Hey! Welcome back to the Creator Economy NYC newsletter, your weekly hit of insights and strategies to help you build, monetize, and scale as a creator.
A few weeks ago, we ran a guide on how creators should think about taking equity in brand deals. Now we want to spotlight a creator who’s actually done it (and the company went on to be sold for $1.3B.)
This week: we sat down with Jack Settleman, founder of Snapback Sports. He built a college Snapchat account into a 15-person media company, and he signed one of the most famous creator equity deals in the space with Underdog Fantasy.
His story is an awesome example of a creator building something genuinely bigger than themselves, and being smart about the business every step of the way.
Let's get into it.
Creator Economy NYC meets Times Square
A huge shoutout to beehiiv for featuring us alongside some incredible NYC creators and brands building on the platform.
What makes it especially cool is that the CENYC newsletter has become such a core part of this community with 139 straight weekly editions sharing the people, ideas, events, opportunities, and stories shaping the creator economy in NYC and beyond.
beehiiv also just launched a new Community feature, which feels very aligned with where newsletters are heading: not just something you read, but something you can actually participate in, with other readers.
The hidden cost of creator equity (and how Jack Settleman built Snapback Sports)
Jack Settleman's first business was flipping sports phone cases out of his dorm room at UT Austin. Pay a meme account $1,000 for a shoutout, sell $4,000 worth of cases, and after inventory, shipping, and ad spend, walk away with $500.
"I was like, I want to own the distribution," Jack told us.
So he started his own Snapchat account instead. Nine years later, that account is Snapback Sports: a 15-person media company with a New York office, over a million followers across platforms, and talent going head to head with networks that have been around for decades.
The instinct that built Snapback: own it or don't bother
That same drive to own his distribution shows up in how he built the company itself. Depending on a meme account for reach and depending on himself to keep the lights on are both still dependency. So he's spent the last stretch de-centering the brand around himself, bringing on talent so the company can run without him in every frame.
He shared some news with us first: college football legend Melvin Gordon is joining Snapback this season as a co-host for their college football coverage, covering games live in the stands and on the field.
They've also never taken outside funding, and they still do what doesn't scale: meeting fans at halftime for photos, game after game. "We're grabbing 25 fans a game, but we've got them for life," Jack said. That loyalty compounds. One of Snapback's summer interns this year is a kid who met Jack and his brother at halftime of a game three years ago.
Know your floor before you take the equity swing
That ownership instinct is also what makes Jack's Underdog equity deal worth studying. He's built a career on owning things outright: the distribution, the team, the relationships built one halftime conversation at a time. Now, equity in someone else's company is the one place that instinct gets tested.
Coming out of COVID, Jack was ready to go full-time on Snapback. With that, Underdog Fantasy offered him a one-year deal worth $250,000 and let him choose the split between cash and equity. He picked roughly 50/50: low six figures in cash, the rest in equity at a $50 million valuation.
The one-year deal turned into six, and Underdog gave him the title of Head of Winning to signal how deep the integration went. "The scope incentivized me to share," Jack said. "If I have a set number of deliverables but I want to continue to promote them, I'm obviously capable of doing so."
Here's the part worth stealing: before he signed anything, Jack built in three checkpoints.
The Floor
He'd already calculated exactly what he needed to cover rent and content costs for the year, and the cash portion of the deal cleared that number. The equity was pure upside from there. If the guaranteed cash doesn't cover what you actually spend to operate, no equity multiple fixes that later.
The Bill
"The thing that people don't think about is, you know, we took six figures in equity. You have to take that as compensation. So you actually have to pay taxes on that," Jack explained.
He paid an estimated $40,000 to $50,000 out of pocket for shares he couldn't sell. That check comes due immediately, whether or not the company ever has an exit.
The Wait
Underdog eventually sold for $1.3 billion, a 30x return on that original valuation. Jack still hasn't fully seen it. "There's dilution. The shares of a public company can drop before you can sell," he said. "It's a sexy thing to have happen, and it was still an incredible return, but my wife and my friends were all disappointed that we have to go back to work on Monday because it didn't hit exactly like that."
And while Underdog is a win, Jack's Carta account is full of equity from companies that went to zero.
Build what you can own 100%
Even sitting on one of the better outcomes in the space, Jack's advice to other creators skips equity deals almost entirely.
"You need such a ridiculous result [to make equity pay off]," Jack said. "They built a unicorn. My advice would be: think about what businesses you can build that you get effectively 100% equity into."
It's the same instinct that got him off that meme account nine years ago. Own the distribution. Own the team. Own the equity outright, or treat it as a bonus instead of a plan.
With AI and low-code tools now letting creators build products at a fraction of the old cost and speed, that advice is more actionable than it used to be. Snapback is following its own logic here, building a sports trivia app and what Jack calls a "Yelp for sports fans," neither of which needs anyone else's valuation to go up for Jack to win.
Steal This Playbook
Three moves to take past this newsletter:
Know your baseline. Calculate the exact dollar amount you need to survive and invest in your business. Never trade that baseline for equity.
Audit your bottleneck. If you want to build a long lasting company, look at your content. Could someone else host it? If not, you're the bottleneck to scale.
Do one unscalable thing this week. Reply to 50 DMs. Host a small meetup. Do the thing the algorithm can't do for you.
Our next event: Sept 9th - Creator Money Moves Mixer with Relay
We’re teaming back up with our friends at Relay for another night bringing together some of NYC’s top creators, operators, and industry leaders.
This time, we’re diving into everyone’s favorite topic: money moves as a creator.
Join us for a night of meeting people worth meeting, drinks, and a live conversation with leading NYC creators breaking down how they’ve turned their audience, expertise, and creativity into real businesses.
Whether you’re figuring out how to turn momentum into something bigger, or already have something big and want it to get BIGGER, come meet the people building alongside you and leave with a few new ideas for your next money move.
Come meet. Come learn. Make some money moves.
Two free tools top creators use to keep themselves moving
The Creator Goal Setting Guide (FREE): A simple but powerful document to help you declare who you want to BECOME in 2026. Get it here.
The Creator Accountability System (FREE): Your visual companion for consistent creation in 2026. Get it here.
Thanks for reading! The creators who build lasting businesses are the ones who know their baseline, do the unscalable, and play the long game with the right partners. Pick one of those three and go deeper on it this week.
F*ck It, Create It,
Brett
With research, interview and editorial support by Taylor Cromwell - a newsletter and creator economy expert and founder of Creator Diaries. Follow Taylor on LinkedIn.