Moneywise

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.

Jace Mattinson, an entrepreneur who transformed a failing 135-year-old business into a $160M exit, provides insights on wealth management and personal fulfillment. He discusses the challenges of spending $40K a month in search of lost time, revealing how leisure can sometimes feel like another grind. Jace shares strategies for aligning time, money, and values while navigating family life with five kids. His unique perspective on turning old businesses into successes and maintaining a balanced life post-exit makes for an enlightening conversation.

Alex Peykoff, a millionaire from the Niagara Bottling family, shares his incredible journey from chasing material wealth to seeking emotional fulfillment. He reveals how his upbringing instilled the wrong values about success and led to a chaotic life marked by drugs and isolation. A pivotal moment with his daughter transformed his outlook, prompting him to prioritize emotional wealth over financial gain. Now, Alex focuses on real estate and sees emotional debt as a significant barrier to happiness, proving that true wealth lies in connections and purpose.

Shane Cultra, a domain investor and plant enthusiast, left his family's five-generation nursery business to forge his own path, amassing a $10M net worth. He shares how watching 'Succession' pushed him to take the leap. Shane discusses his diverse investments in Bitcoin, stocks, and how he built a $300K/year side hustle from blogging. He reflects on the challenges of family dynamics in business, lessons learned from his father, and his approach to redefining wealth, all while advocating for personal growth and the importance of failure in education.