Yishi Zuo on Maximising Serendipity, Expert Network Founder and Creating Optionality - E57

· Founder,Podcast Episodes English

"…even if you want to have serendipity, the world is so vast. You still have to be a little bit more focused so that your energy, the serendipitous energy that's generated, generally pulls you in a certain direction." - Yishi Zuo

Yishi is an entrepreneur and investor. He was born in China and grew up in the San Francisco Bay Area.His first job out of college was as an investment banking analyst at Goldman Sachs in San Francisco. He worked for 3 years at a fundamental-value hedge fund thereafter. After 20 years in the Bay Area, he moved to Boston in 2016 to pursue an MBA at MIT Sloan. While at MIT, he co-founded DeepBench. The company connect customers with experts on any topic in any industry.In 2020, he transitioned away from being the full-time CEO of DeepBench. And he started a start-up studio called Optionality Partners. He uses his own capital and that of a few close friends to build businesses and invest in companies.He also blogs at the intersection of investing, entrepreneurship, and personal growth: https://yishizuo.com. Currently, Yishi lives in Los Angeles.

Jeremy Au: [00:01:25] Well, welcome aboard to the show, Yishi. Yishi is a longtime friend from our UC Berkeley days, but also has had an interesting career across Goldman Sachs to running a startup as a founder and CEO, all the way to Optionality Partners today. I think this journey is not just interesting from a career perspective, but also interesting from a personal history, and what's it like to be in the trenches together, at least living together as former roommates in Boston together? Yishi, welcome aboard. 

Yishi Zuo: [00:01:55] Yeah, thank you. I'm glad to be here. 

Jeremy Au: [00:01:57] Yishi, for those who don't know you yet the same way that I do intimately I guess, how would you describe your professional journey? 

Yishi Zuo: [00:02:06] Yeah, good question. I guess probably good to give you a little bit of life context, give everyone a little bit of life context. I was born in China, moved to the U.S. when I was six years old. I grew up in the San Francisco Bay Area. Went to UC Berkeley undergrad, and then I worked for five years in finance after graduating in 2011. The first two years was in investment banking at Goldman Sachs. I was in San Francisco. I was a generalist. Then I spent three years at a small fundamental value hedge fund called Solstein Capital, also in San Francisco. When I was at Solstein, in my free time on nights and weekends, I kind of caught the entrepreneurial bug in short. I started working on side projects. 

Unfortunately, those side projects didn't really go anywhere, entrepreneurial side projects. But I did realize I wanted to be an entrepreneur. I applied to business school and went off to MIT Sloan in the fall of 2016. With the idea that I wanted to start a business, find co-founders, and just go through the whole process, and just see what it's like. Test myself. Fortunately, I actually stumbled across a pretty neat idea. I started an expert network called Deep Bench where we were using technology to make things more efficient. We were able to find customers while we were in school. We were able to basically grow revenues, significant revenues, while we were students. We hired employees during school. We raised a little bit of angel money, accelerator money, after we graduated. 

From 2018, kind of June 2018 until last year, I was the full-time CEO and founder of Deep Bench. Last year, right around when COVID hit, I decided to take a step back. I actually transitioned away from the CEO role at Deep Bench. I also moved across the country. I was in Boston at the time and I moved to California, Los Angeles. I was figuring out what I wanted to do. I'm still in the process of figuring it out, but I decided that I wanted to stay in the realm of early stage entrepreneurship. I also wanted to use the investor skillset that I had built up over the years prior to starting Deep Bench. I created this hybrid role for myself. I'm part investor, part entrepreneur. That's what Optionality Partners is. The best way to call it is a startup studio, or you can think of it like an incubator. That's a quick three, four minute summary of what I'm doing now and how I got here. 

Jeremy Au: [00:04:43] Amazing. I think there's so much to unpack along the way. There's a couple things we want to talk about. I think the first one upfront was, let's talk about how you and I met. If I remember correctly, it was at UC Berkeley. I had been invited to a party, I believe, at your place. Or at least that's how we connected. I had brought some board games. We had a good time. I remember that both you and I did not... I think I won that first game. Then we kind of made a date to play again, right? 

Yishi Zuo: [00:05:13] Yeah. 

Jeremy Au: [00:05:13] We had to play a few times, until you finally won. Afterwards you won and we never played again, I think. 

Yishi Zuo: [00:05:21] Yeah, yeah. I'm a bit of a board game nerd, as are you. You introduced me to this game called Citadels. It's quite good. I think I got into Settler in sophomore year of college. This must have been 2009, '10-ish timeframe. Then I learned Citadels in 2011 I guess when I was a senior in college. I do remember playing with you and a bunch of your friends that I became very good friends with in college. That was how we met. Board games brought us together. 

Jeremy Au: [00:05:51] Yeah. I think the funny thing about that is sometimes the serendipity of that. If I didn't have board games with you and bring it over, you would never have met your future roommates in the SF Bay Area. Conversely as well, I would not have, almost eight years later I guess, become your roommate as well in Boston together. 

Yishi Zuo: [00:06:10] Yeah, that's just how life is. It's the serendipity of it all. Obviously we had some shared interest, but it was quite coincidental that we both happened to be in Boston eight years later and we became roommates. That was quite the journey. 

