Kevin O'Leary, aka 'Mr. Wonderful,' on crypto, winning in AI and 3 things all business owners must know

Michael Sincere

Financial Writer, Editor & GhostwriterAugust 8, 2026

What Kevin O'Leary learned from Steve Jobs: You only need to get three things done every day. Just three.

By Michael Sincere Aug. 7, 2026

Link to MarketWatch column: LINK

'The demand for data centers is insatiable. Domestic demand right now is about 45 gigawatts, and we have about 4.7 gigawatts under construction. We are way behind.' — Kevin O'Leary

Kevin O'Leary, who made a fortune in software in the 1990s, is now best known as "Mr. Wonderful" from ABC's Emmy Award-winning "Shark Tank."

O'Leary co-founded SoftKey Software in 1986, grew it into the world's second-largest consumer software company with over $800 million in annual sales, and sold it to Mattel for $4.2 billion in 1999. He is chairman of O'Leary Ventures, holds investments in more than 30 private companies, and is a member of the Hamilton Trust, the oldest investment club in the United States.

In this recent interview, edited for length and clarity, O'Leary talks about whether there are still opportunities in cryptocurrencies, where he's putting his money in the artificial-intelligence trade and the one question he asks every entrepreneur that reveals whether they have a real business.

MarketWatch: You've said 97% of crypto value has concentrated into bitcoin and Ethereum. Is that a warning to retail investors?

O'Leary: It's just a fact. Sovereign-wealth funds looked at the crypto market and hired analysts to run the numbers. They looked at market caps and volume across every token and concluded that bitcoin and Ethereum captured 97.2% of the entire market. So why bother with anything else?

As a result, you could see the charts collapse. Some of these tokens went down 80% to 90% and never came back. They had their day in the sun and it's over.

'I talk to S&P 500 companies all the time, and I ask every one of them: Are you planning to use blockchain for inventory, logistics, contract management?' — Kevin O'Leary

MarketWatch: So where's the next big opportunity in crypto?

O'Leary: I talk to S&P 500 companies all the time, and I ask every one of them: Are you planning to use blockchain for inventory, logistics, contract management? And 100% say yes. Then I ask which one. They say they haven't decided.

The next big thing in crypto is whichever chain lands at least one company in all 11 sectors of the S&P 500. The minute that happens, you want to go long that token. Because once standardization forms across sectors, it becomes a winner-take-most situation. That's the moment. And we haven't hit it yet.

MarketWatch: You've moved your company's cash reserves into stablecoins. Why?

O'Leary: Stablecoins are now Securities and Exchange Commission approved and compliant. Let's say you're putting down a $2 million deposit on real estate in Zurich. Fedwire takes three days. Your money earns nothing while it's in the system. ACH transfers are even messier. Those are 60-year-old technologies.

With stablecoin, you do a $100 test transfer, confirm it arrives in five minutes, and complete the transaction. Know-your-client compliance is built in on both sides. You just saved yourself a fortune. More and more of our assets are going into stablecoins. Our cash reserves are basically in stablecoins now.

'I'm a picks-and-shovels guy. I know that data centers need power. I know digital payment systems need infrastructure. I'd rather play on that side than bet on who wins and who loses on the software side.' — Kevin O'Leary

MarketWatch: You control tens of thousands of acres tied to AI and data centers. How do you think about that investment?

O'Leary: The demand for data centers is insatiable. Domestic demand right now is about 45 gigawatts, and we have about 4.7 gigawatts under construction. We are way behind. Each gigawatt of AI compute costs $15 billion. That's an enormous amount of capital we're going to have to deploy if we want to stay competitive.

The reason I'm in land is simple: You can't attach a new data center to the grid anymore. There is no power. If you tried, you'd force electricity prices up 30% in your local community and you wouldn't get a permit. So you have to bring your own power. That's what we're doing.

MarketWatch: Which investment looks brilliant today but could collapse in five years?

O'Leary: With tech, it's very hard to know which horse to bet on. If you're betting on one of the AI stacks — whether it's Claude, ChatGPT or any other — I have no idea where they are in five years. That's not what I invest in.

I'm a picks-and-shovels guy. I know that data centers need power. I know digital payment systems need infrastructure. I'd rather play on that side than bet on who wins and who loses on the software side.

'It's all about CAC — customer acquisition cost — and ROAS — return on ad spend. If you don't know those numbers, you're heading to zero.' — Kevin O'Leary

MarketWatch: After thousands of "Shark Tank" pitches, what makes you say no faster than anything else?

O'Leary: I ask three things: Are you using social media to acquire customers? Do you know your customer acquisition cost? And which AI tools are you using to reduce your content costs? If they stare at me blankly, I'm out. I don't care what the product is. Their competitors are going to destroy them using those tools.

Fifty percent of sales on most domestic startups are now direct-to-consumer or direct-to-business. It's all about CAC — customer acquisition cost — and ROAS — return on ad spend. If you don't know those numbers, you're heading to zero.

MarketWatch: What separates people who want to be rich from those who actually become rich?

O'Leary: The ability to distinguish signal from noise. Great entrepreneurs get an inbound flow of information every minute of the day and deflect the noise. They catch the signals. In entrepreneurship, you only need to get three things done every 18 hours to advance your cause. Just three.

I learned this from Steve Jobs in the early 1990s. I made all his educational software for 110,000 school buildings. He told me, get three things done each day, and the rest is noise. He used to call me at 3 in the morning. He was very difficult to work with, but he was right. When you go to bed, you need to know what tomorrow's three things are.

MarketWatch: Your portfolio is 60% equities, 20% fixed income, 20% alternatives. Has anything changed in 2026?

O'Leary: I've moved more into sports collectible cards and watches this year. My highest return has come from alternative assets. Rare watches — particularly F.P. Journe pieces — have outperformed the S&P over the last five years. A dual Logoman Kobe-Jordan autographed card that my syndicate bought for $12.93 million last August is now worth $21 million. That's a strong return by any measure.

MarketWatch: If you were 25 with $10,000, what would you do?

O'Leary: I'd go to companies and offer to manage their social media and content creation using AI tools. I'd charge 2% of the reduction in their customer acquisition cost per week — measurable, provable results. I have people who used to make $40,000 to $60,000 a year doing this work who now make $600,000 a year because they got on the right side of AI-driven content.

People worry AI is going to eliminate jobs. That's the same fear people had when Ford automated the manufacturing line. The productivity it creates builds economies. The same thing is going to happen here.

Michael Sincere is a freelance financial writer and researcher and the author of several books including "Understanding Stocks," "Understanding Options" and "Help Your Child Build Wealth."