Kevin O’Leary Put $8.5 million Into His ‘Shark Tank’ Investments — How Much Did He Make?

KodySci/Tech2025-07-223230

Entrepreneur and investor Kevin O’Leary is probably most well known as one of the investors on “Shark Tank.” You know, the show, where he and other investors listen to pitches from entrepreneurs and decide whether to put money towards their ventures.

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According to The Street, O’Leary has invested at least $8.5 million in around 40 companies since he’s been on the show for about 16 years.

Although it’s hard to tell how much he’s made in total out of all his “Shark Tank” investments, there have been some businesses that have fared better than others — let’s check them out.

What Are O’Leary’s Most Successful Investments on ‘Shark Tank’?

In 2013, Wicked Good Cupcakes appeared on “Shark Tank” and O’Leary invested $75,000 in the company. In return, he wanted to be paid $1 per cupcake until his initial investment was paid back, then 45 cents for each one afterwards.

Several years later, Wicked Good Cupcakes made $10 million in total sales, according to Food Republic. O’Leary was there to hand out the millionth cupcake sold. It’s safe to say that he more than recouped his investment.

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O’Leary also invested in Basepaws in 2019 that earned him a massive profit, per Yahoo Finance. He invested $125,000 in the company in exchange for a 5% stake and the whole company was valued at $2.5 million.

O’Leary has publicly said that, percentage-wise, Basepaws has been his biggest win so far. The company has reportedly been sold for around $50 million, which could mean that O’Leary earned about $2.5 million from the sale.

Other companies he invested in, Shutterfly and Plated, have since sold for tens of millions of dollars. Safe to say that O’Leary made millions on these deals.

How Much Has O’Leary Made?

We probably won’t know exactly how much O’Leary has made from all of his deals from “Shark Tank,” since he’s had to sign many nondisclosure agreements that prevent him from doing so.

Despite losing half a million on one deal and probably more if you include other deals, this “Shark Tank” investor is still probably coming up on top.

Is it safe to say he earned more than the $8.5 million he’s invested? Probably, but only O’Leary and his accountant will know for sure.

What we do know is that O’Leary doesn’t put all of eggs in one basket. At any time, he probably has around 30 to 40 companies in his private investment portfolio to spread out his risk, according to CNBC. A good percentage of these companies are probably going through the acquisition process and at that time, is probably when O’Leary will be able to know how much his investments have paid off.

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