Interview with Shaun Maguire
Shaun Maguire is venture capitalist. He is a partner at Sequoia Capital.
Roots
Contents
Max Raskin: Before I ask anything, what's the thing on your wrist?
Shaun Maguire: This is a lashon hara bracelet — speak no evil.
I went to Israel shortly after October 7th with Elon for the day that he was in the country. The day after, I went to one of the hospitals to meet with some wounded warriors — these were guys who lost limbs on the entrance to Gaza. There was some guy walking around with these bracelets and just giving them out to people. The bracelet for me means many things — it’s both a reminder of the war and a reminder of the actual concept of trying not to say bad things about other people.
MR: But you weren’t always connected to Judaism; how did that happen?
SM: Look, I'll tell you my journey. Growing up, I was not raised Jewish, and I didn't consider myself Jewish.
MR: Where did you grow up?
SM: I grew up in Orange County, California, in Irvine. I was raised Catholic with no religion at all, but I kind of thought I was Catholic. My dad's side was Catholic, and that was the dominant side in our family from a religious perspective.
But my mom's mom was a kohen. Her name was Amy Cohn. It’s a crazy story. My great-grandfather's name was Arthur Cohn. He was a geologist who went to UC Berkeley. He was a sixth-generation Californian Jew. His family came to California in 1849. My fourth great-grandfather on that side co-founded the first synagogue on the West Coast, Temple Emanu-El, in San Francisco. He was a defector early on, and then co-founded the second synagogue, which is Beth Israel. That fourth great-grandfather's name was Simon Simon.
MR: Simon Simon?
SM: Simon Simon was his name. You can see his name among the founding documents of these synagogues as one of the signatories.
MR: This is all your mom’s side?
SM: This is my mom's side.
Simon was one of the founding signatories of Sherith Israel. I think the reason they broke off was that Emanu-El was primarily German Jews who were very much going into Reform Judaism and most of the founders of Beth Israel were Polish Jews who were unhappy that it was becoming so Reform. My mom's family were some of the only German Jews that went to that other synagogue. Anyways, I had this in my family, but I didn't even know it as a kid. I'm a sixth-generation Californian.
So my great-grandfather who I was mentioning, Arthur Cohn, went back to Europe after graduating as a geologist and was basically doing oil exploration, primarily in the Black Sea. He lived in Romania and Poland and Germany at some point. Before the Holocaust, in the mid-1930s, he and his wife could really feel the antisemitism; they could very deeply feel it.
I don't know the full truth because I never met my great-grandmother, but the family story is my great-grandmother became a paranoid schizophrenic at this time in 1935, 1936. I know that's true because my mom spent a lot of time with her grandmother, my great-grandmother. The thing that's really complicated is the thing that triggered her schizophrenia her whole life afterwards was anything related to Judaism. So if someone wore a Jewish symbol or if you mentioned anything Jewish related or said a prayer or whatever, she would have a full-blown schizophrenic meltdown. It's kind of crazy because she was not wrong in the 1930s. So they went back to California.
MR: Wow.
SM: Fast forward to when I was a kid — my great-grandfather was alive until I was eight years old or something like that. I would see him a few times a week.
MR: The geologist?
SM: Yeah, the geologist. My sister and I would go to his apartment after school a few days a week, and so I knew him unbelievably well. He would watch us for a few hours multiple times a week every week. His whole apartment was filled with rocks, which is pretty cool — tons and tons of crazy rocks and gems from all over the world. He told my sister and me things like his biggest regret in life was not raising a Jewish family.
MR: But his kids were both Jewish?
SM: Well because his wife became paranoid schizophrenic and her trigger was anything Jewish, they basically never talked about Judaism. He raised my grandma and her sister with basically zero Jewish heritage, even though their last name was Cohn.
What’s In a Name?
MR: Did your grandmother marry someone who was Jewish?
SM: No, she did not.
I would hear these stories. When she was at Berkeley, she tried to join a sorority. She couldn't join any of the sororities she wanted to because she was Jewish. She didn't like that, and so she would try to assimilate. I was raised with these stories, but it didn't really mean much to me as a kid.
I really do think there's a lot in your name, and having the name Shaun Maguire, which is a very Catholic sounding…I identified with that side more strongly.
