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.