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.