Moneywise

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.

Tommy Mello, billionaire entrepreneur and CEO of the billion-dollar A1 Garage Doors, shares insights from his remarkable journey. He reveals how he transformed a small business into a massive empire by mastering strategic investing and emphasizing relentless competition. Mello discusses the key sacrifices needed for success, his philosophy on building businesses with an exit in mind, and his passion for creating millionaires among his employees. His wealth-building strategies and commitment to mentorship provide a roadmap for aspiring entrepreneurs.

Rob Hoffman, an entrepreneur and member of the Hampton community, made a life-changing move to Colombia, leveraging geo-arbitrage to triple his wealth. He discusses the financial perks of living abroad and how a frugal lifestyle can lead to significant savings and reinvestment opportunities. Rob emphasizes the importance of community involvement and the ethical responsibilities of expatriates. His journey from an anti-capitalist hippie to a successful business owner reveals a transformative approach to wealth and personal freedom.

Rob Walling, a serial entrepreneur and comic book aficionado, discusses his unique investment strategy. He reveals that over 10% of his net worth is tied up in collectibles, blending passion with financial savvy. Rob highlights the emotional fulfillment of comic collecting, linking it to childhood dreams and financial freedom. He warns of the hidden risks involved and differentiates between investing and gambling. With insights on auction strategies and managing valuable items, Rob showcases how personal interests can spice up investment portfolios.