Underdog Fantasy Sports has been doing some interesting content recently, including launching the “Gil’s Arena” show with Gilbert Arenas and Josiah Johnson in February. They have other notable athlete-hosted shows, including Cut To It (hosted by former NFL star Steve Smith Sr.) and That’s What Sheed Said (hosted by former NBA star Rasheed Wallace). And March saw them launch a Underdog Originals YouTube channel focused on short-form documentaries, which has published five installments so far. Those have ranged from six to 20 minutes in length, and have covered everything from the Brett Favre welfare scandal to Zion Williamson’s shoe issues to Madison Square Garden’s use of facial recognition technology. Underdog VP of content Tim Livingston spoke to AA earlier this year, and said the short-form documentary space seemed like a real opportunity for them relative to traditional longer documentaries.
“I have experience over the last six, seven years pitching a lot of sports docs, and it’s been a very frustrating process,” he said. “Right now, networks are producing less and less despite what I think is solid demand for this type of content. And then there’s also what I call the The Last Dance effect, where network execs, after the obvious and enormous success of The Last Dance, they all want Michael Jordan.”
“The market right now is “Do you have a star attached? What star are you profiling?” It’s really frustrating. I think there’s want for really solid story. And obviously there are producers producing doc content just based on story. But I think right now the first question is ‘Is it true crime, or do you have a star?’ I believe that there’s demand for this content and for great sports storytelling, and we think there’s a business opportunity here.”
What exactly is that business opportunity? Livingston said the first part of it is finding what works as evergreen content on YouTube (which is a big part of the length decision):
“Evergreen content on YouTube in general is a really solid recipe for success. So we looked at similar types of content on YouTube and how well it does and thought ‘We could do that, and we could do it better, and put a lot more production value into it.’ And that’s what we decided to do.”
He said the second part of the opportunity is finding the right talent to produce good content that fits that mold.
“So I gave the keys—for Underdog Originals, we have a producer on my team named Paddy Cotter, and Paddy’s really talented. I originally got connected with him when I did a speaking engagement at Penn State and the professor there, John Affleck, was like ‘You should give this kid a shot.'”
“That was two years ago, and Paddy was initially working with me on my next podcast project after (Tim Donaghy podcast) Whistleblower. He’s just a really talented kid. We brought him over to Underdog, and he’s made an enormous impact. We came up with this concept together and I just gave him the keys. We’ve already seen a lot of interesting data and I think there’s a big opportunity here.”
Back to the length front, Livingston said that works in a couple of ways, both giving them content that works as short-form docs on YouTube now and potentially paving the way for longer-form ones down the road on the topics that take off.
“YouTube loves eight to 12 minute videos. We have a list of 500 stories, and the idea is to produce the most concise version of all these interesting stories. Long term, I want Underdog to have its own 30 for 30esque slate, I want to produce 60 to 90 minute docs and have them of that quality of Untold or 30 for 30 and have them for free on our YouTube channel. That’s the ultimate goal with our originals, to really emulate that model.”
Livingston said he fully recognizes the importance of longer documentaries, and he wants to get Underdog there eventually. But he sees the short-form docs as a way to build an audience and have a lot of data on that audience before making that kind of investment.
“I love that model, I want to produce high-quality full-length documentaries. But the fascinating thing with where we’re at now with this channel is that we have the opportunity to produce the most concise version of each of these stories and then look at the data and say ‘What are audiences interested in?’ This is like a two-year goal down the road, so in two years, we’ll be able to look at all our short-form content and say ‘Oh wow, audiences really like the Zion busted Nikes video.'”
Indeed they do. The Williamson doc has picked up almost 400,000 views over the three-and-a-bit months since its release, the most of any Underdog Originals doc so far. Here it is:
Livingston said the success of the Williamson doc wasn’t necessarily an expected result, but it confirms the value of doing shortform projects and seeing what appeals to their audience rather than taking full-length documentary swings immediately.
“It’s really interesting looking at what we’ve already produced and saying ‘Oh, wow, audiences like this more.’ And the YouTube algorithm doesn’t mess around. …Telling stories this way allows us long-term to look at a lot of data and make intelligent decisions on which full-length documentaries to produce. 30 for 30, Untold, anyone who exists in that model doesn’t really have the opportunity to essentially create this huge data farm for their longform stuff.”
“They’re guessing, and that’s the stress with being a network exec that I think most have. That’s what I love most about this model; we get to produce hundreds of these things, and then look after a couple of years at what works best, and then make a decision on what longform docs would work best for us at that point.”
A notable thing with Underdog Originals is how they’ve been able to land high-profile names despite the company only having a few of these short-form docs published to date. That shone with their Jail Blazers doc with former Trail Blazers Wallace and Bonzi Wells:
Wallace obviously has an existing relationship with Underdog with That’s What Sheed Said, but getting him to the company in the first place was notable. And getting Wells in on this was also notable. Livingston said he thinks his NBA contacts in particular have been helpful in finding high-quality interviews for these documentaries.
