Garry Tan, CEO of Y Combinator, traces his path from a bullied 7th grader who gained social standing by publishing an underground newspaper to a leader who believes writing is the foundational skill for founders, investors, and anyone seeking to live a meaningful life. The episode explores how writing shaped his identity, his career, and his philosophy on startups, communication, and the internet.
Writing as identity and survival
Garry’s earliest experience with writing was creating an underground newspaper in 7th grade using Aldus PageMaker on a PC his parents provided.
His teacher photocopied 150 copies for the class, and suddenly the “short, nerdy, shrimpy kid” who got shoved into lockers became someone people looked up to.
He describes this as the origin of everything he is now known for: having influence, curating ideas, and building a platform.
Writing gave him a sense of agency and individuality, especially as a Chinese American navigating the tension between collectivist family culture and the individualistic Western world.
He struggled with the question of whether he, as an individual, truly existed and mattered.
Putting words to the page made his experience “indelible and available for others” and helped him develop a felt sense of who he was over 20 to 30 years.
He had a rough childhood marked by his father’s alcoholism and abuse, and he retreated into books as a way to understand how other people thought and to escape.
He read voraciously and at random, from Kerouac and Kundera to Ayn Rand’s The Fountainhead, which he credits with making his college essays so off-putting that he was rejected or waitlisted everywhere except Stanford.
He was a rabid atheist as a young person, struggling with theodicy, the question of how a loving God could create a world of such injustice and scarcity.
The internet as a consciousness shift
Garry was obsessed with the internet from age 12, seeing it as an inevitable force that would reshape the economics of information and democratize communication.
He references David Bowie’s famous 1999 BBC interview where Bowie called the internet “an alien life form” and a “shift in consciousness,” and Garry agrees with that framing.
He sees the internet as a global brain where each person is a neuron, and social media is the mechanism of communication between them.
He draws on Girardian theory (mimesis and scapegoating) to explain why platforms like Facebook and Reddit are so powerful: they are extreme carriers of mimetic desire.
Peter Thiel invested in Facebook early based on his study of Girard.
Yuri Milner once told YC that data centers consume about 10% of the world’s energy, roughly the same as the human brain.
He believes the revolution is still coming: most workplaces outside a few elite cities still operate on phone calls and steak dinners, and software has not yet fundamentally changed those dynamics.
Forums, voting, and the shape of online discourse
Garry briefly moderated Hacker News and reveals that Paul Graham once introduced a bug where downvotes weren’t counted for a month or two.
During that period, the consciousness of Hacker News changed dramatically, becoming nastier and scarier.
This illustrates how small design decisions in forum software can profoundly shape community behavior.
He sees forums like Reddit and Hacker News as mechanisms for upvoting what is worthy, interesting, and valuable, a role he now plays at scale through his own platform.
He describes his Twitter/X feed as a “distributed newsroom” that curates voices from dozens of group chats and people who would normally never get attention, much like his old underground newspaper.
Design and writing as paired disciplines
Garry studied computer engineering at Stanford but would have studied rhetoric at Berkeley if left to his own devices. He worked at Adjacency, the design firm that figured out how to make webpages look like magazines in 1996.
He sees design and writing as a matched pair: both are fundamentally about social experiences.
Great design is like a great party: someone greets you, makes you feel welcome, introduces you to friends, takes your coat, hands you a drink.
Writing is the most important part of great interaction design.
He emphasizes that every webpage is in perfect competition with every other interesting thing on the internet, including the front of Reddit and X. You have five to ten seconds or less to prove your value.
Vulnerability and novelty as the two elements of effective writing
Garry identifies vulnerability and novelty as the two essential elements of effective writing.
Vulnerability is a hack: sharing things that scare you or that people might not be okay with creates connection and gives others permission to be real.
He notes a strange inversion: being vulnerable when you have nothing is very different from being vulnerable when you have power and a platform. Early in his life, oversharing was awkward and off-putting; now, as YC CEO, being an open book allows people to see their own humanity reflected.
