We taped Friday's Yak two weeks ago due to everyone's travel schedules, so it seemed like a safe place to break some news. In a pitch that had dated back almost a year ago, I had asked to move to content full-time. My title for my entirety of my Barstool tenure has been Senior Director of Ad Operations. It's a job that I loved, but it is time for a change.
I signed my offer letter for Barstool in August of 2016. I was so excited to make the shift from a big corporate giant to a small, scrappy startup that was completely unfiltered and authentic. I admired how everyone worked and lived. I loved seeing The Dave Portnoy Show, Pardon My Take, KFC Radio, and other programs get made and grow. My job was originally to get programmatic advertising integrated with barstoolsports.com. But we soon tried to start selling our half a dozen podcasts on our own, as an affiliate was handling 100% of the sales at the time and that fell under my jurisdiction. I remember fondly in December 2016, I kept a notepad that I hand wrote all the deals our sales team made for our pods and cross matched those with the affiliate. That soon grow into an excel sheet where we sold 100% of our own inventory, which grew into a whole CRM that now has people that work only on that.
I was a lone wolf for the first few years, making sure all the ads got read correctly and in the right spots. I would sit at my desk every day and listen to Barstool Radio with Dave, Kevin, Liz, and Frankie with Coley or Caleb mixed in on occasion. I always admired Frankie Borrelli for his producing skills on that show. He was younger than me and we actually started at Barstool on the same day, but the fact that he was producing such a quality show with no prior experience was amazing to me. One day, Dave announced we were getting our own channel on Sirius and my mind was racing with possibilities. What would the shows be? Who would produce them? What would they look like? Growing up, we mainly listened to sports talk radio in the car and I was a huge fan of Mike & Mike in the Morning. Radio just seemed like the tops for me at the time, so I bugged the Chief of Content at the time to see if I could get a similar shot as Frankie and produce a show, any show. I'd do it in my free time, no extra pay needed. I'd just be happy to learn and be part of a show. After I bugged him enough times, we got clearance, but there was a catch. The catch was it was 6-7pm every night. But the plus side, it was with Big Cat.
I had known Big Cat from the office but we weren't personally very familiar with each other. I had to meet with him for him to sign off on it and he seemed excited about my eagerness and said of course. We had about a week to put a show together, so we picked a name, got a logo, secured the social handles and got ready for showtime. I set a daily meeting for 30 minutes with the hosts of The Evening Yak, Big Cat, Rone, and Jared Carrabis NAME REDACTED. I came to find out years later Big Cat hated these and in turn, disliked me for a few months to start.
But my big break came a few months before radio started when Frankie noticed I was doing All-22 cut-ups on Twitter. That got Dave's attention and I still remember him giggling as he came down to ask me if he could blog about it. He said he knew I wasn't content, but it was so weird, he had to talk about it. Right after he hit publish, Steven Cheah as you know him was born into the Barstool universe.
Producing The Evening Yak and being on Dave's radar turned out to be a good thing. When Pat McAfee left Barstool he vacated the only other football podcast we had, which we had ad dollars sold against. I was assured that we'd have a show to fill it, but things were coming down to the 25th hour, so they had Dave do the show with Willie Colon and Tommy Smokes. They'd just need a producer who knew ball. That's where I slid in and with Dave thinking I was a total weirdo, it was an easy yes from him. I got a ton of exposure to him that season and got my first 'Welcome to Barstool' moment when I forgot to press record five minutes into a Dave rant. Other than that, the show went well and now I had a content foot squarely in the door.
A few months later, I noticed a gap in our coverage. Nobody was covering the NFL Draft. I was the most qualified, but I had never posted a blog before. I reached out to KMarko to see if he'd be cool if I posted a blog and a day later I had my first mock draft published. I also made my podcast debut hopping on MicksTape to talk NFL Draft. That became an annual tradition which was always a delight. It's crazy to think that all the Draft talk would evolve into the En Eff El Draft Show that I co-host with Rone and Brandon Walker and one of the funnest projects I'll ever work on.
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The following season, Laces Out became The Surf and Turf Podcast Going Deep with myself and Willie Colon. It was an interview based show with former players designed to be raw and unfiltered. We had some great times and it was such a different lens than I was used to seeing NFL players through.
Last year, I made my pitch for full-time content which was supposed to be very on the down low. It was a long process, but in the middle of it, Big Cat suggested I take over Fantasy Football Factory with Ben Mintz. Hank, Rone, and Nick all had other priorities that wouldn't allow them the time needed to be all in on the show so it made perfect sense. While I don't always agree with him, Mintzy is a great guy and I think we make a pretty good tandem. The show was a ton of fun this past year and I was really loved diving into the prop betting market, which is something I've really found a niche in. Follow @TrustTheData on twitter for all my gambling picks.
I also got involved with The Dozen over Quarantine. Jeff D. Lowe had started a remote gameshow and him and I are pals, so I was genuinely flattered when he asked me to play. My first match was on a team with Large and Zah and we narrowly lost. I had a few highlight answers in the match and Jeff decided to move me over to play with Big Cat and Rone as we were all original members of The Yak. That has been a huge blessing to play on a traveling tour with two of our company's biggest stars.
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One day in March 2021, Jeff was on for The Yak to do a bracket style tournament around fast food chains as a bunch of our guys were traveling for March Madness. The episode got pretty good reviews and Jeff told me he wanted to do a project like that on a weekly basis with the same crew. That has become The Bracket which is one of my favorite things I do. It's a weekly show we tape on Tuesday nights discussing the best or worst of one particular topic. But it's really just a veil to rip on stuff and tell jokes amongst friends and after each taping my face usually hurts from laughing and smiling. That's such a joy to do.
While I've been doing all of that, my constant has always been The Yak. I am so ridiculously proud of that show both for what it is and what it's going to become. It's wild how we've grown as a show and all grown closer as friends. It truly makes that hour plus incredibly enjoyable because it's just laughing and joking with your pals. With this move, I'm excited to be able to pour more into that show.
Juggling essentially two jobs has been wildly difficult. I almost exclusively work. I have very few other hobbies or interests. During quarantine I'd be up regularly so late working on building my own brand/content things and catching up on my Ops work that I learned to navigate my home in complete darkness. In the past few months, not much has changed as far as my hours, so I'd first like to thank my wife for just putting up with what has just been my whacky side gig for the past few years. It's scaled up a lot and definitely been stressful and there is no way I could do it without her constant support.
But there are actually so many people, a few who I've mentioned here that have really helped me get to this point. Big Cat has been my biggest advocate internally and always pushing me, which I can't thank him enough for. My boss on the business side Jenn Popack has been in my corner since her first day and really helped get this over the finish line along with our new Chief People Officer, Kim Rayner. Michael West aka Westy has been wildly helpful with advice on how to become a valuable commodity in Penn's eyes from a gambling perspective. Obviously a giant thank you to Dave and Erika who have both supported me over the years doing two roles and now shifting to one. Huge thank yous also to all the content people that had my back in this pursuit and most importantly, thank you to all the Stoolies, especially everyone in the Cheah hive for tailing, reading, listening, watching, and consuming my content. This is a W for us all. I can't wait to get started.
-SC
steven cheah
