save Money and Build Your Wealth. He's also the author of the blog Of Dollars and Data, and the Chief Operations Officer at Ritholtz Wealth Management. We are thrilled to have Nick join us!

Shoot us an email with your personal finance and investing questions at checkyourbalances@outlook.com.

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Inspired by the story of Fred Smith gambling to save FedEx early on, Ross and Dan explore scenarios where wrong financial decisions may have positive outcomes.

Send questions for the show to checkyourbalances@outlook.com to be featured on the show.

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Market got you down? Ross and Dan kick around positive actions that you can (potentially) take in a negative market.

Send questions for the show to checkyourbalances@outlook.com to be featured on the show (and get a CYB mug!).

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On this episode, Ross and Dan are joined by Anna Helhoski - Nerdwallet's authority on Student Loans.   

Read more from Anna by visiting her Nerdwallet profile here:
https://www.nerdwallet.com/blog/author/anna/

Email us at  checkyourbalances@outlook.com if you have any questions or comments for the show!

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This week we're calling it a rant episode. Ross and Dan take on some very broad tax advice being given out on social media, and debate whether you should get excited about stock splits.

Submit your financial planning questions to checkyourbalances@outlook.com to be featured on the show!

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Our former colleague, the recently retired, Sean Gates, joins us to talk about his journey. Sean has embraced the Financial Independence Retire Early (FIRE) movement for his entire career and has just recently made the transition out of full time work. Hear more about his story on this week's show.

To submit your personal finance questions or thoughts tot he show, email us at checkyourbalances@outlook.com.

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This week we are joined by George Mason University professor Dr. Lawrence White. Dr. White has spent his academic career studying monetary systems, banking, and more recently cryptocurrencies. He joins the show to share what is going on in the space and how crypto is being used.

Submit your questions for the show to checkyourbalances@outlook.com to have a question featured!

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Inspired by Dan Pink's new book The Power of Regret, Ross and Dan reflect on how regret has played a part in their financial planning practice.

Also, Dan shaved his beard and head to support St. Baldrick's Foundation.

Send us your questions and thoughts to checkyourbalances@outlook.com!

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Resident "engaged guy" Matt Trogdon joins the show to talk about how he and his fiancée are dealing with combining finances.   

Send your questions for the show to checkyourbalances@outlook.com. 

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Ross sold his home recently and details what an exploration of the iBuying process was like. A farewell episode to "Dirty Mike and the Boys."

Send your questions for the show to checkyourbalances@outlook.com. 

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Of course more money is better than less money (unless you ask Biggie, in which case mo money is mo problems), but how much can a shift in salary impact your retirement trajectory?  Ross and Dan create a scenario for their made up client, Janice McExample, to see how it plays out.

Email us at  checkyourbalances@outlook.com if you have any questions for the show!

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Elon Musk has been in the news for giving away Tesla stock, and the news presented an interesting slant on Donor Advised Funds (DAF). Ross and Dan weigh in with their take on why DAF accounts can be a powerful planning tool and how you might consider using them.

Submit questions to the show to checkyourbalances@outlook.com!

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Ross and Dan explore the basics of estate planning that everyone needs, and how to plan effectively in an area with so many variables. You'll also get to hear about Dan's second career path that could have been at the end.

Submit questions to checkyourbalances@outlook.com to have them featured on the show!

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This week we unpack Morningstar's report entitled: The State of Retirement Income: Safe Withdrawal Rates. Do we need to replace the old 4% rule with the 3.3% rule?  We also address the differences between ETFs and Mutual Funds when it comes to index investing.

You can download Morningstar's report using this link.

Do you have a question or comment you'd like covered on the show?  Email us at  checkyourbalances@outlook.com and maybe the spirit will inspire Ross to mail Check Your Balancesmugs once again.

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What real life lessons about business and investing can we learn from scripted television?  This week, Ross and Dan pull back the curtain on their TV habits and share some moments from The Office and Silicon Valley that ring true in real life.

