Moneywise

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:

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.

What is Moneywise?

This is Moneywise, a podcast where hosts Sam Parr and Harry Morton are joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Check it out at https://joinhampton.com/.