Barstool's Deirdre Lester Named CEO Of Outsider

    • Lester teaming with ex-NFL quarterback Jay Cutler.
    • Lifestyle brand co-founded by entreprenur Shannon Terry.

Deirdre Lester helped Barstool Sports expand to over $200 million in revenue. Now, Barstool’s former chief revenue officer is the new chief executive officer of Outsider, with the goal of growing the new lifestyle company into a billion-dollar brand.

As CEO, Lester will team with former Chicago Bears quarterback Jay Cutler to drive the business of the year-old company, which now reaches more than 20 million monthly users. 

Cutler, who was recently named chief design officer, co-founded Outsider with Shannon Terry, the entrepreneur behind,, and Terry sold to Yahoo for $100 million in 2007. He later sold to CBS Sports Digital in 2015. 

“Outsider is a brand that really celebrates the American lifestyle. So it’s a brand and lifestyle play that will produce media and content,” Lester told Front Office Sports. 

“We have a handful of podcasts in our arsenal already. We will be producing more content shows that really speak to a variety of different areas of American entertainment and American culture that we feel have a theme of commonality – and embrace that Outsider mindset.”

Cutler says Outsider will remain neutral editorially.

“Obviously when you hear ‘Outsider,’ you think outside and outdoorsy things. Hunting and all that. But this brand can go either way,” he said. “We’re in a weird time in the country right now. It’s really politically driven. Extreme right, extreme left. I think there’s a large group of people who are kind of in the middle. They might feel there’s not a home for them — and they’re kind of left out. That’s where we are trying to land.”

The fast-growing Barstool is as much a lifestyle brand as a sports brand, noted Lester. She sees a similar business opportunity for Outsider as the company launches its new lifestyle subsidiary over the next few months. 

The company recently launched a new line of hats designed and created by Cutler, who’s designing other lifestyle products to be released over the next year.

As a hunter and outdoor enthusiast, Cutler “understands and lives” the Outsider brand just as much as the customers it’s trying to reach, according to Terry. The former quarterback retired from the NFL after 12 seasons in 2017.

“[Cutler] has such a talent for creativity and design,” Terry said. “I really believe the products we’re road-mapping could become household products in this space.”

With its headquarters in Nashville, Lester said Outsider will lean heavily into coverage of NASCAR and the country music scene. ESPN reporter Marty Smith, who is also listed as a partner on Outsider’s website, hosts his own podcast

“We’re going deep on NASCAR in a way that a lot of the other sports media companies don’t. We think there’s a hunger and a desire for it from our audience,” Lester said. 

Looking ahead, she expects Outsider to cover more of the “culture around sports” than the sports themselves.

Cutler, breakout star of E!’s “Very Cavallari” reality show with ex-wife Kristin Cavallari, is expected to appear frequently on Outsider’s videos, podcasts, and social media content. 

“He’s a one-liner extraordinaire. He’s really funny, and he’s interesting. At the end of the day, he’s memorable,” Terry said. “You may like him or you may dislike him, but he’s memorable. So he’s definitely going to help us on the media side.”

Founded in August, 2020, Outsider now has more than 50 full-time employees. In January, the startup secured $2.75 million in a Series A funding round led by Stuart McWhorter. 

Over the next 30 days, Terry expects to raise seed money for the new lifestyle company. Terry declined to comment on revenue.

Barstool has recently made headlines over founder Dave Portnoy’ alleged sexual misconduct, according to Business Insider.  

Lester said the media attention has “absolutely” nothing to do with joining Outsider. While “frustrating” and a “nuisance,” BI’s coverage has had little impact on Barstool’s bottom line, she said.

“No, it didn’t hurt the business. There’s always a new article about the controversies at Barstool Sports,” said Lester. “I think the Business Insider articles reflect more on their business model than ours.”

Portnoy has filed a lawsuit against Business Insider, claiming the stories were “false and defamatory.”