John Buckman started with an idealistic vision inspired by Buckminster Fuller — build global conversations that make war impossible. He created Lyris, email software so successful that at its peak, one third of the email on the internet ran through it. But idealism has a shelf life when payroll is due. What began as technology for tracking jelly bean flavor preferences became a tool for political micro-targeting — suppressing paragraphs in newsletters based on a voter's tracked behavior. When John refused to sell to Philip Morris, his sales team learned a simpler lesson: don't ask the boss. And when the White House called asking for 24-hour tech support so they could send an email at 2 a.m. to declare war in Iraq, John knew he'd crossed a line he couldn't uncross. This conversation traces the full arc — from a childhood watching his parents buy a Porsche with a legal settlement while facing bankruptcy, to making $100,000 in shareware donations by age 18, to selling Lyris and creating Magnatune, a fair trade music company with legal provisions so radical his own lawyer resisted. Now in Hong Kong, John builds high-end espresso machines with Decent Espresso, trying to create something that outlives him — not because it makes money, but because it matters. What emerges is a portrait of someone who has wrestled with money, morals, and meaning across a dozen companies and three decades — and arrived at a deceptively simple philosophy: always be ready to die next year. KEY TOPICS COVERED The White House call: How building email software led to being part of the war effort — and the moral reckoning that followed.The slippery slope: How small compromises — feminist porn, political newsletters, tracking dots — compound until you wake up somewhere you never intended to be.The Porsche story: A childhood financial flashpoint — watching his parents buy a Porsche with a legal settlement while facing bankruptcy — that shaped everything.The $3 million rule: A VC's advice on the number you need to never work again, and why John didn't listen until it was almost too late.Fair trade music: Building Magnatune with legal poison pills so no acquirer could corrupt its mission — and convincing his lawyer to draft agreements that screwed the founder.Decent Espresso: Why giving someone a better cup of coffee in the morning became John's most meaningful venture.BookMooch: Creating BitTorrent for books, processing 10 million books a month, and receiving three lawsuit threats from Amazon."Why employees suck": John's contrarian argument that productive people should quit and sell the fruits of their labor instead of their time.The immigrant mindset: Growing up in France until age 10, arriving in the US without English, and choosing to be a nobody again in Hong Kong.Legacy and enough: Trying to build something that lasts five years after you leave — and why that's harder than it sounds. MEMORABLE QUOTES "And I realized at that moment, I was gonna be part of the war effort." 📍 Timestamp: 05:39 "It is absolutely a slippery slope. So I had a rule, which was no porn, no politics. That was our rule. Otherwise, freedom of speech." 📍 Timestamp: 08:49 "They're about to go bankrupt. And they got a settlement and they bought a Porsche." 📍 Timestamp: 21:19 "I've got the moving quality outlook of a Frenchman, but the business acumen of an American. And thank God it's not in reverse." 📍 Timestamp: 29:44 "I'm glad I found my limit. It's much, much worse to have that, could have been a contender." 📍 Timestamp: 01:06:35 "Always be ready to die next year." 📍 Timestamp: 01:12:07 "You gotta live well now. Even if you're working your brains out, if you're having a bad day, you gotta figure out how to get out of that because this might be all you got left." 📍 Timestamp: 01:12:30 ABOUT JOHN BUCKMAN John Buckman is a serial entrepreneur who has started over a dozen companies across email technology, music, publishing, and coffee. He built Lyris, email software that at its peak powered one third of the email on the internet, and sold it after the moral compromises of scale became untenable. He then created Magnatune, a fair trade music company with legally binding ethical provisions, and BookMooch, a book-swapping platform that processed 10 million books a month and drew legal threats from Amazon. Now based in Hong Kong, John runs Decent Espresso, a high-end espresso machine company competing with billion-dollar Italian families. He has served on the boards of the Electronic Frontier Foundation and Creative Commons. He grew up in France until age 10, didn't speak English until arriving in the US, and describes himself as having the quality-of-life outlook of a Frenchman with the business acumen of an American. His guiding philosophy: always be ready to die next year.