“One thing I’ve been able to bring to Underdog are my relationships, and Rasheed and Bonzi are two guys that I’ve been close with for a long time. I think especially in basketball circles, I started working with Gilbert Arenas six, seven years ago, we started No Chill together, and the success of that podcast has earned me a lot of respect in basketball circles. So I have a lot of really great relationships with ex-athletes who are very skeptical of traditional media. So when it came to Jail Blazers, that’s a story…going back to The Last Dance, I spoke to [director] Jason Hehir about the Jail Blazers, and he loved that story and is fascinated by that story, and if he didn’t have literally 18 documentaries on the go, I think he would love to tell it.”
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“But the Jail Blazers story is a really fascinating basketball story, but it’s a really tough market, even with someone like Damon Stoudamire. And Damon was supposed to be there as well. We happened to film that the same week as there was some drama in the Boston Celtics organization, the Ime Udoka stuff was going down, so Damon had to bow out last-minute.”
Livingston also said that part of what helps attract notable participants to these documentaries is the idea that it might translate into something longer (with Underdog or someone else):
“These guys want to get their stories out too. So we think there is an opportunity to team up with really interesting people like Rasheed Wallace and Bonzi Wells and give them an opportunity to put some things in front of a network executive or whoever might greenlight a longer-form doc. I would love to produce [a longer version of] Jail Blazers, there’s a bunch of super interesting people who are really interested in it. Like, the actor Jay Ellis, who was on Insecure, he was an intern for that team.”
He said it helps as well that these are video-focused rather than podcast-focused:
“There’s longform podcast interest as well, and that’s another avenue. But something I’ve experienced producing longform podcasts is that most guys, especially ex-athletes, you want to see them. And that documentary format works so well. So most guys don’t want to do an audio podcast, they want to do docs.”
Livingston said he’s optimistic they can continue building on the documentaries they’ve done so far.
“I hope to use my network and relationships to get some more of those big names. I really want to sit down with Jerry West and hear his thoughts on Winning Time. I’d love to sit down with Reggie Bush and expand on what we’ve already produced around Reggie. And over the course of the next year or two as we expand this channel, we’ll have the opportunity to bring in a lot of really interesting names and tell their stories. So I’m excited to build out this format, because I think there’s a really solid opportunity to get a lot of big names to come on board and tell their story in a trusted environment.”
One particularly interesting early documentary from Underdog Originals was one on Brett Favre and accusations of misused welfare funds. Covering Favre’s connections to the Mississippi welfare scandal has led to litigation against the likes of Pat McAfee and Shannon Sharpe, and while Favre eventually dropped his lawsuit against McAfee in exchange for an on-air apology, his one against Sharpe remains active. That’s led to many people being extremely careful in how they cover Favre. And Livingston said they considered the possibility of litigation (which hasn’t yet happened), but were fine going ahead because of their confidence in Cotter’s reporting.
“Obviously, we thought about that. In my eyes, we made the decision to produce it because the reporting is fantastic. Paddy Cotter went through thousands of pages of documents to produce that. And we crossed all of our proverbial t’s and dotted all of our proverbial i’s, and made sure that the reporting and the journalism were perfect in that, because it had to be. And ultimately, I decided that if this gets big enough where Brett Favre adds us to the baseless Pat McAfee lawsuit, then we have done something right. And we at Underdog, at this point we’re a pretty big company, and if we enter that spotlight and we piss off Brett Favre enough to get sued by Brett Favre, then we’ll take him down; that means that we’re doing our job and we’re doing it very well.”
As of Tuesday, Underdog Originals had more than 26,000 subscribers on YouTube, with Underdog NBA (home of Wallace’s show and more) having more than 45,000, Underdog Fantasy having more than 51,700, Cut To It (featuring Smith’s show) having more than 68,800, and Gil’s Arena (featuring Arenas’ show) having more than 256,000. And Livingston said their plans go well beyond that.
“Our ultimate goal in two and a half years, for football season 2025, is to have a sports network that streams free on YouTube that fans prefer to watch over ESPN. And I think we really should by end of next football season have a million-subscriber YouTube network across our channels.”
He said he thinks they have a useful overall mix of athlete-driven content, expert content, and now these originals, and he thinks that positions them well for major success down the road.
“We have now these use cases where the content is thriving and the athletes love what they’re doing, because we give them all this freedom to create. So keep an eye on us,” he said. “In two and a half years, if we have two, two and a half million YouTube subscribers, and we have these athletes that are synonymous with our network the way J.J. Redick is now synonymous with ESPN, what does that mean? That’s what we’re excited about, and that’s what we’re building.”
[Underdog Originals on YouTube]
