Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-report

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.

Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-report

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.

** Thinking about selling your company? 24 founders told us what really happens after the wire hits. — joinhampton.com/exit-report

Santiago Aparicio built a $500M company, then faced a choice: step away or die.

Here’s what we talk about:

• Santiago shares his $22M net worth and the breakdown.
• He rents instead of owning real estate to keep life flexible.
• Spends freely on watches and Porsches, but says they are assets, not expenses.
• Grew up in Colombia with wealth but strict spending limits, which fueled his drive.
• Joined Rappi early, then co-founded Fitpal, before chasing bigger ideas.
• Built a payroll company from zero to $500M/year fast, but felt miserable.
• Constant comparisons made him feel like a failure despite success.
• Ignored health issues until he developed a severe heart condition.
• Family forced him to choose: company or life.
• Walked away while the company was thriving, leading to an identity crisis.
• Now working with Bryan Johnson on health tech at Blueprint.
• Says success comes at a cost, and many founders hide how miserable they really are.

Cool Links:

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

Chapters:
(01:34) Santiago's Financial Breakdown
(04:09) Luxury Spending Habits
(05:10) Early Life in Colombia
(08:37) Entering the Startup World
(10:37) The Rappi Journey
(13:29) Building FitPal
(17:14) The Y Combinator Playbook
(19:18) The Goalposts Keep Moving
(24:44) The Fleeting Joy of Success
(26:46) Aggression and Overwork
(28:47) Health Scare and Realization
(34:13) Stepping Down and Identity Crisis
(40:47) Reflections on Sacrifice and Success
(43:43) Challenging Hustle Culture
(47:31) Working with Brian Johnson

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.

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

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.

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

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.

Jackie breaks down exclusive data from 127 millionaire founders inside Hampton, revealing how motivation, money management, and mindset evolve as net worth grows, from $1M to over $100M.

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.

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report.

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.

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

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.

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

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.

127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-report

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.