Shiyan Koh on Choosing Bosses, Learning Acceleration & Building Investor-Founder Trust - E60

Koh Shiyan is the Managing Partner at Hustle Fund, a venture capital fund that invests in pre-seed software startups in the U.S., Canada and Southeast Asia. 

Prior to that she was VP Business Operations and Corporate Development at NerdWallet, a Fintech Startup that helps users with a range of financial decisions through content, community and tools. Over the course of six years at NerdWallet, she led product teams, ran business operations and corporate development, and helped grow the company from US$1M to US$150M in revenue. 

Shiyan’s first exposure to technology was as a summer intern writing technical documentation for a small 30 person startup Telenav, that is now listed on NASDAQ. She has also worked in a series of finance and investing roles at JPMorgan, Institutional Venture Partners and Bridgewater Associates before joining NerdWallet.

Shiyan graduated with a Bachelor of Science in Biomechanical Engineering and a Bachelor of Arts in Economics from Stanford University as well as an MBA from Harvard Business School.

You can find our community discussions for this episode at https://club.jeremyau.com/c/podcasts/60-shiyan-koh-on-choosing-bosses-learning-acceleration-building-investor-founder-trust

Jeremy Au: [00:00:00] Welcome to Brave Dynamics. This is your host, Jeremy Au. Leadership is harder than it looks. As a proven founder and Harvard MBA, I interview courageous entrepreneurs, executives and investors every week. I also share my frontline experiences, coaching insights and own professional development journey. If you're stepping up as a new leader, founding a startup, or venturing into the great unknown, this is the podcast for you. 

Hey, Shiyan. Good to see you again.

Koh Shiyan: [00:00:33] Great to see you, Jeremy.

Jeremy Au: [00:00:35] Well, such is life. We were just hanging out a few weeks ago and now here we are.

Koh Shiyan: [00:00:41] Yeah, happy to be on. It's an honor.

Jeremy Au: [00:00:44] Thank you. It's an honor to hear from you. I always love our chats and I'm so excited to share some color of our chats with the world, especially about your professional journey. For those who don't know you yet, about why you're cool, and hip, and awesome, how would you share your personal journey?

Koh Shiyan: [00:01:02] Oh, my gosh. I don't know if they're going to conclude that I'm hip or cool. Yeah, I guess if we sort of start from college, I had the opportunity to go to Stanford for undergrad, and in many ways I think that was a dream come true. My parents, Asian parents, they really wanted me to go to Harvard, and so I early-decisioned Stanford to hopefully not have to do that. I was like, "I grew up in a tropical country! I like being warm." Boston winters just didn't sound like a great time and... it seems like a pretty trivial way to make a choice, went to Stanford undergrad.

I think when you grow up in Singapore, you think that because you're fluent in English, going to school in the US will be really easy. You've watched American TV, you listen to American music, and then you show up on campus and you're like, "Oh, wow. These people are super different." I feel like college, the first year's just  and figuring out what was going on, and kind of being blown away by the quality, the ambition of the people, but also being like, "I don't know anything that they're talking about. I don't watch Seinfeld, I don't watch the Simpsons or South Park or any of these things. What..." just tells you how old I am.

So I majored in econ and, a little bit unusually, I suppose, biomechanical engineering. If I had been smart I should've majored in computer science, probably. But I really loved building things and I had always played sports, all through my life, so I really loved the idea of learning how to build things that could help people, whether it was new knees, new ankles, pieces of body that I would probably need or want when I get older and retire from all my physical activities.

But fate has a lot of funny twists and turns to it. I wound up actually doing an internship in college for JP Morgan in the investment bank. I didn't really know what an investment bank was. I had a friend who had interned for CreditSpace the year before and he'd said, "Hey, I think you would like this." like, "What is it?" He's like, "It'll be good for you," he's like, "and it's only for 10 weeks. You can do anything for 10 weeks." I was like, "Well, I guess that's true." So I read up a bunch of books and it seemed like you had to learn how to DCF things and do math or whatever. I was like, "Okay, I think I can do these things."

I go to the they didn't want to do any of these things that I had practiced for. And now, 20 years later, you kind of know, you've been that person who's had to interview tons of kids and you had to read hundreds of resumes. He didn't actually want to ask me any questions about whatever fake preparation I'd done. He was just like, "Oh, so you play rugby?" And like, "Oh, yeah, I play And he's like, "Oh, I played soccer in college." I'm like, "Okay, cool." We literally just spent the whole time talking about sports.

