Three guests. Three completely different relationships with money. All of them more honest than they probably planned to be.

Neil Patel wrote a blog post in 2014 saying he could be happy on $15,000 a month. He meant it. We brought him on to find out how that became $200,000 a month — and where it actually goes. The answer involves $35,000 in bed sheets, four homes in Beverly Hills, and donations that dwarf his actual lifestyle spend.

Hank — not his real name — built a $3 billion cell phone distribution company, exited in 1996 for $60 million, and eventually found himself standing inside a 24,000 square foot house wondering how it happened. He paid $10 million. Cash. No mortgage. And runs it like a part-time job. He never says his net worth. He doesn't have to.

Taylor Adams grew up in a Los Angeles family with over a billion dollars in assets going back to the 1890s. Got sober at 26. Now helps wealthy families avoid destroying what the first generation built. He has a framework for how that destruction happens. He calls it the Four Horsemen. Every one of them sounds like good advice.

Three clips. Three moments worth rewinding.

This is MoneyWise.

FEATURED GUESTS

• Neil Patel — Founder, Neil Patel Digital & Crazy Egg
• Hank — Anonymous. Cell phone distribution. $60M exit. 24,000 sq ft.
• Taylor Adams — Founder, Belief Partners. Fourth-generation family wealth.

ABOUT MONEYWISE

MoneyWise is a Hampton podcast about what wealthy founders actually do with their money. Not how they made it — what they do after. Real numbers. Real allocation. Real feelings about wealth. Hosted by Daniel Berk.

New episodes in production now.
____________

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://www.joinhampton.com 

This episode's sponsor is Daily Body Coach - achieve your dream body with dailybodycoach.com/moneywise

This episode's sponsor is Daily Body Coach - achieve your dream body with dailybodycoach.com/moneywise

In this episode, we get into: 

• Building Oscar Health 
• How and why he tracks every minute of his day
• The framework he took from Ray Dalio at Bridgewater
• His approach to radical transparency in leadership

Cool Links

• Oscar Health
• Hampton

We're testing something new on MoneyWise. Just like we got radically transparent about money, we want to do the same with company building. Let us know what you think.

In this episode:
Adam White started Front Office Sports as a college project. Now it's worth over $40 million and it's basically the Wall Street Journal of sports. How'd he do it? We break down the branding, hiring, and operations that Adam used to compete with sports industry titans from day one.

Cool Links:
Hampton - https://joinhampton.com/
Front Office Sports - https://frontofficesports.com/

Five founders. Five exits. All around $30 million. So why did one walk away with $30M – and another with just $2M? From taxes and co-founders to deal structure and equity rollovers, the factors that shape a founder's final payout are rarely simple. This episode is your crash course in what really happens when a deal closes.

Here’s what we talk about:

• How Eran Galperin took home ~$30M while still keeping ~50% of his company
• Why Scott Galloway only netted $2–3M from a $33M sale
• How Alex Hormozi earned more from distributions than the $31M exit itself
• The ultra-simple, debt-free deal that netted two Canadian brothers $20M each
• Marshall Haas’ $18M cash payout – and why he held onto equity for peace of mind
• Why the "headline number" often masks the founder’s true financial outcome
• The impact of seller notes, taxes, state residency, and post-sale roles
• What to consider before you sell to avoid regret or burnout
• The myth of the $1B exit – and how one founder only took home $70M

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
  
  

Chapters:

• (0:42) Five Exits, Five Wildly Different Payouts
• (1:37) Eran Galperin: The Gym Desk Power Play
• (4:19) Tax Dodges & Seller Notes: Cash Isn’t Always King
• (5:22) Scott Galloway: $33M Headline, $3M Reality Check
• (7:39) Alex Hormozi: Gym Launch – Cash Out, Cash In
• (8:32) The Sinkinson Brothers: Double or Nothing in Canada
• (11:56) Marshall Haass: The Art of the Partial Exit
• (13:17) Why Smart Founders Never Sell It All
• (15:28) Scoreboard Envy: Don’t Get Played

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: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

What makes a founder truly successful? It’s not blind risk-taking or pure hustle. After two years of interviews and supporting research, we break down the five core personality traits that show up again and again in top-performing founders – from billion-dollar exits to early-stage wins. If you're building a company, understanding these traits might just be your cheat code.

Here’s what we talk about:

• Why openness and curiosity is the #1 trait in founders (with research to back it up)
• How a need for achievement often comes from past pain – and how to harness it
• The powerful drive for agency and autonomy, and why it often makes founders unemployable
• Why emotional regulation might be the most underrated skill in entrepreneurship
• Why successful founders don’t love risk – they just know how to manage uncertainty
• The science behind personality types and founder performance
• When focus becomes the essential balance to curiosity
• How therapy, journaling, and self-awareness are now founder-edge tools
• The myth of the stoic leader – and what really works instead

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/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise
• Rank higher in AI tools and LLM results with Mentions.so

Chapters:

• (0:46) How Curiosity Drives Founder Success
• (2:13) Turning Achievement into a Competitive Edge
• (4:08) Autonomy: The Fuel Behind Entrepreneurial Drive
• (5:39) Building Emotional Resilience for the Long Haul
• (6:53) Managing Uncertainty – Not Chasing Reckless Risks
• (8:17) Grit: The Unseen Force Behind Every Win
• (13:55) What Happens After the Big Exit?

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: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

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 exit
• Flipping a beachfront property for millions (plus cash flow along the way)
• Mining Bitcoin in a basement – and finding millions on an old hard drive
• Geo-arbitrage: the founder who 3x’d his wealth just by moving to Colombia
• Buying small businesses instead of starting new ones
• Mobile home parks, domain names, and other unexpected wins
• Common patterns behind the biggest personal money wins

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/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise

Chapters:

• (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 Works

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: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

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 again
• Why hiring a housekeeper or private chef might save your business (and marriage)
• The health investments founders make – and which ones are worth skipping
• Why some founders spend $100K/year on concierge medicine for their families
• Renting 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/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise
• Tame your taxes today at https://olarry.com/moneywise

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 It

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: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

Everyone 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 explode
• Lifestyle vs. legacy: how founders think about cash flow vs. long-term exits
• Industry winners: finance, pets, and healthcare dominate earnings
• The one funding stage where founders earn the least
• Non-salary perks: credit card hacks, expense runs, 401(k) tricks, and company-backed loans
• A rare peek into the creative (and sometimes questionable) ways founders make it worth their while

Cool 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/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise
• Tame your taxes today at https://olarry.com/moneywise

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 Strategies

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: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

Everyone’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 up
• The dangerous feedback loop of external validation
• How imposter syndrome thrives — even after a $50M exit
• Why goal-setting alone can leave you feeling hollow
• The “post-success” slump that no one prepares for
• Why founders keep building (and chasing) after they’ve “won”
• A better way to define success that doesn’t move the goalposts

Cool 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/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise
• Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywise

Chapters:

• (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 Easier

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: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

Kevin 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 writing
• The moment he realized his million-dollar payday was gone
• How a $9M sale turned into $0 overnight
• What “sweat equity” really means when it’s only a handshake
• How trusting the wrong partner cost him ownership and peace of mind
• Why he still refuses to be angry about it
• What he’s building next (yep, it involves flying cars)
• The lesson behind it all: if you’re going to bet on yourself, go all in

Cool 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/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise
• Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywise

Chapters:

• (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 Yourself

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Adam 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 room
• Why brand aura matters more than ever and how to create it from scratch
• The tweet that led to a $750K investment
• Why he gave up 51% of the business early – and doesn't regret it
• The role of soft touchpoints in landing major deals
• Growing to 800K newsletter subs without chasing SEO
• How an official NFL content partnership changed everything
• Diversifying revenue from newsletters, social, events, and brand partnerships
• The personal side: paying off student debt, buying his mom a car, and defining success as freedom

Cool 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/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise
• Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywise

Chapters:

