• Loading stock data...
Monday, December 15, 2025

Shot Callers: Deirdre Lester, CRO, Barstool Sports

Barstool Sports have grown significantly in revenue generation in the last several years thanks in part to a series of unique brand partnerships and the efforts of Chief Revenue Officer Deirdre Lester.

Lester joins FOS Editor Ian Thomas in the latest episode of Shot Callers to discuss her time with Barstool Sports and the company’s approach to brand partnerships.

Edited highlights appear below:

On the growth of Barstool’s events side (1:54)

Lester: “It’s immensely helpful, especially when we have the opportunity to bring clients or potential customers to an event and let them experience that with the fans. So they get to see the fan engagement, the brand love for Barstool. The fact that we can kind of just show up pretty much anywhere and hundreds, depending on the venue, hundreds or thousands of people will come if we, if we do a ticketed event…to be able to show that up close and personal to brands is really powerful because they want to be part of that experience, part of that environment.”

On importance of being choosy about partnerships (3:50)

Lester: “Authenticity is key. It’s an overused buzzword in the industry, obviously. But for us, we have to remain authentic to Barstool’s tone and voice. And that’s not for everyone…Not everyone is kind of overly obsessed with the words ‘brand safety’ in the industry right now and I think of it as brand suitability. Like if our brand is suitable for you, then your brand is likely to be suitable for ours. It’s just as important for their brand and their brand messaging to be suitable for our brand as it is for our brand to be suitable for them. Otherwise, we’re asking our personalities to create content that isn’t inauthentic or forced. So not only will fans reject it, the talent and personalities won’t feel great about it and that comes through.”

On big partnership categories for Barstool (5:45)

Lester: “Our number one advertising category in 2019 was sports books. So a category that less than 18 months ago did not exist quickly became a really huge partnership for us. So that’s one. You can see there’s a lot of conversations about strategic partnerships and alignments there. Beer and spirits…huge category for us. What we’ve been able to do there, which is exciting, is particularly in the beer and now beer and hard seltzer category, where the lines are getting a little blurry is diversify to have multiple partners by carving out ownership positions and key franchises.”

On misconceptions about the brand (08:30)

Lester: “The average CMO or brand marketer may not be in our demo, right? So ideally what happens, and this happens in a lot of cases, is there is someone… that is a Barstool fan…and understands the power of this brand and seeing what we can do for our partners and is championing that. But aside from that, if we don’t have that person in there, there’s a lot of education that has to happen. How we got to where we are, what we are, how we’ve diversified the brand, how big the brand is and how we’ve outpaced our competitors in a very big way.”

Linkedin
Whatsapp
Copy Link
Link Copied
Link Copied

What to Read

Oct 8, 2025; Bronx, New York, USA; New York Yankees left fielder Cody Bellinger (35) runs off the field after ending the first inning with a sliding catch against the Toronto Blue Jays during game four of the ALDS round for the 2025 MLB playoffs at Yankee Stadium.

Steinbrenner: No Set Budget Yet for Yankees in 2026

The high-spending club faces numerous questions heading into next season.

How NBA Arena Experiences Went Ultra-Luxe

For the most connected guests, the game has become a secondary attraction.
exclusive

Schools Consider Not Signing House v. NCAA Enforcement Memo

Texas Tech’s general counsel has advised the school not to sign.
Caitlin Clark
exclusive

The WNBA’s Million-Dollar Offer Isn’t What It Seems

The league’s most recent offer still includes a six-figure maximum base salary.

Featured Today

How Pickleball Became One Massive Private-Equity Rollup

Pickleball roads lead back to billionaire Tom Dundon.
Dec 9, 2025; Toronto, Ontario, CAN; New York Knicks guard Jalen Brunson (11) dribbles against Toronto Raptors guard Jamal Shead (23) during the first half at the 2025-26 NBA Emirates Cup at Scotiabank Arena
December 13, 2025

The Lucrative NBA Cup Is Here to Stay

The in-season tournament, launched in 2023, is turning into a staple.
The Los Angeles Chargers host executives from UCLA Health on Wednesday, August 7, 2024 at The Bolt in El Segundo, CA.
December 7, 2025

The Multibillion-Dollar Business of Pro Athlete Recovery

What started as ice baths has evolved into a multibillion-dollar industry.
Big League Wiffle Ball
November 29, 2025

Celebrity-Backed Wiffle Ball Has Big-League Aspirations

Big League Wiffle Ball team owners include Kevin Costner and David Adelman.

Fundamentals: Women in Sports

Welcome to the latest episode of Fundamentals, a Front Office Sports interview…
September 22, 2020

Fundamentals: USTA CEO Michael Dowse

Dowse, the CEO and executive director of the national governing body for tennis, discussed the unique challenges of a fan-less US Open and growing the sport in the U.S.
November 17, 2020

Fundamentals: Women In Esports

On this episode of Fundamentals, three guests join the show to discuss the opportunities for women in the gaming industry, as well as the challenges they face.
Sponsored

20 Years of Coastal Cool: How Johnnie-O Became a Force in Golf,..

A style movement powering one of the fastest-growing brands in sports and lifestyle.
July 28, 2020

Fundamentals: RISE CEO Diahann Billings-Burford

Diahann Billings-Burford is the CEO of RISE, a national nonprofit whose mission is to use sports as a means of eliminating racial discrimination and acting as a vehicle for social justice and societal equality.
July 24, 2020

Fundamentals: MLL Commissioner Sandy Brown

Sandy Brown — commissioner of Major League Lacrosse — discusses the logistics and realities of the league’s return to play with a single-location tournament format, along with the growth of the sport as a whole.
July 17, 2020

Fundamentals: Evil Geniuses CEO Nicole LaPointe Jameson

Nicole LaPointe Jameson, CEO of professional esports team Evil Geniuses, discusses the state of esports and what is next for the organization.
July 16, 2020

Fundamentals: The Launch of VaynerGaming

VaynerGaming division lead Darren Glover and VaynerSports EVP Mike Neligan join the show to discuss the new division, and the future of commercial opportunities in esports.