
49 segments available
Learn how the CEO of Y Combinator Garry Tan wrote his way to success in the startup world — and how you can, too. Writing is (and has always been) Garry’s #1 tool to excavate his identity and discover his purpose. In his own words, “Writing is the most potent form of representing your own experience.” TIMESTAMPS: 00:00:00 Intro 00:00:40 Garry's early days on the internet 00:01:40 Garry's underground newspaper 00:04:40 X / Twitter 00:05:00 Early childhood and education 00:08:30 Finding identity 00:12:00 Internet obsession 00:15:00 YouTube scripts 00:17:00 Shilling, marketing, and zero cringe 00:20:00 Online forums like Reddit and Hacker News 00:22:00 Garry's design background 00:24:45 Garry's web development background 00:26:30 Human attention and Reddit 00:27:25 Advice for Y Combinator applications 00:29:20 School 00:30:30 Documentation 00:32:10 Influencers and Y Combinator 00:33:20 Effective Communication 00:34:45 Peter Thiel 00:36:30 Vulnerability and Novelty 00:38:00 Stanford University 00:41:20 Novelty 00:42:45 Building a brand 00:44:55 YouTube 00:48:45 Writing at Y Combinator 00:49:45 Y Combinator writers like Paul Graham and Sam Altman 00:50:55 Learn from successful founders 00:54:45 Human-computer interactions 00:56:30 Writing online SPEAKER LINKS: Website: https://www.ycombinator.com/people/garry-tan Twitter: https://twitter.com/garrytan Instagram: https://www.instagram.com/garrytan/ Blog: https://blog.garrytan.com/ YouTube: https://www.youtube.com/@GarryTan Linkedin: https://www.linkedin.com/in/garrytan WRITE OF PASSAGE: Want to learn more about the next class Write of Passage? Click here: https://take.writeofpassage.school/writing-sprints PODCAST LINKS: Website: https://writeofpassage.school/how-i-write/ Apple: https://podcasts.apple.com/us/podcast/how-i-write/id1700171470 Spotify: https://open.spotify.com/show/2DjMSboniFAeGA8v9NpoPv ABOUT THE HOST: I’m David Perell and I’m a writer, teacher, and podcaster. I believe writing online is one of the biggest opportunities in the world today. For the first time in human history, everybody can freely share their ideas with a global audience. I seek to help as many people publish their writing online as possible. How I Write is a podcast by Write of Passage // Production by Adam Soccolich
Garry Tan discusses the fundamental reason behind writing: to leave notes for one another and to live multiple lifetimes through shared experiences. He emphasizes the importance of being unique and authentic in a world dominated by the internet, suggesting that writing is a powerful tool for self-expression and connection.
"We write in order to leave behind notes for one another. I mean, how do we live 10, 000 lifetimes in one? What advice do you have for writing a good YC application? If I can learn something immediatel..."
Reflecting on his early days, Garry Tan shares his experience of creating an underground newspaper in seventh grade. He highlights how this endeavor allowed him to engage with complex societal issues, fostering a sense of agency and influence among his peers, which shaped his identity as a writer.
"This was before the internet. So like 1991 92. Um, you know, there are these things called bulletin board systems. Sure. And so that was sort of the proto internet. And, you know, being really, really..."
Garry explains how his early writing experiences, including discussions on social justice, helped him develop a passion for ideas and the importance of education. He reflects on how these formative moments contributed to his understanding of writing as a means to express opinions and influence society.
"You know, what if you were going to make a newspaper, what would you write about and it was all kinds of stuff Like I remember one of my best friends at the time wrote about how you know Pete Wilson a..."
Transitioning from writing to coding, Garry recounts how he learned to create web pages while continuing to publish his underground newspaper. He discusses the significance of being recognized for his contributions and how this early success laid the groundwork for his future endeavors in technology and writing.
"you know, 8 11 sheets, it would be like 10 or 15 pages of just, like, writing by the kids in, like, our English class, and, uh, she'd photocopy, you know, 150 copies and then every single person in ou..."
Garry reflects on the influence of literature in his life, mentioning authors like Kerouac and Kundera. He shares how reading provided him with wisdom and understanding during challenging times, shaping his perspective on life and the human experience.