Have you had any "a-ha" moments watching your favorite TV show?  We'd love to hear about it!  Email us at  checkyourbalances@outlook.com to share your takeaways with us.

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A roundtable discussion of how to keep the recent market movement in context and focus on the big picture of your personal financial plan. Ross and Dan are joined by Matt Trogdon to discuss how the market has started 2022, and some strategies that we are using to relax along the way.

Send your financial planning questions to us at checkyourbalances@outlook.com!

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YouTuber, investor, speaker, and author Brian Feroldi joins the show to talk about the inspiration for his series of personal finance graphics and the book he has coming out this spring.

Pre-order Brian's Book: Why Does the Stock Market Go Up

Follow Brian on: YouTube, Instagram, Twitter

Send your questions for Ross and Dan to us at checkyourbalances@outlook.com.

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Ross and Dan were on a mission to bring to life Bill Mann's vision of a Monkey Butt on the blockchain.  They did so by creating the Monkey Butt NFT!  This week, we discuss what the process was like to create an NFT, and we also address a listener question about financial aid for college.

To view the Monkey Butt NFT on Rarible click here.  Worth a chuckle, but not your hard earned dollars.  We don't recommend purchasing it.

If you have personal experience with NFTs or any questions about personal finance, send your notes to checkyourbalances@outlook.com to be featured on the show!

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We kick off the year feeling 22 and addressing listener questions! This week we address improving a credit score, differences in 529 and ABLE accounts, Fully Paid Securities Lending, and even a hint of Payment For Order Flow.

Send your questions to checkyourbalances@outlook.com to be featured on the show!

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As the year comes to a close, Ross and Dan review the performance of several major stock indexes and discuss their takeaways from 2021.  They also address Vanguard's Market Perspectives report which offers their 10 year asset class forecasts.  Have you dozed off yet? 

E-mail us at checkyourbalances@outlook.com with your biggest investing takeaways from the year!

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Do you need last minute gift ideas for the finance nerd in your life? Check out our gift guide for 2021 to help round out your shopping list for the year!

E-mail us at checkyourbalances@outlook.com if you have questions for our year end wrap up show next week, or personal finance questions that we can help with!

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Many of us have experienced inflation to this point in 2021 through rising costs, however there is a flip side to that coin!  Series I Savings Bonds, which pay an interest rate tied to inflation, are paying attractive rates.  In this episode we discuss I Bonds, and Ross takes us through what it was like to purchase one through TreasuryDirect.gov.

Have you reached any personal financial milestones in 2021?  Let us celebrate your success!  Email us at checkyourbalances@outlook.com to potentially be featured!

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This week we welcome Andrew Schear of the Practical Personal Finance YouTube channel to the show. Andrew is a personal finance enthusiast that has documented his own journey and has created a library of more than 180 videos teaching finance concepts in simple, easy-to-understand, language.

To submit a question for our show, email us at checkyourbalances@outlook.com to potentially be featured!

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This week we talk taxes with Kelly Phillips Erb, aka the Tax Girl.  Together we discuss the challenges of navigating the tax landscape, and Kelly offers some controversial takes on home ownership and Roth IRAs.

You can find Kelly's podcast, blog, and more by visiting: https://www.taxgirl.com/

If you'd like to submit questions or air grievances you can contact us at checkyourbalances@outlook.com.

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Once again, Matt Trogdon, CFP joins the show to talk about his experience going through a job transition over the summer which he lovingly refers to as "Funemployment."

You can read his Preservation Mode article that he wrote for Humble Dollar.

And to submit your questions for our show, email checkyourbalances@outlook.com.

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Ross and Dan have real estate on the brain again.  This week they discuss the tough rental market, along with some potential money saving tips whether you already own a home or are in the market for one.

Send your questions for the show to checkyourbalances@outlook.com and receive a CYB mug while supplies last!

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Bill Mann joins the show this week to discuss how to think about international investing, changes to the small-cap landscape, and even... crypto.

