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He Made Hats for His Friends Using a Logo His Mom Drew on a Napkin in the '80s. Now He Counts Gary Vaynerchuk and Aaron Judge as Customers. Max Siegelman spoke with Entrepreneur about the rise of his cult-favorite fashion brand, Siegelman Stable.

By Emily Rella

Max Siegelman
Fashion brand Siegelman Stable founder, Max Siegelman.

The date is October 16, and I'm standing shoulder-to-shoulder, fighting for a good spot outside the gates of Madison Square Garden in New York, all just to get my hands on a limited-edition New York Rangers hat that's being sold tonight, and only tonight, at three select locations in the venue. (And to see my beloved Rangers play, of course.)

"If you're going tonight, cop me one, please, I'll send money," my friend Mikey texts. "I'll send you money instantly."

After twenty minutes of waiting and sprinting up three sets of escalators, I made it to the second point-of-sale location and secure the goods — a limited-edition Siegelman Stable Rangers hat for $73 — the last of the bunch.

"There were probably 70-ish people waiting [that night], like three hours before the game started, just for the hat. Didn't have a game ticket," Max Siegelman, Siegelman Stable's founder, told Entrepreneur. "It was crazy."

"Someone sent me a screenshot of [a hat] on eBay that resold for $399 or $499," he added.

Suddenly a cult-favorite fashion brand, Siegelman Stable is known for its trademark dad- and trucker-style hand-stitched hats seen on celebrities such as MLB superstar Aaron Judge, serial entrepreneur Gary Vaynerchuk, musicians Post Malone and Future, and models Kendall Jenner and Hailey Bieber.

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Now, for the first time, Siegelman Stable will dabble into brick-and-mortar with a showroom experience in Midtown Manhattan. The pop-up is appointment-only starting December 11, then open to the public on December 16 and 17.

Sometimes, the idea is in your backyard — or your horse stables

Siegelman Stable began as many brands have over the last few years — out of boredom and curiosity during the pandemic.

After graduating from SUNY Oneonta in 2012, Siegelman worked in the corporate world while pursuing creative side hustle projects in his free time.

Then, in 2013, his entrepreneurial journey began when we co-founded the social aggregation app Rouse, which brought in rapper LL Cool J as a partner.

Aaron Judge of the New York Yankees fist bumps Max Siegelman during the TCS 2022 New York City Marathon (Jamie Squire/Getty Images)

"That was kind of my segue into the entertainment world and entrepreneurship," he said.

When the pandemic rolled around seven years later, Siegelman was working in consulting and, like so many others, had extra time on his hands, which piqued his interest in a new creative outlet.

He decided to take two logos that his mother hand-drew on a napkin for his father's Long Island-based racehorse stable in the 1980s and turn them into hats and sweatshirts for family and friends — with no intention of selling to the public.

Siegelman's merchandise began to garner attention through word of mouth and on social media, which led him to launch a Shopify store to test out minimal inventory. He intended to take about $300 to $400 of his own money, create the merchandise, invest back the profit, rinse and repeat.

But as consumer interest and business started growing, so did Siegelman's belief that his latest side hustle could actually be the next big thing.

"When I started doing that, I started trying to figure out different ways to get my products into some celebrity or athlete's hands, whether it was through direct relationships I had from previous work, or just creative new ways of doing it," he explains.

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How did he get creative? By infiltrating the infamous NBA bubble during the pandemic.

Index your contacts — and then get creative

The NBA Bubble was a closed-campus safe zone at Walt Disney World Resort near Orlando, Florida, created during the pandemic to finish the last eight games of the 2019-2020 regular season and host the pandemic season of 2020.

Siegelman got the address from a friend who worked in the industry and started mailing.

"I was like, 'Well if this is the one address for the bubble, if I just change the team name and the player name, I could kind of get it in anyone's hands I want,'" he says.

He took the names of about a dozen players who he considered to be the "most fashion-forward" and blindly product-seeded them — and it worked.

"We had a handful of these guys wearing [the products] in the bubble on repeat," he said. "Because you were in a bubble, you weren't getting new clothes every week. So you get these tunnel photos. And that was kind of the start."

That's when Siegelman says the company saw a boost in followers on social media.

"By ramp up I mean we had, like, 250 Instagram followers," he jokes.

The Siegelman Stable Instagram account now has around 20,000 followers.

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After more blind product seeding, the hats made their A-List debut on Kendall Jenner's noggin during Paris Fashion Week in 2022.

Gary Vaynerchuk speaks during the VaynerX Rose Reception on the VaynerX Yacht in Cannes, France. (Lionel Hahn/Getty Images for Vayner)

How he markets and sells his products

Siegelman says he's spent $0 on traditional marketing and instead focused on the strategic product-seeding approach that has become popular in influencer marketing.

This way, brands will send free products to strategically chosen influencers or celebrities in hopes that they will wear the product, garner the interest and curiosity of their following, create a buzz, and eventually, turn a profit for the company.

"It's been very slow, strategic, organic growth," Siegelman tells me. "We're super picky with who we align our brand with."

But giving free products to influencers is only half the battle. Siegelman Stable also uses scarce marketing through selective e-commerce drops to ramp up interest. The products are teased on the company's official Instagram account alongside a countdown ticker to generate hype around the new collection.

"We're trying to get into a system where we're doing two drops a month, collections or collaborations. They typically sell out pretty quick — fingers crossed that continues," Siegelman says.

And while the company has mastered e-commerce, brick-and-mortar retail is a different animal.

"I think that with some of the higher-priced products that we're putting out, it's very tough on your own e-comm to sell those out of nowhere because you can't touch and feel the product," Siegelman explains.

Siegelman Stable now makes all of their hats from scratch in the U.S. with a "conscious effort" towards sustainability and craftsmanship, and, he says, a portion of the company's proceeds go towards equine therapy programs.

Related: Redefining the Modern Man: How Designer Todd Snyder Built an Brand Through Collaboration

Though the quantity made for each skew is "completely different," the company's most recent Winter 2023 drop features dad hats for $76, newer style corduroy hats for $88, embroidered t-shirts for $88, crew necks for $132 and newly made knit sweaters for $282.

Siegelman wouldn't disclose financial or sales numbers, but based on website data, if Siegelman Stable were to hypothetically sell 100 units of one item in the Winter 2023 collection, the company could generate roughly $66,600 from one drop.

Next, Siegelman wants to try runway shows.

"We're in the middle of improving a ton of stuff on the back end in terms of quality and production, as we just keep the ball rolling forward with drops and collaborations," he says. "I think we see ourselves not next year, but maybe the year after, the year after that doing runway shows and stuff — we want to continue to up the ante. We want to continue to up the quality types of pieces that we're putting out."

Looks like Siegelman won't be reining it in any time soon.

Emily Rella

Entrepreneur Staff

Senior News Writer

Emily Rella is a Senior News Writer at Previously, she was an editor at Verizon Media. Her coverage spans features, business, lifestyle, tech, entertainment, and lifestyle. She is a 2015 graduate of Boston College and a Ridgefield, CT native. Find her on Twitter at @EmilyKRella.

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