This CEO went from homeless to starting over 30 businesses before selling or closing them all down — now he works 1 hour a week building multimillion-dollar Airbnbs

How it started

Jenney experienced wealth for the first time at the age of 13 when he visited cousins in New York. The combination of their riches and, more importantly, happiness led him to seek the same. After the trip, Jenney scrounged together some money and bought books to learn about the stock market. He thought his future would be in finance, but in the end he decided it wasn’t for him. His drive to generate wealth, however, remained.

Jenney made his first million dollars via a website-building business. But while the money was great, the lifestyle was not. He spent 14 hours a day behind a screen filling out orders by hand because nothing was automated.

Jenney was also quite young at the time and had no guidance in terms of his finances. He didn’t know how to manage his money, and as a result he blew it all away.

Lessons were learned and Jenney continued to build businesses. However, they were all a one-man show and if he wasn’t interested or invested in it, he’d shut them down. Even if they were successful.

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How it’s going

Over the years, he claims to have started and closed over 30 different businesses that totaled $1 billion in sales, but they weren’t all a good fit. He didn’t want to do something he didn’t believe in and admits at times he “felt like a snake oil salesman.”

By the time he got to building the business he’s most known for, RV Share, Jenney decided he would be all-in on one business rather than work on multiple at a time. While incredibly successful, in the end, Jenney and his partners decided to sell RV Share. He cited burnout as the main reason behind his decision, although he does remain a shareholder.

Despite his financial success, Jenney is quick to admit he’s not a genius. However, he’s equally quick to caution that becoming a millionaire isn’t easy and there is no blueprint and you need to figure out when to push forward and when to stop.

“The world is dynamic,” he said. “You’ve got to learn along the way.”

Now he spends his days — actually, 30 minutes to 1 hour a week — working on his Airbnb business. Jenney buys luxury properties and turns them into one-of-a-kind rentals by adding things like playgrounds, basketball courts and driving ranges.