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.

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.

Nathan Blecharczyk turned a social experiment into Airbnb: a company that would remake travel. But first, it had to survive.

Before it reshaped an industry, Airbnb looked like an idea that shouldn’t work. In this episode, Nathan retraces the moments that almost killed the company: convincing people to trust a stranger in their home, handling their first major crisis, and watching 80% of their business evaporate in a global pandemic. But with each emergency, he developed the philosophies that would engineer real trust in the company.

Alongside Sam Angus, the first advisor who believed in their idea, Nathan shares how they overcame one of humanity’s most instinctual fears and built something that refused to die.

After more than a decade of mixed success with tech startups, Immad Akhund decided to try something even harder: starting a bank.

Today, Mercury is valued at $3.5 billion and serves thousands of startups. But the road to get there was long and rocky. Immad shares how moving from Pakistan to the U.K. left him struggling to belong, how a string of failures nearly led him to leave entrepreneurship altogether, and what kept pulling him back. We also hear from the person who believed in him - really believed in him - long before anyone else: his mom.

Y Combinator is the legendary startup program that has launched more than 5,000 companies, collectively worth over a trillion dollars. Household names like Airbnb, DoorDash, Coinbase, Instacart, and Stripe. And without Jessica Livingston, YC would not exist today.

In this episode, we dive into Jessica’s unlikely origin story. She and her husband and co-founder Paul Graham share never-before-heard stories from YC's founding: the winding career path that gave Jessica an unlikely but perfect skill set, how a husband and wife built one of the most important institutions in startup history, and the secret to what Paul calls "the magic of Y Combinator".

Leap Forward is a show about founders and the people who believed in them before anyone else. Each episode traces the real story behind a company you might know, both from the perspective of the founder, and someone who believed in them before anyone else, like a first boss, early investor, college roommate, or even a parent. Through candid conversations we uncover the story of how companies actually get built, and why it rarely looks the way you might expect.