"Yeah, it's, it's a good line. So then, so you go from, you go from that, and then you're the editor in chief at this magazine called Express? Oh, it's just our school newspaper in high school. So, um,..."
Garry shares a humorous anecdote about how reading 'The Fountainhead' by Ayn Rand impacted his college application essays. He discusses the unexpected consequences of this experience and how it shaped his understanding of writing and self-presentation.
"with the mind very early. Tell me about that. I guess I always sort of expected That we are, we write in order to leave behind notes for one another, um, you know, that's what writing is to me. I mean..."
In this segment, Garry opens up about his childhood struggles with love and identity, influenced by his family dynamics and personal beliefs. He discusses how these experiences fueled his desire to explore deeper questions about existence and purpose through writing.
"What do you mean? Uh, I was, I think, December of, what, 1998, and I was doing, uh, my college essays, and, um, I had sent off my Stanford one already, and then, uh, I remember being in the Fremont Pu..."
Garry emphasizes the role of writing in helping him find a sense of agency and identity. He explains how articulating his thoughts and feelings allowed him to understand his place in the world and the importance of individual expression.
"synesthesia Who knows what it means, but I mean by the synesthesia Oh literally like I can see like a halo around this book and that and like for whatever reason I Needed to read that book at that mom..."
Garry discusses the challenges of navigating cultural identity as a Chinese American in a collectivist society. He reflects on how writing served as a means to assert his individuality and develop a personal narrative amidst cultural expectations.
"But my dad also really struggled with alcoholism. And so, um, you know, whether it was love of family or Actually, growing up, I was a rabid atheist, um, and I really struggled with the idea of uh, th..."
Garry shares his thoughts on the evolution of personal blogs and their significance in the digital age. He argues for the importance of personal expression and the need for more individuals to share their stories online, highlighting the transformative power of the internet.
"I tried to find solace in, uh, the great writers, you know, in, in Kerouac, in Kundera, in like whatever, in even in Rand, right? Like in anything I could find, um, I was trying to understand, like, w..."
In this segment, Garry discusses his belief that the internet is still in its early stages of transforming communication and information sharing. He reflects on the ongoing changes in workplace dynamics and the potential for further evolution in how we connect and share ideas.
"uh, one of the more salient things for Asian Americans often is like this idea of existing of like, and I distinctly remember what do you mean by existing, just, um, Of being? Of being, of, of being a..."
Garry Tan reflects on the transformative power of personal blogs in the digital age, emphasizing their importance in sharing ideas and experiences. He notes that while the momentum of personal blogs has stalled, they remain a vital tool for self-expression and connection in an increasingly digital world.
"intuitive sense of That the internet was gonna radically reshape both economics, especially the economics of information, and that personal blogs were gonna be this liberating thing. Now, I actually t..."
Garry discusses a memorable interview with David Bowie, who described the internet as a 'shift in consciousness.' This segment explores the profound impact of the internet on society and how it continues to evolve, suggesting that we are still in the early stages of this digital revolution.
"Like anytime you walk into most workplaces, like if you leave Silicon Valley or you leave, like, even the top four or five, like, sort of, you know, intelligentsia cities in America and you walk into ..."
In this segment, Garry delves into the historical influence of media technology on society, drawing parallels between the rise of mass literacy and the shaping of national identities. He references Peter Thiel's early investment in Facebook and its connection to societal dynamics, highlighting the role of media in amplifying social behaviors.
"Yeah, have you ever seen the clip with David Bowie talking to that BBC interviewer? Yeah, I love it. Yeah, he's like, The BBC interviewer is like, Yeah, so I don't understand why you keep saying this ..."
Garry emphasizes the significance of writing as a personal expression, particularly in the context of his own memoir. He discusses the struggle between authenticity and the temptation to use a ghostwriter, asserting that true writing must reflect one's own voice and experiences.
"and so, um, I'm really taken aback by, uh, the whole idea that, Peter Thiel invested in Facebook very early because of his, um, you know, studying of Girardian writing. Yeah. Simply because, yeah, lik..."