• (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 Journey

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 Morton

• Founder 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.com

Most 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 founders
• How 47% of founders said they made less than expected from their deal
• Why having millions in the bank can still feel like financial insecurity
• The surprising trap of feeling “poor” after selling
• Why 92% of exited founders build again – retirement is a myth
• The identity unraveling that hits most founders post-exit
• The most common regret: a house, car, or other “reward” that quickly became a burden
• Why trying to time the market almost always backfires
• The #1 post-sale frustration almost no one talks about: losing control of company culture

Cool Links:

• Hampton joinhampton.com/
• Lower Street lowerstreet.co/
• Hampton Wealth Report joinhampton.com/2024-wealth-report

Sponsors:

• Get a team of AI agents that run compliance for you at delve.co/moneywise
• Achieve your dream body with dailybodycoach.com/moneywise
• Join 700+ founders hiring A-players in Latin America at hirewithnear.com/moneywise

Chapters:

• (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 About

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: Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

Alex 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 hustle
• The personal crises that forced him to walk away
• Why he thinks franchising is totally broken – and how brokers quietly take 60% commissions
• What he’s doing differently at Franzy: flat fees, transparency, no bullshit
• Why he’s not taking a salary, even with an $11M net worth
• What it actually costs – financially and emotionally – to scale fast
• The moment he knew he wasn’t the right CEO anymore
• Why he believes franchising could be the path for millions displaced by AI
• How he defines success today: not exits, but impact

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Franzy https://franzy.com
• Alex 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/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

• (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 Founders

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Most 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 food
• Turning a sushi photography hobby into a six-figure uni import business
• Why importing sea urchin taught him everything about supply chains
• How Sendo became one of NYC’s busiest sushi spots – with zero marketing spend
• The “three ingredients” behind every successful restaurant: food, location, brand
• Why most chefs fail at business, and why one restaurant alone is a bad bet
• The real margins of restaurants (and what “good” actually looks like)
• How restaurant investing and profit-sharing actually work
• The surprising scalability of sushi, and how he plans to reach 40 locations
• Building publicly in an industry famous for secrecy

Cool 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=moneywise
• Build web apps quickly with https://bubble.io/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

• 00:00 - The Harsh Reality of Restaurant Ownership
• 00:43 - The Sushi Business Model and Guy’s Background
• 01:35 - Guy’s Pivot from Real Estate Tech to Sushi
• 02:56 - From Sushi Hobby to Social Media Platform
• 05:44 - Importing Uni: Economics and Challenges
• 10:11 - Sushi Quality, Branding, and Market Positioning
• 13:22 - Why Premium Sushi Doesn’t Scale
• 14:47 - Transition from Importing to Restaurant Ownership
• 16:51 - Why Most Restaurants Fail: The Role of Branding
• 18:44 - Building a Restaurant Brand and Early Success
• 22:56 - Financing and Structuring Growth
• 27:27 - The Surprising Upsides of the Restaurant Business
• 29:54 - Scaling to 40 Restaurants and a $50M Exit
• 33:49 - 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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Kory 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 scale
• Why adding debt transformed their trajectory – and nearly broke the company
• What not to do after an exit: the new CEO that lost $12M in 6 projects
• The hidden tax of scale: how managing founders who’ve “already made their money” can kill your business
• How to build trust during M&A, and the warning signs that should make you walk
• Lessons in culture, integration, and the real cost of bad communication
• The burnout that followed a $200M exit, and why Kory walked away
• Sabbaticals, Porsches, and starting over: what post-exit life really looks like
• The secret to finding off-market deals, and why PE firms keep asking Kory for help
• Who 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/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

• (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&A

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Kass and Mike Lazerow built two companies together, sold one for $25M… and the next for $745M. Along the way, they went bankrupt, survived dot-com busts and Facebook booms, and figured out how to build a business without destroying their marriage. 

Here’s what we talk about:

• What it’s actually like to sell your company for $745 million
• The early Golf.com bankruptcy scare, and how Tiger Woods saved the business
• Why their co-founder relationship works (and where it almost blew up entirely)
• Mixing work and love: the brutal fights, trust, and one-liners from the delivery room
• Full breakdown of their first splurge, and what “enough” money really means
• Raising $50M without meaning to sell, and getting a surprise offer from Salesforce
• The $12M flop that reminded Mike why Kass is the only co-founder he needs
• Co-founder red flags, communication rules, and how they manage disagreements
• Living rich vs. feeling rich: the moment they finally felt secure

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Kass and Mike https://kassandmike.com/ 
• Kass and Mike's book: Shoveling $h!t: A Love Story https://www.amazon.co.uk/Shoveling-Story-about-Entrepreneurs-Success/dp/B0DY21NS7W 

Sponsors:

• The modern way to run your business phone is https://www.quo.com/perks/moneywise
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

• (1:26) The $745M Buddy Media exit
• (4:29) What people get wrong about working with a spouse
• (6:22) How Kass and Mike met
• (8:44) The Golf.com story
• (15:33) Managing team dynamics as married co-founders
• (23:17) Handling finances as a married couple
• (28:18) What they did with the money after the exit
• (32:33) Lessons learned and what they'd do differently
• (36:58) Closing thoughts on finding the right co-founder

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Jaclyn Johnson sold Create & Cultivate for $22 million. Then she hit pause – burned out, got divorced, and took a year off to figure out what she actually wanted. Now? She’s back, running the same company she sold, after buying it back for less.

Here’s what we talk about:

• Flipping real estate, investing in 25 startups, and turning $10K into $1.2M
• Spending $17K/month on rent – and not caring
• The number where she actually felt rich: $4–5M liquid
• Her full wealth breakdown: real estate, stocks, startups, and “a little” crypto
• Why angel investing works for her, and the returns that keep her going
• How burnout and divorce forced her to take a full year off
• What it’s like buying back the company you sold – for less
• Why she’ll never run day-to-day again (and how operators changed everything)
• Female founder scrutiny, and why being the face of the brand gets brutal
• Why she’s done chasing status, and how FOMO just disappeared

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Jaclyn Johnson https://jaclynrjohnson.com/ 

Sponsors:

• Get US caliber talent at offshore prices with https://www.oceanstalent.com/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

• (0:25) How Jacqueline Johnson built and sold businesses for millions
• (1:43) The three kinds of success every founder chases
• (7:04) What it actually feels like to have $15M in the bank
• (15:29) How Create & Cultivate became a brand women rally behind
• (18:37) The double standard: What it’s really like being a female CEO
• (23:18) The moments that made Jacqueline feel like she’d “made it”
• (25:37) What happens after you stop chasing FOMO
• (29:38) The money mistakes founders make after a big exit
• (32:04) What Jacqueline wishes every founder knew before selling

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Jordan Schlipf spent a decade building companies optimized for fun, freedom, and friendships. But with years of hindsight, he wonders if he left too much money on the table.

Here’s what we talk about:

• Why Jordan left a lucrative investment banking path to chase startups
• How the Rainmaking model let him share risk (and reward) with fellow founders
• The downside of passion-led business: no investment thesis, millions wasted
• Why he believes he could’ve made way more money doing less exciting work
• What he thinks about his $4M liquid net worth — and why it doesn’t feel like enough
• The moment he realized private equity is a better game than startups
• How he’s now trying to turn around a $10M beauty business without raising capital
• What it really costs to live well in London as a founder with a family
• Why he regrets chasing the “cool” startup dream instead of playing it safe
• What true wealth means to him today: help, time, and optionality

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Jordan Schlipf https://www.linkedin.com/in/jordan-schlipf-0b855174

Sponsors:

• Tam your taxes today at https://olarry.com/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

• (0:49) Breaking Down the Rainmaking Model
• (2:08) Jordan’s Pivot from Investment Banking to Startups
• (4:15) Why He Couldn’t Stay Away from Startups
• (5:43) The Origins & Vision Behind Rainmaking
• (8:48) Biggest Challenges in the Rainmaking Model
• (10:57) Costly Mistakes & Lessons Learned Along the Way
• (13:00) Why Jordan Stepped Away from VC
• (17:05) Taking Over as CEO of a Beauty Brand
• (18:23) Jordan’s Current Finances & Where He Stands Today
• (20:23) Lifestyle Adjustments & Financial Struggles
• (24:32) Life Before Family vs. Life After
• (29:04) What He Wishes He’d Done Differently

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Donald Spann built a multi-million dollar call center from scratch — with no outside capital, no technical background, and no safety net. Even crazier? He sold it for $12M to the first person who ever signed up.