Then the interview ends and I said, "Actually, my team bus is going to pick me up from outside this JP Morgan office in San Francisco and we're going to go play a match."   And he's like, "Oh! That's so amazing!" There's more reminiscing about trips and things like that. Then I get on the bus and all my teammates were like, "So did you get the job?" And I was like, "I don't know! I'm so confused! He didn't even ask me anything that I'd prepared for. We just talked about rugby the whole time."

so I wound up getting the job. My friend was right. I really enjoyed 10 weeks there.  It was the summer of ' 03, so we were kind of in the run-up to the first boom and crash, and it was sort of very intoxicating to be 21 and working on transactions at companies that you had heard of, had used their products. It could be eBay, it could be Cisco, all of these things.

I wound up going back there full-time after I graduated. I spent two years in the investment bank covering tech and healthcare out of San Francisco, and because it was the boom, I did 19 transactions in two years. I don't remember all that much about the two years. I drank a lot of Diet Coke and coffee and I didn't sleep very much. But I think what I learned was a lot about how businesses get financed, because I worked on IPOs, follow-ons, converts, high-yield, investment-grade. And then I also learned that I didn't want to be an investment banker.

I just caught up, actually, with my old boss from that period. He's now a vice chairman at JP Morgan.  a long-time guy, and when I told him I was leaving, he said, "You don't want to grow up to be like me?" I said, "No. I mean, I've seen how you live your life. You're on a plane 15 days a month." He had a sort of six or seven-year-old daughter, he had a stay-at-home wife. And I said, "I don't know what's going to be my future but I'm pretty sure it's not a stay-at-home wife, so I don't think this is going to be particularly sustainable."

jP Morgan San Francisco was a little interesting because it's actually built from the old Hambrecht & Quist teams, which if you remember the first tech boom, they were part of the four horsemen of those boutique investment banks that took a lot of the start-ups public.   So the practice on the West Coast was actually much more growth company-focused rather than on the East Coast, they covered a lot more like the IBMs of the world. I think what I found was, oh, I really like that part of it. I don't need to go sell another revolver or credit facility. That's actually not that interesting. I am much more interested in smaller companies.

  I wound up working for a late-stage venture fund called Institutional Venture Partners. They  are old-school, founded in 1978. Reid Dennis, the founder, is one of the original grand old men of Silicon Valley in Sand Hill Road and got to work on deals like Twitter and Zynga, and then all these enterprise software companies that you've probably never heard of. That, I thought, was a fantastic education because basically you evaluate thousands of deals a year but you end up making maybe six to 10 investments a year. It's a very thorough process to kind of whittle that down.

Then after a couple years there, I wound up going to business school. I think for women, business school is like an insurance policy, I suppose, in a way, a place to mark your career in case you ever do take time out or you'd work for smaller companies that people hadn't heard of. And, also, I realized that I actually had no real, I guess, formal business training. I'd learned a lot from the financing side but I hadn't really actually thought about businesses all that much. I didn't really know anything about marketing, or sales, or all these functions, right? I knew a lot about financial statements.

So I go to business school, and I think this is also a great reminder of how narrow my view was, I just remember very clearly the practice case. HBS is a case method, so every case has this expository essay about the founder and the problems they were considering in their head, and blah, blah, blah, and then at the end there's always financial statements. So these practice case was about an ice cream distributor business. I flip to the back and I look at the financial statements and I was like, " 2% net margin? I mean, why do these people even get up in the morning? What kind of business is this?" I had just been so brainwashed by software businesses that it was actually really hard for me to think about non-software businesses.

I thought business school was a great widening of my field of view,  I think both in terms of types of businesses in the world and also types of people, right? I think you've met people from all over the world who you never would have met or hung out with in any sort of more standard professional capacity, right? So people who had served in the military, people who worked in more traditional industries, kind of you name it, someone had done it.

There was a girl in my section... I mean, it was kind of intense. I think she was Polish, she had trained to be a professional musician, she came from a family of professional musicians, and then she decided she was bored. She became a professional competitive ballroom dancer, and then consultant. People just, like, super crazy bundles of skills and experiences that showed up. I thought that was just fascinating. Of course, you go for the network and what not.

I guess the fun fact about business school is: I wound up living off-campus and my apartment wound up being super start-up-y and entrepreneurial. The first year, one of my roommates was Kat Lake, the founder of StitchFix, and the second year, one of my roommates was Justin McLeod, the founder of Hinge. Any of you who are using Hinge, it started in our living room in Cambridge, Massachusetts. That's kind of funny to think about, and for StitchFix, too. It's crazy to kind of think about where they started and the sizes, how those businesses have grown.

