Aaron Caulfield dives deep with high-achieving entrepreneurs, CEOs, and founders of startups. He gives you an inside look, unscripted at the dreams as well as the emotional challenges they face as leaders. Aaron previously worked for Accenture in Silicon Valley and studied finance at the Wharton School of Business at the University of Pennsylvania.
Alchemy went from public launch to a half-billion-dollar valuation in eight months.
The company is the world’s leading blockchain developer platform powering $30+ billion in transactions with 10+ million users in 197+ countries worldwide.
Founded by Nikil Viswanathan (@Nikilster) and Joe Lau (@thejoelau), Alchemy has been likened to the Amazon Web Services (AWS) of the blockchain industry. They provide the best tools and products for developers to use in building NFTs, marketplaces, protocols, and more.
Investors include Stanford University, Coinbase, Pantera Capital, founders and executives of Charles Schwab, Linkedin, PayPal, Yahoo!, Dropbox, NYSE, as well as John Hennessy, Jay-Z, Reid Hoffman, Will Smith, Balaji Srinivasan, the owners of the Tampa Bay Buccaneers and Manchester United, and more.
They recently raised their Series B funding round of $80 million led by Coatue and Addition (started by Lee Fixel in 2020).
Previously, Nikil and Joe co-founded Down to Lunch, a social app that rose to #1 in the App Store and was featured in The New York Times and other international media publications. The two met at Stanford, where they studied computer science and were co-TAs for an online class on databases, a precursor to Coursera.
In this episode, Nikil and I discuss:
Nikil's entrepeneurial lessons include:
For more information, go to: https://www.aaroncaulfield.com/podcast-feed/nikil-viswanathan-on-reaching-a-1/2-billion-dollar-valuation-in-eight-months
Nikki Adamson is the founder of Hustle Hunters, a recruiting firm for early stage startups.
They help teams attract, support, and retain top talent and create more diverse, equitable, and inclusive (DEI) organizations.
Candidates in their network include people that have historically been excluded: moms, women, caregivers, people who identify as LGBTQ+, Black, Indigenous, and people of color (BIPOC), Asian Americans, and more.
In this episode, we discuss:
Nikki's tangible takeaways include:
For resources, organizations, and people mentioned go to: https://www.aaroncaulfield.com/podcast-feed/nikki-adamson-how-to-create-a-more-diverse-equitable-and-inclusive-startup-team
Justin Shenkarow is an actor, voice actor, producer, writer and director from Los Angeles. He’s best known for his roles as Matthew Brock in Picket Fences, Simon Holmes in Eerie, Indiana, and the voice of Harold Berman from the Nickelodeon animated series, Hey Arnold!
Justin recently participated in NFTHack, a hackathon hosted by ETHGlobal, where he formed a team with Felipe Faraggi, Brennan Fife, and Pablo Palomo.
They created Hashink to enable celebrities, actors, musicians, athletes, artists, and more to sign autographs digitally, interact with fans, and receive royalty perks.
NFTHack featured 634 participants, 182 NFT projects, and 10 winning teams, of which Hashink was one.
Disclaimer: My guests and I are not investment advisors. All opinions are my guests’ and mine alone. There are risks involved in placing any investment in bitcoin, ethereum, cryptocurrencies, or any other investment vehicle. Nothing discussed today or anytime is intended to form the basis for any offer or recommendation or have any regard to the investment objectives, financial situation, or needs of any specific person. Everything discussed is for informational and entertainment purposes only.
For resources, organizations, and people mentioned go to: https://www.aaroncaulfield.com/podcast-feed/justin-shenkarow-on-winning-nft-hack-and-more
Claude Cayemitte is a NARM-certified, award-winning psychotherapist based in West Palm Beach, Florida.
He works at a health center and runs a private practice, Clear and Connected Counseling, for individual therapy with adults and adolescents.
I met Claude through the NARM Training Institute, where I’m training to be trauma informed in my coaching and consulting work. NARM stands for NeuroAffective Relational Model and is designed to help people address complex trauma.
Disclaimer: Claude is a licensed psychotherapist, but I am not. As such, this episode and blog post are for informational purposes only, and nothing is intended as professional or medical advice in any capacity. If you are intending to recover from trauma, please contact a licensed psychotherapist or medical professional.
In this interview, Claude and I discuss several types of trauma including:
We also cover:
Claude’s lesson for listeners is to embrace vulnerability. As leaders, we can create spaces for ourselves and others to be vulnerable. If you embrace vulnerability, your life will be transformed.