Send your questions for the show to checkyourbalances@outlook.com and receive a CYB mug while supplies last!

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On this week's episode the team tackles a listener question which spurs a conversation on balancing short- and long-term goals.  Ross lets us in on a wedding planning hack.  And where in the world is Tyler?

Submit any comments or questions you may have for the show to checkyourbalances@outlook.com and receive a free mug while supplies last!

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Ross and Dan welcome Matt Trogdon, CFP to the show for the first time to share financial planning horror stories from celebrity life and beyond! Make sure you don't miss this special Halloween episode of Check Your Balances.

Submit horror stories or any questions you may have for the show to checkyourbalances@outlook.com to receive a free mug while supplies last!

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Mat Sorensen,  an attorney and the CEO of Directed IRA,  joins us on this week's show to discuss how IRA funds can be used to make investments beyond traditional securities. This week's show explores a broader investment universe through a lesser known structure.

You can learn more about Mat Sorensen and Self-Directed IRAs here on his website.

Send your questions for the show to checkyourbalances@outlook.com to receive a CYB mug!

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A new term in financial planning to unpack, and one of the key problems that could prevent it from working for you! Check out this week's show on what the Coast FIRE movement is and how little choices make the difference on it working.

Email us at checkyourbalances@outlook.com with your Coast FIRE plans or any stories of personal lifestyle creep that you've experienced!

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On this week's episode we welcome William Green, author of Richer, Wiser, Happier. His book draws on his interviews with some of the world's greatest investors and highlights the principles and habits that make them successful.   In his chat with Dan, they discuss how many of these lessons extend beyond the world of investing.

You can learn more about William Green and his work by visiting https://www.williamgreenwrites.com/.

E-mail us at checkyourbalances@outlook.com to submit questions for the show!

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People often grow comfortable with buying stocks, but how should you think about selling them?  Ross and Dan talk about a few of the situations where you should say goodbye to shares within your portfolio.

E-mail us at checkyourbalances@outlook.com to submit questions for the show!

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What personal finance lessons can we take away from a Will Ferrel movie? Check out this week's show to find out as Ross and Dan break down personal finance lessons from some popular movies.

E-mail us at checkyourbalances@outlook.com to submit questions for the show!

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In a world where yield is hard to come by, learn how you can leverage simple options strategies to boost portfolio income.  

Email your questions for the show to checkyourbalances@outlook.com to potentially have your question featured!

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As kids head back to school for the fall, Ross and Dan breakdown what would be in their financial literacy course if they got to design it for high school students.

Email your questions for the show to checkyourbalances@outlook.com to potentially have your question featured!

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This week Ross and Dan are joined by Alan Moore.  He is the CEO and co-founder of XY Planning Network, which has created a community of over 1,000 fee-only advisors focused on serving Gen X and Gen Y clients.  

To submit questions or topics for the show, email us at checkyourbalances@outlook.com!

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Dr. Terri Friedline is the author of Banking on a Revolution and a professor at University of Michigan. She joins Ross and Dan to talk about underbanked and unbanked communities and structural reform that is needed in the banking system.

To submit questions or topics for the show, email us at checkyourbalances@outlook.com!

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The blog post Go Big, Then Stop by Nick Maggiulli inspired Ross and Dan to think about advice they would give to their younger selves.  They reflect on the early days of their careers, the power of compounding, and the risks of faking it until you make it.

Submit questions or feedback to the show using checkyourbalances@outlook.com!

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A mailbag episode, Ross and Dan read listener responses to how they'd spend lottery winnings and answer questions on net worth and 401(k) rollovers. There's a lot to unpack this week!

Submit questions or feedback to the show using checkyourbalances@outlook.com!

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We examine the math on how lottery payouts are actually made and then apply those same fundamentals to a much more likely scenario... pension planning! Check out this week's episode whether you're thinking about your pension or the Powerball.

Receive a Check Your Balances mug by sending in great questions for the show at checkyourbalances@outlook.com (while supplies last!).

