The Sweet Truth About Entrepreneurship: Lessons from Georgetown Cupcake Founders

Highlights from my conversation with the well-known DC cupcake entrepreneurs, Katherine Kallinis Berman and Sophie Kallinis LaMontagne. From baking at dawn to navigating a hit TV show, their journey is honest, inspiring, and full of lessons for any entrepreneur. Want to hear the full conversation? Listen to the latest episode of the Founding DC podcast.

What happens when you follow your passion and start your own business? 

On Valentine’s Day in 2008, sisters Katherine and Sophie took a leap of faith – and baked their way into one of Washington, DC’s most iconic food brands: Georgetown Cupcake. But behind the frosting is a story every entrepreneur should hear. 

Katherine and Sophie left stable corporate jobs to open their small bakery. They had no investors, no road map – just two ovens and a dream to build something by hand, from scratch. 

Their first week brought unexpected press from The Washington Post, followed by The New York Times. A TLC producer discovered them in line, leading to the hit reality show, DC Cupcakes, which aired globally for three seasons.  

Their journey seems sweet on the outside, but the real lessons lie behind the scenes. 

What challenges did they face as entrepreneurs? 

One of the biggest early hurdles? Too much demand, too fast. 

“Sometimes too much business can be as damaging as not enough,” Sophie said. 

Customers lined up around the block. They sold out daily, closed, baked more, and reopened. They maxed out credit cards, slept at the bakery, and did everything themselves. 

This is the stretch where many businesses break. But Katherine and Sophie powered through it by staying close to their purpose and each other. 

How did Georgetown Cupcake grow while staying true to its values? 

Katherine and Sophie made a bold choice: growth with intention. 

They turned down private equity. Kept baking everything from scratch. Chose family over scale. And they never lost sight of what made their brand special. 

“We’re probably leaving money on the table,” Sophie shared. “But it still feels like our business – and that matters more.” 

In a world obsessed with “more,” they chose enough. They chose to love what they do, every day. 

How do they manage working as sisters? 

Their secret? Radical honesty. No politics. No sugarcoating. 

“If one of us doesn’t like an idea, we just say it,” Katherine said. 

Their family bond gives them a superpower most co-founders don’t have: trust without fear. But their advice for solo entrepreneurs? Don’t go it alone. 

Build your circle. Find advisors. Create a space for real talk. Entrepreneurship is lonely, and community makes it bearable. 

Can you run a business and raise a family? 

Katherine was direct: “It doesn’t do women justice to say you can have it all. You can’t do everything, all the time, perfectly.” 

They spoke honestly about the guilt of working during family time—and the gift of flexibility that entrepreneurship can offer. When their mom was sick, they stepped back. When their kids need them, they can show up. 

That’s not a perk—it’s the point.  Entrepreneurship is about creating a life that fits your values. 

What do entrepreneurs need to know about discomfort? 

"You live in a constant state of low-grade panic,” Sophie said. “But once you accept that smooth days don’t exist, it gets easier.” 

That’s the unsung truth: chaos is the constant. Your business will always have fires to fight. The key isn’t eliminating them—it’s learning to lead through  them. 

“You’ve got to be willing to get on the roller coaster and ride it,” Katherine told me. 

What’s next for Georgetown Cupcake? 

The sisters are now thinking about the future of the brand—succession planning, legacy, and how to protect what makes Georgetown Cupcake special. 

They’re not chasing a billion-dollar exit. They’re building something to last. Something that still feels like them. 

What can other business owners and entrepreneurs learn from Georgetown Cupcake? 

Katherine and Sophie have shown that you don’t need to follow the standard playbook to win. 

They’ve built a company around: 

• Quality over quantity 

• Values over valuation 

• Purpose over pressure 

Their story is a masterclass in authentic entrepreneurship. And a reminder that growth, when intentional, is sweeter than scale for scale’s sake. 

How to hear my full conversation with Katherine & Sophie from Georgetown Cupcake? 

Don’t miss the interview with Katherine and Sophie on the Founding DC podcast. It’s a candid, behind-the-scenes look at what it really takes to build a beloved brand—and a meaningful life—on your own terms. Available HERE on all major podcast platforms.