Kevin O’Learyalso known Mr WonderfulShe has made many bets over the years. He is best known for his appearance at Shark Tank, where he invests in many startups. While his shark tank deals are well known for happening in front of millions on live television, his other startup investments tend to be more private and not as easy to follow.

O’Leary has invested approximately $8.5 million in startup companies since Shark Tank debuted in 2009. However, one of his biggest bets on startups right now could be worth more than five times that amount. So what’s this $50 million bet? The start is Start the engineand Kevin O’Leary owns 1,997,374 shares of the company’s stock, which is collectively valued at over $49.9 million.

For example, Kevin O’Leary, in 2018, O’Leary sold one of his shark tank investments, Groovebook, to Shutterfly for $14.5 million. O’Leary also saw a big payday with his investment in Wicked Good Cupcakes in 2013. Wicked Good Cupcakes was recently sold to Hickory Farms in 2021.

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Some of O’Leary’s other notable Shark Tank exits are Basepaws, which was acquired by Zoetis, and Talbott Teas, which was acquired by Jamba Juice.

The investment fits O’Leary because StartEngine helps everyday people invest in startups. StartEngine is currently the leading equity crowdfunding platform in the US, but it’s likely most people haven’t heard of it since equity crowdfunding has only been legal since 2016.

Equity crowdfunding was created by the Jumpstart Our Business Startups (“JOBS”) Act of 2015, which was signed into law by President Barack Obama and gave anyone the ability to invest in startups. O’Leary appeared as a paid spokesperson and consultant for StartEngine, accumulating a large position over the years.

Although the stock crowdfunding market is still relatively small compared to the overall stock market and venture capital markets, it is growing rapidly. In 2020…