For resources, organizations, and people mentioned go to: aaroncaulfield.com/podcast-feed/claude-cayemitte-on-types-of-trauma
On this episode Abhishek Gutgutia interviews me as a potential customer for the platform he’s building.
Abhishek is the Chief Product Officer at Chronicled and is creating a platform on the side of his full-time job to help fellow entrepreneurs succeed.
By providing resources, tools, coaching, feedback, best practices, and other support, he plans to celebrate and support founders of companies, especially first-time founders.
Inspired in part by the trend of “building in public,” whereby startups receive valuable feedback early on from potential customers, investors, and coaches, Abhishek would like to create a one-stop shop for founders to share their journeys and receive support.
His mission is to demystify and democratize entrepreneurship and help people all over the world start companies, rather than only those in Silicon Valley and other hubs.
For resources, organizations, and people mentioned go to: aaroncaulfield.com/podcast-feed/abhishek-and-aaron-on-democratizing-entrepreneurship
Marquis Lupton, co-founder and CEO of the TCP Network, struggled with stuttering while growing up.
To overcome his speech impediment, he worked with speech coaches and practiced speaking in front of the mirror: making eye contact, squaring his shoulders, and wearing a microphone.
Determined to be a radio personality or news reporter, he started two radio shows in college under the DJ name Quiet Storm. After college he worked for WLAN FM97 as a club DJ and board operator. He later landed a job in production for CNN in Washington, D.C., where he worked on the Pentagon unit and The Situation Room with Wolf Blitzer.
Marquis then spent several years in the field as a news reporter for TV stations around the Northeast. But he noticed that people of color, especially men, were disproportionately reported on in crime stories. There’s a phrase used in the industry: “if it bleeds, it leads,” meaning that fear-based stories, especially about minority groups, tend to get top billing.
After several failed attempts, Marquis partnered with Billy Way, Brandon Way, and Whitney Lupton to start the TCP Network, which stands for The Cultured Professional.
They’ve grown the radio station to over a dozen original shows on topics such as the morning news, hip hop, politics, pop culture, and sports.
Marquis and his team share the stories and voices of marginalized people and serve the community through initiatives such as the Spread Love Campaign.
In this interview, we discuss:
Marquis's entrepreneurial lessons include:
For resources, organizations, and people mentioned go to: aaroncaulfield.com/podcast-feed/marquis-lupton-on-overcoming-stuttering
Connect:
April Frazier is the founder of FRWD Confidence Coaching.
She was a technologist who wrote code and led software development teams for 18 years before realizing that her true passion is in serving others through coaching.
Through 1-on-1 and group coaching, she helps emerging entrepreneurs turn their ideas or side hustles into purpose-driven businesses. Serving dozens of female founders, April says “I help women remember how powerful they are.”
Like many entrepreneurs, clients of April’s struggle with imposter syndrome, doubts, worries, and limiting beliefs around money. She helps people overcome these challenges through a series of shifts in mindset.
In this interview, we discuss:
April's entrepreneurial lessons include:
For resources, organizations, and people mentioned go to: aaroncaulfield.com/podcast-feed/april-frazier-on-overcoming-failures
Connect:
Since starting Ranch Rider Spirits at the end of 2019, Quentin Cantu and Brian Murphy have expanded operations from Texas to Arkansas, Oklahoma, and Tennessee with plans to be in Louisiana, Arizona, California, Florida, Georgia, New Mexico, and Nevada soon.
Their idea for cocktails came while running their food truck Ranch Hand, which they started as University of Texas at Austin MBA students. They noticed a gap in the market for spirit-based ready-to-drink beverages, sold their food truck, and went all-in on Ranch Rider Spirits.
Offering four flavors, they hit $3.6 million in sales in 2020, which Quentin attributes to their sales and marketing team creating a brand that takes stances but also pokes fun at themselves as well as a production team that has nailed their recipes in a way that stands out in the market.
In this interview, we discuss:
Quentin's entrepreneurial lessons include:
For resources, organizations, and people mentioned go to: aaroncaulfield.com/podcast-feed/quentin-cantu-on-creating-a-lifestyle-brand
Connect:
Drishay Menon co-founded Bottlecode to help men take care of their skin. The company matches customers with skincare and personal-grooming products to solve their specific problems.
For Drishay and co-founders Jeff Meyers and Rob McIntosh, this is part of a larger mission to help men be happy, healthy, and more confident.
