"I Thought I Had the Midas Touch": How an $80M Success Led to a Major Failure

We just hit our 25th episode! To celebrate, we’re doing a special recap of the best lessons from all our past conversations. Sam’s looking back at the standout advice from founders, entrepreneurs, and experts who opened up about what really happens when you hit major financial success—and the stuff no one talks about. You’ll hear insights from Mike Beckham on why giving back keeps lifestyle inflation in check, Dr. Becky’s take on raising resilient kids in a world of privilege, and advice from founders who’ve faced the mental rollercoaster that comes after big exits. We also dig into what it means to live a low-key, fulfilling life, even if you’re worth millions. This is Moneywise, a podcast where hosts Sam Parr and Harry Morton are joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022. Who is Harry Morton? Harry Morton is the CEO of Lower Street, a company specializing in premium podcast production that he founded to transform brand narratives through audio storytelling. His expertise has made Lower Street a leader in the podcast industry, working with diverse clients from startups to Fortune 500 companies to enhance their market presence and audience engagement. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Chapters:  Lesson 1: Finding Purpose After Early Retirement (01:47) Lesson 2: Raising Resilient Children in Wealthy Environments (04:28) Lesson 3: The Impact of Giving (06:55) Lesson 4: Stress and Growth vs. Peace and Letting Go (09:22) Lesson 5: Jennifer's Story: Financial Red Flags in Relationships (13:57) Lesson 6: Financial Stress: A Wild Story of Loss and Resilience (16:32) Lesson 7: Beware of Burnout: Lessons from Ryan and Pete (18:46) Lesson 8: Small Town Success: Travis's Story (21:25) Lesson 9: Knowing When to Walk Away: Laura and Jeff's Insights (24:14) Sam’s Personal Top Takeaways (27:45) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

Jess Mah is worth half a billion dollars—and she’s tired of pretending otherwise. Jess Mah, entrepreneur and founder of InDinero, dives into the power of radical transparency and how it’s impacted her personal and professional life. Raised by an entrepreneurial mother, Jess aspired to success from a young age, but her path to wealth wasn’t always smooth. By 34, she has built ownership stakes in several companies, but more importantly, she’s learned to stop caring what others think about her wealth. In this episode, she shares intimate details of her finances, including how she manages her wealth, why she doesn’t worry about having liquid assets, and why she prioritizes personal cash flow over big exits.  We also get into how radical honesty has reshaped her relationships—both romantic and platonic—and how she balances being a CEO with maintaining a fulfilling life. This is Moneywise, a podcast where hosts Sam Parr and Harry Morton are joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022. Who is Harry Morton? Harry Morton is the CEO of Lower Street, a company specializing in premium podcast production that he founded to transform brand narratives through audio storytelling. His expertise has made Lower Street a leader in the podcast industry, working with diverse clients from startups to Fortune 500 companies to enhance their market presence and audience engagement. This episode also features an interview conducted by Andrew Namanny. Check out his podcast Permission to Shine. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Chapters: Jess's Net Worth Breakdown (03:19) Early Life and Career (04:28) Wealth Philosophy (08:28) Jess’s Spending (19:04) Dating Challenges (23:30) The Wall Street Journal Bounty (34:26) Transparency with her Employees (36:56) Dealing with Haters (39:14) The Value of Brutal Honesty (43:08) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

What’s the true value of money when faced with a life-or-death situation? Mitch found out the hard way when his wife was diagnosed with cancer. As a highly successful entrepreneur with a net worth of nearly $100 million, Mitch had built a life of financial security. But when faced with his wife’s illness and his own health scare, he discovered that no amount of money could buy control over life’s toughest moments. Mitch's story is one of resilience, from his early entrepreneurial days, selling candy out of his locker, to growing a business worth millions. He reflects on the emotional and personal costs of his financial success and how his near-death experience completely shifted his perspective on wealth, work, and family. This is Moneywise, a podcast where hosts Sam Parr and Harry Morton are joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022. Who is Harry Morton? Harry Morton is the CEO of Lower Street, a company specializing in premium podcast production that he founded to transform brand narratives through audio storytelling. His expertise has made Lower Street a leader in the podcast industry, working with diverse clients from startups to Fortune 500 companies to enhance their market presence and audience engagement. This episode also features an interview conducted by Aaron Hayslip. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Chapters: Mitch's Early Entrepreneurial Spirit (03:25) First Taste of Wealth and Career Choices (05:24) Health Scare and Perspective Shift (13:30) Reflecting on 2019: A Pivotal Year (21:36) Turning Down a Billion-Dollar Offer (22:03) Starting from Scratch: The Independent Journey (24:08) Facing a New Challenge: Breast Cancer Diagnosis (28:48) The Emotional Toll and Family Struggles (30:27) The Role of Wealth in Healthcare Access (33:41) Reevaluating Wealth and Power (37:35) Investing in Experiences (39:37) The Limits of Wealth and Final Reflections (40:40) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

