In a recent video shared on his official Instagram on April 10, 2025, Shark Tank investor Kevin O’Leary opened up about some of his past financial missteps. O’Leary emphasized that the most significant error he made was not paying attention to his instincts and overlooking the valuable lessons drawn from years of experience in business.
“Not listening to my experience, my intuition, and my gut feeling. What is gut feeling? It’s experience. Always listen to it,”he remarked.
Reflecting on a substantial investment that went wrong, O’Leary noted he had poured a considerable sum into a venture despite harboring doubts about its potential. Ultimately, he lost all of his investment, prompting him to advise his followers to trust their instincts and withdraw from deals that seem questionable.
The caption of O’Leary’s Instagram post succinctly encapsulated his regret:
“$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.”
Kevin O’Leary on Losing $750,000: “It Went to Zero”
The Shark Tank star reiterated that his largest financial blunder stemmed from ignoring his gut feelings. He recalled a specific instance where he made an initial investment of $250,000 followed by an additional $500,000, only for the entire amount to evaporate.
“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 highlighted the importance of avoiding emotional attachment to investments, sharing that his emotional involvement contributed to his unfortunate loss. He candidly expressed his feelings, recalling how he cried “like a baby”after the setback.
Despite the heartache, O’Leary reflected on the experience as a crucial learning opportunity, vowing never to repeat the mistakes that led to his financial loss.
The Path to Success: Setting Goals and Building Confidence
On April 5, 2025, Kevin O’Leary shared another insightful video on Instagram, emphasizing the critical role self-confidence plays in achieving business success. He underscored that while emotional detachment from financial decisions is vital, self-belief is equally important.
“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,”O’Leary advised.
O’Leary encouraged his followers to remain resilient and realistic when setting their goals, underscoring that perseverance is key to not missing any opportunities.
Common Mistakes New Entrepreneurs Make, According to Kevin O’Leary
In a video released on March 25, O’Leary discussed prevalent pitfalls faced by novice entrepreneurs. He emphasized that many newcomers err by presuming they will receive subsequent rounds of funding after their initial efforts.
“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 warned.
O’Leary explained that every dollar raised in the initial round holds significant importance, reiterating that it’s unwise to assume further support will follow. He urged entrepreneurs to be resourceful and strategic in utilizing their funds.
“If you waste money, there won’t be any more,”he cautioned.
For those interested, Shark Tank episodes are available for streaming on Hulu.