Teen Entrepreneur is on a Roll

Appears in the June 2023 issue.

By Peter Gianopulos

Jenna Swain

For posterity’s stake, remember this name: Jenna Swain. The 14-year-old from Wheaton already has her own business, selling cups of rolled ice cream—ultra-rich cream that’s spackled onto a cold griddle, frozen into pancake-thin sheets, then scraped into what looks like icy fruit roll-ups.

She launched her portable pop-up, which she dubbed High Rollers, when she was just 12. She bought her first griddle—special thanks to mom and dad for allowing her to test it in the family living room—and taught herself how to pour, freeze, and roll. By then, she’d developed a reputation for selling her handmade bracelets—plus store-bought suckers—to kids at her school for a profit. “I just like making things and finding creative ways to sell them,” Swain says. So she did just that, setting up shop at the Wheaton French Market.

Rolled ice cream from High Rollers

Immediately, she dazzled folks by folding Oreos and homemade caramel—and later on, cotton candy—into her ice cream. She never squandered her profits; she reinvested them in her business. Now, she has four griddles plus cotton-candy machines and crepe-makers. She still scrapes away at the Wheaton French Market but also will sell at the at Wheaton Town Square marketplace, Cream of Wheaton fest, and the Downers Grove summer concert series. (Check highrollerscompany.com for her schedule).

So do yourself a favor: Go buy some ice cream from Jenna. Years from now, when she’s a titaness of industry, it’ll make a hell of an ice breaker at parties to say you used to buy Peep’s flavored ice cream from her way back when.


Photo: High Rollers Company