Jeremy Au: [00:06:25] Yeah. It's good life advice to all the people out there, right? Hangout over board games, I guess. At that time, I remember I was part of a social impact consulting club called The Berkeley Group. I was the president. I was thinking to myself I would either join the Gates Foundation or vaccine research. I think that's when I first met you. Eventually, I transitioned. I realized they wouldn't really hire non-Americans, so I transitioned to being... that's what my mentor told me, which was an interesting left road, right road kind of decision. For you, you went off to iBanking, right? At the time you were a student body senator, then you went iBanking. Can you just tell us a little bit more about why you chose to go into iBanking at Goldman Sachs? 


Yishi Zuo: [00:07:03] Great question. I think it's good to explain my personal background. I'm sure people listening to this podcast will come from all different cultures, geographies, and socioeconomic backgrounds. Just to begin with, I immigrated with my parents to the U.S. when I was six years old. Growing up, we didn't have a ton of money. We were never destitute, but we were definitely lower middle class. As I went to elementary school, middle school, high school, we gradually climbed the economic ladder. Kind of the typical American dream story. We actually bought a house when I was in college. Very much so kind of just climbed the ladder, American dream story. Because of the fact that I came from a background of not having a lot of money growing up, I knew only one thing that I wanted to do after I graduated college, which was I wanted to have a stable, lucrative career. 

Of course, what can you do in college at this point, like 2010, 2011? The obvious path for someone who is business oriented is either consulting or investment banking. I basically just chose investment banking because I think honestly, it was more prestigious. It paid a little bit more. Obviously Goldman Sachs was a great brand that I was able to get a job out of that firm. That's the honest truth of why I chose investment banking. I knew I wanted to work hard, and start my career on a good path, and make some money early on. 

Jeremy Au: [00:08:24] Yeah, I think that's a fair point. I think the truth is that you and I both chose, at that time, I think the two most popular or cool jobs on campus I guess, when we were on campus at the time. Which was McKinsey, BCG, MBB management consulting, and you did iBanking, right? 

Yishi Zuo: [00:08:40] Exactly. 

Jeremy Au: [00:08:41] Times have changed. I don't think they're the coolest jobs on the campus anymore, especially with technology being there. I think one thing I can take away from what you just said was, yeah. I often tell people, "Hey." People are like, "I need to take this job because I need to cover my student debt, but I want to set up a startup." I just tell them, "There's absolutely no shame. I think you should be proud that you can get a job that's paying well. Just do it and cover your student debt and help your family, and do the startup on the side. There's time. Your life is not over when you're 21." 

Yishi Zuo: [00:09:13] Yeah, this is actually something that I've thought a lot about. This is something I care a lot about because I've done some reflection recently in the past, over the past few months. I've had some more time to reflect since I left the CEO role of my last company which is, why didn't I do entrepreneurship earlier? I actually wrote an essay about this. I read a blog. The essay is called The Privilege of Taking a Risk. Basically, I think there's a U-shaped curve, the way I think about it. At the far left end, you have people so destitute that you have no choice but to do entrepreneurship in certain countries who don't have a lot of options. On the other end, you have, you grew up in wealth. You have a trust fund and you might as well take a risk. The world is your oyster. That's a small percentage of people. 

For most of us probably who listen to this podcast today, we probably come from middle class-ish backgrounds. There's an opportunity cost to taking risk. We have our family to think about. We really could use a $150,000 job at an investment bank or a software big tech company. Not everyone can just take a risk and not have to think about the consequences.  I've been thinking a lot about that. I'd like to, and it's part of my, maybe I'll talk about this later, it's part of my longterm goal to make entrepreneurship more accessible to more people. But that's separate from maybe the topic at hand. 

Jeremy Au: [00:10:37] I never thought about it that way and I think that's really true. My own family history is the same. My grandfather immigrated from China and he was destitute. He was working on a plantation and he had to save money to set up his own small business, but this is a story for another day. But he made the entrepreneurship bet to set up a small business. If he hadn't made that decision, the truth is, my father on that side of the family would never have been educated. If so, then I wouldn't have made it. I think It's the U-shaped curve, to be honest. That's only possible because my grandfather was on the other end of the U-shaped curve. I think that's a really good insight. I'm going to be definitely using that and referring to that. Quickly, what's your website? People will know where to find this.

Yishi Zuo: [00:11:15] Yeah, sure. It's my first and last name .com. Y-I-S-H-I-Z-U-O, Yishi Zuo, .com. 

Jeremy Au: [00:11:22] Right. If you go to JeremyAu.com, there will also be a show notes and transcript of this conversation. It will also hyperlink to the essay itself as well as the blog and his social media handles. Let's double click on that. That's where you transitioned to becoming a founder at some point in time. What was that? You had carved out a few years at Goldman Sachs iBanking. I don't know, did you ever sleep under your desk? Made a lot of money, go to the bars I assume and that's it. But after that, what happened? I'm just kind of curious. 