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At the end of 2019 a major piece of tax legislation was signed into law.  The SECURE Act may have flown under the radar of many Americans as our focus quickly shifted towards a global pandemic.  On this episode Ross and Dan review some major provisions of the SECURE Act and what they might mean for you.

E-mail us at checkyourbalances@outlook.com with your questions or feedback for the show!

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How much cash is too much in your portfolio? Ross and Dan launch from a listener question into their theory about allocation bands and how you choose to treat risk in your portfolio. They also react to Malcom Gladwell's enthusiasm for self-driving cars.

E-mail us at checkyourbalances@outlook.com with your questions or feedback for the show!

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Kimberly Palmer, author of "Smart Mom, Rich Mom" and personal finance expert at NerdWallet, joins the show to talk about budgeting.  Ross and Dan have historically considered themselves "anti-budgeters", but Kimberly flips them by offering a simple and practical framework for regaining control of your spending.

E-mail us your personal finance questions or topics at checkyourbalances@outlook.com.

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Ross and Dan ambitiously try to tackle life insurance, disability insurance, and long-term care insurance in a single episode. How to think about what you really need, and what products get sold in all the wrong ways.

E-mail checkyourbalances@outlook.com to submit questions or feedback to the show!

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Ross and Dan answer a listener question on relocation, provide a helpful (free) resource for estimating your costs, and unpack what the bond market is currently telling us to expect in terms of inflation.

Shoot us an email at checkyourbalances@outlook.com to let us know where you're thinking of relocating to in retirement or with other questions for the show!

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Ross and Dan compile a list of 10 of the most powerful concepts, mantras, and lessons they have learned about investing. Whether they help with your mindset, developing good habits, or combating a dangerous bias, we hope you take something positive from this week's show.

Shoot an email to checkyourblaances@outlook.com to share your favorite investing lesson or a question you'd like Ross and Dan to weigh in on!

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Dr. Michelle Fritsch, author of Preventative Maintenance for a High Mileage Life, joins the show to talk about health when making the transition into retirement. Her background as a pharmacist uncovered gaps that need addressing in the medical field that she is actively working to solve.

Learn more about Michelle at retirewellness.com or email her at michelle@retirewellness.com.

E-mail us your personal finance questions or topics at checkyourbalances@outlook.com.

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Ross and Dan weigh in on one of the biggest debates in the investing world: active versus passive investing.  

E-mail us at checkyourbalances@outlook.com with questions for the show or anything you'd like us to weigh in on!

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A new Dalbar study suggests that investors with variable annuities did better in 2020. Ross and Dan unpack some of the possible reasons and discuss whether data like this  would alter our traditional thinking around retirement income.

E-mail us at checkyourbalances@outlook.com with questions for the show or anything you'd like us to weigh in on!

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Ross and Dan receive an email from a "listener" in need of assistance.  This spurs a conversation about common scams and some preventative measures people should be taking.

Send us what you're excited to do with your free time to checkyourbalances@outlook.com or submit questions or topics you'd like to hear us cover on our show!

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Could a new framework around what retirement means let you get to the fun stuff early? Ross and Dan discuss different ways to think about what retirement could be and what they learned in starting their business about financially preparing for mini-retirements.

Send us what you're excited to do with your free time to checkyourbalances@outlook.com or submit questions or topics you'd like to hear us cover on our show!

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How realistic are TV shows like Ballers and Entourage?  This week we invited Jordan Josephs to answer that question and more as he gives us a glimpse into his life.  Jordan has been named as one of Billboard's top business managers for 2021 and awarded Variety's "Business Manager Elite" title.

Email us at checkyourbalances@outlook.com for questions or topics you want us to cover on our show!

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Taylor Swift is in the process of recording fresh versions of her first six studio albums.  She is doing this because she does not own the master recordings of those original tracks, and hopes to regain control of her music by creating new versions ("Taylor's Versions" as she calls them). 

