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Shark Tank investor Kevin O'Leary recently discussed his financial mistakes in a video posted on his official Instagram account on April 10, 2025. He shared that the "biggest financial mistake" he had ever made was ignoring his instincts and the experience he had gathered by being in the business for years.
"Not listening to my experience, my intuition, and my gut feeling. What is gut feeling? It's experience. Always listen to it," he said.
The Shark Tank investor recalled investing a significant amount of money in a business despite feeling uneasy about it and losing all of it. He urged his fans and viewers to always follow their instincts and withdraw if an investment felt off.
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The caption of his post reads:
"$750,000 - GONE. Why? I didn't listen to my gut. Your gut is just experience talking. If something doesn't feel right, don't do it. I learned the hard way, but I won't make that mistake again."
"It went to zero" — Shark Tank star Kevin O'Leary recalls losing $750,000
Shark Tank panelist Kevin O'Leary stated that his "biggest financial mistake" was not listening to his gut. He then recalled how he lost $750,000 by overlooking his instincts.
"I made an investment, $250,000, and it didn't feel right. I followed up just a couple of months later with another $500,000, and it went to zero," he said.
O'Leary also urged his viewers not to get emotionally attached to an investment. The business owner believed he lost the $750,000 capital because he allowed his emotions to come into play. He also revealed that he cried "like a baby" after losing the money.
Regardless, O'Leary stated he learned a lesson from it and would never repeat his mistakes.
"Be able to set goals and achieve them" — Shark Tank star Kevin O'Leary shares his opinion on becoming successful
On April 5, 2025, O'Leary shared another video on his Instagram account, in which he discussed the importance of self-confidence and believing in oneself for success in business. While he stated that avoiding emotions from factoring into financial decisions played a key role in achieving success, he also believed that having faith and trust in oneself added to the success rate.
"It's focusing on what I can do and setting goals and achieving them. It's the same for you too. If you wanna be successful, you have to be able to set goals and achieve them," Kevin said.
The Shark Tank investor then motivated his fans not to let "anything get in the way." He asked them to "be realistic" about their goals but not miss them since that mattered most.
Shark Tank fame Kevin O'Leary comments on the biggest mistake entrepreneurs make
On March 25, O'Leary shared another video in which he commented on the entrepreneurial mistakes made by newcomers. He stated that the most significant fault of such individuals was assuming they would get a second round of funding after the first one.
"You gotta go into the first saying it's the last money you raise. You can't make the assumption that people just want to keep pouring money on losses," he added.
The Shark Tank panelist explained that "every cent" mattered on the "first raise" and reiterated that it was naive to assume there would be a second round. He urged entrepreneurs to "make it work with every dime" they had by saving and not wasting money.
"If you waste money, there won't be any more," O'Leary stated.
Shark Tank episodes are available to stream on Hulu.
