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by 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.
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- 4 days ago37 min
I Have $12M But I'm Broke Every Month
We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He sold his company for a headline $54 million — the number that actually hit his account was $12 million.Brandon Harris is the founder of Playmaker, a sports media company he built starting with $15 shoutout posts on Facebook pages and grew into a business with 20+ million followers and shows featuring athletes like Shaquille O'Neal and Jalen Brunson. The deal that sold it carried a $54 million headline — but between a brutal, near-failed first year with the acquirer and an earn-out he ended up negotiating his way out of early, what actually hit his account was $12 million. Today all of it stays invested, he borrows against it instead of selling, pays himself just $75,000 a year at his new startup, and hasn't taken a single day off since the deal closed.This episode gets into the real mechanics behind a $54 million number — the earn-out structure, the ugly first six months with a Danish acquirer that nearly tanked the whole deal, and the negotiation that got Brandon out early. We go deep on exactly where his money lives today: a 60/40 portfolio, a $600,000 "high risk" Robinhood account, and a $3 million credit line he taps instead of ever selling a share. Brandon also opens up about the 2008 crash that cost his family everything, the tattoo on his shoulder that explains why he can't stop building, and the one regret from the whole Playmaker run that still bothers him.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps:00:00 — Intro: the $54M headline, the real number that hit his account, and how he funds his life today without selling a single share01:30 — Growing up "very privileged" — until his dad's real estate portfolio got wiped out in the 2008 crash02:07 — Supporting his family financially at 18: "basically roller coaster"04:14 — Buying $15 shoutout posts on Facebook pages — the move that led him into media05:06 — Inside the $54M Better Collective deal — "one of the most complicated structures" he's dealt with07:42 — "Where I netted out was about 12 million total"09:48 — The first six months of the earn-out: missing a $17M revenue target by more than half12:18 — "That was probably the least healthy I've been personally in my life"12:51 — The turnaround: landing Shaq and Jalen Brunson, "the thrill of my career"15:56 — Where the $12 million actually lives today — a 60/40 portfolio and a credit line built to avoid capital gains17:35 — The $600,000 Robinhood account for his concentrated AI and robotics bets18:28 — The real debt picture: $3 million tapped on the credit line, $1 million left on the mortgage19:01 — Why he only pays himself $75,000 a year — "a big discount from the corporate 250 I was making"22:19 — His actual number before he can stop working: "I'd like to get to 20 million"24:13 — Zero days off since the exit: "No time, no time"25:09 — The tattoo on his shoulder and the "trauma" behind the drive to keep building33:51 — The regret that still bothers him: "no wins really mattered"Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
- 1 weeks ago39 min
He Sold For Over $40M. Here’s His Exact Cut.
We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.He got his first $5M check and expected to feel superhuman. The next day was one of the most disappointing of his life.Jesse Pujji walked away from a Goldman Sachs job where he made $500K at 25 — with a boss making $3M and a group head making $20M — to bootstrap an ad agency on $33K per partner and a stack of Amex cards. Ampush cracked the Facebook arbitrage before almost anyone: $100K in monthly revenue in June 2010 became $2M a month with $600K in EBITDA fourteen months later. He scaled it to half a billion in annual ad spend and 250 employees without raising a dollar, turned down $25M at 27, sold 20% to Red Ventures in 2015, and sold the whole thing to New Mountain Capital in 2022 for somewhere between $40M and $60M on a 35% stake. He never got the nine-figure number he made up in his head, and he says chasing it was the mistake.This episode gets into the exact allocation of a post-exit portfolio, why Jesse refuses to let his advisors put illiquid startup equity on his balance sheet, what $500K a year of "normal" spending actually buys, and why he asked his financial advisor how people possibly spend more than that. He's honest about the gap between the money he expected to change him and the money that didn't. And we spend real time on the part most founders avoid: three kids who never saw him grind, a Greenlight allowance split into thirds, a $63 JCPenney paycheck at 16 that taught him more than any of it, and the question of whether to leave them anything at all.