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Tuesday, July 1, 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.”

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