Deirdre Lester tapped to lead Outsider.com as CEO

NASHVILLE, Tenn., March 9, 2022 – Outsider.com, a rapidly growing digital media and lifestyle company, announced today that former Barstool Sports Chief Revenue Officer Deirdre Lester has been appointed new CEO of the company. 

“Deirdre completely understands the brand mission and opportunity with Outsider,” said Outsider Co-Founder and former NFL Quarterback Jay Cutler. “She is extremely talented, has years of experience and a known track record in the industry, but what impresses me most is her team-first attitude and leadership skills.”

Lester will be tasked with expanding the media and lifestyle company’s mission of celebrating American culture through real stories and authentic goods. 

“Barstool was an amazing experience for me, having an opportunity to be a part of staggering growth and work along so many dedicated, passionate, and talented executives and talent,” said Lester. “I will forever look back on my experience as one of my proudest professional moments.”

“I’ve been keeping up with Outsider from the sidelines and when the opportunity to lead the company as CEO was presented, It was without question the entrepreneurial leadership role I’ve been building towards for years. The Outsider mission to build a community that celebrates American entertainment and culture has endless potential and I’m thrilled to be at the helm of building this company to be an industry force.”

Outsider’s media division is building a portfolio of podcasts and shows, featuring production from Co-Founder Jay Cutler and “The Marty Smith Podcast”. In addition to the media division, Outsider recently launched its lifestyle store, with a small offering of custom-built hats. The company has plans to release a full line of products serving the Outsider lifestyle in the near future.

“When the search for our CEO began, Deirdre was our first call. She has executed at the highest levels at best in class digital brands her entire career,” said Outsider Co-Founder Shannon B. Terry. “Deirdre’s portfolio of experience puts her in rarified air. She had unlimited opportunities to lead an organization, and her choosing Outsider is a testament to our enormous opportunity.”

About Outsider.com
Outsider is a media and lifestyle company built to celebrate American culture through genuine stories, authentic goods and portfolio of podcasts and shows, featuring “The Marty Smith Podcast.” Outsider reaches more than 22 million users and more than 7 million social followers. Along with former NFL quarterback Jay Cutler, Outsider was created by the founders of On3.com, Rivals.com (acquired by Yahoo! In 2007), 247Sports (acquired by CBS Sports in 2015), and Pop Culture Media (acquired by CBS Interactive 2017).

About Deirdre Lester
Deirdre Lester has over 20 years experience in the digital media industry, with a focus predominantly on sports & entertainment brands. She began her career in media at CNET Networks in the late nineties and went on to work at ESPN as her foray into the sports business. Deirdre has held executive level positions at Rivals.com, MLB Advanced Media, Whistle Sports and most recently was the Chief Revenue Officer at Barstool Sports where she led Advertising & Sponsorship and Brand Licensing. She has been names a Top 25 Women in Sports by Forbes (2016) and Top Digital Executive by Mediapost.

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Jay Cutler to lead Outsider’s Lifestyle Division

BRENTWOOD, Tenn., Feb. 3, 2022 – Outsider.com, a rapidly growing digital media and lifestyle company, announced today that former NFL Quarterback Jay Cutler will be leading the company’s Lifestyle Division as Chief Design Officer.

Cutler, a founding partner in Outsider.com, will be tasked with expanding the lifestyle division and the company’s mission of celebrating American culture through real stories and authentic goods.

“Obviously, Jay has many talents, but those that know him will tell you that he is a creative savant,” said Outsider co-founder Shannon B. Terry. “He led the efforts to develop the Outsider mark and brand mission and is now creating a portfolio of products that are built from the ground up, with the highest quality of materials and craftsmanship.”

Outsider has also launched its lifestyle store, with a small offering of custom-built hats designed and created by Cutler. The company has plans to release a full line of products serving the Outsider lifestyle in the near future.

“I believe in the Outsider mission and see this as a great opportunity to build a brand that can impact so many people in a positive way,” said Cutler. “Outsider is a natural extension of my everyday lifestyle. It is the things I do and what I love. I look forward to sharing this experience as I enter the next journey of my life.”

About Outsider.com
Outsider is a media and lifestyle company built to celebrate American culture through genuine stories and authentic goods.

Outsider reaches more than 22 million users and more than 7 million social followers. Along with former NFL quarterback Jay Cutler, Outsider was created by the founders of On3.com, Rivals.com (acquired by Yahoo! In 2007), 247Sports (acquired by CBS Sports in 2015), and Pop Culture Media (acquired by CBS Interactive 2017).

About Jay Cutler
Jay Cutler played in the NFL for 12 seasons after being selected by the Denver Broncos with the 11th pick in the 2006 NFL Draft. He played with the Broncos for three seasons, the Chicago Bears for eight seasons and the Miami Dolphins for one. He officially retired from the sport in 2017.

Cutler currently hosts ‘Uncut with Jay Cutler,’ a podcast in which he hosts friends, fellow athletes, and experts to talk about their lives and current events. Former guests of the show include Mark Cuban, Danica Patrick, Mike Rowe, and Eric Trump. Since its launch in August 2021, the podcast’s 24 episodes have amassed over 570 thousand downloads and over 300 thousand YouTube views.