Then I thought I was going to try to come back to Singapore after business school.  This was 2011, there wasn't as much venture capital then and I figured it'd be pretty hard to try to get a venture capital job. In a very strange series of events, I wound up getting a hedge fund job because I thought, "Oh, there will be way more finance jobs in Singapore." I wound up working for a hedge fund in Connecticut called Bridgewater. It's one of the world's largest hedge funds. The founder, CEO, Ray Dalio, is pretty well-known for his writing. First, I think, many asset managers read Bridgewater's daily notes, and then subsequently, Ray has written a lot as well about his management philosophy, the Principles. If you want to talk about that, we can get a beer and talk about the Principles.

I was there for a year. I was on the investment team. I worked on FX trade strategy. I think what I learned was I didn't like public markets all that much. I didn't like living in Connecticut and I really just wanted to be back with smaller companies, closer to the action, things that felt more tangible to me.

We were living in New York at the time. My now wife was working at a start-up, so I was like, "Okay, I'm going to find a start-up job in New York." I started networking, doing some small consulting projects for people, trying to find teams or businesses that I liked to work with. I was really struggling. I did a bunch of projects and I was like, "Hey, I don't really care about fashion. I don't really care about jewelry. I don't really care about advertising technology," which is a lot of what was in New York at the time.

I wound up chatting, getting drinks with an old friend. He had been in New York ever since college, and so I said, "Hey, you've been here for a while," he was working on his own start-up, "can you tell me what are some interesting start-ups in New York that you recommend that I go reach out to?" He said, "Oh, I don't really pay attention to anybody else's company. I'm too busy working on my own business." He's like, "You should come work with me." I was like, "What do you do again?" Because we were social friends, basically. He said, "Well, let me show you."

This was Tim, of NerdWallet, which at that point was him and Jake, the co-founder, and a couple people they'd hired off of Craigslist. They had just made the decision that they were going to try to really build and scale it. They'd kind of been running it just the two of them for a while. So I'm like, "Okay, well, tell me more." I was like, "That's interesting. Show me the books. Right? Show me what you guys have been doing."

I don't really know how to explain it, but as he was talking, and walking me through the business, and explaining how it worked, I just had this feeling. I was like, "There's something there. I don't really know what it is, but there's something there there." I said, "Okay. Well, theoretically, suppose I did come work with you. What would I do?" Tim says, " What do you want to do? There's so many things to do." And me, you know, being the idiot MBA, I was like, " Would you let me be a product manager?" That was the pinnacle, right? And he's like, "You want to manage the engineers?" I was like, "Yeah! Can I do that?" He said, " Sure." He's like, "Whatever." He's like, "So much to do. Whatever you want."

I was like, "Okay, make me an offer." He makes me an offer. I call Katharine. I was like, "Hey, I just got this offer to be a product manager at my friend's company." Small detail, they're in San Francisco because he'd just moved the business to California, I said, "But I can commute." Because Katharine's like, "We just got here. We just moved to New York a year ago. I like it here. I'm not moving."

so I take this job. And it's very funny because I always get calls or questions from fresh grads or MBA grads. They're like, "How do you make the decision to join an early-stage start-up? What's in your framework? What metrics..." and I was like, "Look, it was pretty basic. The way I thought about it was, I think this is a big market. I think Tim is a high-integrity person. I believe the thesis, because there's some sort of early signs, but it's super early, right? I'm going to give it a year, and if it works, hey, I'm a genius. If it doesn't work, I'll get another job, it's fine. But if it doesn't work, it won't be because someone screwed me or there wasn't a market. Right? It'll have not worked because we didn't do a good job. We didn't execute properly, which is a bet I'm willing to take, right? I'm betting on myself, essentially, and this team."

 The first year I was at NerdWallet, it was 2012, I spent commuting back and forth between San Francisco and New York. I would do three weeks on, three weeks off. In San Francisco, I slept on people's couches for the whole year. I slept on every single of the management team's couches. As we grew the team, I slept over at everyone's house. Then I also had a home-couch with some business school friends, which, actually, included Russ Heddleston, who's the founder of DocSend that just got bought by Dropbox. I think I paid them $400 a month to have the right to sleep on their couch. I would buy booze periodically for their fridge, and I thought this was a real steal because, if you can imagine, a one-bedroom in San Francisco at the time was like, I don't know, $2,800, and we were already paying rent in New York, right? I wasn't going to be paying rent in two expensive cities on a start-up salary.

