Every once in a while we back a founder who makes you think: how has nobody built this yet? Jessica Chen Riolfi is one of them. She spent a decade watching fintech democratize everything — and then asked why nobody had fixed the thing that stresses the whole country every April: taxes 🫠.
As with any great founder story, Jessica’s journey is full of twists and turns. Read on for a dose of inspiration (I bet you didn’t think you could be inspired by taxes! Ha).
Tell us who you are and what your company does — in plain language, like you’re explaining it to a friend at a dinner party.
I’m Jessica, co-founder and CEO of Uprise. We’re a premium tax firm for complex earners: people with a small business, real estate, or stock comp bouncing up and down all year. They’ve graduated beyond TurboTax, but the Big Four is out of reach. So they’re stuck in a messy middle — and it’s getting worse as independent CPAs retire and leave people without great options. We do tax filing plus year-round advisory, embedded inside the platforms and advisor relationships clients already trust.
What problem were you personally frustrated by that made you think “someone needs to fix this, and that someone is me”?
It wasn’t tax at first. I grew up in fintech — I started at Wise in 2015. Over the years I watched the same pattern repeat: customer-first products coming in to serve people the legacy players had been underserving for years. I came to believe that’s the most important work in this industry. And that it’s nowhere near finished.
It was only after doing advisory work for complex earners that the tax problem came into focus. For this audience, the vast majority of financial decisions we helped with came back to tax. And I had lived it myself — I got a tax notice in the mail, went for a second opinion, and found out my returns had been filed incorrectly for three years. That’s when I realized: tax wasn’t a side issue. It was THE issue.
What’s the biggest thing you’ve had to unlearn from your life before founding?
That there’s a right way to do things. Our entire education trains us to believe this — follow the process, get the grade. But as a founder, the only thing that matters is the outcome. I argue with myself about this constantly: the old Jessica who wants to do it the perceived correct way, versus the founder Jessica who’s learned you don’t get a sticker for how you did it.
We’re so proud to have Jessica as part of our portfolio!