He publicly discussed his childhood trauma and abuse for the first time on a podcast, and found that it helped others integrate their own adverse childhood experiences.
Novelty does not mean impressing people you respect or being exhaustingly original like the Velvet Underground.
The most useful novelty is the stuff that comes up all the time but seems too obvious to say.
The best founders and writers focus on the commonplace, everyday problems and explain them clearly rather than trying to be avant-garde.
Writing for startups and YC applications
When reading YC applications, Garry prefers plain-spoken writing where he can learn something immediately.
The biggest problem is conformity: people describe ideas that have been tried thousands of times, and the writing blends together.
He advises founders to lean into their own weirdness and distinctiveness rather than writing to fit in.
He references Naval Ravikant’s idea that there is literally only one person who can be you, and in an internet-connected world, being uniquely yourself is a massive advantage.
He believes school is toxic for writing because it teaches conformity: write book reports, hit the middle of the bell curve, don’t stand out.
The internet age rewards the opposite: being “incredibly weird and unique and yourself and having the courage to do that is really, really important.”
Communication, influence, and being present without being there
Garry is deeply influenced by the idea that great writing allows you to be present in a room without physically being there.
He references Jesus as the ultimate example: his presence isn’t in his presence, yet he shapes the world every day through scripture.
He sees the same dynamic at Founders Fund with Peter Thiel, whose ideas and one-liners shape decisions even when he’s not in the room.
Thiel once forwarded an email from a Columbia CS senior to Garry with no comment; Garry hired him, and that person went on to become the CEO of Adapar.
He believes that in the internet age, you don’t have to market anything other than what you stand for and what you believe. Like-minded people will seek you out.
Creating at scale: YouTube, blogs, and parasocial relationships
Garry writes all his own YouTube scripts and resists using a ghostwriter because he wants his book or memoir to be truly his own words.
His most-viewed video is titled “How to Get Rich” and features an excerpt of Alan Watts on the nature of money, elevating a base search query into a philosophical idea.
He describes his creative output as a river: topical, top-of-mind, raw, and immediate rather than polished works crafted over years.
He has never made writing his primary thing; it has always been something he did on the side while grinding as a founder and engineer.
He believes his best work hasn’t been created yet.
He takes his parasocial relationships seriously: when someone approaches him who has watched 20 to 30 hours of his content, he feels obligated to learn about them and carry on the conversation.
He sees media less as the outcome of a process and more as a way of building relationships and understanding his place in the world while helping others understand theirs.
What writers can learn from successful founders
The best founders have a clear outcome in mind that goes beyond surface-level goals like fame or money.
Brian Chesky, for example, is driven by a deep “why” about connecting people.
Great founders, like great filmmakers, create until their fingers bleed and then create some more.
Garry’s advice for writers mirrors his advice for founders: confront the scariest question, which is who you are, where you came from, and what is deep down real for you.
The most resonant writing comes from zooming into your own individual reality, finding something small and specific, and magnifying the universal human experience within it.
He experienced this himself when he published a deeply personal essay and felt destabilized, as if he had carved out a part of his identity and shared it with the world, but felt compelled to do it anyway.
The democratization of writing and the promise of the internet
Garry was drawn to Milan Kundera’s concept of “graphomania,” the desire to write books to a public of unknown readers, because it captured what he felt as a teenager putting his zine online.
As a 12- or 13-year-old, having people take his writing at face value alongside CNN was intoxicating. “On the internet, nobody can tell you’re a dog.”
The internet removed the need for editorial boards, printing presses, and access to wealth, making thorough communication available to everyone.
He sees online writing as one of the places where the internet is at its best: anonymous writers influence people in Congress, and anyone can have influence from anywhere.
Thirty years later, he is amazed and a little scared by what is happening, but the core promise of democratization is being fulfilled.