What happens when you don’t sell your company and keep growing it for decades?  For Oscar, it means you become a billionaire. Oscar bought a company every six weeks for 20 years and now his business is worth about $50 billion. Yet, he still wears $15 t-shirts and lives by the values that helped him achieve success. In this episode, he shares how he became a billionaire while always putting family and faith first. He discusses his humble beginnings, the influence of his father, and how he’s now passing on his wealth through a generational trust. From managing a $3 billion stake in his company to owning 300 classic cars and a $49 million private jet, Oscar’s story offers a glimpse into life after massive success—without ever sacrificing who he is. This is Moneywise, a podcast where hosts Sam Parr and Harry Morton are joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022. Who is Harry Morton? Harry Morton is the CEO of Lower Street, a company specializing in premium podcast production that he founded to transform brand narratives through audio storytelling. His expertise has made Lower Street a leader in the podcast industry, working with diverse clients from startups to Fortune 500 companies to enhance their market presence and audience engagement. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Chapters: Oscar's Lifestyle and Major Expenses (02:32) Military Service and Its Impact (11:18) Building a Business Empire (13:59) Walking Out on Investment Bankers (22:54) Sacrifices for Business Growth (24:58) Family Support and Business Success (28:10) Wealth Management and Generational Planning (32:47) Investment Strategies and Mistakes (37:01) Advice for Young Entrepreneurs (39:29) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

Can success create a false sense of invincibility? For Pete, it did—and it cost him millions. After selling his business for $80 million, Pete felt unstoppable. But his overconfidence led him into a risky venture that didn’t pay off. Determined to prove he wasn’t a one-hit wonder, Pete ignored the warnings, thinking his past success guaranteed future wins. Instead, he faced one of the hardest losses of his career. In this episode, Pete shares how his upbringing shaped his hunger for security, how overconfidence after a major exit led to a business failure, and how he’s rebuilding emotionally and financially. This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Chapters: Pete's Humble Beginnings (01:45) Early Entrepreneurial Ventures (05:00) The Big Exit and Its Impact (07:03) Post-Exit Lifestyle and Spending (09:13) The New Venture and Its Challenges (10:56) Realizing the Mistake (22:57) Financial and Emotional Impact (23:52) Lessons Learned and Moving Forward (28:17) Redefining Success (35:31) Conclusion and Final Thoughts (36:48) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

How Do You Stop Hustling When You’ve Already Won? Laura Roeder told herself that at $5 million liquid she could live the life she wanted and refocus her life on what matters most: living. Unlike a lot of entrepreneurs who get caught up in the game and keep chasing more, Laura stayed true to that goal and quit hustling harder than she had to. But how did she avoid the endless treadmill for more? Laura Roeder, founder and successful SaaS entrepreneur, joins the show to share her journey of hitting her financial target, choosing simplicity, and focusing on what matters most. With a net worth of over $15 million, she explains how she prioritized lifestyle over accumulation, and how her upbringing played a key role in shaping her financial mindset. In this episode, Laura discusses how she hit her financial goal and resisted the temptation to keep pushing for more. You’ll also hear about her business philosophy, why she believes in running a business for lifestyle and not just growth, and the importance of knowing when enough is enough. Plus, she dives into her personal investments, expenses, and how she balances wealth with family time. This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Chapters: Laura’s Financial Foundation (03:54) Balancing Lifestyle and Financial Goals (07:14) Starting and Scaling Businesses (13:21) Selling the Business and Life After Exit (19:13) Lifestyle Business vs. Growth Business (21:41) Laura's Investments and Expenses Breakdown (24:18) Balancing Work and Personal Life (30:09) Avoiding the Comparison Trap (32:54) Final Thoughts on Wealth and Happiness (36:33) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

Ever wondered what it feels like to be the richest person in a tiny town in the middle of nowhere? Today’s guest, Travis, is worth $50m, yet he’s never been tempted to leave his hometown of 2400 people. Travis has already had an exit of $25m, and he’s about to double that with a second exit. Now he’s navigating life as the local big shot. From curious neighbors asking about his money to balancing wealth without being flashy, Travis shares the surprising perks—and awkward challenges—of being a big fish in a very small pond. In this episode, Travis shares why he chose to keep his family and business in a small town and why he believes more people should consider doing the same. He reveals the highs and lows of small-town life after wealth, from nosy neighbors to giving back to his community in ways that wouldn’t be possible in a big city..  This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Chapters: Travis's Business Journey (02:48) Challenges of Wealth in a Small Community (11:44) Spending and Lifestyle Choices (15:29) How He’s Invested (20:30) Impact on the Community (24:27) Raising Kids in a Small Town (34:12) Conclusion and Advice (37:14) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

