Leap Forward

From Design Thinking to $1 Billion Healthcare IPO: Omada’s Sean Duffy + His Former Boss

When Sean Duffy was a medical student interning at IDEO, he came face to face with a hard truth: millions of Americans with chronic disease weren’t getting the support they needed to actually get healthier. In this episode, Sean tells the story of how an unlikely mix of medicine and design thinking led him to spend a year refining an idea that would eventually become Omada - a company that’s since helped over a million people and gone public. We also talked to his former boss at IDEO, David Webster, about the intern application that fell on the floor, and the rare combination of expertise that Sean brought to a huge problem. It’s a story about how ideas don’t arrive fully formed, but get found, tested in strangers’ living rooms, and built through steady commitment.

Created By Humans: Trip Adler & His Dad

Scribd took off fast - then hit a wall that nearly broke the company. In this episode, Trip Adler tells the story of building the “Netflix for books,” only to face the moment every founder dreads: when everything comes tumbling down, as growth stalled and much of the team walked away. But while others quit, Trip stayed - spending years rebuilding the company and eventually growing it to more than $300 million in revenue. We also talked to his dad, John Adler - an entrepreneur himself - about the question at the heart of it all: how do you decide if a company is still worth fighting for? Trip’s journey, from Scribd’s hard earned success to starting Created by Humans, shows that sometimes making it simply comes down to not giving up.

Bobbie: Laura Modi & Her Mentor

It’s common for a tech startup employee to start their own tech startup. It’s rarer for a startup employee to go on to build a baby formula company.  When Laura Modi showed up at Walgreens at 11pm to buy baby formula for the first time, she felt ashamed and afraid. So she started a company that didn't just create a healthier formula, but built a community, participated in activism, and made business decisions that didn't sell more, but grew trust. Bobbie became the fastest growing formula company since the 1980s. And a major source of Laura’s business savvy? Her time at Airbnb, under the hospitality legend Chip Conley, who transformed her understanding of a “product.” In this episode, the unusual story behind a fast-growing startup that built a deeper social movement.

Plug: Jimmy Douglas & His First Investor

Jimmy Douglas didn’t learn how to fundraise in business school. He learned it at 14, selling vacuum cleaners on commission to help pay the bills after his father - an entrepreneur who once ran a semiconductor company - passed away.  In this episode, Jimmy tells the story of growing up on a Christmas tree farm in Oregon, feeling out of place, working sales jobs to make rent, and eventually leading used car sales at Tesla before deciding, on paternity leave, to finally start his own company: Plug. A marketplace for used electric vehicles that has raised two wildly successful rounds of funding.  We also talked to his first investor, Ann Miura-Ko of Floodgate, about what stood out about Jimmy that made her want to chase him down to start a company. Jimmy’s story shows how our most difficult circumstances shape our sharpest skills, and how good founders avoid getting attached to their first idea.

Segment: Peter Reinhardt & His College Roommate And Cofounder

Peter Reinhardt co-founded the analytics firm Segment, and built it into a company that sold for $3.2 billion. But before it worked, everything else they tried didn’t.  In this episode, Peter and his co-founder, Calvin French-Owen, share their humbling story of finding product-market fit: hospital panic attacks, a crisis of faith, and how, with just a few weeks of runway left, they published a Hail Mary concept on Hacker News -- that blew up. It’s a story about how giving up control finally led them to build something people wanted. And forced them to mourn their attachment to vision. Since then, Peter has only increased his ambitions: he launched another successful company, Charm Industrial, that permanently sequesters carbon underground, and is also the CEO of Revoy, that converts semi-trucks into electric vehicles.