In this introspective segment, Garry shares his belief that creation is essential for establishing one's identity. He reflects on the fulfillment he derives from expressing himself through writing and design, suggesting that without creation, he feels a sense of emptiness.
"Otherwise, you know, it's someone else's experience or someone else's beliefs that are sort of, uh, merged with my own. And then to what we were saying earlier, like, I do think about creation as, um,..."
Garry discusses the balance of authenticity and cringe in marketing, proposing that a certain level of cringe is necessary for genuine expression. He shares his approach to promoting remarkable individuals and ideas, emphasizing the importance of being true to oneself in the process.
"Yeah, I'm totally with you. I guess as an investor, the other weird thing that I really like is that, um, I want people to know that when I, you know, for whatever reason, the internet seems okay with..."
In this segment, Garry expresses his preference for novelty and the excitement of meeting diverse individuals. He reflects on how different life experiences can teach valuable lessons, reinforcing the idea that embracing uniqueness enriches personal and professional interactions.
"be authentic. Being yourself is always a little bit weird. That seems interesting. Let's pull on that thread. I guess that's what I like about just meeting all sorts of people. And you know, my job no..."
Garry shares insights on the role of online forums like Reddit and Hacker News in shaping the internet. He likens the internet to a global brain, where individual contributions and interactions create a collective consciousness, highlighting the importance of community in digital spaces.
"Like, if I was just, um, I mean, maybe this is why earlier in my career, like, When I graduated from college studying computer engineering, like I applied to the gap thinking like, oh, maybe I could b..."
In this segment, Garry recounts his experience as a moderator for Hacker News and discusses the significant impact of downvotes on community dynamics. He reflects on a bug that temporarily disabled downvotes, leading to a shift in the platform's atmosphere and user interactions.
"What have you learned about forums? And how they have shaped the Internet. I think it goes back to what we were saying earlier. Basically, the Internet's turning into a global brain literally. Um, and..."
Garry shares a thought-provoking statistic about the energy consumption of data centers, comparing it to the energy usage of a human brain. This segment explores the implications of our digital infrastructure and its parallels to biological systems, prompting reflection on the future of technology.
"weren't being counted, um, and I think it's just very interesting, like, um, we're sort of at this moment, I'm very obsessed even today about, like, new types of organizations, because, you know, I th..."
Garry discusses how his background in design informs his writing process. He draws parallels between effective design and writing, emphasizing the importance of creating engaging experiences that resonate with audiences, much like a well-hosted party.
"Yeah, that sounds smart. Therefore, it's true. I mean, but I think that there's something to this. How does your background as a designer shape your writing? I think design is very helpful in that. It..."
In this reflective segment, Garry looks back at his early writing style, acknowledging its flamboyance and evolution over time. He discusses the importance of pushing boundaries in writing while recognizing the value of clarity and authenticity in effective communication.
"I remember when I was spending a lot of time working with companies, like, almost all of it was. Uh, a lot of people think, think of design. They think of, Oh, what color is the button or, you know, s..."
Garry explains how his experience as a web developer shapes his approach to writing. He highlights the importance of design in creating engaging content and the technical challenges of early web development that influenced his understanding of user experience.
"I actually, uh, left to my own devices, I probably would have studied, uh, rhetoric at UC Berkeley instead of computer engineering at Stanford. Is that right? Yeah. No complaints over here. It all wor..."
Garry Tan elaborates on the fierce competition for human attention on the internet. He discusses the challenges of creating engaging web content that stands out among countless distractions. This segment underscores the necessity of making an immediate impact within seconds of a user's visit.
"Like it sort of loads and it's there. Um, you know, the opposite I think of is, you know, for a wedding, you have to get very fancy stationery. Right. Like a webpage, um, is actually somewhat adversar..."
Garry offers advice on crafting compelling applications for Y Combinator, stressing the importance of originality and clarity. He highlights the common pitfalls of redundancy in startup ideas and encourages applicants to embrace their uniqueness. This segment serves as a guide for aspiring entrepreneurs seeking to stand out.
"What advice do you have for writing a good YC application or just broadly any grant application or something like that? I guess personally, I always like, um, very plain spoken and then if I can learn..."
