Moneywise

• $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.

  --------  

  46:46

  --------

  46:46
• $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.

  --------  

  25:07

  --------

  25:07
• 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.

  --------  

  36:55

  --------

  36:55
• 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.

  --------  

  46:06

  --------

  46:06
• How Much Does It Really Cost to Fly Private?

  127 founders (net worth: ~$1M–$100M+) opened up their personal books. Want to see how your finances stack up? https://www.joinhampton.com/wealth-reportIs 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/prestonholland6Preston’s Newsletter: https://prestonholland.com/bioChapters:(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 ThoughtsThis 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 LamportNot really the host, but the producer.Wrote this sentence.

  --------  

  41:23

  --------

  41:23

Weitere Wirtschaft Podcasts

Trending Wirtschaft Podcasts

Über Moneywise

Moneywise: Zugehörige Podcasts