John Lilly has had a front row seat to almost every major shift in technology over the last thirty years, and he has sat in almost every chair while it happened.

He was a Senior Scientist at Apple in 1997, when the market cap was two billion dollars and most people assumed the company was finished. He co-founded Reactivity, later acquired by Cisco. He became CEO of Mozilla and led Firefox past 450 million users, running an open source nonprofit at a time when nobody else in Silicon Valley was doing anything like it. Then he spent over a decade as a General Partner at Greylock, where he led investments in Instagram, Dropbox, Figma, Tumblr and Quip. He sits on the boards of Figma, Duolingo and Nuro, and recently joined Gigascale Capital as an Advising Partner, backing companies rebuilding the physical economy.

In this conversation with Jessica Neal and co-host Jeff Markowitz, John walks through what he actually saw in the founders everyone else missed.

He tells the story of chasing Kevin Systrom for six months, wiring the money on a Thursday, and getting the call three days later that Instagram was selling to Facebook. He explains the moment a friend showed him Instagram and what clicked was not the filters, it was the distribution. And he describes meeting a 19 year old Dylan Field at a Starbucks in Palo Alto, telling him his product did not matter, and then spending the next decade watching him prove it wrong.

He is also honest about the parts that are harder to hear. Why some partners at Greylock wanted Dylan replaced. Why he thinks micromanaging the right things is a feature of good leadership, not a flaw. Why he does not tell CEOs anything, and what he does instead. And why, at a moment when OpenAI and Anthropic are pulling talent out of every company on earth, the answer is not matching the money.

He closes with something a colleague at Mozilla told him years ago that he still carries: we had a chance to make the world we wanted, and we did it.

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WHAT WE COVER

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THE FOUNDER QUESTION

→ How John spotted Dylan Field at 19
→ Why recruiting senior people is the strongest early signal
→ The trait every great founder shares: relentless about getting help
→ Why non-defensiveness beats raw intelligence
→ The lunch where they told Dylan he had to build a go to market

THE INVESTMENTS

→ Chasing Kevin Systrom for six months
→ The underwater photographer who explained Instagram to him
→ Why the network mattered and the filters did not
→ The four day flip to Facebook and what he told his LPs
→ The Adobe Killers that came before Figma and why this one was different

LEADERSHIP AND SCALE

→ Going from 12 people to a quarter of the internet at Mozilla
→ Why he never learned the delegation lesson everyone teaches
→ Larry and Sergey reviewing every resume and what that signals
→ Learning to be simpler in your message as you grow
→ Deciding you would rather be successful than comfortable

THE TALENT WAR

→ Why every great person is now a free agent
→ The spreadsheet exercise he gives every CEO
→ Tour of duty and the bilateral deal between company and employee
→ Never making an offer until you know it will be accepted
→ Why money is rarely the only reason people leave

THE CURRENT MOMENT

→ Why leadership now means stability without pretending anything is stable
→ The collision of faster scaling and total vulnerability
→ Why org size no longer scales with impact
→ Alpha nerds, Tim O'Reilly, and following the most technical people around
→ Investing in transformers, copper recycling and rare earth supply chains
→ Why none of the AI future is settled and it is all still to play for

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CONNECT WITH JOHN LILLY

LinkedIn: linkedin.com/in/johnlilly

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Truth Works is hosted by Jessica Neal, former Chief Talent Officer at Netflix, with co-host Jeff Markowitz.