Most guys, including me, have struggled with skin issues but don’t talk about them openly. We’re left searching for solutions online, lots of trial and error, wasted time, money, and energy, and, in my case, using products that were actually the direct opposite of what I needed based on my skin type.
Bottlecode, based in Chicago, solves these problems by providing an outlet for men to identify skincare problems, receive personalized guidance backed by estheticians and doctors, and purchase products that meet their needs.
In this interview, we discuss:
Drishay’s entrepreneurial lessons include:
For resources, organizations, and people mentioned go to: aaroncaulfield.com/podcast-feed/drishay-menon-on-developing-confidence
Connect:
In light of the racial tensions following the murder of George Floyd, among the many other wrongful deaths at the hands of police violence, Sam Interrante launched Faces Against Racism.
He photographed over 100 people, each of which donated $100. Together the people of Lancaster, Pennsylvania, raised over $11,000, all of which was given to Lancaster-based black-owned community organizations: Advantage Lancaster, Deca City Farms, Lancaster NAACP, and three artist grants through the help of Lancaster LGBTQ+ Coalition.
As an entrepreneur, Sam balances passion projects such as this with projects that generate consistent, sustainable revenue such as headshots for LinkedIn profiles, websites, and other outlets.
In this interview, we discuss:
Sam’s entrepreneurial lessons include:
For resources, organizations, and people mentioned go to: aaroncaulfield.com/podcast-feed/sam-interrante-faces-against-racism
Connect:
Randy Paris is the CEO of Brewbike, a coffee company that exists to empower young people through entrepreneurial experience.
Brewbike gives college students opportunities to run coffee businesses, thereby equipping them with leadership, decision-making, and real-world skills.
Randy attributes his team’s high-performing nature in part to their willingness to have uncomfortable conversations.
Randy and I discuss handling conflict, such as that between Randy and Lucas Philips, which they worked on together for several years through coaching and individual psychotherapy, a process that has led to an even stronger relationship in the long run.
Randy’s entrepreneurial lessons include:
For resources, businesses, and people mentioned go to: aaroncaulfield.com/podcast-feed/randy-paris-building-a-high-performing-team
Connect:
ProtoTaste is a low-cost food truck rental program. Restaurants and chefs can use ProtoTaste’s food trailers to go to events and test new markets, thereby reducing the costs and risks associated with doing so.
CEO Chris Sempeles and his team handle all of the logistics, including the clean-up, so members can focus on serving their customers.
It’s a small B2B play, but Chris and co-founder, Kyle Pellman, have big plans. Their goal is for ProtoTaste to be in every city in the U.S. Currently located in Denver, they’re growing in spite of COVID-19.
Chris and I have been friends since childhood and in this interview we caught up about entrepreneurs and celebrities we look up to: Jay Z, Kobe Bryant, Gary Vaynerchuck, and Warren Buffett among others.
We also discuss the ups and the downs of entrepreneurship: the thrill of signing your first client, the devastation of losing clients, such as when COVID-19 hit, and everything in between.
Chris’s entrepreneurial lessons include:
For resources, businesses, and people mentioned go to: aaroncaulfield.com/podcast-feed/chris-sempeles-helping-restaurants-and-chefs-grow-their-businesses
Connect:
Sophie Roman co-founded The Pop’d Shop in 2017 with Mark Wieder.
They met at The Great Social Enterprise Pitch in Sophie’s hometown of Lancaster, Pennsylvania, where they ran the business for several years.
Earlier this year they moved the company to Puerto Rico.
The move was both strategic for the business: they now source fresh, natural ingredients from local fincas (farms), and deeply personal for Sophie: she is part of the diaspora—millions of Puerto Ricans from all over the world who are reconnecting with their roots, a subset of which are returning to Puerto Rico to build the local economy.
With this interplay of business strategy and cultural significance as the backdrop, Sophie is as optimistic as ever for the future.
She recently stepped into the CEO role and is focused on scaling the company. The Pop’d Shop now ships whole-fruit sparkling tonics to anywhere in the US and Puerto Rico.
When asked what she would tell young entrepreneurs, Sophie said, “You don’t have to face the starving artist. You can create opportunities for yourself through art...Entrepreneurship, if you’re creative, can be the biggest exercise in creativity.”
Resources mentioned include:
Connect:
Villond Cook spent 32 years, 2 months, and 3 days in prison, most of which were in maximum security.
At the age of 12, Villond started selling marijuana on the streets of Los Angeles. He later sold crack, joined a gang, and was making thousands of dollars per week in “fast cash.”
