Why Payment Companies Want a Piece of Your Pop-Up Shop

A hat brand built from a napkin sketch now has some of the biggest names in commerce wanting to stand next to it. That says as much about the companies chasing founders as it does about the hats.

Siegelman Stable started during the pandemic, when Max Siegelman took two logos his mother hand-drew on a napkin in the 1980s for his father's Long Island racehorse stable and turned them into hats and sweatshirts for friends and family, he told Entrepreneur. He launched a Shopify store to test small batches, planning to put in US$300 to US$400 of his own money, reinvest the profit and repeat. His father, Robbie Siegelman, established Siegelman Racing Stable in 1982, a year that now shows up on the merchandise, according to Dan's Papers.

How did a hat side hustle become a pop-up brand?

Through athletes first, then rooms. Siegelman told Entrepreneur he mailed product to players inside the NBA's pandemic bubble by tweaking the team and player name on a single address. The hats ended up on people like Aaron Judge and Gary Vaynerchuk, and in 2023 the brand tested brick and mortar with an appointment-only showroom in Midtown Manhattan.

The bigger step came in late 2024, with a holiday pop-up in SoHo that WWD called the brand's first extended store since its 2020 founding. WWD also reported that Siegelman Stable had previously run two weekend pop-ups with Shopify. By fall 2025 the brand was back with a seasonal SoHo shop at 430 West Broadway, timed to its biggest collection yet, Hypebeast reported. That followed a summer pop-up in East Hampton that ran from June 27 to July 20, 2025, according to Dan's Papers.

Siegelman's case for all this is simple. "It's important for people to come and touch and feel our product and try on and feel the cuts, and understand what we're building," he told Dan's Papers, adding that in-person visits help turn shoppers into repeat online customers.

Why are payment companies so interested in founders' pop-ups?

Because founders are customers worth winning. Shopify, which is headquartered in Ottawa, put its name behind Siegelman's 2024 SoHo pop-up. "At Shopify, we support entrepreneurs at every stage, from their first sale to their first million," Jessica Williams, Shopify's head of brand marketing and partnership, told WWD. Siegelman added that using the Shopify space in spring 2024 "reopened our eyes as to why it is so important for an e-commerce founded brand to bring our story and clothing to life."

Card issuers are working the same angle. In June 2025, Chase introduced Sapphire Reserve for Business, which it called its first premium travel-focused credit card for businesses, saying it was "designed to meet the needs of business owners at scale," according to the company's launch announcement. The bank already builds live experiences around cardmembers, from a Chase Freedom lounge at Dreamville Fest to NBA All-Star Weekend courts featuring stars like Jalen Brunson, BizBash reported.

That overlap is no accident. Brunson is also one of the Knicks players Highsnobiety has tied to Siegelman Stable's hats. When a fashion brand already owns the cultural moment, a financial company can rent some of that credibility and meet the exact business owners it wants as cardholders.

What are Canadian banks and card issuers doing?

Mostly grants, mentorship and storytelling, rather than branded shops. American Express Canada and the DMZ at Toronto Metropolitan University reopened their Backing Canadian Small Businesses program this spring, offering $10,000 each to 100 businesses plus mentoring, according to the companies. Amex Canada says it has handed out $3.5 million to 350 Canadian small businesses since 2021.

RBC, meanwhile, publishes founder stories that read like pop-up playbooks. Its profile of Fruit of the Land traces how Stacey and Michael Kurtz opened a single holiday pop-up at Promenade Mall in Thornhill, Ontario, in 2003, pitched empty mall space to landlords as "a win-win," and grew into seasonal shops at the Eaton Centre and Yorkdale before going permanent.

What can Canadian founders take from this?

First, treat a pop-up as a test with an exit. Big brands do the same thing. In Toronto, Eataly kept the small Distillery District store it opened in 2025, which started as a pop-up, BNN Bloomberg reported in a piece on retailers shifting toward smaller formats.

Second, know what a partner wants before you sign. A platform or card issuer sponsoring your space is buying access to your customers and your credibility with them. That can cover rent and add polish, but the brand story still has to be yours, which is why Siegelman keeps pointing back to his father's stable.

Third, timing matters. Siegelman's longest runs have landed in the holiday season and in summer resort towns, where foot traffic and gifting budgets peak. For a Canadian founder with a loyal online audience, a few weeks in a busy neighborhood, backed by a partner who wants small business customers, may be the cheapest way to find out whether the internet hype converts in real life.