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwTimestamps:00:00 — Jesse's origin story: immigrant household in St. Louis, a snow shoveling business in middle school, and $33K each plus Amex cards to start Ampush02:00 — The Facebook arbitrage that changed everything: $100K/month in June 2010 to $2M in revenue and $600K in EBITDA fourteen months later02:49 — "Sandbox entrepreneurship" — Facebook cold-calls them: "Who the hell are you guys? You're one of our top 100 advertisers"04:24 — Why he left Goldman at 25 making $500K: "I would rather make half of my future expected earnings and do something I feel excited about"06:18 — The $25M offer two years in, why they said no, and the $3M dividend they took instead — $1M each, which bought his SF house07:30 — The made-up number that wrecked them: hoping for $150M, getting $60–75M offers, and turning down $190M in Marin stock09:24 — The Red Ventures deal and $5M after tax: "I thought I would get wings or superhuman strength... nothing changed"11:16 — 2022: selling to New Mountain and walking away without going with the deal13:12 — The exit number, on the record: a $40–60M range on a stake "a little bit more than a third"16:04 — The Zone of Genius framework, and why being a CEO sat in his zone of excellence — good at it, drained by it17:52 — Gateway X by the numbers19:06 — Whether the scarcity ever goes away: "nine days out of ten" became "one day out of ten," and the coach question he couldn't answer20:16 — The Deer Valley condo, and finally understanding why people buy vacation homes21:08 — Full portfolio breakdown and why he tells his advisors to mark his startup equity at zero23:24 — Annual spend 26:52 — The schedule that makes it work: Tuesdays and Thursdays he misses bedtime, Monday/Wednesday/Friday he doesn't, and he deletes Slack on vacation28:16 — The thing that keeps him up: "They've gotten all the fruits of the grind without actually observing the grind"29:23 — Greenlight, allowance equal to their age, and splitting it into thirds — spend, save, give30:19 — Running a Starbucks P&L with his 9-year-old daughter in the store32:30 — The four-bucket framework: spend it, give it to the government, give it to charity, or give it to your kids34:44 — A Schnucks family board member on generational wealth: "Money doesn't ruin kids. Lack of values does."35:36 — What Jesse wants said at his funeralSponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Mone
- 2 weeks ago47 min
This Guy Tips Strangers $10,000 After 9-Figure Exit
He pastored for 30 years, then sold his company in a ~$500M deal — and gave away $1.5M the same week.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwDean Sweetman spent 30 years as a pastor before founding Tithe.ly at 51 — a giving platform for churches that Excel KKR acquired in a deal in the hundreds of millions. The same week the wire hit, he moved $1.5 million into a donor-advised fund he can never take back. Today he's worth $30–50M, gives away 10–15% of it every year, and still budgets like he did when he ended each week with $150 to spare.This episode covers the anatomy of his exit — upfront cash, rolled equity, earn-outs — and where every dollar sits now: 95% liquid, 50% indexed, 5% of net worth in debt. Plus the $10,000 tips he leaves strangers in airports, why he calls himself a "biblical capitalist," the dollar amount where he stopped thinking about money, and what he plans to do with all of it when he's gone.Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
- 3 weeks ago53 min
Craigslist Founder on Why He Turned Down $11B
Craig Newmark turned down an $11 billion offer for Craigslist, and he's already given away $570 million of his own money chasing a number even bigger than that.This podcast is made by Hampton, a community for founders doing on average $25 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you're a founder, apply here: joinhampton.com/mwCraig founded Craigslist off a mailing list in 1995. He turned down that $11 billion offer, and since then has given away $570 million through his foundation, aiming for a billion before he dies. He funds NYPD bomb squad gear, an NYU cardiologist's AI research, Wikipedia, journalism schools, and pigeon rescue. He's 73, hasn't owned a car in ten years, and just upgraded from $50 Skechers to $80 Skechers.This one gets into what happens once a founder's number stops being the problem, the Sunday school lesson behind his moral compass, why his own headline net worth is wrong, the two causes eating most of his giving budget, and his plan to train an LLM to keep making his philanthropic decisions after he's gone. It closes on Take Nine, his campaign for the nine-second pause that stops most scams.Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
- Jul 1, 202650 min
He Sold For $1.5B But Will Never Retire
He had $15 in the bank and a $1M judgment against him. Eight years later, Nestlé bought his company for $1.5B — then shut it down.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "What the heck, let's make it public." If you are a founder, apply here: http://joinhampton.com/mwMichael Wystrach built Freshly out of the wreckage of a failing restaurant, with $15 in the bank and a personally-guaranteed lease that left him with a $1M judgment against him. Six years later he sold the company to Nestlé for $1.5B — then watched it get shut down. He never took time off. He started a veterinary platform with his sister, raised a $75M venture fund, and put almost his entire payout back to work.This episode gets into what really happens to your bank account after a nine-figure exit — secondary sales, earn-out math, his actual living costs, his real estate philosophy at 2% interest rates, and what it felt like to lose the company he built after selling it. He also shares why he believes the first $10M matters more than the hundredth, and why he plans to keep building for the rest of his life.
