• Loading stock data...
Tuesday, August 26, 2025
Front Office Sports Honors winners are here! View the 2025 winners
exclusive
Tuned In

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
Deirdre Lester

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 Rivals.com, 247Sports.com, ComicBook.com and PopCulture.com. Terry sold Rivals.com to Yahoo for $100 million in 2007. He later sold 247Sports.com 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.”

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

‘You’re Going to Get Beat Up’: The Liberty’s All-Male Practice Squad

A select group suits up weekly to take on the defending champs.
exclusive

Ohio State Bars Dave Portnoy From Stadium in Fox Debut

Portnoy will appear on “Big Noon Kickoff” but not inside the stadium.
A'ja Wilson
exclusive

New WNBA CBA By Oct. 31 Deadline Appears Increasingly Unlikely

The sides could avoid a work stoppage with an extension.

The Honey Deuce Effect: How Tennis Perfected the Signature Cocktail

Sold every 1.5 seconds, they total more than $12 million in sales.

Featured Today

Dec 21, 2024; Austin, Texas, USA; Texas Longhorns quarterback Arch Manning (16) warms up as the Texas Longhorns prepare to play the Clemson Tigers in the first round of the College Football Playoffs at Darrell K Royal Texas Memorial Stadium.

Schools Are Hesitant to Allow PE Into Their Athletic Departments

Regardless of budget, schools don’t believe the risk is worth the reward.
Oct 2, 2024; Rosemont, IL, USA; Big Ten commissioner Tony Petitti speaks with the media during the 2024 Big Ten Women’s Basketball media day at Donald E. Stephens Convention Center.
August 22, 2025

‘Not Ready to Jump In’: Power 4 Commissioners Aren’t Sold on PE

Top leaders in college sports have yet to see a satisfactory proposal.
Nov 23, 2024; Minneapolis, Minnesota, USA; Penn State Nittany Lions head coach James Franklin looks at quarterback Drew Allar (15) during the first quarter against the Minnesota Golden Gophers at Huntington Bank Stadium.
August 22, 2025

Private Equity Enters College Sports—Without the Equity

As college football starts, lending agreements have become PE’s best way in.
Sep 8, 2024; East Rutherford, New Jersey, USA; New York Giants running back Eric Gray (20) returns a kickoff against the Minnesota Vikings during the first half at MetLife Stadium.
August 18, 2025

‘Fauxbacks’ Throw Back to a Retro Uniform That Never Existed

Many throwback jerseys are brand-new designs or “Franken-Unis.”

6 Burning Questions About Reimagined MLB Rights Deals

MLB’s rights are changing significantly, but questions still remain.
August 25, 2025

Netflix to Stream Entire 2026 World Baseball Classic in Japan

Netflix picks up Japanese rights to the upcoming international tournament.
August 25, 2025

YouTube TV, Fox Standoff Puts CFB Viewers in Jeopardy

Subscribers could find themselves without access to marquee matchups.
Sponsored

Building A Pro League From Scratch

Front Office Sports and Gainbridge® spotlight what it takes to build a professional women’s soccer league.
August 25, 2025

Former Tennis Channel CEO Sues Sinclair Over Voided 8-Figure Payday

The former network executive cites a financial pretext to his firing.
August 24, 2025

Bill Belichick Tells UNC Football Team Hulu Series Is Happening

FOS reported last month that the Hulu series was nearing finalization.
Jul 13, 2025; Atlanta, GA, USA; MLB Commissioner Rob Manfred announces the pick for the Athletics pick during the MLB Draft at The Coca-Cola Roxy.
August 21, 2025

MLB Confident New Rights Will Exceed $550M ESPN Deal

MLB would redistribute rights forfeited by ESPN back in February.
August 21, 2025

NBC’s MLB Chase Built on Vision for Yearlong Sunday Night Sports

NBC Sports is gunning for a Sunday night slate rivaling “The Sopranos.”