Here’s what we talk about:

• Dropping out of college because he knew he’d never work for anyone else
• Building a cleaning business off a Reddit thread… then using it to launch something way bigger
• Accidentally going viral and getting 65,000 applications on a mom blog 
• Why he’s never raised a dollar of capital — and never plans to
• His $12M exit from a bootstrapped call center (and how the buyer was his first-ever customer)
• Breaking down his finances: no real estate, no advisor, just stocks and angel bets
• Growing up Black in a private school bubble and how that shaped everything
• Living on $10K/month in Mexico and self-funding a new mezcal brand

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/

Sponsors:

• Tam your taxes today at https://olarry.com/moneywise 
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Chapters:

• (1:26) Donald’s Net Worth & Current Ventures
• (3:57) Early Life, Education, and First Lessons
• (7:40) First Businesses & Getting Into Y Combinator
• (10:49) Building and Selling the Cleaning Business
• (14:02) The Successful Exit of Vicki Virtual
• (18:54) Personality, Confidence, and Entrepreneurial Edge
• (22:41) Meritocracy, Hard Work, and the Role of Luck
• (25:40) Reflections on Success & Personal Growth
• (29:02) Race, Identity, and the Entrepreneurial Journey

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Rajiv Khaneja made tens of millions running an ad tech company, but still lives in the same city he grew up in, wears the same clothes, and told friends he rented his house—even though he owned it. Here’s why.

Here’s what we talk about:

• How Rajiv built a profitable tech business as a teenager (and hired adults while still in high school)
• Turning down a $2.5M acquisition offer... then heading back to chemistry class
• What 25 years of “anti-lifestyle inflation” looks like
• The impact of immigrant parents and a “worst-case-scenario” money mindset
• Why he lived undercover for years, and how finding a peer group unlocked everything
• How he built AdButler into an 8-figure, bootstrapped business
• Rajiv’s idea of a lifestyle upgrade: attentional freedom > private jets
• Happiness optimization: spending $7M on a home to be closer to friends 
• His new obsession: using AI to help cure cancer
• Co-founding Arvita Therapeutics — and why he’s still building, even with $50M+ in net worth

Sponsors:

• Tame your taxes at https://olarry.com/moneywise
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• AdButler https://www.adbutler.com/index.html
• Arvita Therapeutics https://www.arvita.co/
  
  

Chapters:

• (0:00) Teen Millionaire: How Rajiv Made His First Money
• (0:45) Living Cheap on Purpose: Why He Drives a Prius
• (1:59) Managing Wealth & Long-Term Investing Strategy
• (3:36) Monthly Spending Breakdown & Frugal Habits
• (9:02) The Origin Story: From Web Polls to Ad Butler
• (19:16) Family, Upbringing & Money Values
• (24:49) Social Life, Hiding Wealth & Finding Founder Friends
• (31:56) Resisting Lifestyle Upgrades After a Big Exit
• (35:40) Choosing the Right Life & Business Partner
• (41:29) Future Bets: Biotech, Longevity & Playing the Long Game

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Ali Abdaal didn’t sell a startup. He didn’t raise money. He didn’t even plan to leave medicine. He just turned himself into the business, and ended up happier, wealthier, and more free than he ever expected.

Here’s what we talk about:

• Why Ali says money hasn’t made him more happy, just removed the stuff that made him unhappy
• His net worth (between $1M and $10M) and how it breaks down
• How a scammed MacBook deal sparked a business that made £1M+
• What he learned after hitting $6M/year in revenue, and why he stopped trying to scale further
• How flying business class and skipping trash day became his personal luxuries
• Why “$100M in the bank” wouldn’t change how he spends his time
• How coaching, meditation, and philosophy reshaped his relationship with money
• The moment Lewis Howes helped him break his identity as a doctor
• His rule of thumb: “Freedom comes from leaving money on the table”
• Why he's building software to reduce his dependence on content
• His real goal: $2M/year profit so he can work when he wants, on what he wants

Sponsors:

• Get US caliber talent at offshore prices with https://www.oceanstalent.com/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Protect your upside and get your time back at https://www.cressetcapital.com/moneywise

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Ali’s stuff: https://aliabdaal.com/

Chapters:

• (0:00) Introduction & Ali's Philosophy on Wealth
• (1:48) Net Worth Breakdown & Investing
• (3:17) Life in Hong Kong: Renting vs. Owning
• (4:54) From Medicine to Entrepreneurship
• (6:09) Early Business Lessons & Getting Scammed
• (7:44) Building and Selling the First Business
• (9:02) YouTube Journey & Passive Income
• (12:00) Revenue Growth, Plateau, and Lifestyle Design
• (16:01) Money, Happiness, and Scarcity Mindset
• (24:00) Motivation, Fulfillment, and Final Thoughts

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Rob Townsend says you’re wrong about financial advisors… mostly. And he’s built an 8-figure firm to prove it.

Here’s what we talk about:

• Why $3M liquid is Rob’s version of “f*** you money”
• How he went from $0 to 8 figures by modernizing financial planning
• Why the old guard of wealth management is failing founders
• What most people get wrong about index funds
• The simple investing mistake that wipes out 44% of stocks
• Why the happiest clients aren’t the richest ones
• How sabbaticals change Rob’s life (and business) every time
• His full portfolio: Dimensional Funds + a little Bitcoin
• The real reason private deals feel better than they perform
• The toxic mindset that plagues people with $25M+ net worth

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
  
  

Sponsors:

• The best phone system for teams at http://www.openphone.com/moneywise
• Achieve your dream body with https://www.dailybodycoach.com/moneywise

Chapters:

• The Financial Advisor Debate (00:00)
• Rob’s Personal Money Story (00:43)
• Growing Up & Early Influences (01:53)
• Lessons from Rob’s Uncle (05:39)
• Breaking into Wealth Management (06:31)
• Mistakes in Investing & Learning the Basics (09:01)
• The Case for Financial Planning (14:15)
• Building a Modern Wealth Firm (15:26)
• The Defense of Financial Advisors (19:14)
• Psychology of Wealth & Happiness (37:53)
• Final Thoughts: Money as a Tool for Life (45:53)

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Everything you need to know about turning art into a real (and risky) investment strategy.

Carlos Cardenas is a Private Wealth Advisor at Austin Wealth Management, bringing over 20 years of experience in alternative asset management. His background spans commercial real estate, technology, and healthcare ... but with a particular passion and expertise for the most alternative of asset classes: the fine art market.

Carlos spent nearly two decades in Paris, where he worked as a private art dealer and advisor, collaborating with leading institutions like Christie’s,

Sotheby’s, and the Picasso Family Office. His rare blend of financial acumen and art world savvy allows him to help clients navigate both traditional and nontraditional investments with insight and creativity.

