O’Leary looks for three qualities in the people he chooses to do business with. The 71-year-old investor tells Fortune the most critical trait is having “founder’s mindset”: adopting a frame of mind that prioritizes “signal,” or what has to get done in the next 18 hours, while drowning out the “noise” of everyday life and complications. He witnessed this demeanor while working with Jobs, when Apple was partnering with O’Leary’s $4.2 billion software company SoftKey Software Products. He requires that the founders he invests in have that same leadership ethos—even if it’s a quality that’s hard to come by. 

“The ability to see all the noise coming at you and filter it out, and focus on the three to five things you’re going to get done, that’s a remarkable attribute,” O’Leary tells Fortune. “You find that in 30% of the people. Then you want to back those people, because if they’re not successful in their first mandate, they’re going to figure it out. That attribute is very important.”

When it comes to the signal versus the noise, he currently operates on a 80:20 balance, just like Jobs did while running Apple, and looks for entrepreneurs who can keep their eye on the ball.

O’Leary admits that he didn’t always have the right ratio in embodying the founder’s mindset—but now has achieved it, and looks for it in others.

“You have to decide everyday, every 18 hours, what three to five things you have to get done,” O’Leary says. “It’s not the big vision. It’s what you have to get done in the next 18 hours that matters.”

The two other traits a founder needs to have O’Leary’s backing

O’Leary has heard hundreds—if not thousands—of entrepreneurs plead their business case while starring on Shark Tank. Thanks to his intuition from decades in the game, he’s worked alongside and invested in a lot of winners.

In 2014, O’Leary put $150,000 down for 80% of licensing profits of small photo-book subscription service Groovebook, which was later bought by Shutterfly for $14.5 million, making it one of the show’s biggest acquisitions.

He also had luck with sustainable cleaning-products business Blueland, investing $270,000 for 3% equity and $0.50 per unit royalty until principal was recouped. By 2022, Blueland made over $100 million in lifetime sales and profitability, with its products now flying off the shelves of Target and Whole Foods every 10 seconds.

It’s clear the serial investor has developed a keen eye for what will work well. In addition to the “founder’s mindset,” the serial investor also emphasizes the importance of having a balanced listening-to-talking ratio and strong executional skills, which he says is “impossible to find.” 

He says he didn’t always get the talking-to-listening balance right. Wall Street and Silicon Valley executives may think they should be the loudest and most outspoken people in the room—but taking a backseat and giving others the floor is important, too. Not enough listening and too much talking may stifle great business ideas that get drowned out.

“Reverse the ratio of talking and listening. Most people love to hear themselves talk—I was guilty of that for years, and I’ve reversed it,” O’Leary says. “I listen two thirds of the time, and I talk one third of the time. That’s my new ratio, and it’s much more powerful.”

Lastly, the baby boomer investor looks for unparalleled executional skills. Coming up with the next billion-dollar business venture is one thing, but getting it off the ground is another.

O’Leary looks for founders and teams that can get the job done—even if it takes more than one try. Being an excellent executor doesn’t always mean hitting a home run your first time at bat. Sometimes, O’Leary says, investors and entrepreneurs need a little karma and luck. 

“Great ideas are dime a dozen—executional skills are impossible to find,” O’Leary continues. “I’ve invested in lots of teams over the years that screw up their first deal, they go to zero, and then I invest again, and I get a huge hit, because I know they’re good.

“I’m working on a deal right now with a team that I just finished a great execution with, and hopefully will be good on the second one. I like to work with people that I know have proven executional skills.”