What happens when the big exit doesn’t fill the void?

Josh Payne thought selling his company for $80 million would be the defining moment of his life. Instead, it sent him into one of the darkest periods he’d ever experienced.

Josh’s story is a testament to the complexity of success. As the founder of StackCommerce, Josh grew his company from $0 to $32 million in annual revenue, eventually selling it for a life-changing sum. But with his emotional wellbeing tied so closely to his business success, he found himself struggling to find purpose once his goal was achieved.

In this episode, you’ll learn how Josh’s early years in the Midwest shaped his drive for entrepreneurship, what it felt like to grow a company from nothing to millions—and why he struggled when growth slowed, the challenges and emotions of selling his business and suddenly becoming a multi-millionaire, as well as how he found his way out of post-sale depression through therapy, family, and physical challenges like completing an Ironman and why Josh is now building a new company—but this time, with a focus on joy, service, and sustainability.

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.

Check out Sam’s Companies:

Hampton

Sam’s List

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:

Josh's Finances and Origin Story (02:37)

Early Career and Entrepreneurial Drive (06:37)

Founding Stack Commerce (08:44)

Revenue Growth and Financial Success (08:58)

Emotional Struggles and Existential Threats (10:18)

The Exit Process (14:04)

Post-Exit Realizations (16:14)

The Illusion of Financial Fulfillment (18:02)

Reassessing Values and Spending (24:36)

New Business Ventures and Goals (30:35)

Reflections on Success and Fulfillment (34:38)

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

Army Ranger Turned Entrepreneur - Grant Quezada