Throughout his teenage years, animosity brewed between Villond and a rival crew. They followed him home several times, flashed guns, and threatened his mom and others. One night, after they showed up at his then girlfriend’s home, Villond decided to take matters into his own hands. Furious, he grabbed his gun, drove to their hangout spot, and opened fire. He shot and killed one person and harmed two others.
At 18 years old, Villond was charged with one count of first-degree murder and two counts of first-degree attempted murder.
While incarcerated, he contemplated suicide. Drugs are easily available in prison and Villond considered overdosing on heroin in his cell. But he had what he calls a “spiritual awakening,” in which he vividly saw his grandmother telling him that everything would be okay.
His grandmother passed away shortly thereafter, but Villond immersed himself in various spiritual traditions, including Ifá, a way of life that originated in Nigeria and includes the idea that “anything that’s mentally conceivable is physically achievable.”
He read hundreds of books and took personal-development and victim-sensitivity courses, in which he learned to take responsibility for the ripple effect of his actions as well as to gain an understanding of the conditions that lead to his lifestyle.
After 32 years, 2 months, and 3 days, Villond was paroled and released in March of 2020.
When asked about his release, Villond said, “it’s still sinking in as far as I’m actually free, that I’m not living in a cage anymore…I can walk on the beach and listen to the ocean, I can sit under a tree and feel the breeze, I can go to a park with grass and watch children play and laugh…I can’t really find an adjective to describe or express what it’s like to be given a second chance at life basically; it’s like I’m being reborn again.”
Since his release, Villond has been volunteering and mentoring people who were incarcerated on how to re-enter society successfully. An entrepreneur at heart, he’s been taking culinary classes and has a vision of starting his own food truck or bistro.
In this episode, I'm being coached by Rich Litvin. Rich is an expert at taking high-achievers to the greatest levels of success. He's been a mentor and coach of mine for years.
Here he's helping me with my branding as an executive coach and strategy consultant for startup CEOs.
We draw out two potential chapters of my future book, which are "single point of leverage" and "solitary confinement."
Rich gave me permission via email to share this session. You can find him at richlitvin.com.
Resources mentioned include:
Connect:
On this episode, Aaron answers questions from three up-and-coming startup CEOs: Naman Trivedi, Caroline Caselli, and Randy Paris regarding:
Naman Trivedifounded Wattbuy in August 2017 to help millions of Americans choose cheaper, greener electricity plans and advance the global transition to a clean-energy economy. They raised a $2-million seed round, which enabled the team to identify a solid product-market fit in real estate and energy. They’re now at an inflection point in the company’s history. To continue to grow, they’re wondering whether to capitalize on a strategic opportunity with a partner company or raise a next round of funding.
Caroline Caselli (@cmcaselli) and her team at Haven Connect are on a mission to get more people into affordable housing. They connect low-income applicants and affordable-housing property managers to get people into units faster. They raised their $2.4 million seed round in 2019 and are scaling the company. Caroline is curious about how to create psychological safety and get buy-in from her team members.
Randy Paris is the CEO of BrewBike, a startup that serves coffee on multiple college campuses in three states via bikes and retail locations. This year they launched an e-commerce shop to serve thousands of online customers. To date, they’ve sold over 100,000 cups of coffee, paid student employees over $150,000 for their work, and raised over $2.5 million in funding. Because of the company’s growth, Randy is interested in managing people even more effectively rather than doing the work himself.
Aaron mentions the following resources:
Ishmael Jackson, founder and CEO of The Body Academy, grew up in abject poverty in Liberty City, Miami.
He's faced discrimination based on skin color and sexual orientation since he was a kid.
As Ishmael comments, “[I’m] an African American, recently married, my partner is male, in a country that is still to this day grappling with what each means.”
Ishmael speaks openly about the portrayal in his youth of African Americans on television as “bad guys,” and describes being fearful of police officers. “The anxiety that one would feel in the body—the feeling that I needed to run and hide—those things don’t leave us,” Ish says.
Yet through these and other challenges, Ishmael continues to put himself out there as an entrepreneur, and is writing a book to help others maximize their performance.
Ishmael has honed his skills in a specific area: movement. He helps clients unlock their mind-body connection through specific movements, which translates into breakthroughs in other areas of their lives, including business and relationships.
The working title of Ishmael’s book is Move through Life: Rediscover the Mind-Body Connection and Maximize Your Performance.
