Sep 22, 2026 · 1 hr 11 min · 15 segments
Jack Settleman is the founder of Snapback Sports, the sports media company that started as a Snapchat account in 2017 and became one of Underdog's earliest creator partners. Jack breaks down the bets…
Francis ZiererHostTom
What was Snapback? What was Jack Silliman doing in 2021 in terms of the media, in terms of the content? Not the money, but what were you creating? What was your audience scale back then in 2021?
And so Snapback Sports, which was called Real Underscore Sports, name changed not only because you can have an underscore in your LLC and media company name, but because HBO also had a very famous show called Real Sports with Brian Gumbel.
And then Omar Raja, who's now at ESPN and is one of the best in our industry, he sold to Turner and Bleacher Report.
And they brought that in-house, paired him with the rights, and they were allowed to kind of go do things there.
And then built it up large enough to build leverage and then turn into original content.
Now, back in 2017, when I started the Snapchat account, the whole thing was...

What was Snapback? What was Jack Silliman doing in 2021 in terms of the media, in terms of the content? Not the money, but what were you creating? What was your audience scale back then in 2021?
And so Snapback Sports, which was called Real Underscore Sports, name changed not only because you can have an underscore in your LLC and media company name, but because HBO also had a very famous show called Real Sports with Brian Gumbel.
And then Omar Raja, who's now at ESPN and is one of the best in our industry, he sold to Turner and Bleacher Report.
And they brought that in-house, paired him with the rights, and they were allowed to kind of go do things there.
And then built it up large enough to build leverage and then turn into original content.
Now, back in 2017, when I started the Snapchat account, the whole thing was...
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