Moneywise

Ronan Berder, a founder who built an 8-figure consulting agency, shares his unexpected journey from burnout to passion projects in open source. He reflects on the obligations that kept him in a business he didn’t love, the anticlimactic nature of his sale, and how true fulfillment often lies beyond monetary success. Ronan also dives into his investment strategies, the lessons learned about discipline and grit, and how minimalism shapes his work-life balance today.

Jay Berard, a financial powerhouse with a $10M net worth and $2.5M cash flow, reflects on his unconventional journey from a risk-laden Craigslist job to financial security. He values control over lucrative buyout offers, redefines wealth beyond money, and shares insights on his lean lifestyle. The discussion tackles the tension between comfort and ambition, personal growth, and how his mindset has transformed his spending habits. Berard also delves into the impact of fear and anxiety on success, offering a candid look at the entrepreneurial journey.

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.

Andrew Wilkinson, the founder of MetaLab and Tiny, achieved immense wealth in his 20s but faced harsh realities along the way. He shares his journey from reckless spending to near bankruptcy, emphasizing that luxury doesn’t guarantee happiness. The impact of wealth on relationships and identity is explored, along with the complexities of giving back and the emotional burden of ownership. Andrew reflects on the lessons learned, advocating for meaningful investments and the importance of financial transparency in fostering genuine connections.

Jess Chan, founder of Longplay, is a powerhouse entrepreneur with a worth of ~$10M. She opened up about her journey from hustling to embracing profit over revenue, sharing how this shift helped her avoid burnout. The conversation highlights her experience in fostering feminine leadership and redefining success away from traditional metrics. Jess emphasized simplicity in finances, living on just $6K monthly, and learning the art of spending wisely. She encourages finding contentment while maintaining ambition, reshaping the conversation around wealth and happiness.

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.

Auren Hoffman, an accomplished angel investor and entrepreneur who made $60M from the exit of LiveRamp, shares insights into the reality of angel investing. He reveals why it’s not as glamorous as it sounds and explains his unique approach to tracking spending. Auren discusses the surprisingly complex relationship between money and happiness, the importance of resilience in entrepreneurship, and the significance of community support among founders. He also emphasizes that investing isn't suited for everyone, especially those without substantial financial resources.

Nick Huber, an entrepreneur with an impressive 8-figure net worth, discusses his journey from humble beginnings to significant wealth through startups and real estate. He emphasizes the importance of avoiding lifestyle creep, meticulously tracking his finances, and keeping a monthly burn under $25K, even while owning a private jet. Huber shares insights on the emotional rollercoaster of managing cash flow and significant tax bills, highlighting his paranoia about fixed costs and his ambitious goal for reaching $1M monthly profit without succumbing to media fame.

Anastasia Koroleva, who navigated the tumultuous aftermath of a nine-figure exit, shares her journey through divorce, burnout, and identity loss. She discusses the traps many second-time founders fall into, including rushing into new ventures and losing self-awareness. Anastasia emphasizes that wealth alone doesn’t guarantee fulfillment and offers her personal portfolio strategies focused on flexibility. With insights into rebuilding life post-exit and the emotional challenges faced, she aims to guide others in avoiding similar pitfalls.

Adam Robinson, a visionary founder who was on the brink of a $70M exit, shares his rollercoaster journey in finance and entrepreneurship. He talks about the shock of a collapsed deal and how it forced him to pivot, leading to his current $25M ARR business. Surprisingly, he discusses impulsive spending on crypto and land, coupled with an unexpected 60% tax bill. Adam emphasizes that high income doesn't guarantee peace of mind, revealing insights on financial discipline, lifestyle choices, and the importance of steady wealth building over sudden windfalls.