Here’s what we talk about:

• What makes a banana duct-taped to a wall worth $6 million — and what it says about the art market.
• Carlos Cardenas shares how he went from private art dealer in Paris to advising wealthy clients on fine art investing.
• Why art can offer 8–12% returns — but only in a narrow slice of the market.
• How to start investing in art (even with less than $10K) — and when it becomes a serious wealth play.
• The real reason most people lose money in art — and how to avoid rookie mistakes.
• Passion, status, and profit: the three reasons people buy art (and why you need all three to succeed).
• Inside the elite world of art fairs, private dinners, and collector circles — and why art collecting is a powerful networking tool.
• Fractional ownership, tax loopholes, art-backed loans, and other financial hacks of the ultra-wealthy.
• How NFTs and digital authentication could transform the future of art investing.
• Why collecting art might just be the emotional outlet you didn’t know your money needed.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Austin Wealth Management https://austinwealthmgmt.com/
• Carlos's LinkedIn https://www.linkedin.com/in/carloscardenastx/
• Carlos's Instagram https://www.instagram.com/chicobeef/?hl=en

Sponsors:

• Get US caliber talent at offshore prices with https://www.oceanstalent.com/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Thinking of selling your company? Don’t leave millions on the table check out https://www.promissory.com/moneywise

Chapters:

• The $6.2 Million Banana & Art Market Hype (00:00)
• The Story of Art Collector Eli Saka (01:27)
• Meet Carlos Cardenas: Art, Wealth, and Passion (03:22)
• Art as an Investment: Returns & Blue Chip Art (04:44)
• Building an Art Collection & Diversification (07:06)
• Why Most Art Investments Don’t Pay Off (09:36)
• Reducing Risk & The Importance of Provenance (12:15)
• Big Wins, Big Losses, and Market Speculation (18:19)
• Fractional Ownership, Masterworks, and Modern Strategies (22:44)
• The Emotional Value of Art & Is It Worth It? (30:23)

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

This podcast is for educational purposes only and do not constitute financial advice.

You Host - Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

Inside Alex Hormozi’s decade-long climb from $0 to $200M+.

Here’s what we talk about:

• A transparent breakdown of his $200M+ net worth: $95M in liquid assets, $100M+ in illiquid equity
• The Gym Launch explosion: from near-bankruptcy to $42M in distributions and a $31M cash sale by age 31
• Why selling made him feel poorer, and why he’ll never cut off his “cash flow firehose” again
• Launching Acquisition.com the day after his exit to build a “forever business” using capital, skill, and leverage
• His high-yield side plays: hard money lending, minority equity deals, and how he’s made six figures a month in interest alone
• Lifestyle spending habits – including losing a $20M Vegas dream home
• Why most founders shouldn’t bank on an exit, and the slim statistical odds of selling successfully
• The mindset shift he’s working on now: being in a better mood regardless of success, stress, or circumstances

Sponsors:

• Get US caliber talent at offshore prices with https://www.oceanstalent.com/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• Thinking of selling your company? Don’t leave millions on the table https://www.promissory.com/moneywise

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
  
  

Alex Hormozi's newest book, $100M Money Models, launches at a live virtual event Saturday August 16th. Register free: https://register.acq.com

The book will teach you how to get more customers to spend more, in less time, over and over again, ultimately eliminating cash flow as a constraint to growth of any business.

Chapters:

• (1:22) Alex Hermozi’s Net Worth & Background
• (3:49) How Alex’s Assets & Where He Invests
• (5:28) Alex’s Fitness Philosophy
• (6:10) College Years & Early Ambitions
• (10:18) First Venture: Defense Contracting, Then Entrepreneurship
• (13:20) Building Gym Launch & Selling for $60M
• (31:47) Lifestyle, Spending Habits, Plus a Wealth Mindset
• (38:43) Personal Growth & Finding Fulfillment
• (40:02) The True Value of Success & Seeking Validation

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: Sam Parr

• Founder of Hampton, a private, highly vetted community for high-net-worth founders.
• Previously sold his last company for tens of millions.

Chuck Yates rode the wildest wealth rollercoaster: $150M up, $82K down, now back at $20M. In oil & gas private equity, he made (and lost) fortunes and never flinched. For Chuck, money’s just part of the story. Mindset is everything.

Here’s what we talk about:

• How Chuck went from $150M to $82K and why he wasn’t phased
• What it’s like to build wealth in the high-stakes world of energy PE
• The absurd economics of buying a plane
• How he managed to tour with celebrities
• Why your relationships matter more than your balance sheet
• The mindset shift that came after divorce, getting fired, and starting over
• How Chuck accidentally became a podcaster and ended up co-founding an AI startup
• Why self-worth shouldn't be tied to net worth and how Chuck redefined success on his own terms

Sponsors:

• Get US caliber talent at offshore prices with https://www.oceanstalent.com/
• Achieve your dream body with https://www.dailybodycoach.com/moneywise
• The best phone system for teams at http://www.openphone.com/moneywise

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
  
  

Chapters:

• (0:00) Chuck's Bold Introduction
• (3:01) Living Comfortably with $20 Million
• (3:25) The Rise in Private Equity
• (6:36) Early Career and Entry into Energy
• (10:41) The Wild World of Oil & Gas
• (13:12) Personal Life Changes and Divorce
• (13:46) The Van Halen Plane Era
• (22:50) Getting Fired and Hitting Bottom
• (31:22) The Comeback: Digital Wildcatters and AI
• (35:52) Life Philosophy and Values

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Amber Lee was literally brought back to life, and then decided to start over.

Here’s what we talk about:

• After a near-death experience in 2020, Amber finally launched her dream matchmaking business from the hospital.
• She bought her mom a house and moved to Puerto Rico, prioritizing freedom over wealth.
• Year one: $1M revenue. Now: $3M+ with fewer clients and higher margins.
• Matches high net worth and high profile clients, with fees from $65K to $1M.
• How matchmaking for the wealthy works.
• Why successful women struggle to date, and why confidence matters more than cash.
• A billionaire fell for a $200K-a-year locksmith… proof that values matter more than money.
• Why fear, not logic, leads many high achievers to sabotage relationships.
• How unrealistic checklists and surface-level filters ruin real connection.
• Tips for finding love without spending six figures on a matchmaker.
• The right partner can make you richer, healthier, and happier.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/

Chapters:

• (0:00) Amber's Near-Death Experience
• (4:31) Early Career and Path to Matchmaking
• (7:36) The Car Accident That Changed Everything
• (13:02) Building a Multi-Million Dollar Matchmaking Business
• (14:18) Inside the World of High-End Matchmaking
• (25:29) Why Successful People Struggle with Relationships
• (29:09) Advice for High Net Worth Singles
• (35:50) The Benefits of Finding the Right Partner

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

How Ronan Berder accidentally built a consulting agency, scaled it to 8 figures, and sold it, despite never enjoying the work.

Here’s what we talk about:

• Why Ronan stayed in China running a business he didn't love, and the deep sense of duty he felt to his team.
• Walking away from an opportunity to follow his passion in order to focus on scaling the business that already had momentum (despite not enjoying it).
• Navigating two failed acquisition attempts before finally exiting for 8 figures.
• The surprising anticlimax of selling his business and realizing… nothing really changes.
• His brutally honest reflections on burnout, entrepreneurship, and why he feels most alive under pressure.
• A transparent look at his current investment portfolio, from fixed deposits to high-conviction plays in AI and Bitcoin.
• Why Ronan says success comes down to discipline, stubbornness, and grit, not genius or perfect strategy.
• How it feels to finally focus on his true passion.

Sponsors:

• Get US caliber talent at offshore prices with https://www.oceanstalent.com/

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
  
  

Chapters:

(01:08) Ronan's Current Life in Singapore

(03:02) Transition to Coding and Open Source Projects

(09:39) Early Life and Career Beginnings

(11:47) Starting a Business in China

(17:43) Growth and Realizations in Business

(21:19) Living a Minimalist Life

(22:24) Balancing Work and Personal Life

(24:23) Business Challenges and The Impact of COVID-19

(28:27) The Final Push and Burnout

(29:36) Selling the Business

(32:05) Life After the Sale

(38:55) Financial Management Post-Sale

(41:35) Reflecting on the Journey

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Jay Berard’s never sold a company, but with $2.5M in cashflow and $10M net worth, is he confidence-rich or risk-blind?"