In this thought-provoking segment, Garry discusses the importance of individuality in writing and creativity. He contrasts societal pressures to conform with the necessity of embracing one's unique perspective. This conversation encourages listeners to lean into their distinctiveness and authenticity.
"hanging out with the bar, at the bar with my friends. That's true. Conformity is actually totally what society, uh, teaches you to do. Of course. And most people have to write in sort of a school cont..."
Garry explains the significance of good documentation in technical writing and its parallels to effective essay writing. He emphasizes the need for clarity and understanding, suggesting that the best documentation anticipates user struggles. This segment highlights the importance of user feedback in refining written communication.
"Mm hmm. How does good documentation work as someone who has no experience coding? What, how does good documentation read and is it different from reading an essay? Hmm. I guess documentation is really..."
In this segment, Garry discusses the intersection of writing and startup success. He emphasizes that great writers can simplify complex ideas, making them accessible to a broader audience. This ability to communicate effectively is crucial for convincing customers and investors alike.
"How many? Influencers have you invested in at YC and is that a path you want to go down more or is? writing and running startups directly Oh, I think they work really well together, honestly. Um, I th..."
Garry reflects on the influence of writing, using examples from the Bible and Peter Thiel's impact at Founders Fund. He explores how powerful writing can create a lasting presence and influence, even in the absence of the writer. This segment delves into the idea that narrative shapes perceptions and decisions.
"What have you learned about effective writing from reading the Bible? I guess the number one thing from Girard is actually just this idea of monesis period that, um, writing is, um, the most potent fo..."
Garry discusses the dual elements of effective writing: vulnerability and novelty. He shares personal experiences that illustrate how being open and authentic can resonate with others. This segment emphasizes the balance between sharing personal truths and maintaining a sense of safety in writing.
"But at the same time, he's not always in the room, and if you talk to people who are there, they say, yeah, Peter's not in every single meeting. And that idea that through writing, through narrative, ..."
Reflecting on his college days at Stanford, Garry shares his struggles with vulnerability and authenticity. He recounts awkward moments of oversharing and the challenge of finding the right balance in expressing oneself, particularly in a high-achieving environment.
"time, like, I mean, it's crazy vulnerable, right, like, things that could open you for attack or, um, or close people off, um, I think you have to be careful with it, right, like, on the other hand, f..."
Garry emphasizes the significance of sharing personal experiences to create deeper connections with others. He discusses how vulnerability can lead to a sense of community and understanding, allowing individuals to feel less alone in their struggles.
"And, um, you know, I've, they're definitely like, absolutely obsessed with words. And sometimes I would, like, Yes, I think I, like, sent some, uh, you know, overshare type emails to, um, I think my p..."
In this segment, Garry explains why he writes: to verbalize his experiences and gain a sense of grounding. He reflects on how writing can articulate feelings and thoughts that are often difficult to express, fostering a sense of connection with readers.
"I did not mean that as part of the metaphor. It might be this, it might be vulnerability, right? But so far, um, I was saying earlier, uh, you know, I have this weird tendency of doing, uh, therapy wi..."
Garry discusses the importance of community and connection, particularly in small, trusting groups where individuals can share their fears and challenges. He highlights how the internet has enabled these connections, making it possible to find support and understanding in a broader context.
"A lot of the writing that has moved me the most was some feeling that either I didn't feel alone, or somebody was putting words to an experience that I'd only felt but never actually verbalized. And I..."
Garry contrasts the obsession with novelty in writing with the importance of authenticity. He advises that new writers should focus on sharing common experiences rather than trying to impress others, emphasizing that the most impactful writing often stems from relatable, everyday truths.
"How crazy is that? Yeah, well, we talked about vulnerability talked about novelty. I guess I think people are really obsessed with novelty. And when people first start writing, um, they're not really ..."
In this segment, Garry reflects on the challenge of maintaining authenticity while establishing a personal brand. He discusses the balance between evolving as an individual and the need for consistency in creative expression, drawing parallels to the pressures faced by artists and creators.
"All creative acts really are, like, sort of establishing, you know, you as an individual. Yeah. Sort of sounds like artistry at that point. How do you think about the establishment of you as an indivi..."
Garry shares his philosophy on creativity, likening it to the intensity of filmmaking. He discusses the pressure to produce meaningful work quickly and the emotional investment required to create content that resonates with audiences.