Yishi Zuo: [00:11:53] Yeah. I mean, it wasn't really about the money. When you're in your 20s and you don't have a lot of ties, you can do a lot of things. I just thought, oh, all these smart, ambitious people are doing startups. Obviously it's risky, but what do I have to lose? Let me give it a shot. When I was still working in finance, at the time, I was working in the nights and evenings. The things I did didn't really get me anywhere. I wasted like thousands of dollars working with freelancers on different projects. I just wasn't going about it the right way. I knew I wanted to dive deeper into entrepreneurship. I thought that, oh, business school is probably a good transition. Even if I don't end up doing entrepreneurship, it's a good learning experience. I've heard great things about business school. That's why I decided to apply. I stumbled across, and I use the word stumbled because I think it's fortuitous almost the way Deep Bench, my last company, came about. I just happened to come across customers given my previous background. During school, we started generating revenue. That's how it all started. 

Jeremy Au: [00:12:57] Yeah, I think there's a lot of truth there. Before we go into how the startup itself, but why the MIT MBA? What appealed to you about it at that stage? 

Yishi Zuo: [00:13:08] I was deciding between a couple of options. I chose MIT because, I mean, it's been so long. I'm trying to think. One reason was definitely the entrepreneurship ecosystem. Boston as a whole has a strong entrepreneurship network. The culture is pretty strong there. It's a small city. Actually, the most European city of all American cities. Very small, great public transportation. A college town for sure, and so I liked that. I also like the small class sizes at MIT. We both went to UC Berkeley. It's one of the largest universities in the world, so large class sizes. A lot of things to do. You can really do a lot, but I wanted that smaller, more close knit experience at MIT as well. That's basically why I decided on MIT and I had a great experience.


Jeremy Au: [00:14:00] MIT. Tell us, what was it like? I always loved the campus at MIT. is Harvard because it has all the, I don't know, the Ivy and the red brick. It's very like in the movies. But I actually found MIT a very, very fascinating campus because of how smart everybody was. Harvard folks were I would say less smart than the MIT folks on campus, I would say. I don't know, what do you think Yishi? What was it like being at MIT? 

Yishi Zuo: [00:14:25] That's a good point. I actually don't know if anybody is less smart or more smart than the other. I will say though, MIT has a reputation. It's scientists and engineers. MIT has a reputation for being "nerdy." I actually think it's a very valid reputation. I don't mean that in a pejorative, negative way at all. MIT is a place where you can be a nerd. When I say nerd, I think that means you get to be your true self. You get to explore your own niche interests. I think a way the system is designed, the courses. Just the resources that are available. There are a lot of niche resources. You really have to just pursue it. That's how MIT is designed. Everyone is free to be their inner nerd. 

Jeremy Au: [00:15:09] I think maybe just riffing on that, maybe I think MIT looks for the really spiky people. People who have one giant spike in something, like nano photonics, which is I think one of my bosses, he's a partner. He did undergrad, master's, PhD in one thing. I think Harvard is much more fuzzy? I don't know if that makes sense. They tend to be a bit more... I guess you could say well-rounded is a nice way of saying it. I think MIT is really spiky. You are really free to nerd out and get really deep on one, one, one thing. 

Yishi Zuo: [00:15:41] Yeah, perhaps. I haven't met that many people from HBS. I mean, definitely dozens. I think everyone is generally equally... everyone is smart at MIT, Harvard, and anywhere else. People that listen to the podcast, I'm sure they could do well at either place. It's hard for me to tell exactly, but I think you have a point there. 

Jeremy Au: [00:16:03] Yeah. Let's go a little bit deeper. You're on campus. You're hanging out with your MBA friends. How did Deep Bench as an idea appear? 

Yishi Zuo: [00:16:12] Yeah, Deep Bench. We are an expert network. We find experts on demand for like one hour phone calls. Clients and customers pay us one price. We find the expert and pay them a lower price, and the difference is our profit. It's a relatively straightforward, easy to understand business model. I used to be a customer of these things when I worked at an investment firm. You can imagine it's useful to be able to talk with people, to learn about things and then use that knowledge to make investment decisions. I saw an opportunity in this space and I just thought, oh, okay. If I see the opportunity, if I build a service product, if I can try to find potential customers, let's just get started. We have a business. 

That's what we did. We found customers, told them we can help them, and enough of them gave us a shot. That's how it started. We started with an insight that customers needed this. We found the customers, sold them on a product that didn't exist yet. Then once they gave us the mandate to, "Hey, find us some experts," we would execute on that request and then find experts on demand. That's how Deep Bench began, and that's by in large still what we do now. 


Jeremy Au: [00:17:21] Let's Zoom in even one layer deeper because some people want to know what the shining moment was. Was it like, you're in the shower and this came to you? To the best of your recollection, what was that journey of at least the initial hunch, whatever that was? 

Yishi Zuo: [00:17:34] Okay, I like this. Digging into the past.  It was me, myself, and two other MIT Sloan classmates. It was October 2016. We were brainstorming different ideas. I remember Deep Bench was one of eight ideas we had written on a whiteboard. We were just deciding, okay, which one should we explore? I think we were exploring more than Deep Bench. We just got the furthest with Deep Bench the quickest. I just started calling up my former colleagues, friends in the industry. Someone said, "Hey, yeah. Actually, we need experts right now. Can you find them for us?" That was it. Within a couple weeks, we found a customer willing to pay us thousands of dollars. As business school students, this was crazy. All of a sudden, from zero to thousands of dollars of revenue. Why not start a business around this? That's really how it started. We were exploring ideas and it just so happened, again, we got lucky. We got a customer. I think it was a friend from Berkeley actually. He was working for an investment firm and he happened to need our service at that point in time. 