- Jun 23, 202642 min
He Sold 4 Companies for $1.5B. The $13M Exit Changed His Life.
We did something nuts: we got 50+ founders to reveal their net worth, portfolios, income, expenses. Its free and right here: https://joinhampton.com/mw-wrWhy this podcast exists:Hampton is a community for founders. Members do an ave of $20m/year in revenue.Tons of the convos within the community are about money: how to invest, how to spend, how much to pay yourself...all this stuff you can't Google.We thought "Let’s just make these convos public". And thus, this podcast Moneywise came to be.We publish weekly. Click the subscribe button and the goodness will be delivered. Also...we've done 100+ episodes. If you want the aggregate info of all the numbers, meaning the net worth, spending, income of 50+ founders ranging from $10m to $1 billion: https://joinhampton.com/mw-wrOk, so let's talk David Royce, today's guest:He built the same pest control company four times — $13M, $30M, $135M, $1.5B — and says the first exit was the most life-changing.David Royce sold four pest control companies — Moxie, Eco First, Altera, and Aptiv — each bigger than the last, culminating in a $1.5B sale of Aptiv when it was doing $508M in annual revenue. He kept 100% equity through the first three, gave 25% of the last one to his employees, and personally walked away with hundreds of millions across the run. He's now on an indefinite sabbatical, investing through Iconic (the firm that manages Zuckerberg's and Dorsey's money), with half his net worth in S&P 500 and the rest in private equity, direct deals, and alternatives — including multiple Anthropic investments.This episode covers the exact mechanics of each asset-sale exit, why David kept restarting instead of holding, his full portfolio framework (including the 4-year cash buffer strategy), the "the answer is just a little more" moment that hit every entrepreneur in the room, and the story of flying his dying father on a private jet from a New Orleans hospital to Cedars-Sinai at 2am — made possible only by one call to a CEO WhatsApp chain.Timestamps:00:01:39 — David's full intro: four companies, four exits, what actually happened with the money01:55 — First company (Moxie): nearly went bankrupt the first year, how a cash flow crisis taught him "cash was king"03:14 — The asset-sale strategy: selling customers and technicians to Terminix while keeping the sales operation04:57 — "Pretty close" — David confirms Forbes' reported $13M and $30M exit figures05:37 — Why he gave 25% of Aptiv to employees and stepped back as chairman06:23 — Aptiv was doing $508M in revenue; Daniel and David settle on $1.5B as the sale range07:13 — What he actually took home: cap gains, California taxes, "hundreds of millions"08:37 — Net worth today: "do the math backwards and figure it out"09:09 — Portfolio breakdown: 4-year cash buffer in fixed income, S&P 500 with tax-loss harvesting, alternatives11:31 — "I just invested in Anthropic — three different times in the last year and a half" via Iconic14:35 — "The one that was life-changing was the first one" — $13M from nothing hits differently than $1.5B17:46 — Why pest control? A starving college student, a friend who made $25K in a summer, and zero sales for five days straight21:16 — His boss's question that changed everything: "What on earth would you go work for somebody else?"27:31 — Fifth grade through eleventh grade: watching his family nearly lose the house, the fear that built everything36:35 — Flying his dying father on a private jet from New Orleans to Cedars-Sinai at 2am39:36 — What he wants to be remembered for: "The sign of a good leader is not how many followers you have, but how many leaders you create"Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.comSubscribe to Moneywise: https://www.youtube.com/@themoneywisepodcastFollow Daniel on X: https://x.com/danielcberkListen on Spotify / Apple Podcasts: [search "Moneywise Hampton"]
- Jun 16, 202647 min
She Has $115M and Spent $340K on Knicks Tickets