Fast forward to when I was about 21, I went to Israel for the first time.
MR: Why?
SM: I went because one of my best friends, Boris Hanin, whom I love, was doing math research for the summer at the Weizmann Institute. Boris and I had met each other at an undergraduate math camp for really good math kids. We were both at Stanford. I had started grad school there. He was an undergrad and we did our problem sets together and all that. Boris is now a professor at Princeton. Boris signed my ketubah. He's a very close friend. He was just in Israel doing research for the summer, so I went to visit him. It was truly an out-of-body experience. From the second I got off the plane, I just felt this very, very, very deep connection to the place in an almost indescribable way.
MR: What year was this?
SM: This was probably 2008. It was the same year I learned those things about myself and my background that I didn't know before.
MR: Who told you everything? How did you find out?
SM: It is honestly pretty funny, but there were people in my family that considered themselves Jewish before me. My sister is one. My sister had gone on Birthright before I went to Israel. And one of my aunts is a professor and very into history. My sister and my aunt had almost in hiding been doing all this Jewish family history research for us for years. I didn't even know they were doing it. I want them to be framed in a very positive light, but I think they were almost a little embarrassed or afraid to share that they were doing this work. In the culture I grew up — California is different than New York — there were fewer Jews, and the Jews had assimilated so deeply. You’re looked down upon — you're seen as different if you're Jewish.
I'm literally wearing a lashon hara bracelet, so I am not speaking ill of my grandma who is an unbelievable woman. I really love her so much. I miss her so much. But my read is she was ashamed to be Jewish, really. I don't mean that in a negative way. I think that's a very understandable thing. So some of this research was being done in the background quietly, and I didn't even know that it was happening.
I had never felt anything like I felt after I went on this Israel trip — and I’d already been to probably 50, 60 countries at that point in my life. I knew I needed to know more about our family history. And as I just asked basic questions, everyone told me I needed to talk to my sister and my aunt because they’d been doing all this work, and they knew everything. I had relatives that were rabbis, and I didn't know that as a kid.
There were also things in the family history that were major sources of pride. For example, relatives of mine donated the land for the San Francisco Opera building. I had been to the opera a number of times and didn’t know my family donated the land for it. We have the newspaper clippings on that. I just didn't know that I had all these very deep roots.
It Starts with Legos
MR: When you get into something, do you really get into it?
SM: Yes, I really get into it.
MR: When you were 13 or 14 what were you really into?
SM: I'll go even further back. From about three to seven, I was obsessed with Legos.
MR: What was your favorite Lego set?
SM: My family didn't have much money when I was that age, and so I would just build and recycle all the Legos I had. It was more creative building.
MR: Do you remember something that you built that stands out in your mind right now?
SM: Someone gifted me one of the early Lego train sets. I was obsessed with that and would just build all sorts of stuff around it.
Then I had a cousin help me build my first computer when I was seven. Building a computer in 1993 was not common and not easy. That was very formative for me. This was MS-DOS. I was obsessed with the computer. I literally spent all my time on the computer for years.
MR: What were you doing on the computer?
SM: I was just exploring. I know that sounds crazy, but I was really just exploring the operating system. At the time, it wasn't a visual interface. It was command line, and you would have to type the pathway.
MR: Would you play any command-line games?
SM: Yeah. The computer had a game called Commander Keen.
MR: Oh, I know that. That's so nerdy.
SM: That was the only real game that the computer had, and so I played a lot of Commander Keen. To figure out where you were going, you had to navigate to the right file pathway. It was like finding treasure on the computer. I didn't have anyone to help me with this. There was no internet, or at least I didn't have access to the internet. I didn't have any friends that were into this stuff. So you'd go C://programfiles/directory/whatever, and you'd find a whole new branch of the computer.
From Counter-Strike to General Relativity
MR: Are you still a tinkerer and explorer?
SM: This is going to sound weird, but at this point, I’m more of a tinkerer and explorer in my mind, trying to understand the world, rather than electronics.
The phases were Legos to hardcore, maximum computer explorer. That didn’t end until I was probably 25 or so.
MR: Do you ever play video games seriously?
SM: Unbelievably competitively.