"one body of work and then boom, you're a success. And within, you know, 12 or 18 months, you got to hit them with like the next thing. And how could you do that? That would like match that first, like..."
Garry reflects on his journey as a creator, expressing pride in his ongoing work rather than focusing solely on past achievements. He emphasizes the importance of continuous creation and the relationships built with audiences through shared experiences.
"Yeah. So, um. YouTube videos? The obvious one is there's my top viewed video is, uh, how to get rich. And, uh, I almost feel silly. It seems to be a fairly effective title. Yeah, but I feel good about..."
Garry discusses the scale of communication at Y Combinator, highlighting the importance of writing to connect with a vast community of founders and alumni. He emphasizes the need to treat these communications as media, aiming to foster connections and support among a diverse group.
"Yeah. But, I mean, that's the tricky thing, like, I came up through blogs, I came up through YouTube videos, like, these things are not books. Mm hmm. Like, they are, uh, almost meant to be, you know,..."
Garry reflects on the strong writing culture at Y Combinator, mentioning influential figures like Paul Graham and Sam Altman. He discusses how clear thinking and effective writing contribute to the success of founders, marking a cultural shift that YC aims to promote.
"Like this past weekend we had 2, 700 people together and um, it felt like a massive reunion cause literally everyone who you could meet, we all had the same set of values and um, it felt like home. We..."
Garry shares insights on what writers can learn from successful founders, emphasizing the importance of having a clear vision and purpose. He contrasts superficial motivations with deeper, more meaningful goals that drive impactful entrepreneurship.
"celebrating. Well, we need to keep going. I mean, the outcome is that we just want more abundance. Like, we just want more people to actually succeed. Um, I think the thing that got me was realizing w..."
In this introspective segment, Garry discusses the challenges of understanding one's identity through writing. He reflects on his personal journey and the significance of confronting past experiences to carve out a clearer sense of self.
"There's like a why that is way beyond like sort of the classic, you know, tropes or the classic things that you might run across. Like when you meet most people, it's like, Oh, I want to be more famou..."
Garry talks about the emotional experience of publishing personal essays that reveal intimate aspects of his life. He describes the destabilizing effect of sharing his identity with the world and the compulsion to express himself through writing.
"Like, all of these things were happening to me. I had, like, certain skills. I had, you know, certain things that I, like, didn't understand. Um, I was dealing with, like, something that, you know, ho..."
Garry explores the paradox of writing about personal experiences and how it resonates universally. He emphasizes that by delving into individual emotions and struggles, writers can connect with a broader audience, highlighting the power of authenticity in storytelling.
"Deep things that had happened in my life beliefs that I hadn't made sense of things that felt intimate and private and revealing and then I published it and I just shared it with the world and Of cour..."
In this segment, Garry discusses the concept of human-computer symbiosis and the evolution of technology in writing. He reflects on how computers can enhance human capabilities while relying on human intuition, drawing parallels to the development of large language models.
"experience. There's something paradoxical and profound about that. I guess that's what media is to me. It's actually less the like outcome of some process and more about building relationships. Unders..."
Garry reflects on the historical context of writing and communication, discussing how the internet has democratized access to publishing. He shares his excitement and apprehension about the current landscape of online writing and its potential for broader influence.
"at while relying on, um, you know, human intuition and reasoning. And I guess what's tricky is now that we say it, the large language model might be beyond it because, you know, there are aspects of t..."
Garry highlights the significance of anonymous writers and their influence in today's digital landscape. He celebrates the original promise of the internet as a platform for diverse voices and perspectives, emphasizing the power of online writing.
"been with you the entire time. And as I looked at your career through the lens of that kid, I just saw this fire that radiates everything that you do, and had I not seen that. I would have thought abo..."
In the closing segment, Garry expresses gratitude for the opportunity to share his thoughts on writing and identity. He reflects on the enjoyable nature of the conversation and the importance of discussing these themes in the context of entrepreneurship and personal growth.
"right? So, uh, but that was the beauty of it that, um, without their permission, you know, without their Having an editorial board come and see it like without having to, you know, have access to a pr..."