awaken* newsletter: Garry Tan on Startups, Advocacy, and Overcoming Cultural Mindsets

Few people in Silicon Valley are as high-profile as Y Combinator’s President and CEO, Garry Tan. Garry has worn many different hats over his illustrious career. In addition to leading the world’s most successful startup accelerator, Garry was the 10th employee at Palantir, co-founded Posterous (one of the earliest blogging sites), founded Initialized Capital (a VC fund with over $3.2B AUM), and has even ventured into the world of politics, becoming a prominent activist in San Francisco local politics. I got the chance to pick Garry’s brain about how being Asian has affected his life, and I hope that his answers can help and inspire our readers. Without further ado:


My experience is that children of working class parents (especially Asian immigrants) tend to have a sticky mindset of scarcity–even when they improve their socioeconomic status. Garry has previously talked about his “$200 million mistake”. That is–he declined Peter Thiel’s offer to be a founding member at Palantir. To me, this seemed like a manifestation of this mindset, so I asked Garry how he overcame it:

I was able to realize that these things were two-way doors. Quitting a big tech company on good terms actually means you can go back anytime. There are one-way doors and two-way doors. For people who grow up with our upbringing, everything feels like a one-way door. But if you can recognize when that is wrong, then you have reclaimed some of the privileges those who come from money have by default.

The one-way vs two-way door framework is something Amazon founder Jeff Bezos has talked about extensively. You can hear him go more in depth here.

The stigma around mental health in the Asian community is another mindset that is gaining more attention. Personally, because my immigrant parents had to fight tooth and nail for survival, I don’t feel that I have the right to complain about my mental health since my life is comparatively easy. I asked Garry if this resonated with him and how he overcame this mental block:

I pretended I didn’t have any problems and spent a lot of time just trying to blend in, but in the end things about my childhood or unusual trauma-based reactions would pop up in my professional life. At some point I started going to therapy individually and it helped me immensely. All these things I didn’t have control over suddenly became something I could integrate and be aware of, and make better choices about. Carl Jung says if you don’t make the unconscious conscious, it will rule you, and you will call it fate. 

A third common mindset I see among Asian Americans is to keep their heads down and avoid rocking the boat, even if it means holding in their thoughts. Given that Garry is a very outspoken person, I asked him how he developed his confidence:

I remember in high school, I was editor of the school newspaper and noticed that students in our poorer high school got much more harsh sentences and expulsions for the same infractions that would get a slap on the wrist at the rich school. I was so angry about it, and I wrote an article exposing it but that was censored by my high school newspaper teacher. I was already going to graduate and go to Stanford so I let it slide, but deep inside me there was an anger at being silenced that I never forgot. Before newspaper, I would publish underground newspapers using Pagemaker and my English teacher would photocopy the newspapers for the class – it gave me a power I never forgot because otherwise I was the scrawny Asian nerd in the corner, but when I could channel the words of my community it gave me standing. I never forgot that.


On the topic of communities, I asked Garry about what motivated him to become a fierce advocate for the Asian community:

I feel strong solidarity with my Asian American community in San Francisco. We are a major part of the city but we are not seen. We are not heard. The local leaders would even denigrate our attempts at securing safety for our Asian American elders. Now I know I need to fight for those who don’t have a voice. One of the coolest things I found was a nonprofit called Dear Community that connects Asian Americans new to SF, often young professionals, to each other and to the existing SF Chinatown communities. It’s amazing to see smart driven people come together around that, and fight for our people in this city.

I also pointed out how he recently went to Singapore to attend a startup event called SWITCH, and asked him how he felt about the startup scenes popping up in Asian countries:

Startups are happening all around the world. You can learn from YouTube and the web. YC alums are everywhere in the world. I’m excited to see that what started in the Bay Area is now a global phenomenon and only growing.


On a friend’s recommendation, I asked Garry “Who are some non-technical Asian founder role models I might want to look towards? In terms of working at an early stage startup as a non-technical employee, what are the most valuable skills to learn?” Garry’s response kind of challenged the premise of my question:

In startups and in technology, being technical is a key strength. Be technical if you can be. And then be a polymath: it’s far easier for a technical person to pick up the soft skills than the other way around. 

In hindsight, I will admit that it seems silly to expect to get an outlier outcome (in the positive direction) in the tech industry if you aren’t willing to put in the effort to become technical. He got me on that one.

Lastly, I asked Garry the same question I ask all our guests–how does he think about his Asian-ness in the context of being a founder:

I didn’t think about it until much later. Frankly I tried to pretend it wasn’t an issue, even though there was absolutely a bamboo ceiling even for me. I was passed over for promotions and/or people didn’t think I was capable of doing what I have done. I would rage-quit jobs and it would work out, but I could see it going a different way. As a founder, I found that I needed to up-level my ability to speak up and speak out, and especially be as assertive as possible when I knew I was absolutely right. I had an unspoken desire that I was not even aware of for harmony, and without being aware of it I would sometimes self-abandon, and then be passive aggressive about it later. I don’t do that anymore, and it was a key step in my development as a leader. I wish I developed it earlier, and it was all because of unconscious programming from my childhood. 

The biggest lesson I took away from this interview was how the infallible and outspoken Garry Tan was not always so, and that at one point he was very much like the stereotypical Asian kid. Garry’s story proves that with self-awareness and determination, anybody can undergo tremendous growth and become an industry leader.


If you have an ambitious startup idea and want to be part of an amazing community of founders, apply to Y Combinator! Y Combinator runs batches twice a year–in the winter and summer. Applications for the summer 2024 batch are open, you can apply at

Thank you Garry for the interview!

Featured Image Source: Y Combinator