MR: What video games did you play?
SM: I played Counter-Strike basically professionally. I played in the top league in North America, which is called CAL-Invite. I was on some of the best teams in North America for years. But I would also go to LAN tournaments all over the place. I won some LAN tournaments with the teams I was on. I never won anything at CPL. CPL was the biggest LAN tournament for Counter-Strike. The best Counter-Strike players in the world would make $50K, at most $100K. By the end of when I played, 3D was the best team in the world. There was this guy, Ksharp. I don't know what he was making, but my estimate would be between like 50 and 100K.
MR: Would you only play Counter-Strike?
SM: I played a lot of games, but I'm obsessive when I get into something, and I want to be the best in the world. So for probably two to three years, I would play Counter-Strike 10 hours a day.
MR: What was the last video game you played?
SM: I played Overwatch 2 yesterday.
MR: How long will you carve aside to play?
SM: Video games are the number one way that I can de-stress myself. I have an unbelievably active brain, and I deal with a lot of stress in my work and in my life. If I'm doing anything else, say, a Pilates class, I'm thinking about work the entire time. I'll walk out of there with endorphins, and that's great, but honestly, I’ll walk out even more stressed because my brain will be throbbing with all the things I have to do.
When I play video games, I still play seriously. I want to win when I play. In Overwatch 2, I oscillate between high Diamonds, low Masters. It's not good for a 16-year-old, but it's good for a 39-year-old that doesn't have that much time to play. So when I play, I’ll usually play for two to three hours at a time, and I'll do that once or twice a week. When I do it, everything else in the world goes away because the game is so complex that I just don't have space to be thinking about work and other things. As crazy as this sounds, I come away really relaxed.
MR: What other phases were there for you?
SM: So, at the age of nine, I became obsessed with space which became an obsession with special relativity starting when I was about 12 or 13.
MR: Did you like Ed Witten and Brian Greene?
SM: Well, Ed Witten is a legendary physicist, but to be very honest, I didn't really like Brian Greene's books when I was a kid. I didn't need them. The most powerful ideas in physics are simple to state but hard to understand deeply. So special relativity was the first idea I was truly obsessed with in physics. You can basically understand all of it just from what's called the equivalence principle and the concept that nothing goes faster than the speed of light. You can work everything out from there.
What It Takes to Be a Legendary Venture Capitalist
MR: What about after physics?
SM: Then I was pretty obsessed with the public markets. But once I was obsessed with one thing, I was still doing it when I became obsessed with the next. So I was still doing computers, I was still doing space.
MR: What were you reading investing-wise? Buffett? Macro?
SM: I was following specific stocks and trying to understand the companies and what was moving the prices. In terms of books, I loved these books called Market Wizards. They're just interviews with legendary traders. Obviously, Buffett's a legend, but I was not as interested in value investing as I was in macro-trading.
I love the Market Wizards books where they would ask legendary investors questions like, “What's the most important thing to be a great investor?” Most people would say managing your own psychology. That was extremely consistent.
MR: Let me ask that question: What’s the most important thing to being a great venture capitalist?
SM: VC is extremely different than public market investing. For public market investing, I think the most important thing is managing your own psychology.
MR: Do you still invest in the public markets?
SM: It's extremely hard at Sequoia because I have to get every trade approved. But I will get back to it someday. I'm obsessed with it. I love it. I truly love it.
Mike Moritz from Sequoia was one of the most legendary VCs of all time. I think Mike encapsulates very well what it takes to be a legendary VC.
I think the two things that he was just unbelievably good at were: One, being able to dream about what happens if everything goes right. He was an early backer of Google, he was early backer of Stripe, Instacart, Yahoo, and many other great companies. If you take any of these, they're obvious in hindsight, but they all had serious flaws at the time of initial investment. He was able to look past one or two flaws, inexperience, management team, whatever, and really just dream what if everything goes right. It's a very important trait as a VC.
Two, I think you just have to have an uncanny ability to read people. So much of being a great VC is just identifying outlier humans that oftentimes might look different and be underappreciated at the time. Sequoia was the second investor in Apple. There were stories of Steve Jobs showing up to investment pitches barefoot. This is a time when people were wearing suits to pitch, and this guy showed up barefoot in a T-shirt talking about doing LSD in his presentation.
