David Rusenko interviews the founders of companies like Airbnb, Y Combinator, and Twitch, alongside the people who first believed in them. A mom. An early boss. A college roommate. Together, they reveal the intimate, unpolished stories of how successful companies actually get built, and why it rarely looks the way you might expect.
How Reddit Was Born, Sold, Broken…and Rebuilt: Steve Huffman & first employee Chris Slowe
Today, Reddit is the sixth largest website in the world. But it almost stopped existing. A few times. In July 2015, more than 2,000 subreddits went dark, the CEO resigned, and Reddit looked like it might not survive. At the center of its dramatic turnaround is the company’s founder, Steve Huffman, who returned to Reddit to save it from itself.
In this episode, how Reddit went from a tiny apartment in Cambridge to become one of the most important spaces for conversation online. And how they’re wrestling to keep that conversation human in the age of AI.
8 Jul 2026
Season 1: What We Learned
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.
24 Jun 2026
The Strange Origins of Live Streaming: Twitch's Michael Seibel & His Co-founder Justin Kan
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 to survive: the swattings, the stretches with only weeks of cash left, and a reality show built around one...
10 Jun 2026
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 ...
27 May 2026
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...
13 May 2026
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 ...
29 Apr 2026
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 compan...
15 Apr 2026
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 fina...
1 Apr 2026
Airbnb: Nathan Blecharczyk & Their First Advisor
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...
25 Mar 2026
Mercury: Immad Akhund & His Mom
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 - rea...
25 Mar 2026
Y Combinator: Jessica Livingston & Paul Graham
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 sk...
5 Mar 2026
Season 1 Trailer
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.
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