The point of money is to make life easier. To give you security, comfort, and the ability to do the things that make you happy.

So if you’ve made enough to take care of that for life, you can just stop making more… right?

Retiring early is a dream for many, but what happens when you actually do it?

In this episode we explore the story of two guests who did just that, though they came about it in different ways.

Our first guest, “Ryan”, made over $20 million after selling his business, then decided to step away from working and enjoy his money. “Jeff” however, made his money in a series of smaller sales and soon realized he had accumulated enough where his investments outperformed his work income.

Since retiring, both “Ryan” and “Jeff” have gone through similar stages of appreciation, loss, and rediscovering purpose in their lives.

In this episode, we explore the ups and downs of retiring early, how much money they have that allows them to live off their investments and what they do with it. They’ll tell us about the external pressure to start something new, how they dealt with the feelings of loss, and what they do with their time now.

Check out Ryan’s blog After The Exit.

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:

How Ryan and Jeff made their money (3:30)

Why they decided to step away (8:13)

The feeling of loss (11:25)

Facing the “what’s next” pressure (16:50)

The importance of finding a new passion (18:45)

Ryan’s take on financial advisors (21:50)

Stock market anxiety (26:25)

Will they go back to work in the future? (30:19)

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

The Realities of Retiring Early

Episode description