She sold for $88M, almost bought a lake house she didn't want, and spent $340K on Knicks playoff tickets — then gave two away because it felt better.We're still surprised people did this but... 50+ founders worth $10M to $4B reveal their personal finances. Here it is: https://joinhampton.com/mw-wrWhy do we do this? Because if you're an aspirational person or someone who runs a business and is making money, it's incredibly challenging to figure out what to do. Information is impossible to find — and that's what we put together: the net worth reveal and why we do this podcast, Moneywise.Also, this podcast is made by Hampton, which is a community for founders doing on average $20 million a year in revenue. We saw a lot of these money conversations happening privately behind closed doors and we thought, "Why not, let's make it public." If you are a founder, apply here: https://joinhampton.com/mwAnne Mahlum built Solid Core from $175,000 of her own savings into an $88M exit. Two years later, her net worth is $115–120M, with $65M in public equities and $15M in a single stock alone. But the numbers are the least interesting thing that's happened since.After the sale, she secretly launched a second fitness company, had panic attacks she's never talked publicly about, shut the whole thing down, and spent two years in legal fallout. Then she had a baby, pulled an accepted lake house offer the morning after making it, and started forcing herself to spend $200K a month just to stop the money from piling up.This episode covers the full portfolio breakdown two years post-exit, why she's done with private investments, the Ambition story she's never told, what a baby did to how she thinks about money and time, and what she actually wants to be remembered for — which has nothing to do with net worth.Sponsors: Daily Body Coach - achieve your dream body with https://moneywise.dailybodycoach.com
- Jun 9, 202653 min
This Scientist Studied 38,000 People and Says Your Money Habits Are Genetic
JOIN HAMPTON:These episodes often come directly out of conversations happening inside Hampton, a private community for founders and CEOs with $3M+ in revenue or $10M+ exits. Members range from $5M net worth to billions. They wrestle with these same questions off the record. Apply at http://joinhampton.com/mw.HOW FOUNDERS ARE BUILDING WEALTH:How much do founders actually make, spend, invest, work, and keep in net worth? Hampton surveyed founders directly and put the answers into one report. Download it for free here: https://joinhampton.com/mw-wrEPISODE DETAILS:Most founders spend years learning how to make money. Almost none of them prepare for what their brain does once they have it.Henrik Cronqvist is a behavioral finance professor who trained under Nobel laureate Richard Thaler and has spent 25 years studying exactly that. His research has been cited over 7,000 times. He has studied 38,000 people to answer one uncomfortable question: how much of the way you save, spend, and invest is actually hardwired into your DNA?The answer will change how you think about every financial decision you make after an exit.This episode covers the science behind why the traits that made you a great founder may work against you as an investor, what actually happens in your brain the day the wire hits, and the one thing Henrik says every founder should do before making a single investment.TIMESTAMPS:00:00 — The traits that made you a great founder will make you a bad investor 01:45 — What is behavioral finance and why should founders care 04:35 — How Henrik got into this research (the Stockholm subway story) 06:39 — The 38,000 twin study: how much of your money behavior is genetic 10:56 — The first thing to do when the wire hits your account 12:49 — Loss aversion, performance chasing, and home bias explained 20:35 — Your personal mortgage predicts how you'll run your company's finances 30:08 — Why your brokerage app is designed to work against you 37:07 — Why founders feel depressed after selling (the science behind post-exit emotions) 47:14 — "I think I'm the exception" — and what the data actually says about that
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About Moneywise
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.
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