Here’s what we talk about:

• His early days: a Craigslist job ad, 100% commission, no safety net… and a one-way ticket from Winnipeg.
• Jay’s net worth: ~$10M, mostly liquid, mostly public equities, and why he values his business equity at zero.
• He makes ~$2.5M/year in personal cash flow, but keeps fixed expenses surprisingly lean.
• Why he turned down acquisition offers and sees more value in control than an exit.
• From saving every penny to flying business class to how his spending evolved with his mindset.
• Why “rich” should mean more than just money and how he’s redefining wealth on his terms.
• What a “big life” really means and the tension between comfort and growth he’s wrestling with today.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
  
  

Chapters:

(01:19) Jay's Financial Philosophy

(05:07) Personal Cash Flow and Lifestyle

(06:32) The Concept of Safety Net

(12:50) Early Career Struggles and Successes

(17:48) The Role of Fear and Anxiety in Success

(21:35) Struggling with Consistency

(22:12) Deep Work and Self-Improvement

(25:20) Revenue Journey and Business Growth

(32:19) Balancing Work and Personal Life

(35:49) Defining Success and Living a Big Life

(38:42) Future Goals and Business Aspirations

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Here’s what we talk about:

• Why financial security stops being a motivator after $50M—and what takes its place
• The "F*** You" number: What real numbers show is the threshold for total financial freedom
• Wealth allocation shifts: Crypto disappears, bonds and real estate dominate at the ultra-high end
• Surprising insights into monthly cash burn, and how spending changes (or doesn’t) across net worth tiers
• Take-home income jumps dramatically past $50M—especially at the $100M+ level
• Time vs. money: Wealthier founders are working fewer hours, but that doesn’t guarantee happiness
• What motivates founders at every stage—and why some feel lost after hitting their big number
• Real quotes from founders like Brian Johnson and Alex Peykoff on why they build, invest, and spend the way they do

$50M is when founders stop caring about money entirely. Want to see what other millionaire money secrets we uncovered in the full report? https://www.joinhampton.com/wealth-report

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
  
  

Chapters:

• (00:29) Survey Insights: Wealth Allocation and Trends
• (01:02) Understanding the Respondents
• (03:09) Motivations and Milestones of Millionaire Founders
• (04:13) Case Study: Bryan Johnson's Unique Motivation
• (05:47) Financial Security and Lifestyle Changes
• (08:47) Money Management: Crypto, Bonds, and Real Estate
• (10:46) Cash Flow and Spending Habits
• (16:14) Work-Life Balance and Happiness

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

You Host - Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.
• Older than I appear, I promise.

Andrew Wilkinson became rich in his 20s — but early wealth came with hard lessons. In this episode, Andrew opens up about:

• How he went from buying everything he wanted to nearly going bankrupt in 2008
• The emotional rollercoaster of building and losing wealth while still young
• What it's actually like to cross the nine-figure mark
• Why luxury spending doesn’t always bring happiness
• How wealth impacts family, friendships, and personal identity
• His thoughts on giving back, donating money, and the real ROI of generosity

Chapters
(00:00) Introduction
(00:21) Meet Andrew Wilkinson: Early Success and Challenges
(02:38) The Reality of Wealth: Lessons Learned
(03:14) Building Businesses: From Design Agency to Diversification
(06:54) The First Big Sale: A Turning Point
(09:28) Spending Habits: What Worked and What Didn't
(20:39) The Impact of Wealth on Family and Relationships
(23:00) The Complexity of Doing Good with Money
(27:02) Conclusion: Reflections on Wealth and Happiness

Sam Parr
Founder of Hampton, a private community for 7-figure founders. Previously sold his company, The Hustle, to HubSpot for tens of millions.

Jess Chan scaled to 7 figures fast, then tore it all down. Today, she’s worth ~$10M, spends less than ever, and says profit > revenue every time.

Here’s what we talk about:

• Jess hit $40K/month as a freelancer, then walked away to build her agency, Longplay.
• Why chasing $1M in revenue nearly burned her out, and what she did to rebuild.
• The shift from ego-driven growth to sustainable, profitable business.
• How embracing feminine leadership transformed her company and her life.
• Her net worth is ~$10M, but her monthly spend has dropped to ~$6K.
• The underrated skill: learning how to spend money well.
• Why contentment and ambition can coexist and how chasing more can actually cost you.
• Jess’s financial setup: super simple. Mostly ETFs. Barely checks it.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/

Chapters:
(00:00) Introduction to Jess Chan's Journey
(00:58) Early Revenue Chase and Freelancing
(02:03) Building and Scaling Long Play
(02:55) Challenges and Burnout
(04:42) Rebuilding and Stabilizing
(06:14) Shifting Focus from Revenue to Profit
(08:20) Embracing Feminine Leadership
(15:03) Redefining Wealth and Success
(19:37) Breaking Free from Business Metrics
(20:21) Childhood Reflections and Entrepreneurial Drive
(22:09) The Unexpected Path to Entrepreneurship
(27:41) Transparency in Financial Success
(31:57) Personal Finance and Contentment
(37:00) Balancing Ambition and Contentment

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Is flying private a waste of money, or the ultimate time hack for the ultra-wealthy? In this episode, we break down what it really costs, who it makes sense for, and why even billionaires think twice.

Here’s what we talk about:

• Private aviation expert Preston Holland explains the true cost of flying private, from charter to full ownership.
• When does it make financial sense? Around $2M in income and $20M net worth.
• Why fractional ownership is trending, even for people who can afford full planes.
• Guests like Andrew Wilkinson, Josh Payne, and Nick Huber share how and why they fly.
• The real costs: pilots, insurance, hangars, maintenance, and depreciation.
• Who flies private most: rural founders, franchise owners, post-monetary entrepreneurs.
• Flying yourself? FinTech founders and control freaks, take note.
• A PSA: Jets don’t make money, don’t fall for “fly for free” scams.
• Jackie reflects on patience vs. buying back time.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Preston’s Twitter https://x.com/prestonholland6
• Preston’s Newsletter: https://prestonholland.com/bio

Chapters:

• (00:00) Introduction and Andrew Wilkinson's Private Flying Experience
• (00:48) Exploring the Costs and Benefits of Flying Private
• (01:51) Types of Private Jet Ownership
• (03:12) Chartering vs. Owning: Financial Considerations
• (05:06) Fractional Ownership and Co-Ownership
• (07:52) Full Ownership: Pros, Cons, and Costs
• (12:28) The Realities of Owning a Private Jet
• (15:16) Entrepreneurs and Private Flying
• (32:20) The Environmental and Financial Costs of Private Jets
• (34:41) Conclusion and Final Thoughts

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances. Inspired by real conversations happening in the Hampton community.

You Host - Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.

Auren Hoffman reveals the unglamorous truth about angel investing—why he still does it, what he’s learned, and why it’s not for everyone.

Here’s what we talk about:

• Auren Hoffman made $60M—and then became an angel investor.
• He shares why angel investing isn’t as sexy as it sounds.
• The truth about money: yes, it did make him happier.
• How he tracks spending (only big and small stuff—never the middle).
• Why he never sets goals and doesn’t chase happiness.
• His step-by-step guide to being unhappy (for real).
• How trash-talking saved LiveRamp from a PR meltdown.
• The right way to invest after a big exit (hint: take it slow).
• Why most people shouldn’t even think about investing before hitting $3M.
• Sam and Auren go deep on process vs. planning—and what really drives success.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Auren’s Twitter https://x.com/auren

Chapters:
(00:00) Auren Hoffman's Big Exit
(00:17) The Reality of Angel Investing
(00:53) Introducing Moneywise
(01:02) The Hampton Community
(02:23) Auren's Early Entrepreneurial Journey
(03:39) First Million in the Twenties
(06:47) LiveRamp and the $60 Million Exit
(07:52) Handling Wealth and Lifestyle Changes
(12:00) Navigating Business Challenges
(13:56) Entrepreneurial Mindset and Resilience
(15:33) The Importance of Community for Founders
(17:17) Navigating Uncertainty in Business
(17:40) Insights from Successful Founders
(18:26) Auren's Journey Post-Big Exit
(19:44) Balancing Work and Personal Fulfillment
(21:05) The Philosophy of Happiness and Success
(28:52) Advice on Angel Investing

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: Sam Parr

• Founder of Hampton, a private community for CEOs.
• Sold his last company, The Hustle, for tens of millions.

