15 Years Doing What I Hated… 8-Figure Exit. Worth It?
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportHow 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 JourneyThis 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 MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.
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$10M Net Worth. $2.5M Cashflow. No Plans to Exit.
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportJay 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 AspirationsThis 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 MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.
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$10M vs $100M: The Difference Between Being Rich and Really Rich
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 placeThe "F*** You" number: What real numbers show is the threshold for total financial freedomWealth allocation shifts: Crypto disappears, bonds and real estate dominate at the ultra-high endSurprising insights into monthly cash burn, and how spending changes (or doesn’t) across net worth tiersTake-home income jumps dramatically past $50M—especially at the $100M+ levelTime vs. money: Wealthier founders are working fewer hours, but that doesn’t guarantee happinessWhat motivates founders at every stage—and why some feel lost after hitting their big numberReal 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-reportCool 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 HappinessThis 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 LamportNot really the host, but the producer.Wrote this sentence.Older than I appear, I promise.
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Re-Up: I’m Worth ~ $500m. Here’s What I Regret (And Don’t) Spending On with Andrew Wilkinson
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 2008The emotional rollercoaster of building and losing wealth while still youngWhat it's actually like to cross the nine-figure markWhy luxury spending doesn’t always bring happinessHow wealth impacts family, friendships, and personal identityHis thoughts on giving back, donating money, and the real ROI of generosityChapters(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 HappinessSam Parr Founder of Hampton, a private community for 7-figure founders. Previously sold his company, The Hustle, to HubSpot for tens of millions.
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I Let Go of the Hustle. Embraced Feminine Leadership. Built $10M.
127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportJess 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 ContentmentThis 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 MortonFounder of Lower Street, a podcast production company helping brands launch and grow top-tier podcasts.Co-parents a cow named Eliza.
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/.
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