Jeremy Au: [00:18:40] Yeah, I think I like that because you're just very frank about it. I think many, people look at startup ideas... I think the press also likes  to make it sound like the immaculate conception. It just came out of nowhere. I think almost every person is actually a very frontline search. Very kind of white boarding, confusion, pivoting, switching, changing dynamic. Those are the early stages for every founder. I think it just doesn't write well. I don't know, the press doesn't really say something like, "This great startup today was because this person spent five months working over a white board with a couple of his student classmates to figure this shit out." 

Yishi Zuo: [00:19:26] Yeah, I mean, it gets messier than that. I remember I told you I was working with two MIT Sloan classmates on that particular, on Deep Bench, in October 2016. By November, one of them left. Then another MIT classmate joined. Then in March, one of the original two people who were still with me, that guy left too. We had picked up another person along the way, then we added another person in April. There's a lot of messiness in the early histories of Deep Bench that you Google us and you Google the history, it's like, oh. Four MIT co-founders started this. That's actually not exactly true. Yes, by April 2017, there were four of us. But three of them weren't there in October 2016, so it's kind of funny how it all comes about. 

Jeremy Au: [00:20:09] Yeah, it is exactly spot on. I think I have some experience that goes again, where we had a search process. We were initially targeting postpartum depression. Well, to be honest, we were initially targeting depression. Then we zoomed in on postpartum depression. Then we figured out that they were depressed for a multitude of reasons, which the biggest one was a lack of childcare and the ability to go back to work. Then we decided to go for it and solve it from an education perspective. Just that logic path alone shows there were so many ways we could have gone to a different idea or a different iteration. You're right, I also had different co-founders come in. No, different candidates for co-founders working in different phases and go out, and then some of them have built successful startups of their own separate universe. But that doesn't compress well into the 40 word introduction of the company on the company website or the press. 

Yishi Zuo: [00:20:57] Exactly. 

Jeremy Au: [00:20:58] I remember you reaching out because I was already at Harvard for an MBA for a year already. I think you came in a year later. You reached out. You're like, "Hey, dude. Let's reconnect." I was like, "Of course." Then we hung out probably at a Chinese restaurant. 

Yishi Zuo: [00:21:12] Yeah, what was that restaurant? Shanghai Fresh, I remember. Shanghai Fresh. 

Jeremy Au: [00:21:15] Oh yeah, Shanghai Fresh. Was it that one? Yeah, that was great. 

Yishi Zuo: [00:21:17] It was delicious. 

Jeremy Au: [00:21:17] That was super dope. That was like the only legit Shanghainese food in Boston. 

Yishi Zuo: [00:21:25] I hope they stayed in business. 

Jeremy Au: [00:21:25] Oh yeah, that's another matter. I was checking COVID, my maps, my maps of favorite food. A lot of them are not open anymore. Okay, Shanghai Fresh. Great food, I highly recommend. So, we hung out and then we stayed in touch. I think about a year later, in around... I'd say probably whenever we hung out, I was already starting out of CozyKin already. Because you were a year in. I just finished the planning and starting to work. I think somewhere along the way, you started informing me about what you were working on since the fall. Then I hit my graduation from Harvard. 

I think you were still at Sloan, and I remember that I was like... I had basically decided that I wanted to room with other founders because I needed a peer support group, which was great. Because I was like, "We have a whole bunch of different founders." Luna, Matt, Rebecca. And actually all three of them, tremendous horsepower. Great founders. Luna figured it out and was doing VR. Matt was doing some materials and got quiet. Then Rebecca obviously continued working on the social enterprise - she's also from UC Berkeley. We both know her. We were living together, but I always remember that there was one bad thing about the founders, was that making rent consistently and staying in one spot all the time. There's a reason why they want... they say you want your roommate to be a banker or with a steady job. Anyway, the startup founders. Then it turns out I think you were looking for someone. Then we ended up hanging out and then deciding to room together. 

Yishi Zuo: [00:22:53] Yeah. I graduated from MIT Sloan in June of 2018. That summer, I did an accelerator in San Francisco. I think I came back to Boston at the end of September, early October. For those people who don't know Boston, basically all leases begin and end on September 1st. It's very hard to find housing in October. I ended up finding a place to live on Craigslist. It was fine, it just wasn't the best. My roommates were friendly, but we weren't super close. I wanted to move out after a couple more months. It just so happened I think Jeremy got married in December of 2018. I think it was at your wedding where I was talking to you about, "Hey, I'm looking to move out." You were like, "Oh, I'm looking for a roommate." I think I moved in in January 2019. I think that's how it happened. 

Jeremy Au: [00:23:43] Yeah, it actually is. You just jogged my memory. I'm getting old. but yeah, that's exactly how it happened. Again, the serendipitous thing. If it didn't turn out that you were invited to the wedding and you came over, we wouldn't have... 

