Weird Side Bets That Made Founders Millions

Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/Not every smart investment starts with a pitch deck or a business plan. Some of the best returns come from personal bets founders make with their own money. We pulled together five that actually paid off – big. From a $10K angel check that became $1.2M, to flipping a beach house for a $2M profit, and mining Bitcoin before it was cool.Here’s what we talk about:The overlooked angel check that quietly turned into a seven-figure exitFlipping a beachfront property for millions (plus cash flow along the way)Mining Bitcoin in a basement – and finding millions on an old hard driveGeo-arbitrage: the founder who 3x’d his wealth just by moving to ColombiaBuying small businesses instead of starting new onesMobile home parks, domain names, and other unexpected winsCommon patterns behind the biggest personal money winsCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Sponsors:Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseChapters:(0:00) The $10K Bet That Became $1.2 Million(4:49) Beach House Windfalls & Real Estate Flexes(8:01) Triple Your Net Worth – Just by Moving?(10:25) Oops, I Mined a Million in Bitcoin(12:48) Crypto: When 3% Becomes 30%(14:48) Why Founders Buy Businesses Instead of Building(16:59) Three Wealth Rules Every Founder Follows(18:15) The Boring Stuff That Actually WorksThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Jackie LamportNot really the host, but the producer.Wrote this sentence.

Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: https://joinhampton.com/Everyone thinks the “rich person” life is about fast cars, fancy watches, and designer flexes. But when we talked to over 150 high-performing founders, the things they actually spend on – and swear by – were surprisingly practical. Some luxuries just look good on Instagram. Others change the way you live, work, and feel every day.Here’s what we talk about:The #1 luxury nearly every founder says they’ll never go without againWhy hiring a housekeeper or private chef might save your business (and marriage)The health investments founders make – and which ones are worth skippingWhy some founders spend $100K/year on concierge medicine for their familiesRenting at $17K/month: outrageous flex or return-on-happiness?The emotional ROI of experiences (and the trip one founder spent $500K on)Business class vs. private jets: which travel upgrade is actually worth it?How these purchases impact kids – and the fine line between “comfortable” and “entitled”Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Sponsors:Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseTame your taxes today at https://olarry.com/Chapters:(1:18) Stuff You Buy vs. Stuff That Matters(1:58) Buy Back Your Time (Not Just Watches)(3:04) The Housekeeper Dilemma: Freedom or Softness?(4:23) Health Hacks: Trainers, Gyms & Biohacking(6:11) Therapy, Insurance, and the $100K Checkup(7:22) Dream Homes: ROI on Happiness(10:53) Experiences > Things: The Data Says So(12:00) Cancer, Family, and $500K on Memories(15:13) Connection, Curiosity, and Intentional Spending(15:33) The Business Class Trap(16:44) The Real List: What’s Actually Worth ItThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Jackie LamportNot really the host, but the producer.Wrote this sentence.

Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comEveryone wants to know what founders really earn, but most of the numbers out there are either outdated or just plain wrong. We gathered fresh data from 150+ high-performing founders, and the results reveal just how differently they think about paying themselves. Some take home millions, others nothing at all, and the logic behind those decisions says more than the numbers themselves.Here’s what we talk about:8% of founders take no salary at all — why? (and whether they’d do it again)The sweet spot for founder take-home pay: how much is too much?C-Suite compensation breakdown: who's earning what, and where bonuses explodeLifestyle vs. legacy: how founders think about cash flow vs. long-term exitsIndustry winners: finance, pets, and healthcare dominate earningsThe one funding stage where founders earn the leastNon-salary perks: credit card hacks, expense runs, 401(k) tricks, and company-backed loansA rare peek into the creative (and sometimes questionable) ways founders make it worth their whileCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Sponsors:Get a team of AI agents that run compliance for you at delve.co/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseTame your taxes today at https://olarry.com/Chapters:(1:37) Base Salaries(3:14) Founders Who Pay Themselves Nothing(3:56) Salary Distribution and High Earners(4:34) Additional Payouts and Bonuses(5:11) Two Types of Founders: Reinvesting or Cashflow(6:14) Take Home Pay by Net Worth(7:18) C-Suite Salaries and Bonuses(8:43) Industry Salary Breakdown(9:24) Highest and Lowest Paying Industries(10:03) Compensation by Funding Stage(10:52)  Creative Compensation StrategiesThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Jackie LamportNot really the host, but the producer.Wrote this sentence.

Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comEveryone’s chasing success — but what does that actually mean? Founders hit milestones, sell companies, and still feel unsatisfied. After 150+ interviews, the most consistent lesson is that most people are aiming at the wrong definition.Here’s what we talk about:Why the traditional founder definition of success doesn’t hold upThe dangerous feedback loop of external validationHow imposter syndrome thrives — even after a $50M exitWhy goal-setting alone can leave you feeling hollowThe “post-success” slump that no one prepares forWhy founders keep building (and chasing) after they’ve “won”A better way to define success that doesn’t move the goalpostsCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Sponsors:Get a team of AI agents that run compliance for you at delve.co/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseJoin 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseChapters:(1:00) Founders Who “Make It” Still Feel Unsatisfied(2:57) Defining Success: Objective vs. Subjective(4:27) The Founder’s Scoreboard and Moving Goalposts(5:11) The Emptiness After Achieving Big Goals(6:36) Internal Fulfillment vs. External Markers(8:23) Connecting Goals to Personal Fulfillment(8:44) The Search for Purpose After Success(9:25) Rethinking Purpose: Determination Over Destiny(10:30) Lifelong Fulfillment vs. Chasing Milestones(10:48) The Trap of Confusing External and Internal Success(12:01) Why Internal Success Makes External Success EasierThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Jackie LamportNot really the host, but the producer.Wrote this sentence.

Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comKevin Bartchlett built a $9M compost toilet company from the ground up – and walked away with nothing. No contract, no payout, just a handshake. That blind faith turned into a hard lesson in trust that cost him everything – and now, the reason he’s rebuilding on his own terms.Here’s what we talk about:Building a $9M business from scratch – with zero equity in writingThe moment he realized his million-dollar payday was goneHow a $9M sale turned into $0 overnightWhat “sweat equity” really means when it’s only a handshakeHow trusting the wrong partner cost him ownership and peace of mindWhy he still refuses to be angry about itWhat he’s building next (yep, it involves flying cars)The lesson behind it all: if you’re going to bet on yourself, go all inCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Kevin Bartchlett https://www.linkedin.com/in/kevin-a-bartchlett-262233ba/ Sponsors:Get a team of AI agents that run compliance for you at delve.co/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseJoin 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseChapters:(1:58) Building a Compostable Toilet Empire – The Dream of a Big Exit(3:22) When Expectations & Reality Collide(4:24) Picking Up the Pieces: What Happens After the Deal(6:01) The True Cost of Not Getting It in Writing(9:41) Why Compostable Toilets?(11:21) Meeting His Future Partner & Early Roles(14:56) Overinvested, Under-Rewarded: The Ownership Dilemma(20:28) Chasing Success, Counting the Cost(22:28) The Road to Resignation(24:49) Finding Empathy for His Partner(27:02) New Ventures: Flying Cars(29:12) Reflections – Betting on YourselfThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Harry MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.

Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comAdam White didn’t set out to build a media company – he just wanted a job in sports. So at 19, he started posting informational interviews on a Wix site. Today, he runs a $20M brand with NFL partnerships and no background in media. Because in the end, it wasn’t about who he knew – it was about who knew him, and how he got in the right rooms by outplaying legacy media at their own game.Here’s what we talk about:Building Front Office Sports out of his dorm roomWhy brand aura matters more than ever and how to create it from scratchThe tweet that led to a $750K investmentWhy he gave up 51% of the business early – and doesn't regret itThe role of soft touchpoints in landing major dealsGrowing to 800K newsletter subs without chasing SEOHow an official NFL content partnership changed everythingDiversifying revenue from newsletters, social, events, and brand partnershipsThe personal side: paying off student debt, buying his mom a car, and defining success as freedomCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Front Office Sports https://frontofficesports.com/ Adam White https://www.linkedin.com/in/adam-white-85ab4389/Sponsors:Protect your upside and get your time back at cressetcapital.com/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseJoin 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseChapters:(0:42) Building Front Office Sports: Growth & Early Days(1:40) Revenue Milestones(3:40) Building Brand Aura & Early Partnerships(10:34) Attracting Investors & Business Model Shift(13:24) Audience Growth During COVID(16:04) Monetization & Revenue Diversification(17:44) Philosophy on Investors(19:08) New Investors, Professionalization, & Validation(22:07) NFL Partnership (25:44) Networking Secrets(28:31) Personal Growth as a CEO(30:45) Personal Financial Journey & Mindset(33:40) Motivation, Competition, & Enjoying the JourneyThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Harry MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.