He’s worth 8 figures, owns a private jet, and still tracks every dollar. Nick Huber says avoiding lifestyle creep is harder, and more important, than getting rich.

Here’s what we talk about:

• How Nick Huber built an 8-figure net worth from sweaty startups and smart real estate plays.
• Why he keeps over $2M liquid and doesn’t touch stocks.
• His exact monthly burn (yes, including the jet) and how he keeps it under $25K.
• The psychology behind lifestyle creep, and why he’s borderline paranoid about fixed costs.
• Why he’d rather live modestly than risk losing what he’s built.
• The emotional rollercoaster of lumpy cash flow, $900K tax bills, and late-night financial dread.
• How he justifies buying a private jet.
• His next goal: $1M/month in personal profit, and why he's not trying to be a media mogul along the way.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Nick’s Stuff  https://www.nickhuber.com/

Chapters:

• (00:00) Introduction to Nick Huber's Success
• (00:48) Nick Huber's Financial Journey
• (01:20) Breaking Down Net Worth and Assets
• (03:12) Cash Flow Management
• (05:16) Nick's Humble Beginnings
• (08:49) Entrepreneurial Lessons and Challenges
• (13:44) The Rise of Storage Squad
• (17:42) Maintaining Frugality Despite Wealth
• (20:10) Managing Lifestyle Creep
• (22:09) The Justification for Owning a Jet
• (24:11) Avoiding Fixed Costs
• (24:56) Balancing Ego and Humility
• (30:45) The Role of Media in Entrepreneurship
• (35:57) The Emotional Roller Coaster of Entrepreneurship
• (39:16) Conclusion and Final Thoughts

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

After a nine-figure exit, Anastasia Koroleva went through divorce, failure, and identity loss. She reflects on what she didn’t see coming.

Here’s what we talk about:

• Anastasia’s journey from a bootstrapped nine-figure success to divorce, burnout, and identity loss
• Why second businesses often fail, and how success the first time around can actually work against you
• The four biggest traps post-exit founders fall into: rushing into something new, chasing unfamiliar industries, losing self-awareness, and falling into “Sudden Wealth Syndrome”
• How to rebuild your life after selling a company using frameworks like Maslow’s hierarchy and cognitive dissonance theory
• Why wealth alone doesn’t create fulfillment, and what actually does
• Anastasia’s personal portfolio strategy: no wealth manager, heavy in private credit, designed for low stress and high flexibility
• A real look at her post-exit lifestyle, including two homes and $650K to $1M in annual spending
• How long it truly takes to feel whole again after an exit, and why slowing down might be the smartest move
• Why she now spends her time helping other founders avoid the same mistakes

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Anastasia’s Podcast https://www.exitparadox.com/
  
  

Chapters:

• (00:00) Introduction: The Big Picture Trap
• (00:56) Meet Anastasia's Net Worth
• (03:14) Anastasia's Early Life and Career Beginnings
• (04:19) The Silicon Valley Leap and First Ventures
• (07:25) The Emotional Rollercoaster of Success
• (09:25) Post-Exit Challenges and Personal Struggles
• (17:55) The Psychology of Second Ventures
• (24:26) Understanding Sudden Wealth Syndrome
• (28:20) Minimizing Psychological Discomfort Post-Exit
• (29:37) The Paradox of Wealth and Freedom
• (31:30) Confronting Financial Freedom
• (32:48) The Third Level of Wealth
• (33:30) Emotional Challenges and Evolution Post-Exit
• (34:49) Rebuilding the Basics: The Maslow Pyramid
• (35:44) The Goldilocks Approach to Post-Exit Life
• (48:07) Managing Wealth Post-Exit

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Adam Robinson was days away from a $70M exit… then the buyer walked. But the deal collapsing turned out to be a blessing.

Here’s what we talk about:

• His current company now does $25M ARR with $1M monthly profit.
• He accidentally spent millions before the deal closed on land, crypto, and a new mortgage.
• Then came a surprise 60% tax bill, thanks to a little-known IRS rule.
• Adam explains why high income doesn’t equal peace of mind.
• He shares how Wall Street shaped his risky money habits.
• His spending: $750K/year, two kids, boat, Aspen trips, wellness lifestyle.
• He admits he wasn’t ready for a big exit and still might not be.
• Now, he’s focused on structure, restraint, and building wealth slowly.
• And why cash flow feels better than a windfall… at least when you’re winning.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/

Chapters:
(00:00) The Big Exit That Never Happened
(00:54) Adam's Financial Resilience
(02:25) From Wall Street to Startups
(06:59) The Startup Struggles
(10:31) The Almost Sale and Its Aftermath
(12:35) Crypto Craze and Financial Lessons
(15:13) Rebounding and Learning from Mistakes
(19:21) The Genius Trade of the Century
(22:38) Financial Anxiety and Business Risks
(25:26) Tax Surprises and Financial Planning
(29:27) Spending Habits and Lifestyle Choices
(36:28) Balancing Wealth Building and Lifestyle
(37:14) Conclusion: The Exit That Wasn't

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

After a $100M+ exit, Jace Mattinson blew $40K a month chasing lost time, until living the dream nearly ruined it.

Here’s what we talk about:

• Jace shares how he turned a failing 135-year-old business into a $160M exit.
• Why buying old and boring beat building from scratch.
• He hit a $5M net worth—then spent $40K/month trying to “make up for lost time.”
• The moment he realized leisure can become just another grind.
• How he and his wife navigated the emotional hangover of success.
• Why founders struggle with freedom, and how he learned to enjoy it.
• His strategy for protecting wealth and living fully.
• His monthly expenses for a family with 5 kids under 7.
• The framework he uses to make time, money, and values actually align.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Book mentioned: Die With Zero by Bill Perkins

Chapters:
(00:00) The Grind and Delayed Gratification
(01:41) Financial Breakdown and Investments
(03:37) From Corporate Life to Entrepreneurship
(05:10) The Influence of Upbringing
(07:03) Meeting His Wife and Changing Perspectives
(08:47) Turning Around a Struggling Business
(14:21) The Exit and New Challenges
(15:49) Life After the Sale
(18:47) Balancing Family and Personal Time
(19:18) Indulging in Expensive Hobbies
(20:50) Spending on Experiences vs. Investments
(23:26) Finding Balance in Hobbies and Work
(27:05) Intentional Living and Regrets
(30:18) Current Monthly Expenses and Hobbies
(35:55) Future Plans and Bucket List

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

What happens when you grow up alongside a billion-dollar company, lose yourself chasing money, drugs, and approval,  and have to rebuild your life from scratch? That’s what happened to Alex Peycoff.

Here’s what we talk about:

• Why growing up in a soon to be billionaire status family taught Alex the wrong lessons about value and self-worth.
• How wild drug-fueled nights and empty relationships left him feeling more isolated than ever despite immense wealth.
• The life-altering moment with his daughter that redefined his understanding of success, money, and emotional presence.
• How Alex rebooted his life, built "emotional wealth," and developed a purpose beyond material success.
• Why he keeps all his money in real estate and avoids markets and crypto.
• Alex’s personal definition of emotional debt and how clearing it created the biggest transformation of his life.
• His current net worth ("north of a couple hundred million dollars") and how he manages it differently now.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Alex’s stuff https://www.alexpeykoff.com/home

Chapters:

• Introduction to Alex Payoff's Story (00:00)
• Early Life and Family Background (01:38)
• Struggles with Wealth and Identity (04:25)
• The Wild Years: Drugs and Excess (06:17)
• Turning Point: Realizations and Reflections (13:26)
• Embracing Emotional Authenticity (19:12)
• Redefining Success and Happiness (19:34)
• Financial Freedom and Personal Crisis (20:08)
• The Car Obsession (21:48)
• Emotional Wealth vs. Emotional Debt (23:49)
• The Value of Real Estate Investments (32:20)
• Building Emotional Wealth (35:08)
• Join the Hampton Community (36:20)
• Podcast Production by Lower Street (37:05)

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances.