Yishi Zuo: [00:23:52] Yes. 

Jeremy Au: [00:23:53] Become roommates. We became really close during that time as well. 

Yishi Zuo: [00:23:57] Yeah, maximizing serendipity. There's something to that. 


Jeremy Au: [00:24:02] I remember that you were great as a founder roommate. Obviously there was a part where... 

Yishi Zuo: [00:24:07] Thanks. 

Jeremy Au: [00:24:08] No, it was good. Your rating of roommate, 5/5 would recommend. 

Yishi Zuo: [00:24:14] I'm glad. Anyone listening to this, I don't know if I'll need a roommate in the future, but good to know. 

Jeremy Au: [00:24:19] Good to know. 

Yishi Zuo: [00:24:20] Good to have that cred. 

Jeremy Au: [00:24:21] I think one thing that you shared that was interesting, that I found of course, beyond the fact that you use straightforward, frank conversations around financials and cleaning, blah blah blah. But we were both as founders going through shit together, right? 

Yishi Zuo: [00:24:36] Oh, yeah. 

Jeremy Au: [00:24:36] I think that was a fun experience. We would come home and look at, discuss, work in a decompress way. I think that was an interesting set of conversations we had there. 

Yishi Zuo: [00:24:47] Yeah. One thing I really liked was that you were like the social hub for me. You brought over a lot of friends from a very diverse group of friends. Mostly people from Harvard MBA, but from all different interest groups. It was really culturally, ethnically, gender, very diverse group of friends. Everyone was super interesting, so I really liked that. I think I told you this before, but that was one of the best parts about living with you as a roommate. 

Jeremy Au: [00:25:18] I think that's true. I guess it kind of carried on to today. I think I didn't really self-identify that aspect of my own personality until years later as part of the reflections for the next career in my chapter. I think that was a big part of it. I think that wouldn't have been possible, to be honest, without you, Yishi. Because I think what I realized as well was, there was a stint where I was living by myself. I wasn't being social at all because I needed someone to have that... I don't know, copilot. I don't know what to call it, cohost vibe. I think that was great. I think you brought some great people along as well from the MIT ecosystem, but also from the SF side. I think what I remember is that we also had a whiteboard at home. There was always a lot of impromptu sketching of random stuff in our conversations, either one on one or with a group. 

Yishi Zuo: [00:26:07] Yeah, it was good. I think you inspired me to bring some friends together. I'm sure people listening, and you probably have friends too Jeremy, that they're friendly. They have a big social net circle, but they're kind of separate, purposely separate different social groups. They never intermingle. I think that's a little bit of a shame because I love it when my different friend groups overlap. I think it makes the bond stronger over time and I think it becomes a richer relationship as a result. I'm always very excited when my friends introduce me to their other friends. I'm always eager to introduce my friends to others as well. It goes both ways. We're talking about maximizing serendipity. I think that's a key aspect of maximizing serendipity. Just be generally open to intermingling. Who knows what will happen? I think you're one of the most inclusive people I've met actually. Obviously you're starting this brave dynamics, this clubhouse thing. I think that's really cool. It meshes with your personality very well. 

Jeremy Au: [00:27:11] Thanks so much. Hey, I wouldn't have described it as my personality years ago. I would probably describe myself as, oh, I'm a founder and I'm a CEO. I'm a Harvard MBA. These are the big labels and I got to play to those roles. I think one of the things, yeah, it's true. I was taking improv as well because after graduation, I wanted to have a hobby and everything. I always remember that one thing I realized was that being a founder and CEO, I think you have to obviously to some extent have the skills necessary to do it. But even if you don't feel like you're operating it in the moment, you just have to act and improvise as if what a tier one founder and CEO would do in that situation. You know what I mean? 

When there's a really tough... I think decision making of course is very different because that requires you to think through the problem, so on and so forth. I think when you're dealing with tough interpersonal issues, like there's two people debating or one person is very stressed and frustrated. I think even if you don't feel like it, even if you as Jeremy Au feel like you want to be just as frustrated or push back hard, depending on the situation. I think you have to improvise and act what a type one founder or CEO would look like. I think we discussed that a lot during those times as well. 

Yishi Zuo: [00:28:29] Yeah, I'm still learning that today. I don't feel like I'm qualified to really apply what a top tier CEO does. I can only try to act. Like I said, it's situational as well. I try to do my best in every situation and try to kind of listen to people. I think that's the biggest takeaway. You kind of alluded to this too. If anything, over the years, I've gotten a lot better at listening, behind more conscientious. Actually, when I was back at... when I used to work at Goldman Sachs and then Solstein, I've gotten performance reviews, feedback reviews. I did a 360 degree review right before I left Solstein. I got people at Solstein, the hedge fund I worked at, as well as a bunch of my closest friends from different groups. Former colleagues at Goldman to review me. The most common constructive feedback was, "Yishi needs to listen better. Yishi needs to be more aware of the things he's saying." 