Get the full exit report here: https://joinhampton.com/rich-or-dead-reportStop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comMost exit stories are told in headlines and highlight reels. We wanted the truth. So we surveyed dozens of exited Hampton founders and pulled insights from 100+ interviews to uncover what really happens after the deal closes – from broken earnouts and identity loss to why nearly everyone regrets something they bought.Here’s what we talk about:Why deal structure matters more than the sale price, and how earnouts quietly screw foundersHow 47% of founders said they made less than expected from their dealWhy having millions in the bank can still feel like financial insecurityThe surprising trap of feeling “poor” after sellingWhy 92% of exited founders build again – retirement is a mythThe identity unraveling that hits most founders post-exitThe most common regret: a house, car, or other “reward” that quickly became a burdenWhy trying to time the market almost always backfiresThe #1 post-sale frustration almost no one talks about: losing control of company cultureCool Links:Hampton joinhampton.com/Lower Street lowerstreet.co/Hampton Wealth Report joinhampton.com/2024-wealth-reportSponsors:Get a team of AI agents that run compliance for you at delve.co/moneywiseAchieve your dream body with dailybodycoach.com/moneywiseJoin 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywiseChapters:(1:21) Deal Structure: Where the Real Money’s Made(4:22) Why a Big Payout Can Still Feel Small(6:43) The Retirement Myth: You’ll Build Again(8:32) Selling Isn’t Just Business, It’s Personal(11:33) The Big Purchase Trap(13:20) Timing: Stop Waiting for Perfect(15:26) Nine Lessons from Founders Who’ve Been There(17:00) The Culture Shift Nobody Warns You AboutThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Jackie LamportNot really the host, but the producer.Wrote this sentence.

Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comAlex Smereczniak built a $100M laundry business and sold 118 franchise locations in just 14 months. But just as the business took off, life hit hard. After a series of personal and professional crises, he stepped down as CEO. Now he’s back – not for another big exit, but to fix a franchise industry riddled with bad incentives and hidden fees.Here’s what we talk about:Building a $100M brand from a college dorm laundry hustleThe personal crises that forced him to walk awayWhy he thinks franchising is totally broken – and how brokers quietly take 60% commissionsWhat he’s doing differently at Franzy: flat fees, transparency, no bullshitWhy he’s not taking a salary, even with an $11M net worthWhat it actually costs – financially and emotionally – to scale fastThe moment he knew he wasn’t the right CEO anymoreWhy he believes franchising could be the path for millions displaced by AIHow he defines success today: not exits, but impactCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Franzy https://franzy.comAlex Smereczniak https://www.linkedin.com/in/alex-smereczniak-%F0%9F%A6%81-40310329 Sponsors:Get US caliber talent at offshore prices with https://www.oceanstalent.com/Achieve your dream body with https://www.dailybodycoach.com/moneywiseProtect your upside and get your time back at https://www.cressetcapital.com/moneywiseChapters:(0:41) Early Entrepreneurship: College Laundry Business(1:31) Selling the First Business & Lessons Learned(2:47) The Moment Alex Reconsidered Corporate Life at Ernst & Young (3:37) Returning to Laundry: The Startup Vision(6:07) Raising Capital & Startup Growth(10:40) Team Building, Hiring Challenges, and Culture(13:15) COVID-19, Franchising, and Business Model Shift(18:21) The Franchise Broker Problem & Franzy's Solution(20:45) Franchising as a Path to Wealth(24:03) AI, Job Displacement, and the Future of Work(28:30) Alex’s Personal Wealth, Fulfillment, and Impact(31:00) Reflections on Net Worth, Liquidity, and Success(34:40) Community, Support, and Peer Groups(40:02) The Sweet Spot: Wealth, Happiness & Freedom for FoundersThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Harry MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.