To learn more about Taylor Swift's efforts, and to more broadly explore intellectual property rights, we welcome Scott Lloyd to the show.  He is a principal with the law firm Offit Kurman and does work in the intellectual property space.   

Email us at checkyourbalances@outlook.com with questions or ideas that you want us to share on the show!

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Ross and Daniel discuss side hustles, offer their thoughts on rental real estate, and share why you should beware if you happen upon raccoons in your attic.  

Email us at checkyourbalances@outlook.com to submit questions or topics for discussion on the show!

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Ross and Dan unpack some of the financial statements on a single deli that trades as a public company with an eye popping valuation, as well as review an incredibly prominent financial product that you may have in your 401(k) right now.

Email us at checkyourbalances@outlook.com to submit questions or topics for discussion on the show!

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The "Credit Card Queen," as we appointed her, Sara Rathner from Nerd Wallet joins the show this week to talk all things credit cards! We also dive into the importance of bringing nuance to financial media.

Email us at checkyourbalances@outlook.com for questions or topics you want us to cover on our show!

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We are thrilled to welcome Together We Bake to our show to share some of the great work they are doing in the Northern Virginia community to support women in the area. We also kick off financial literacy month with some shortcuts for math and quick tips that we use as planners.

Email us at checkyourbalances@outlook.com with questions or ideas that you want us to share on the show!

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The founders of Crooked Crab Brewing join our show to tell the story of how three friends put their combined skills together to create an award winning up-and-comer of a craft brewery.

Email us at checkyourbalances@outlook.com if you've got feedback, finance questions, or topics you want to hear us cover!

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The language of investing is constantly changing - are you keeping up to date? Join Ross and Dan as they explore a few acronyms showing up more frequently in the world of finance. Be sure to stick around until the end for their rapid fire "meme-talk" round.

E-mail us at checkyourbalances@outlook.com to submit your questions for the show!

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It has been shown that people hate losing money about twice as much more than they like making it.  How does that translate to the way you look at your portfolio during turbulent markets?  Ross and Dan discuss their philosophy on managing the downside in this week's show. 

E-mail us at checkyourbalances@outlook.com to submit your questions for the show!

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Is the Roth IRA for you? When should you file Social Security? When does it make sense to accelerate your taxable income? Ross and Dan talk through three common planning issues in this week's show.

E-mail us at checkyourbalances@outlook.com to submit your questions for the show!

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Investing icon Warren Buffet writes a letter to Berkshire Hathaway shareholders each year. Ross and Dan break down the 2021 letter and share their top 10 takeaways that you can apply to your financial life and investing.

E-mail us at checkyourbalances@outlook.com if you had a different take or with any questions that you think we should cover in upcoming shows!

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The chef and restaurateur behind the award winning Clarity restaurant in Vienna, VA joins us to talk about his journey and what it has been like adapting a restaurant in the pandemic. There are lessons for all business owners and entrepreneurs in the way chef Krinn has been able to navigate the situation.

E-mail us at checkyourbalances@outlook.com with any feedback, questions, or to participate in this week's gift card challenge! And visit clarityvienna.com to learn more about our guest and his establishment.

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College savings plans, picking stocks your kids will understand, and more. Our resident Advisor-Dad takes you through his process and what you need to be thinking about if you're interested to get your kids started on their investing journey.

E-mail us at checkyourbalances@outlook.com with questions you want us to cover and feedback!

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Should you make it a goal to payoff your mortgage? Do you need to convert to a dividend focused portfolio? What's the right allocation for your age? This week Ross and Dan unpack 3 common myths that investors have as they approach retirement.

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Morgan Housel, author of The Psychology of Money and partner at The Collaborative Fund joins Ross and Dan to discuss his book. 

Check Your Balances is a journey through investing, personal finance, and business with an emphasis on always understanding the tradeoffs. Ross and Dan unpack common financial planning anecdotes and lore to help listeners get down to what will really make the most impact for them. Subscribe so you don't miss an episode!