I think I'm still working on it, but I've definitely gotten a lot better at it. I think part of that comes from one, just getting older. Two, it comes from having had that founder experience and I made mistakes along the way. But I think it's something I consciously try to work on. I think that's actually the most critical part of being a good leader in any sense, like any organization. Being able to listen to people and really understand what people are saying, and reading between the lines, and so on. 

Jeremy Au: [00:29:51] I  think you used this phrase that was interesting called, "You need to grow that skill." Being the father of a three-month-old daughter called Arden. 

Yishi Zuo: [00:29:58] Right. 

Jeremy Au: [00:29:58] One thing, obviously being on the education as well for the last company, you're aware that a human literally has to grow the ability to think of what other people are thinking of themselves. Literally, a three-month-old cannot empathize. They cannot understand what the other person is thinking about them. They have no sense of other. I love that sense of growing. At literally zero years old, you don't have any ability and it's okay to still be growing that physically, biologically, in your 30s. 

Yishi Zuo: [00:30:26] Yeah,  everyone talks about how everyone wants to be a lifelong learner and learn throughout their lives. It's easier said that done. How do you actually become a lifelong learner? Things that I started to do, and continue to try to do, and I hope I'll continue to do in the future, is I have an executive coach that I... I'm a pretty frugal guy, but I actually pay decent money for that. It's in the hundreds of dollars per hour. One of the most expensive things I pay for. It's very useful for me personally. I seek out mentors, and sometimes the mentorship is a book. I read a lot, so reading has helped me over the years as well. 

Jeremy Au: [00:31:02] Yeah, that's so good. I think something you opened up my eye on was you really open up a whole stack of books, reading articles that were deeper in thought. They acted as intellectual role models. I'd love to hear more about those role models that were churning out these materials that you were always sharing with me. 

Yishi Zuo: [00:31:21] Oh, yeah. So, you're looking for good books I might recommend? 

Jeremy Au: [00:31:25] Well, both. Good books and your role models. 

Yishi Zuo: [00:31:28] Oh, yes. 

Jeremy Au: [00:31:29] I mean, there's a big Venn diagram overlap for you on this one. 

Yishi Zuo: [00:31:32] Yeah, I can talk about books second. I'd love to talk about role models first because I think... [Hazid] mentioned you might ask me that. I actually put a little bit of thought into it. He said especially, I think in your directions, "Hey, think of real people, not like Warren Buffet and people like that." I actually did some thinking. I thought of three people. These three people, I actually consider them my peers. They both teach me something different, but I think it's very telling. There's something similar for all three of them. I'll go through them very quickly. The first is a guy named Jayesh Kannan. He's a friend from business school. He's not an entrepreneur, but I've learned a lot from him professionally. He's super polished and proper. He's good at a lot of the small things in life that make a big difference. 

As an example, he'll send me and all his friends, close friends, holiday cards regularly. He'll always remember to wish you happy birthday, and all of these small things that frankly I'm not very good at. If I'm telling someone, "My mom is doing this or that," a few weeks later he'll ask, "Yishi, how's your mom doing?" I'm like, "Holy crap. How do you even remember this stuff?" More so than anyone I've met, he's just really good at that stuff. He really cares about his friends and pays attention to detail. He's a role model for me in that sense because I'm trying to... I'm getting better at this stuff. I'm really learning from him on that one aspect, so that's role model number one.

 My second role model, his name is Eric. I don't think he'll want his last name mentioned, so I'll just say that for now. He's a friend from high school. We had a mutual friend, Eric and I, who was pretty sick. He had cancer or something a few years ago. Eric visited him multiple times in the hospital. Visited him more times than anyone else in our friend group, there was like four or five of us, combined. I don't know, I always found an excuse or I just didn't even think much about it. But Eric was there for our friend more so than any of us combined. He's just a really loyal, dependable guy. Later on, he helped that friend as well as another friend from high school that I don't know as well. He helped multiple of his friends from high school get hired at this company he was at. He's just a guy who really cares about his friends, really moral and reliable. Someone you can just count on. He's one of my best friends from high school. For me, he's a role model because he keeps me grounded. He's just someone who I actually look up to in many ways. That's my second role model. 

Then the third role model, so I won't say his name for now, but he was my roommate for a brief period. He's always super social and brought a lot of people together. You can probably guess. It's you, Jeremy. Beyond the surface level stuff, I think the stuff you do, and this is where it gets a little bit deeper, is that it's super intentional. Things you do kind of feed into each other, like Brave Dynamics, your podcast, and your personal brand. What you're doing now, Clubhouse. It's also very aligned with your personality. You're building a community. That's obviously very valuable as a business. You work at a VC, so there's a lot of scalability, cool stuff about that, that I see as well. But it's also very aligned with your personality, which is very important if you want to be genuine and honest. 

Even before, years and years ago, you were I think my first close friend that started doing entrepreneurial things. I think it was like 2013, 2014, or maybe 2012. You were working on Conjunct. You were the first person I saw doing anything entrepreneurial, you kind of like paved the path. Not directly, but you showed me that oh, people are doing this. I didn't grow up in a super business, entrepreneur environment. I paid attention. The people that I followed, emulated, were people like you. I think you were kind of a role model in that sense. I think you were the first person, one of the first people I was close friends with, who had their own domain name, JeremyAu.com. 