Stop making million-dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comMost founders start their restaurants in the red. Guy Allen did the opposite, turning a 12-seat sushi bar into a $3M business with lines out the door and plans for a $50M exit. He’s the founder proving restaurants can scale – if you treat them like startups.Here’s what we talk about:Leaving real estate tech after a decade to start over in foodTurning a sushi photography hobby into a six-figure uni import businessWhy importing sea urchin taught him everything about supply chainsHow Sendo became one of NYC’s busiest sushi spots – with zero marketing spendThe “three ingredients” behind every successful restaurant: food, location, brandWhy most chefs fail at business, and why one restaurant alone is a bad betThe real margins of restaurants (and what “good” actually looks like)How restaurant investing and profit-sharing actually workThe surprising scalability of sushi, and how he plans to reach 40 locationsBuilding publicly in an industry famous for secrecyCool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Sendo https://www.sendo.nyc/ Sponsors:Get your app built at https://zeroqode.com/?ref=moneywiseBuild web apps quickly with https://bubble.io/Achieve your dream body with https://www.dailybodycoach.com/moneywiseProtect your upside and get your time back at https://www.cressetcapital.com/moneywiseChapters:00:00 - The Harsh Reality of Restaurant Ownership00:43 - The Sushi Business Model and Guy’s Background01:35 - Guy’s Pivot from Real Estate Tech to Sushi02:56 - From Sushi Hobby to Social Media Platform05:44 - Importing Uni: Economics and Challenges10:11 - Sushi Quality, Branding, and Market Positioning13:22 - Why Premium Sushi Doesn’t Scale14:47 - Transition from Importing to Restaurant Ownership16:51 - Why Most Restaurants Fail: The Role of Branding18:44 - Building a Restaurant Brand and Early Success22:56 - Financing and Structuring Growth27:27 - The Surprising Upsides of the Restaurant Business29:54 - Scaling to 40 Restaurants and a $50M Exit33:49 - The Need for Transparency in the Restaurant Industry This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Harry MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.

Stop making million dollar decisions alone. Hampton gives you a personal board of eight vetted founders in your city who meet monthly to tackle your hardest problems. Find your group: joinhampton.comKory Mitchell built a blue collar asbestos business and sold it for $200M. When he stepped back, everything started to fall apart. A new CEO lost millions. The culture cracked. Kory came back to fix it, then walked away on his own terms. This is what happens when scaling works…until it doesn’t.Here’s what we talk about:Buying blue collar businesses: the unsexy but ultra-profitable path to serious scaleWhy adding debt transformed their trajectory – and nearly broke the companyWhat not to do after an exit: the new CEO that lost $12M in 6 projectsThe hidden tax of scale: how managing founders who’ve “already made their money” can kill your businessHow to build trust during M&A, and the warning signs that should make you walkLessons in culture, integration, and the real cost of bad communicationThe burnout that followed a $200M exit, and why Kory walked awaySabbaticals, Porsches, and starting over: what post-exit life really looks likeThe secret to finding off-market deals, and why PE firms keep asking Kory for helpWho shouldn’t do M&A (and why doing it while your house is on fire is a terrible idea)Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Kory Mitchell https://www.linkedin.com/in/korylmitchell Sponsors:Get US caliber talent at offshore prices with https://www.oceanstalent.com/Achieve your dream body with https://www.dailybodycoach.com/moneywiseProtect your upside and get your time back at https://www.cressetcapital.com/moneywiseChapters:(01:54) Growing Up Blue Collar & Family Business Roots(03:09) Taking the Leap: Debt and Aggressive Growth(05:53) Merging, Scaling, and Learning from Private Equity(08:19) Managing People: The Human Side of M&A(13:18) Integration and Building Company Culture(19:25) The $200M Exit and Stepping Away(21:48) Crisis: Post-Sale Struggles and Turnaround(25:22) Burnout, Sabbatical, and Starting Over(27:47) Lessons Learned: Who Should (and Shouldn’t) Do M&AThis podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.Your Host: Harry MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.