Rebecca Matchett is a serial entrepreneur, fashion innovator, and now tech founder who’s built her career around solving real-world problems. From co-founding Alice + Olivia to developing a patented women’s sizing system called TrioFit, Rebecca has consistently combined creativity and practicality to build impactful businesses. Now, she’s channeling that same drive into Synchrony—a new social app designed to help neurodivergent adults connect and combat loneliness in meaningful ways.

On this episode we talk about:

How Rebecca transitioned from fashion and retail into tech entrepreneurship

The story behind founding Alice + Olivia and what she learned about branding and innovation

Why ideas alone aren’t enough—and how to validate your market before launching

The challenges and benefits of self-funding vs. outside investment

How Synchrony is using technology to address the loneliness epidemic among neurodivergent adults

Top 3 Takeaways

Great businesses start by solving problems you truly understand—personal experience is a powerful indicator of market need.

Validation matters more than inspiration. Don’t build before you know who actually wants your product.

Bootstrapping gives you control, focus, and creative freedom that investors often limit.

Notable Quotes

“Ideas are easy. Execution and validation are what separate entrepreneurs from dreamers.”

“When you solve a problem for yourself, you’re often solving it for thousands of others.”

“Connection is the most human need we have—and we’re building a tool to make that accessible again.”

Learn more about your ad choices. Visit megaphone.fm/adchoices