Inspired by real conversations happening in the Hampton community. Check out Hampton: https://www.joinhampton.com/

Your Host: Harry Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Shane Cultra walked away from his family's five-generation nursery business—triggered, in part, by watching Succession. Along the way, he built up a $10M net worth, stacked Bitcoin, turned a blog into a domain empire, and made peace with a father who didn’t speak to him for a year after he left.

Here’s what we talk about:

• How Shane went from pit trader to plant farmer
• The domain side hustle that cashflows $300K+ a year
• Breaking down his $10M net worth: Bitcoin, land, stocks, and side gigs
• Why his dad thought success would make him lazy
• The real cost of working with family—and why he’d still do it all over again
• How Succession mirrored his life and led him to finally walk away
• The awkward equity breakdown: 33%, but no control
• Selling a blog for $75K and going all-in on digital real estate
• Why he’d rather make $18K for himself than $100K working for someone else
• Letting his daughter fail—and why that’s the lesson his dad never learned
• His exact monthly spending: $5,600/month, no mortgage, travel-heavy lifestyle
• From Porsches to a two-door Bronco: redefining what rich looks like
• $4M in stock holdings (including a $10K Apple investment for his daughter that grew to $400K)
• Why he's not pushing the family business to the next generation—and what legacy really means

Cool Links:

• If you’re a founder or CEO with $3M+ in revenue or funding, or you’ve sold a company for $10M+, check out Hampton: https://www.joinhampton.com/
• If you want a cool podcast like this one, check out Lower Street https://www.lowerstreet.co/
• Check out Shane's blog! https://www.botany.com

Chapters:
A Family Legacy in Crisis (00:00)
Shane's Financial Journey (00:31)
The Nursery Business Dynamics (04:51)
Shane's Early Career and Return to Family Business (09:12)
Navigating Family and Business Conflicts (11:49)
The Importance of Land Value (16:25)
Venturing into Domain Names (17:27)
The Unexpected Offer: Selling My Blog (21:07)
Family Tensions: Side Income and NFTs (21:43)
Measuring Wealth: Personal Stories (23:01)
Leaving the Family Business: A Tough Decision (24:59)
Reconciliation and Moving Forward (30:42)
Advice for Founders with Kids (33:41)
Financial Overview and Spending Habits (35:37)
Final Thoughts on Family Legacy (39:10)

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

Mike Brown built an oil & gas empire, scaled his net worth to nearly $20 million, but ended up cash poor, losing $1.8M in a failed bet, and borrowing money from his wife to pay taxes. Now, he’s rebuilt his fortune, redefined what wealth really means, and is living a life designed around freedom, not just big numbers.

Here’s what we talk about:

• How Mike went from $2K in his bank account to making millions in oil & gas deals
• The "gold rush" mentality that led him to reinvest everything and regret it
• Why he thought $100M was the magic number (it wasn’t)
• The dangers of illiquid assets and chasing wealth at all costs
• Losing $1.8M on a distressed e-commerce acquisition 
• How divorce and bad bets forced a complete financial rethink
• Mike’s personal framework for financial freedom (12 months of liquidity, 5–7 years cash cushion, escape velocity)
• Why liquidity and cash flow > net worth
• His full portfolio breakdown today: fixed income, oil & gas, index funds, and zero angel investing
• The mindset shift: from "grow at all costs" to "invest for safety and joy"
• What it really feels like to sell your Lamborghini and love it
• How he's building a life he never wants to retire from — and helping other founders do the same

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Mike’s Wealth Business https://unbreakablewealth.com/

Chapters:
(00:00) Introduction to Mike Brown's Financial Journey
(02:36) Mike's Early Life and Money Lessons
(05:07) Navy to Entrepreneurship: The Million Dollar Deal
(07:24) The Gold Rush: Rapid Wealth Accumulation
(16:54) The Downfall: Divorce and Financial Struggles
(19:23) The E-commerce Disaster: Losing It All
(22:28) Rebuilding and Relying on Support
(24:55) Rebuilding with Cash Flow
(25:42) Lessons from Failure
(27:02) Current Portfolio Strategy
(28:41) Cash Flow and Investments
(31:11) Financial Freedom Levels
(33:53) Personal Monthly Burn and Joy
(36:17) Redefining Wealth and Happiness
(42:12) The Irony of Wealth
(47:24) Final Takeaways and Community

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 Morton

• Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
• Co-parents a cow named Eliza.

There is no amount of money that will make you happy. There is also no amount that will stop making you more happy. 

Both of those things are true.

Our producer is not rich. But she has talked to 100+ people who are, and she (I) has learned a lot about your kind (is that wrong to say?).

In the Moneywise pilot, we asked the question “at what point will more money stop making you happy”. Turns out, that was a pretty stupid question. So in this episode, we’re fixing that.

This is an episode of Moneywise unlike any other. This is a solo essay-style inside-outsider's take on wealth and happiness, based on the past year of peaking behind the curtain at what truly makes millionaires lives better… and worse. Backed up by quotes from our guests and of course, real studies.

Here’s what we talk about:

• Money doesn’t make you happy. It can only remove stress.
• The “happiness number” is a myth but knowing your “freedom number” changes everything.
• Most people don’t want money, they want the freedom they think money will give them.
• Hitting your financial goal won’t feel like you imagined.
• Founders often feel lost post-exit because they unknowingly traded hope for cash.
• Wealth adds new stress.
• Money can’t buy you meaningful experiences, and you need to stop thinking it can.
• If you expect money to do the emotional heavy lifting in your life, you will never be satisfied.
• Money is the key, not the door. It unlocks your potential but it won’t add anything more to your life.

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
  
  

Chapters:
(00:00) Introduction and Confession
(00:35) Reflecting on 50 Episodes
(02:24) Revisiting the Happiness Threshold
(03:09) Money as a Subtractive Tool
(03:48) The Freedom Number vs. Happiness
(05:07) Studies and Research on Wealth and Happiness
(14:39) The Hedonic Treadmill and Wealth's Paradox
(17:45) Hope and the Entrepreneur's Journey
(25:26) Concluding Thoughts and Freedom Numbers

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances.

Inspired by real conversations happening in the Hampton community.

You Host - Jackie Lamport

• Not really the host, but the producer.
• Wrote this sentence.
• Older than I appear, I promise.

References:

• Kahneman, D., & Deaton, A. (2010). "High income improves evaluation of life but not emotional well-being." Proceedings of the National Academy of Sciences, 107(38), 16489-16493. DOI: 10.1073/pnas.1011492107
• Jebb, A. T., Tay, L., Diener, E., & Oishi, S. (2018). "Happiness, income satiation and turning points around the world." Nature Human Behaviour, 2, 33-38. DOI: 10.1038/s41562-017-0277-0
• Killingsworth, M. A. (2021). "Experienced well-being rises with income, even above $75,000 per year." Proceedings of the National Academy of Sciences, 118(4). DOI: 10.1073/pnas.2016976118
  Link, B. G., Phelan, J., Bresnahan, M., Stueve, A., & Moore, R. E. (1995). American Journal of Orthopsychiatry, 65(3), 347-354. DOI: 10.1037/h0079653
• Donnelly, G. E., Zheng, T., Haisley, E., & Norton, M. I. (2018). "The Amount and Source of Millionaires’ Wealth (Moderately) Predicts Their Happiness." Personality and Social Psychology Bulletin, 44(5), 684-699. DOI: 10.1177/0146167217746340
• Luthar, S. S., & Becker, B. E. (2002). "Privileged but Pressured? A Study of Affluent Youth." Child Development, 73(5), 1593-1610. DOI: 10.1111/1467-8624.00492.