MR: Nowadays if someone shows up to your office in a suit, you're like, "What's this guy doing? He probably doesn’t even microdose LSD."
SM: Yes, today’s version is not to disqualify someone who shows up in a suit and have an open mind.
Signal, Noise, and Tillamook Cheddar
MR: Do you floss?
SM: Yeah, of course.
MR: Every day?
SM: Every day.
MR: Would you describe yourself as an organized person?
SM: Medium.
MR: You must get a torrent of information all day. Do you have any interesting tech or apps you use to stay organized?
SM: No. This is going to sound weird. I am simultaneously very high tech but also very low tech. I think you would be shocked at how little time a day I spend getting information. Almost all of my time is spent just thinking.
MR: You must have a lot of people texting you all day.
SM: I do, and I barely even look at the messages. Right now I have hundreds of unread messages. It's too much noise. My superpower my entire life has been an ability to think through things obsessively.
MR: Do you know what your screen time is on your phone?
SM: My screen time is high, but it's mundane stuff, like sending emails and phone calls. It's probably four hours a day or something like that. But of that, it's two minutes a day on Instagram.
I do spend time on X. It's like an hour a day on X, and that's my information.
MR: Do you meditate? Do you pray?
SM: Video games is how I unwind.
MR: What does your diet look like?
SM: I have coffee every morning, but I skip a lot of breakfasts. I really try to just listen to my body. I try to eat almost no processed foods.
MR: When you would play Counter-Strike, what would you eat?
SM: Shit. At that point, I was eating absolutely horrible, shitty food.
MR: What was your go-to?
SM: Dude, you don't even want to know. Just eating blocks of Tillamook cheddar cheese and not good food. I’d make quesadillas on repeat because it was fast and easy and good.
MR: What about Mountain Dew?
SM: No, I've never really been a big soda drinker. I think soda is horrible, really horrible.
MR: How do you read books? Do you write marginalia?
SM: No. I’ve read books obsessively for most of my life. I'd read over a hundred books a year, and I have an extremely good memory. My memory is less good now than it was. Honestly around 21, my memory basically phase transitioned. I had a borderline photographic memory until I was about 21. My memory really changed around that age. Then it really changed again when I started a company. I think it's less age and more that I got to the point where I was taking in so much I couldn't. I used to remember most of my life almost like a movie where I could visualize basically everything that had ever happened to me. I lost that ability around 21. My sister still has that ability.
Chess
MR: Are you good at chess?
SM: It's funny you ask that. I never really played chess. But one of my great-grandfathers beat a world champion. He was a grandmaster. He beat Alexander Alekhine who was the world champion.
MR: And his cat was named Chess!
SM: My great-grandfather’s name was Richard E. McBride. He has a couple of recorded games — one where he beats Alekhine and one where he beats Frank Marshall who was the U.S. Chess Champion.
His name was not actually R.E. McBride. He took that name at Ellis Island. This guy never shared anything about his childhood with my family, so we really don't know. He came from Europe after World War I. We really don't know anything about his life. But he was just obsessed with chess.
But anyways, this guy just played chess all day, and he was never there for my grandfather. So my grandfather hated chess, and so he told me not to play chess as a kid. But I think I have the genetics for it.
MR: I'm going to go out on a limb and say if you played chess, you'd be good at it. There's a great line from Paul Morphy, “The ability to play chess is the sign of a gentleman. The ability to play chess well is the sign of a wasted life.”
SM: Yes.
Hunter Biden and To-Do Lists
MR: How did you meet your wife?
SM: I met my wife randomly at a pool party in Los Angeles in February 2016. It was at my friend Diego Berdakin's house. He had a Super Bowl pool party on a very warm LA February day. It was literally love at first sight.
MR: Amazing.
SM: She's a Persian Jewish woman with strong family ties to Israel. Her grandfather had fought in the War of Independence.
MR: Do you guys do anything for Shabbat dinner?
SM: Oh, yeah, of course. We just do big Persian-style Shabbat dinner every week.
MR: Do you cook or does she cook?
