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.

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.

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

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.

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

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.

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

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.