Dating is already weird and vulnerable, but when you’re wealthy, talking finances can feel like dropping a bombshell.

In this episode, we explore the complexities of dating with significant wealth and how to handle the inevitable conversations about money.

Today's guest, who we'll call Alex, is worth around $133 million. His journey to wealth began with a company he founded with his now ex-wife, and he’s here to share his experiences on navigating the dating world post-divorce.

Alex started his entrepreneurial journey with multiple failed ventures before hitting success with his third company, which he co-founded with his ex-wife. After a difficult and non-amicable divorce, which involved complex asset division, Alex found himself back on the dating scene. 

In this episode, Alex opens up about the unique anxieties of dating with a substantial net worth. He discusses how he avoids flaunting his wealth to prevent attracting the wrong kind of attention. We delve into the challenges of sharing financial details with new partners and the importance of finding someone who shares similar lifestyle values. Alex also shares practical advice on how to approach the conversation about money with transparency and integrity, and his personal experiences in navigating these waters.

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:

Meet Alex (02:02 )

Alex's Modest Lifestyle and Financial Transparency (04:15 )

Navigating Relationships with Wealth (06:54 )

Alex's Approach to Dating (11:06 )

Power Imbalance and Financial Compatibility (18:50 )

Final Thoughts and Advice (26:17 )

This podcast was produced in partnership with Lower Street and distributed by Morning Brew.