Investor Kevin O’Leary may have made millions investing in businesses on “Shark Tank,” but he’s the first to admit that some of his best financial moves were the deals he never made.
Mode Mobile developed a smartphone called EarnPhone, which allows users to earn and save money by playing video games, listening to music and reading the news. With the phone priced at an affordable $99, the barriers to adoption are low.
Earning Opportunity for All Smartphone Users
Mode EarnPhone
State-of-the-art smartphone device includes built-in earning features.
EarnOS
Proprietary earning software turns smartphones into EarnPhones.
Sometimes Saying No Pays Off
“The smartest investments I ever made? The ones I walked away from,” O’Leary said in a recent post on X. “Not every shiny pitch is a winner. Sometimes your gut tells you it’s a mess, listen to it. The money I didn't lose was my biggest gain.”
Don't Miss:
- Hasbro, MGM, and Skechers trust this AI marketing firm — Invest before it's too late.
- Maker of the $60,000 foldable home has 3 factory buildings, 600+ houses built, and big plans to solve housing — this is your last chance to become an investor for $0.80 per share.
In a video posted with that message, O’Leary elaborated, saying, “Sometimes you make the deals you don’t do. I’m not kidding—there’s so many deals that I looked at, was tempted to do, and didn’t. And just waited a year later, and they were zeros.”
O’Leary, known as “Mr. Wonderful,” has invested millions into dozens of companies on the show. While some bets paid off, like his investment in a meal-kit company, Plated, which later sold for $300 million, not all pitches result in profit.
One $500K Mistake Still Stings
One of his worst deals cost him $500,000, and it’s a mistake he still remembers vividly. In a 2022 interview with CNBC, O’Leary said, “In my stomach, I didn’t feel right about it … I ignored it, and it cost me half a million bucks.”
Trending: ‘Scrolling To UBI' — Deloitte's #1 fastest-growing software company allows users to earn money on their phones. You can invest today for just $0.30/share with a $1000 minimum.
He initially put $250,000 into a telecom startup. A few months later, the founder came back asking for more money. “My gut said, ‘No,'” he recalled. “But because I knew the guy and I liked him, and he was a friend, … I gave him another [$250,000].”
That second round of funding disappeared in just 60 days. O’Leary never got a dime back.
What He Learned
That failure wasn't just about the money. It became a turning point in how he approaches investing. “The lesson is: Listen to your gut, because that is your experience [talking],” he told CNBC.
O’Leary also pointed out a common thread in his losing deals: founders who refuse to pivot. “They can’t get out of their own way,” he said. “They won’t listen to anybody else.”
He added that it’s crucial to find reliable business partners and stick with them once you’ve made a commitment.
“You make 10 investments, you get two to three huge hits. And it pays for the other seven [failed investments],” he explained in the CNBC interview.
But above all, O’Leary believes the key is knowing when to walk away. As he said on X, “Don’t invest in everything. You don’t have to.”
Read Next:
- Invest where it hurts — and help millions heal: Invest in Cytonics and help disrupt a $390B Big Pharma stronghold.
- Deloitte's fastest-growing software company partners with Amazon, Walmart & Target – Many are rushing to grab 4,000 of its pre-IPO shares for just $0.30/share!
Image: Shutterstock
© 2025 Benzinga.com. Benzinga does not provide investment advice. All rights reserved.
Trade confidently with insights and alerts from analyst ratings, free reports and breaking news that affects the stocks you care about.
