O'Leary: Execution from the basement beats office attendance

Forty percent of the roughly 10,000 people working across Kevin O'Leary's more than 50 portfolio companies still haven't returned to the office as of January. The Shark Tank star wants to keep it that way.

He laid out the case bluntly on social media this year. "If you have to be in an office, why? Is my question?" O'Leary said in a video posted to X. "We do have people that sit in cubicles, but I'd rather hire somebody who can execute and sit in their basement or in their backyard."

The founder of O'Leary Ventures is betting that execution—not attendance—decides who climbs the modern corporate ladder.

Why does O'Leary keep his team remote?

He pointed to a single employee hired more than a year ago in the United Arab Emirates. The worker, unnamed in O'Leary's telling, rose quickly because "the kid can execute."

That template, O'Leary said, applies to every generation—and Gen Z most of all. "If you're a Gen Zer and you can execute, and you can hit your mandate and deliver it on time, you move up and you make more money," he said. The quote came from a video earlier this year.

O'Leary's own staff sits in London, Los Angeles, and Canada. He treats remote work less as a perk than as a filter: top performers deliver from anywhere.

Who's pushing the opposite view?

Corporate America's biggest names. Amazon kicked off the full five-day return in tech at the start of 2025, sparking a wave of mandates. In February 2026, Instagram CEO Adam Mosseri ordered most staff back five days a week, citing a "winning culture."

Microsoft, for its part, asked Seattle-area employees back three days a week starting late last month. O'Leary reads that strategy as a self-inflicted talent wound.

In a January Instagram video, O'Leary warned: "If you're trying to say to people, 'Oh, you got to work in an office,' and that's the talent you want to hire, you'll just get the bottom quartile people that have no choice." Then, blunt as ever: "I don't want those people. I want my competitors to hire those people."

What do the numbers say about worker preferences?

The trade-off for in-office work is steep. A Harvard study last year found workers would accept a 25% pay cut to choose fully remote or hybrid jobs over full-time in-office roles.

O'Leary says his own data confirms the math. In 2022, he claimed 55% of the 10,000 people across more than 50 portfolio companies hadn't come back. By January 2026, that share had dropped to 40%.

When his firms threatened job loss, employees shrugged. "They said, 'Great, I'm going to go work for somebody else,'" O'Leary recounted. The threat, in his view, only accelerates the flight to remote-friendly rivals.

Does O'Leary buy the loneliness argument?

Not really. He says isolation isn't new and doesn't track to remote work specifically. "That's not really what's at play here," he told his audience.

What is at play, in his telling, is a war for the same talent. "They're just delivering, and they get rewarded because the whole team wants the people that can execute. That is the nature of the economy today," O'Leary said.

His pitch lands as AI-fueled displacement anxiety rises across white-collar ranks and flexibility keeps contracting. O'Leary's bet is straightforward: execution-heavy teams will out-build attendance-heavy ones, and the employers now forcing five-day returns will pay for that choice in lost talent over the next hiring cycle.