SM: We alternate sides. We go to her grandmothers, every other week. Her grandmothers love hosting Shabbat. I think it still gives them a lot of meaning in life. They just love having their whole family at their house. Someday we'll do it ourselves. But for now, the grandmothers want to do it, and it's hard to take it away from them.
MR: Can I ask about the Hunter Biden situation?
SM: You can ask whatever.
MR: Is that a fun story?
SM: Hunter was my family's tenant for well over a year. He was an absolute not positive thing, and he stopped paying rent after a while. He owes over a year’s worth of rent, was just an absolute jerk about all of it, and also completely trashed the place.
MR: Do you listen to music?
SM: Not really. I listen to just background music sometimes, either electronic or classical music, but very rarely with words. It is just kind of flow music. I think it's not a very important part of my life.
MR: What email client do you use?
SM: Just Gmail.
MR: What do you use to take notes?
SM: My head.
MR: You don't have a written to-do list?
SM: No.
MR: Do you watch TV?
SM: I go through phases where sometimes I do. In the last three years, I've watched very little TV. I get 100 times more joy playing a video game than watching TV. So I would say basically no. Call it 10 hours a year of TV.
Freshly Squeezed Orange Juice
MR: What is the place you think you've eaten most in Los Angeles?
SM: I've lived in different parts of LA. The place where I’ve probably eaten the most was, when I lived in Venice Beach for a long time, I used to go to Gjelina all the time. It's an amazing restaurant. I used to go there every day.
MR: What would you get there?
SM: I would go there for breakfast at 9:30 a.m. or so. I would get smoked salmon on toast and orange juice because they have these small truly freshly squeezed, very delicious orange juice, and a macchiato. I'd get that every single day for years.
MR: Are you a creature of habit with these things?
SM: I am a creature of habit with food.
When I was doing my PhD at Caltech, I used to go to this place called Euro Pane every day. It used to be amazing. It's no longer good. It changed owners. But it was amazing.
MR: I have a question about freshly squeezed orange juice. You're an extremely smart person, and you're probably going to be one of the people that gets us to Mars or invents cold fusion or something like this. Why can't they make orange juice that is not freshly squeezed taste like it’s freshly squeezed?
SM: Well, so there are many reasons, one of which is things oxidize over time.
MR: Can you create some kind of ester or additive that at least makes it taste fresh-squeezed?
SM: As I said earlier, I eat almost no processed foods, and I eat almost nothing that has additives in it. I think that is extremely bad for human health. So from my perspective, I would much rather drink water than drink the fake fresh orange juice. I think it's a flawed line of thinking to even try to make fake orange juice that tastes like fresh orange juice. I think that that will just be bad for you.
MR: Almost certainly.
SM: In terms of why it's hard to do, look, to me, we don't even understand what food is right now. Let me try to explain. I think food is basically a complex system. When you eat food, there are natural bacteria in there. There's all the macronutrients that are easy for us to measure, like how many carbohydrates and how much fat. But all of the micronutrients, it's very hard for us to measure. I don't trust our ability to create fake food anytime soon because I don't think we even know what food is. I think there are lots of subtle things that we don't properly take into account that are actually very important for us.
Big Questions
MR: Do you believe in an afterlife?
SM: I'm going to take this in a much bigger way. We started with Judaism. I have a very deep connection to Judaism. I learn an incredible amount from Judaism. If you ask me, "Do I believe in God?" my answer is, "I don't know." I don't have a strong point of view. On an afterlife, I also don't know. I don't have a strong point of view. But I deeply believe two things. One is that I think Judaism contains incredible amounts of profound ancient wisdom that we still don't really understand the depth of. Something as simple as Shabbat, is, I think, way more profoundly impactful for living a healthy life than other things.
MR: Are you offline for Shabbat or no?
SM: I'm not shomer Shabbat, but I think it's better to be.
MR: Do you think you ever will be?
SM: I should be, and I think that I will be someday.
Anyways, there's just incredible profound ancient wisdom in Judaism. I really believe that, and I believe there's a lot we don't understand now. I would say on the bigger level, whether it's God, whether it's an afterlife, I do believe there's a lot more order in nature than we appreciate now. There's an incredible amount that’s outside of the knowledge of physics and science today. There's all sorts of miracles that happen that I cannot explain at all using science.