13 million dollars is a lot. But is it enough to retire on? For pre-epiphany Ryan Begelman, the answer is no. Ryan built his wealth working in the corporate world, then decided to risk it all and bought into Bisnow. That risk paid off, and Ryan made a huge profit. But despite his successes, he found himself grappling with lifestyle inflation, misguided investments, and financial uncertainty. In this episode, Ryan opens up about his struggles with managing wealth after a big exit, how flashy spending left him unprepared, and why life coaching became the tool that helped him find real security. We dive deep into his financial epiphany, his coaching career, and how he halved his spending while learning to respect money in a whole new way. This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Chapters: Ryan's Early Career and BizNow Success (02:32) Financial Mismanagement and Realizations (06:09) Family Influence and Flashy Spending (09:37) Life Coaching and Personal Epiphany (12:38) The Start of a Coaching Journey (20:05) Financial Success and Security (20:45) Existential Financial Concerns (22:44) Modeling for Financial Future (23:17) Spending Adjustments and Reflections (26:56) Endurance and Self-Care in Business (32:38) Final Thoughts and Reflections (38:24) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

Worried that your wealth might turn your kids into spoiled, unmotivated adults? Dr. Becky’s here to show us how to raise resilient, grounded kids even when money isn’t an issue. She’s the force behind "Good Inside", often called the "millennial parent whisperer." With a clinical psychology background, and her own experience parenting young kids while founding a rapidly growing successful business, she’s full of valuable insights on how to raise kids in a wealthy environment without them becoming spoiled and entitled. In this episode, Dr. Becky explains why it's crucial for kids to experience challenges, even when you can afford to remove obstacles, and why you too need to do more hard things. She provides actionable tips on setting boundaries, managing a demanding career while being present for your family, and encouraging internal motivation. We also explore how your behavior and energy as a parent shape your children's growth and resilience. This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Chapters: Dr. Becky's Journey and Good Inside (02:41) Balancing Business and Family Life (07:57) Teaching Kids Resilience and Handling Frustration (13:04) Self-Improvement and Parenting (21:57) Small Steps for Big Changes (23:09) Managing Anxiety and Productivity (24:23) Balancing Family Time (25:50) Teaching Financial Responsibility (28:41) Legacy and Parenting Philosophy (33:36) Good Inside App (36:45) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.

Imagine waking up one day to find nearly everything you've worked for is gone.  Today’s guest, Domenic, lived through that nightmare. His story begins at Facebook, where he was one of the early employees during the dawn of the social media era. He wisely took as much equity as possible, which paid off handsomely when the company went public. Despite his newfound wealth, a series of unfortunate decisions—risky investments, a poorly negotiated acquisition, and unforeseen personal losses—led him to lose nearly everything he had earned. Domenic’s tale is not just about loss but about resilience. From growing up in a modest household in Southern Virginia to navigating the high-stakes world of Silicon Valley, he shares his experiences of building wealth, facing devastating setbacks, and the philosophy that keeps him moving forward. This is Moneywise, a podcast where host Sam Parr is joined by high-net-worth guests to explore exclusive insights into personal finance and lifestyle tailored for other high-net-worth people, or those on their way. They'll get radically transparent about the numbers, revealing things like their burn rates, portfolios, and spending habits. Who is Sam Parr? Sam is a serial entrepreneur and the co-founder of The Hustle, which he sold to HubSpot in 2021. He's also the co-host of one of the world's top podcasts for entrepreneurs, My First Million. Known for his insightful business acumen and candid communication style, Sam Parr continues to be a prominent figure in the world of media and entrepreneurship. Sam's newest and biggest venture yet is Hampton, which he co-founded in 2022. This podcast was made for the Hampton community, a private, highly-vetted, peer membership community for founders and CEOs of fast-growing, tech-enabled startups. Chapters: Early Facebook Employee (0:29)  The Facebook IPO and Domenic’s Net Worth Impact (12:53) Life After Facebook: Investments and Mistakes (17:29) Losing It All in a Bad Acquisition Deal (24:46) Rebuilding from Scratch (31:55) Final Thoughts and Takeaways (38:50) This podcast was produced in partnership with Lower Street and distributed by Morning Brew.