Eran Galperin bootstrapped a niche SaaS for Brazilian Jiu-Jitsu gyms, sold it for $32.5 million, moved to Japan, and is now quietly living the FIRE dream — with a few luxury upgrades.

Here’s what we talk about:
- How Eran went from $15K in the bank to a $32M exit (with 90% equity!)
- Why he ignored VCs and chose to bootstrap — and how it paid off years later
- The long, slow ramp: 4 years to $12K MRR, 8 years to $3M ARR
- The FIRE mindset that guided his financial decisions from day one
- How and why he moved to Japan — including taxes, cost of living, and lifestyle
- What it actually cost to move abroad and build a luxury home in Tokyo
- His full post-exit portfolio breakdown (hint: most of it’s in index funds)
- What it’s like working after the exit — and why he’s still showing up
- The one splurge that changed his mindset about spending
- The emotional reality of selling your company — and why it felt more like relief than celebration
- Why he's mentoring early-stage founders and learning real estate development — just for fun

Cool Links:
Hampton https://www.joinhampton.com/
Lower Street https://www.lowerstreet.co/
FIRE Subreddit https://www.reddit.com/r/Fire/?rdt=37862
fatFIRE Subreddit https://www.reddit.com/r/fatFIRE/

Chapters:
(00:00) The $32 Million Exit
(01:48) Why FIRE
(08:31) The Slow SaaS Ramp of Death
(12:49) The Big Move to Japan
(14:32) Financial Optimization and the Exit Strategy
(19:05) The Final Deal: $32.5 Million Sale
(23:25) Financial Breakdown and Initial Investments
(26:03) Post-Exit Financial Planning
(28:19) Lifestyle Changes and Spending Habits
(33:49) Building a Dream Home in Tokyo
(38:52) Continued Work and New Ventures
(42:30) Final Thoughts and Future Plans

This podcast is a ridiculous concept: high-net-worth people reveal their personal finances.
Inspired by real conversations happening in the Hampton community.

Harry Morton
Founder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.
Co-parents a cow named Eliza.

Vinay Hiremath co-founded Loom and sold it for nearly $1 billion… then walked away from $60 million, gave most of his early money to his parents, and now he’s looking for internships.

Here’s what we talk about:

• How Vinay went from broke stoner to $50–70 million exit
• Why he voluntarily left tens of millions on the table—and doesn’t regret it
• The emotional crash that came after the deal closed
  What happens when your ego, identity, and wealth all collide
• The moment he paid off his parents’ mortgage—and why it meant more than the money
• His portfolio breakdown (hint: half of it’s just sitting in cash)
• Why he’s now learning physics and applying for internships in robotics
• The surprising amount of money he thinks you actually need to be free

Cool Links:

• Hampton https://www.joinhampton.com/
• Lower Street https://www.lowerstreet.co/
• Vinay’s Blog Post: I’m Rich and Have No Idea What To Do With My Life vinay.sh/i-am-rich-and-have-no-idea-what-to-do-with-my-life
• Kubera – Net Worth Tracker https://www.kubera.com/
• Monarch Money https://www.monarchmoney.com/

Chapters:

(00:00) Introduction and Personal Struggles

(06:24) Vinay's Early Life and Education

(08:43) Starting Loom and Early Challenges
(12:40) Loom's Growth and Success
(17:18) Vinay's Personal Finance Journey
(22:25) Reflecting on Wealth and Identity
(26:40) The Viral Blog Post
(29:15) Overcoming Childhood Challenges
(30:10) Selling the Company: Mixed Emotions
(32:37) Post-Exit Life: Investments and Strategies
(34:49) Embracing Chaos and Self-Discovery
(42:41) Financial Habits and Spending
(48:00) Pursuing New Passions and Learning
(53:21) Calculating Financial Freedom

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:
Sam Parr

• Founder of Hampton, a private community for CEOs.
• Sold his last company, The Hustle, for tens of millions.

Chris Cooke is a socialist Buddhist who sold his company for $30 million… then blew most of it on a weed farm, a beach house, and a comedy club in Thailand.

Here’s what we talk about:

• How Chris accidentally “won” capitalism—despite deeply skeptical views of money
• What happens when your values, ego, and bank account collide
• Why he spent nearly his entire fortune in six months—and doesn’t regret it
• The real estate investments that unintentionally saved him from going broke
• How Buddhist detachment helped him take huge risks—and make millions
• Why giving money to friends was harder than it sounds (and cost him relationships)
• How he's now building a business focused on sustainability, not just growth
• The real meaning of success for a Buddhist entrepreneur

Cool Links:

 Hampton – Join the Founder Community https://www.joinhampton.com/

 Lower Street – Podcast Production https://www.lowerstreet.co/

Chapters:

(00:00) Introduction: The Paradox of a Capitalist Buddhist

(03:23) Early Life and Entrepreneurial Spirit

(06:01) Building and Growing a SaaS Business

(11:41) The Decision to Sell and Its Aftermath

(17:26) Spending the Fortune: Investments and Losses

(22:05) The Comedy Club and Financial Struggles

(25:49) Lifestyle Changes and Generosity

(27:07) The Downside of Lending Money to Friends

(29:56) Reflections on Wealth and Happiness

(30:54) The Rollercoaster of Post-Exit Life

(36:44) Buddhist Values and Business Success

(40:12) Current Financial Situation and Future Plans

(44:11) Conclusion and Final Thoughts

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 Morton

• Founded and runs Lower Street, the leading branded podcast production service in the world.
• Hampton Member.

Inspired by real conversations happening in the Hampton community.

If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.

Dan Berger sold his company Social Tables for $100 million in 2018. But his net worth today hasn’t moved at all. Why?

Here's what we talk about:

• How Dan went from bootstrapping websites to an eight-figure exit
• Why his net worth hasn’t grown in seven years (and he’s totally fine with that)
• His biggest post-exit financial mistakes: angel investing, dumb NFTs, and a $7.5M NYC apartment
• The hidden struggles of founders post-exit—why selling doesn’t solve your problems
• How Dan’s early-life struggles led to a lifelong search for belonging
• What entrepreneurs get wrong about identity, success, and relationships
• His perspective on the Die With Zero philosophy—and how he’s ACTUALLY living by it.
• How he rebuilt his sense of purpose

Your Hosts:

Sam Parr

• Founder of Hampton, a private community for CEOs.
• Sold his last company, The Hustle, for tens of millions.
• Big fan of first-class flights (unlike Dan).

Harry Morton

• Founded and runs Lower Street, the leading branded podcast production service in the world.
• Hampton Member.

Cool Links:

• Hampton – Join the Founder Community https://www.joinhampton.com/
• Lower Street – Podcast Production https://www.lowerstreet.co/
• The Quest by Dan Berger – A book on belonging and identity. https://www.belongingquest.com/
• Die With Zero by Bill Perkins – The book that inspired Dan’s financial philosophy. https://www.diewithzerobook.com/welcome

Chapters:

Meet Dan Berger: The $100 Million Exit (01:08)

The Journey of Social Tables (01:49)

Life After the Big Sale (03:47)

Financial Transparency and Mistakes (08:10)

Living the Die With Zero Philosophy (18:01)

Rediscovering Success (22:39)

Financial Insights: Investments and Income Sources (23:40)

The Belonging Crisis: A Personal Journey (24:21)

Adoption, Abandonment, and Immigration: Early Life Struggles (24:45)

Building Belonging: From Company Culture to Personal Connections (26:02)

Addiction and Recovery: A Path to Belonging (30:01)

Men in Crisis: Addressing Modern Masculinity (36:58)

Post-Exit Reflections: Investing and Finding Purpose (40:51)

Creating Community: The Birth of Hampton (45:44)