I don't know what year you registered that. I think I registered mine just a few years ago. Now more and more people were doing it, but you were thinking about your personal brand way before anyone else. You're always just an early adopter to this stuff. I'm on Clubhouse now, so I'm following your lead again. We'll see how this goes. I thought you're a role model in that way. You're very intentional and you are big about your personal brand. You're very aligned and very genuine I think. Everyone I mentioned, like my first friend Jayesh from business school, Eric from high school and you, you guys are all... what makes you guys similar, what ties it together, is you guys are all very caring people. Very open when you bring people together and care about your friends. That was my thinking around role models. 

Jeremy Au: [00:36:20] Thank you so much, Yishi. I obviously am really inspired by the other role models and I'm also very touched by you saying I'm one of yours. Obviously we can talk a little bit more about why, but I think maybe one thing that came up to me was this. I really enjoy being with other founders. I really like hanging out, getting feedback from them, giving them feedback. It's like this army buddy kind of feeling. I think that's why you've been a role model for me too, because you were the first person I knew personally who was doing deeper thinking, because you were writing the articles. Your hobby on the side was, oh, I want to write and think through this... I wouldn't say theory, but this framework or this way. I always appreciated it, and we would riff on those ideas together. I think where I am today is very much because of that year and a half we spent rooming together, because I got to basically learn from you, basically about what it means to be a thought leader on one angle. But also get to hangout with you and just have that creativity and comradery together. 

Yishi Zuo: [00:37:27] Yeah. I think just having the right people in your life can make a big difference. I think you were very, again, intentional about you wanted to live with co-founders. I was living with people off Craigslist. It's worked out for me in the past. I just didn't put as much emphasis on that. Now as I grow older, I'm putting a lot more emphasis on that. I'm more thoughtful, more intentional about the types of people I live with and spend time with. I've learned that over the years. We all do things that work for us. We all grow. It's part of serendipity. I'm pretty carefree with a lot of things. Overtime, you realize what really matters and what doesn't. It's just different personalities. I tend to focus on certain things, like big picture things, a little bit more. 

Jeremy Au: [00:38:11] Yeah, I think serendipity is our key phrase here because it's underrated, I think. A big part of it today is about how do we become more intentional versus default? But I think a way to be intentional is to look to maximize your own serendipity. That's really key. How have you been looking to maximize serendipity in life? 

Yishi Zuo: [00:38:31] Man, that's a great question. I'm putting, I think first and foremost, doing some introspection. Thinking about what I really want. Because even if you want to have serendipity, the world is so vast. You still have to be a little bit more focused so that your energy, the serendipitous energy that's generated, generally pulls you in a certain direction. For me it's like, okay, I want to be an entrepreneur. I want to start businesses and I want to invest. If I want to build a personal brand to attract more of that stuff, I can write, but I can write more things that are investing oriented or entrepreneurship oriented. I do write, but I'm also somewhat intentional with what I put out there. I'm conscious about how I spend my time working on those skills. 

I recently joined this writing collective called Compound Writing. It's like $100 a month, like $300 a quarter or something. I think they recently announced YC funding. It's a bigger thing for any writers out there. It's a private community where people help each other edit and become better writers. That's an investment I'm making in myself because no matter what I do, I don't know if I'll be investing in startups forever, ever. I don't know if I'll be starting companies from scratch forever, ever. But I do know that I want to be writing for a long time. It is something that I want to get better at. That was an intentional investment in my skillset. It's a balance between just doing random things, because it's like I don't need extra impetus for me to do random things. That's going to be a part of my personality no matter what. If anything, I need to focus my randomness a little bit more by being more intentional. I don't know if that fully answers your question, but it just really depends on what you need and what your weakness is actually. For me, I probably need to be a little bit more focused. 

Jeremy Au: [00:40:24] Well, I think it's interesting because I think that organization that you formed, the title Optionality Partners was very Yishi when you first announced it. I was like, "This is a topic you've written about. This is a topic we've discussed about in our pajamas. This is something that I can really see is really important to you." Tell us more about Optionality Partners. Less about what it does because you've explained it before, but why the name Optionality Partners? 

Yishi Zuo: [00:40:53] Yeah. I think it comes about from my own entrepreneurial journey. I as a founder, I've been in positions where we had to do things a certain way. We had to raise money to keep the company going, and had to have co-founders. Had to do this, had to do that. Honestly, there were certain mistakes I made that if I had something like Optionality Partners that gave me, to use a lack of a better term, more optionality, I think things would have turned out even better. Or certain mistakes I made in the past I wouldn't have made. It's really about alignment with individuals. That's kind of where it all comes from. It comes from my own personal experience. 

Jeremy Au: [00:41:35] That reminds me of many founders and VCs. They're very much like, "You've got to burn the boats." I use that analogy quite often as well. "You've got to burn the boats on the beaches so that there's no way but attack and win." 

Yishi Zuo: [00:41:46] Yeah. I could go on for a while about the misalignment between VC investors as well as individual founders. I think you know this quite well, Jeremy. This could probably take up another whole podcast. Just look at, for listeners out there if you're curious, look at the funding, the incentive structures, the fee structures of all the VC funds. One of the sayings is, "Follow the incentives. The incentives will lead you to the outcomes that you get." It's very telling how the fund structures, the fees are set up. 

