Moneywise
Hampton
This is Moneywise, a podcast where host Daniel Berk is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Check it out at https://joinhampton.com/.
Episodes
Mentioned books
22 snips
May 12, 2026 • 36min
He Made $400k/Month Before 30... Then Realized It Meant Nothing
Nathan May, founder of a fast-growing newsletter growth agency and former BCG consultant who started by selling Minecraft maps, tells a wild rise from childhood poverty to $400k months. He talks about early Minecraft entrepreneurship, leaving consulting to build a multimillion-dollar agency, the tight IRL founder community he calls the Media Mafia, and why wealth failed to deliver meaning.
112 snips
May 5, 2026 • 60min
He Made $3M a Year and Decided He Had Enough
Jonathan Goodman, entrepreneur and author who built a $35M fitness education business from a one-bedroom apartment. He reveals his $14M net worth and why $7M felt like a safe number. He explains living part-time abroad for 14 winters, how he spends during Toronto months vs travel months, and why chasing tax havens felt unappealing.
74 snips
Apr 28, 2026 • 40min
Does Making $100M Make You Happy?
Steve Weiss, founder who grew MuteSix from homelessness to a nine-figure sale, reflects on life after a $100M-plus acquisition. He recounts the moment the wire hit, the unexpected emotional fallout, and how he spends and protects his wealth. He also discusses obsession with insurance, the post-exit search for purpose, and where he’s channeling his energy now.
59 snips
Apr 21, 2026 • 54min
He Has $70M And Flies His Own Plane Wherever He Wants
John Arrow, serial entrepreneur who bootstrapped Mutual Mobile to huge exits and now invests in AI projects like FreedomGPT. He recounts building a company from a $0.99 app to a $70M outcome. He talks flying his own plane, radical financial transparency, risky stories like the Cuba trip, and his approach to investing and building uncensored AI.
55 snips
Apr 14, 2026 • 37min
This 23-Year-Old Dropout Bootstrapped His Company to Millions
Josh Suggs, 23-year-old founder of Street Talk who bootstrapped an ad/content agency to millions and speaks openly about ADHD and startup life. He discusses growing up in Westport, early hustles from magic to barbershop content, refusing outside capital, heavy cash holdings, monthly spending habits, and why he left school to chase momentum.
27 snips
Apr 7, 2026 • 49min
$200k/Month, a 24,000 Sq Ft House, and a Billion-Dollar Trust. Our Best Moments.
Taylor Adams, founder of Belief Partners and a fourth-generation heir, helps wealthy families steward multi‑generational wealth. He discusses finding purpose after inheritance and his sobriety pivot. He outlines how families lose legacies with his Four Horsemen framework and explains reframing net worth as fuel for value creation.
171 snips
Mar 24, 2026 • 34min
Matt Paulson has $25m a year in personal income - nice.
Matt Paulsen, founder and CEO of MarketBeat and serial investor, built a high-margin financial media business and owns real estate and multiple firms. He discusses bootstrapping from small-town roots, huge company financials and personal take-home, why he doubled down on real estate, buying a private jet, philanthropic priorities, family-first choices, and simplifying his investment portfolio.
110 snips
Feb 26, 2026 • 14min
Why The Founder of a $4BN Company Tracks Every Minute of His Life...
Mario Schlosser, co-founder and former CEO/CTO of Oscar Health, an insurance tech leader valued over $4B. He describes tracking every minute of his life in a spreadsheet and how that forced focus. He explains using radical decomposition to build resilient systems. He also discusses radical transparency, confronting founder conflict early, and rebounding after IPO-related mental-health struggles.
25 snips
Feb 17, 2026 • 12min
He Turned $40 into a $40M Sports Media Empire
Adam White, founder of Front Office Sports, turned a college project into a $40M sports-media brand. He talks about investing heavily in premium branding and design to appear larger from day one. He explains creative stunts, strategic partnerships, and a metrics-driven weekly performance pack. He also outlines a hiring framework using Culture Index and defined role profiles.
93 snips
Dec 30, 2025 • 19min
Five Founders, Same Exit Value – Wildly Different Payouts
This discussion features Scott Galloway, a renowned entrepreneur and professor, and Alex Hormozi, a successful business strategist. They dissect the stark contrasts in founder payouts from similar exit values. Galloway reveals his experience of a $33M sale that netted only $2–3M due to taxes and equity splits. Hormozi shares how he gained $42M in prior distributions, surpassing his $31M exit. Insights on seller notes and tax implications underscore the complexity of these financial outcomes.
