A little less than five years ago, in September 2021, I sat down with Underdog founder and CEO Jeremy Levine. He had launched Underdog less than two years before that.
Underdog was the third company Levine had founded in the fantasy space. The first was StarStreet, which he sold to DraftKings for an undisclosed sum. The second was Draft, which he sold to what was then Paddy Power Betfair for $48 million.
Both of those companies were purchased by competitors, and both took those companies out back behind the woodshed and killed them.
Stretching the pun, it appeared in that 2021 interview that Levine was a bit gun-shy about the idea of jettisoning Underdog.
I asked him if people were already looking to buy Underdog.
“Absolutely,” he said.
I then asked if he was looking to sell, and his answer was unequivocal.
“Absolutely not.”
Well, things have a way of changing over five years. That was in stark relief Thursday, as Levine sold his baby (puppy?) to IG Group Holdings for $1.3 billion.
No wonder things changed.
Looking back at the rest of the interview, it now reads like less of a feature, and more of a “Hey dummy, pay attention, the guy is telling you exactly what he’s going to do and if you’re smart you’ll ask to get in as a small-time investor, but you’re not smart and as a result are writing this story instead of depositing a fat check.”
Here are some highlights of what Levine told me back then, followed by my obvious-in-hindsight take. Remember, the company was less than two years old at the time.
Big, bigger, biggest
“We want to be the biggest company in the space. No one in this industry can build product, innovate, or provide great customer experience like we can. I’m a believer in product and innovation and treating customers well. And I think that’s a massive advantage we have.”
At the time, Underdog was running best ball and pick ‘em contests. That’s it. That was the whole ballgame. No one in the space was talking about prediction markets. No one could spell “CFTC,” never mind tell you what it was.
And while I’m not going to sit here and tell you Levine saw the future, it’s notable that this quote, this mindset, clearly allowed Levine to push for entry into prediction markets and make a giant splash. According to the documents IG Group released as part of the deal Thursday, Underdog is the “third-largest US prediction markets venue by US regulated notional volume flow.”
The Underdog prediction market was launched in September 2025. Not too shabby.
Providing a full suite
“It’s always been a view of ours that winning companies in this space should have multiple pieces, multiple platforms, more than just being somewhere to place a bet. The same customers like fantasy sports, March Madness brackets, survivor pools, collecting sports cards. They’re playing poker, they’re doing a whole bunch of things. It’s very clear to me the biggest companies in the space need to have the full suite of platforms. And we believe we can build this better than anyone else.”
He said this because Underdog had just launched a sportsbook, and he was convinced that not only would it succeed, but it would be just one piece of a larger business model.
Well, the sportsbook ended up shuttering this May after Underdog completed its purchase of Aristotle Exchange’s designated contract market (DCM) and derivatives clearing organization (DCO) business, allowing it to have its own CFTC-blessed prediction market.
Again, no way Levine saw the coming prediction market wave, but he — at minimum — saw it as another piece of an ever-growing puzzle for Underdog to put together. Now, a few short months later, he was proven correct to make these moves.
Speaking of that sportsbook …
Compared to DraftKings, FanDuel?
“It was apparent to me when PASPA was repealed that DraftKings and FanDuel were going to be the two largest players in the space because of the inherent structural advantage they have of being able to draw players from their daily fantasy offerings. And we have those same advantages, basically having a huge database of players that are sports bettors and have money in their account. That’s a big difference than a database of loyalty rewards players who signed up three and half years ago.”
Again, the sportsbook was shelved as prediction markets rose. Levine was not the only sportsbook operator to realize prediction markets might be the future, but he was certainly the only one to completely fold up shop and put all his eggs in prediction markets. Not to say DraftKings and FanDuel should do that — obviously not — but the fact Underdog did is notable. If it had kept on the sportsbook path … well, we wouldn’t be reading this right now, would we?
Also notable: Underdog is beating both DraftKings and FanDuel in the prediction market game.
Absolutes
“Absolutely not” (in response to the 2021 question about interest in selling).
Yeah, well, if someone dangled $1.3 billion under my nose, I also would roll back any “absolutely nots” I may have said to some dork interviewer five years previous.