Jeremy Au: [00:42:20] We have to go into it a little bit, now that you have this juicy thing. Yes, we will have another podcast a little bit more about it. I think first off, you're right, because we have all these great VCs. We have Sequoia, we have Benchmark, these great names out there. Obviously Monk's Hill as well. Then we also have companies that are great thought leaders and community builders, like Wide Company, the First Round Capital. They're doing tremendous thought leadership, so on and so forth. We see the façade of it. I think there's a real hype to it because of how they select, but I think one is really talking about the business model about what they're doing as well. It's interesting to see that if I listen to the CEO of Exxon Mobile say something, I will take it with a grain of salt. Does that make sense?

Yishi Zuo: [00:43:08] Right. 

Jeremy Au: [00:43:09] Then if I listen to the CEO of Nike, I would also take it with a grain of salt. If I listen to the lead investor of an incubator, then suddenly I switch it off for some reason. Yishi, do you want to talk a little bit more about that? 

Yishi Zuo: [00:43:25] Yeah. I mean, I think everyone is going to have their biases. I'm bias, everyone is bias. You just have to take everything with a grain of salt. With respect to VCs, and it's not just VCs, but a lot of large mutual funds have this issue too, where they make more money from the management fee than they do from the carry. The incentive is to just not rock the boat. Get as much AUM, assets under management, as possible. That's kind of the short of it. That in the startup world leads to certain incentives. You want to make bets that don't pay off for a long time. You want people to make bigger and bigger bets. It drives validations up, but are you actually generating revenue? Arguably, it doesn't really matter, but it's a different mentality. It's not exactly... I don't know if I want to build that kind of startup again, or that's the type of startup that makes sense for me to fund. But there are other ways that I've discovered, learned over the years. Other ways of creating businesses that create more optionality for the founder. 

Jeremy Au: [00:44:28] Yeah. We're coming up to time here, but I think that's such a great insight. I wish I had another hour to go with you into that. I think what you're reminding me of is that you're one of the few people who have an understanding of both sides of the VC side. As the hedge fund at Goldman Sachs, you saw what LPs do, what they're requiring of GPs. You actually see GPs asking as financial stewards of money, or the LPs that put money together for. You actually see as it flows downwards as an industry. That's one angle that I think we really need to delve into in a future podcast together. I think the second part of it is really true. VC is only one way of setting up a business. I think that different shades, to be honest from my perspective, good VCs who are picking and obviously sourcing these deals, and startups, and investing in them, and being a good picker. But I think the great human VCs are very I think humble, and very aware, and very clear that raising VC money is not the only way to build a great business. They're not only able to say that out loud, but be able to say that to the right company that comes along that is figuring it out. And to say, "Maybe we're not... don't chase a dream." "Don't chase the dragon" I think is what they say. 

Yishi Zuo: [00:45:49] Yeah, I would agree with that. I've definitely met a lot of great VCs in the past and I'm friends with many of them, so I definitely respect what they do. I think it's just not exactly the type of approach that I'm taking with optionality. To your point, yes. There's not a lot of people I know that came from a hedge fund analyst background, and also started an operational startup business. If you know any, I'd love to talk with more of them. It's obviously an interesting blend of skillsets. As an investor, you go broad across different industries, use the mental models and become a better investor. It's all about pattern recognition. Then as an operator, obviously you've got to delve deep into the details. You've got to get into the nitty gritty. Then there's also motivating the team, communicating the vision, all that kind of stuff. It's very much so a different kind of skillset, sometimes at odds with being an investor. As an investor, you have to be very rational. As a CEO of an early stage company, you have to sell the vision and grow into that. It's kind of like reflexivity. I think George Soros came up with that term. Anyway, there's a little bit of tension there. I've done both sides of it. It's kind of interesting. 

Jeremy Au: [00:47:01] Coming on time here in the next one minute. Could you just share, if you could go back in time 10 years ago, that means we were what, juniors at that time. Or it was senior year, right? What advice would you give Yishi 10 years ago? 

Yishi Zuo: [00:47:17] That's a good question. I don't know if I thought too deeply about that. I would have started writing earlier because I have a small following, not a huge following. I write largely because it helps me think. It's helped me clarify my thoughts and become a better thinker, become a better leader in many ways. I would've started a blog like 10 years ago. That would have been, I think, very helpful for me in many ways. That's the advice I'd give myself 10 years ago at age 21. 

Jeremy Au: [00:47:49] How would you give that advice? Would it be over coffee? Would it be over a beer? How would you give that advice? Would you be very kind? Would you be very top down like, "You should do this?" 

Yishi Zuo: [00:47:59] Probably, yeah. Over coffee, over beer. That's a good setting to give that kind of advice. 

Jeremy Au: [00:48:07] Awesome. Well, thank you so much, Yishi, for sharing what you have. 


Yishi Zuo: [00:48:11] Okay. See you, Jeremy. Take care. 

Jeremy Au: [00:48:13] See you, Yishi. All right, bye-bye.

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