Leap Forward

This summer, Leap Forward is a short break. We’ll be back this fall with more episodes.  Listen for a look back on Season 1 and a taste of what’s next, including a family crisis over a wiped thesis, and some very big ambitions to change the way we think about energy.

Live streaming feels inevitable now. But it started as what Michael Seibel called a "dumb idea." In this episode, Michael traces the unlikely path from a post-Yale road trip to a 24-hour streaming experiment called Justin.tv. Years of pivots and spin-outs later, it grew into Twitch and created the $100 billion live streaming market that's now part of daily life.  But first, it had t...

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...

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...

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 b...

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...

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 Hai...

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 busi...

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 al...

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...

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 actua...