328. Why unhappiness is a requirement for entrepreneurialism, switching seats from CEO to Chair, and buying versus building a business with Joel Holland, CEO of Harvest Hosts

The Inner Chief

“I feel that if you understand finance and economics, you understand how most of the world works.”

In this episode of The Inner Chief podcast, I speak to Joel Holland, CEO of Harvest Hosts on why unhappiness is a requirement for entrepreneurialism, switching seats from CEO to Chair, and buying versus building a business.

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Joel is the CEO of Harvest Hosts, a membership program that connects RVers (caravaners) with unique overnight experiences at 5,000+ wineries, farms, breweries, museums, golf courses and other interesting destinations in the US and Canada.

Earlier in his career, after stints in investment banking and in media organisations, he founded Storyblocks, the world’s first stock media subscription service, which was purchased by private equity firm Great Hill Partners in June 2020.

Joel has been named one of the "Top 25 Entrepreneurs Under 25" by BusinessWeek Magazine, and "Young Entrepreneur of the Year" by the United States Small Business Administration, and "Entrepreneur of the Year" for the Greater Washington DC Region by Ernst & Young, and also recognised on the Inc. "30 Under 30" list.

When he isn't working, Joel is outside as much as possible with his family in Vail, Colorado. He is proud to be a member of Vail Mountain Rescue, the search and rescue team for Eagle County.

In this episode we talk about:

✅ How in high school he hosted a show where he interviewed celebrities, athletes, politicians and Fortune 500 CEOs, including Arnold Schwarzenegger and Steve Forbes.

✅ Switching seats from CEO to Chair at Storyblocks, and why burnout forced such a move.

✅ The incredible operational principles which help him achieve success but also balance in life, and

✅ How he took Harvest Hosts from a solid business and on an explosive growth trajectory, and why he suggests building a business first, and buying thereafter.

Deal hope,

Greg

Thanks to former guest, Shane Russell, for introducing us to Joel.

Connecting with Joel Holland

You can connect with Joel via LinkedIn, and you can view the Harvest Hosts website.

Books and resources

• Storyblocks - a stock media company

• All Trails - an app for hiking

Similar Episodes on buying companies

• Jaimie Fuller, former CEO of SKINS on coping with rapid growth

• Julie Mathers, CEO of Snuggle Hunny on first-mover advantage

• Ben Simon, Partner of Rose Partners on diffusing heated negotiations and identifying red flags during a deal

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