Ishmael and Aaron discuss the importance of feeling validated, recognized, acknowledged, seen, and heard.
Lucas Philips founded BrewBike while he was in college at Northwestern University in 2015.
Pre-coronavirus, BrewBike had expanded to UT Austin, Texas State, and the University of Miami, sold over 100,000 cups of coffee, paid student employees over $150,000 for their work, and raised over $2.5 million in funding.
But the shutdowns brought on by the pandemic left BrewBike in a tough situation. College campuses had been the lifeblood of the organization; BrewBike, like many food-service businesses, had to adapt overnight.
So they launched an e-commerce shop featuring cold brew kits, original blend coffee, and whole beans.
As Chief Product Officer, Lucas was instrumental in these efforts.
Yet he did so without a team reporting specifically to him. In the past few years, Lucas passed leadership and management responsibilities to CEO Randy Paris and COO Kelsie Hernandez, so that he could focus on growth and innovation.
Now Lucas would like to bring someone onto the team to help him, but he’s terrified that doing so will slow him down.
Aaron and Lucas explore where that terror might be coming from. Aaron offers a quote by Carl Jung, “that which we do not bring to consciousness appears in our lives as fate.”
This episode is an interview with Giovanna Marino, an entrepreneur based in Camp Hill, Pennsylvania.
Giovanna self-published her book How to Draw Graffiti Art: Learn to Master Tags, Wildstyle Technique, Urban Lettering and Creative Piecingon Amazon in November 2019, only 11 months after starting.
She continues to profit each month through her sales on Amazon.
For Giovanna, her book is part of a bigger dream to pay off debt, build profitable businesses, and move to New York for dance and music.
Selected links from the episode include:
Tucker Max on Choosing the Right Publishing Option(Traditional vs. Self Publishing vs. Hybrid)
99designs
Kdp.amazon.com
Workana
CanvaFiverr
Naman Trivedi is the CEO and co-founder of WattBuy, an online electricity marketplace that helps residents save money and go renewable with their home electricity.
As coronavirus continues to spread throughout the US and world, Naman was asking himself what he should be doing as a leader. How much should he share that he's afraid?
Much of Naman's team is in India on lockdown for at least three weeks, unable to leave their homes. He's concerned about his employees, family, friends, and himself.
Aaron helps Naman define a set of principles or values he can lead by in this crisis and beyond.
Aaron and Naman draw from Ray Dalio's book Principles.
This episode was recorded before coronavirus spread significantly to the US and Puerto Rico.
Mark Wieder got three degrees and worked as an attorney before jumping ship to start his own company.
The Pop'd Shop, which he founded with his business and life partner Sophie Roman in Lancaster, Pennsylvania, makes delicious soda with freshly pressed real fruit juice.
Mark and Sophie recently moved to Puerto Rico which puts Mark on the path of becoming an international businessman and more importantly, lays the foundation for Mark and Sophie to grow closer.
Aaron guides Mark to step out of his comfort zone and take on a month-long challenge of doing something special every day for Sophie.
Aaron mentions the work of John Winelandas well as the book Getting The Love You Want by Harville Hendrix.
Benji Leibowitz is a data scientist at Tempus where he is working diligently to accelerate cancer research.
He has visions of helping cure diseases, starting with cancer and ultimately slowing down aging.
Like many of us, he feels held back by not valuing himself at a deep level, which he and Aaron trace back, at least in part, to old wounds from childhood.
At times growing up Benji felt like an outsider or was embarrassed. These patterns may be playing out today.
Aaron recommends a two-pronged approach: meditating and healing deep wounds, as discussed in A Path with Heart: A Guide Through the Perils and Promises of Spiritual Life by Jack Kornfield.
Frank Corrigan is a husband and dad of two kids. He's currently the director of supply chain performance for a large retailer.
Recently, he ran the Houston Marathon in 2 hours and 34 minutes.
Frank has held leadership positions for years, but now he's ready to commit to following a more direct path in data science.
To some his move may look like a step down, but to him it opens up multiple sources of inspiration and income.
Follow Frank's blog at frank-corrigan.com.
Himalaya Mehta is a health actuary for a Fortune 500 company, a data science student pursuing a Masters from Northwestern, and a professional athlete for the Philadelphia Phoenix ultimate frisbee team.
Now he's looking to create more of an impact in sustainability.
Aaron guides Himalaya to take action on his 20-year vision in the next six months.
By using 20% of his time on a sustainability project and taking tiny, courageous actions, he has the opportunity to move closer to his dreams.