Moneywise

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.

Mike Brown, a former oil & gas tycoon who once reached a net worth of nearly $20 million but faced cash flow crises, shares his transformative financial journey. He reveals how the 'gold rush' mentality nearly derailed him and how losing $1.8M forced him to rethink wealth. Mike emphasizes the importance of liquidity over net worth and advocates for a life designed around freedom rather than just numbers. He discusses his framework for financial stability and the joy he found in simplifying his wealth approach, including selling luxury items.

If you're a founder doing at least $3M/year in sales, check out Hampton: https://www.joinhampton.com/.There is no amount of money that will make you happy. There is also no amount that will stop making you more happy. Both of those things are true.Our producer is not rich. But she has talked to 100+ people who are, and she (I) has learned a lot about your kind (is that wrong to say?).In the Moneywise pilot, we asked the question “at what point will more money stop making you happy”. Turns out, that was a pretty stupid question. So in this episode, we’re fixing that.This is an episode of Moneywise unlike any other. This is a solo essay-style inside-outsider's take on wealth and happiness, based on the past year of peaking behind the curtain at what truly makes millionaires lives better… and worse. Backed up by quotes from our guests and of course, real studies.Here’s what we talk about:Money doesn’t make you happy. It can only remove stress.The “happiness number” is a myth but knowing your “freedom number” changes everything.Most people don’t want money, they want the freedom they think money will give them.Hitting your financial goal won’t feel like you imagined.Founders often feel lost post-exit because they unknowingly traded hope for cash.Wealth adds new stress.Money can’t buy you meaningful experiences, and you need to stop thinking it can.If you expect money to do the emotional heavy lifting in your life, you will never be satisfied.Money is the key, not the door. It unlocks your potential but it won’t add anything more to your life.Cool Links:Hampton https://www.joinhampton.com/Lower Street https://www.lowerstreet.co/Chapters:(00:00) Introduction and Confession(00:35) Reflecting on 50 Episodes(02:24) Revisiting the Happiness Threshold(03:09) Money as a Subtractive Tool(03:48) The Freedom Number vs. Happiness(05:07) Studies and Research on Wealth and Happiness(14:39) The Hedonic Treadmill and Wealth's Paradox(17:45) Hope and the Entrepreneur's Journey(25:26) Concluding Thoughts and Freedom NumbersThis 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.References:Kahneman, D., & Deaton, A. (2010). "High income improves evaluation of life but not emotional well-being." Proceedings of the National Academy of Sciences, 107(38), 16489-16493. DOI: 10.1073/pnas.1011492107Jebb, A. T., Tay, L., Diener, E., & Oishi, S. (2018). "Happiness, income satiation and turning points around the world." Nature Human Behaviour, 2, 33-38. DOI: 10.1038/s41562-017-0277-0Killingsworth, M. A. (2021). "Experienced well-being rises with income, even above $75,000 per year." Proceedings of the National Academy of Sciences, 118(4). DOI: 10.1073/pnas.2016976118Link, B. G., Phelan, J., Bresnahan, M., Stueve, A., & Moore, R. E. (1995). American Journal of Orthopsychiatry, 65(3), 347-354. DOI: 10.1037/h0079653Donnelly, G. E., Zheng, T., Haisley, E., & Norton, M. I. (2018). "The Amount and Source of Millionaires’ Wealth (Moderately) Predicts Their Happiness." Personality and Social Psychology Bulletin, 44(5), 684-699. DOI: 10.1177/0146167217746340Luthar, S. S., & Becker, B. E. (2002). "Privileged but Pressured? A Study of Affluent Youth." Child Development, 73(5), 1593-1610. DOI: 10.1111/1467-8624.00492.

Eran Galperin, founder of a successful SaaS company for Brazilian Jiu-Jitsu gyms, shares his journey from a modest $15K to a spectacular $32.5 million exit. He discusses the power of bootstrapping over venture capital and the slow growth process that led to his success. Eran reveals his decision to move to Japan for a balanced lifestyle and financial security, diving into the costs and adjustments of his new life. He also reflects on the emotional landscape after selling his company and why he continues to engage with early-stage founders.

Vinay Hiremath, co-founder of Loom and now worth nearly $50 million, shares his transformative journey from startup success to personal exploration. He discusses his surprising choice to leave millions on the table and the emotional aftermath of his company’s sale. Vinay reflects on paying off his parents' mortgage and the meaning of wealth beyond money. Now exploring physics and robotics, he reveals the paradox of financial freedom and the search for identity amidst newfound wealth, provoking thought on what it truly means to be free.

Chris Cooke, a former skeptic of capitalism turned millionaire, shares his unique journey post-sale of his company for $30 million. He talks about how he spent most of it within six months on a weed farm, beach house, and comedy club in Thailand, all while embracing his Buddhist principles. Chris candidly discusses the conflicts between his values and financial success, the challenges of managing relationships after sudden wealth, and how he’s now focused on building a sustainable business rather than just chasing growth.

Dan Berger, who sold his company Social Tables for $100 million, shares the surprising truth about his unchanged net worth since then. He dives into his biggest financial blunders, like angel investing and a lavish NYC apartment. Berger reflects on the deeper issues founders face after a big exit, including the quest for belonging and personal identity. He discusses living by the 'Die With Zero' philosophy and how early life challenges shaped his journey. Through his insights, he emphasizes the importance of relationships and community for true fulfillment.