I did this for a whole year, and then that spring, my mom flies in for the engagement party, which is in Sonoma at Katharine's aunt's house. She lands at SFO and she's like, "Where's your apartment?" I was like, "Oh, I don't have an apartment." She's like, "What do you mean you don't have an apartment?" I was like, "Well, we have an apartment in New York but I don't have an apartment here." She's like, "What are you talking about?" I was like, "Oh, I just sleep on people's couches." She's like, "This is unacceptable." So the whole time we're driving to Sonoma, she's on the phone with realtors setting up viewings.

Saturday's the engagement party. Sunday we drive around the city and look at apartments. Sunday night she's at the lounge at SFO flying out and she's calling me. She's like, "Did you sign a lease yet? Did you sign a lease yet? Did you sign a lease yet?" So I signed a lease and then we moved full-time to San Francisco.

I was at NerdWallet 2012 through 2018. It was six years. We bootstrapped that business the first three years I was there. We didn't raise money externally until 2015. IVP, my old fund, led the round. It was a $69 million series A, so it was a pretty big series A, but at that point we were probably doing about 52 million revenue run rate. I don't even know what that would be in today's market. I shudder to think about that.

Tim kept his promises. In the early days, I managed engineers in Russia, Pakistan, Vietnam, Brooklyn. The first two years we ran outsource teams because as a bootstrap business, we couldn't really afford Bay Area engineers. Then, after we raised, we really pushed hard to bring engineering in-house, so I ran a couple product teams, and then my last couple years there, I ran business operations and corporate development. We acquired a couple businesses, integrated those.

I think as most in start-up life know, you do whatever you need to do at the time that you need to do it. I make the joke that I have done, I think, almost every job at the business. Hired a lot of people. When I left, I think NerdWallet was 400 people. I think I knew the first 300 employees all by name. Then I had maternity leave, so then there was a four-month period where people arrived and I had never met them. Then when I came back from maternity leave, there was a big catch-up to try to learn all these new names.

But, yeah, it was an incredible crazy ride. Business continues to do well. It's growing, it's profitable. They've done another couple acquisitions this year, so it's really cool to see that and to remember where we started. I think what's even cooler is to see all the people we hired as fresh grads who've grown up in the business, who've left, either to start their own companies or to take really good jobs at other neat businesses.

Yeah, and then I decided... we decided we were going to move back to Singapore in 2018 and I had to figure out what to do. I think the choices were: start a company, join a company, start a fund, join a fund. I spent a few months traveling in the region, meeting with entrepreneurs and VCs. I think where I landed on it was I felt like I was at a point in my life that I wanted to found something. If I was going to work my ass off, I kind of wanted to work my ass off with a little bit more control.

Then this opportunity with Hustle Fund came along. My partners, Eric and Elizabeth, are actually old friends from college. Elizabeth and I actually have known each other since we were five, so we have a long history together. We've all tried to hire each other. I tried to hire Eric at NerdWallet, I tried to buy Elizabeth's company at NerdWallet. Liz has tried to hire me the start-up before. It's kind of like... we've always tried to do stuff and then this was kind of our chance to all work together.

I feel like with Hustle Fund, I kind of get really the best of things. I get to start something. Emerging management funds are just like start-ups. You are constantly raising money and constantly figuring things out, and I get to hopefully give back to a nascent ecosystem and share some experiences and kind of hopefully build an institution that endures, right? Not just one or two funds, but I think if you really think about the great funds of Silicon Valley, they're institutions. They survived generational transition, and that's something we aspire to.

Jeremy Au: [00:19:03] Well, that was fun. I got so much to unpack here, so many questions I want to ask, right? Well, for those who don't know, but... well, there was a couple of things that jumped out. You mentioned a whole bunch of names like Hinge, StitchFix, NerdWallet, Bridgewater, which are, if you're in the States and you're in the know, you're like, "Whoa, these are high-signal grade companies." And if you're in southeast Asia, you're like, "What is Hinge and what is StitchFix?" I mean, it is a big deal. Yeah, StitchFix went public, I know a lot of couples who met on Hinge. I think I was at a bar in New York, there were friends who brought their plus-ones, and I was like, "Oh, how did meet your plus-one?" And they were all like, " Oh, I met them on Hinge." I was like, "Whoa, I got to... what is Hinge doing that clearly Tinder and everything's not?"

I think the second thing that obviously jumped out to me was that you talk about your career journey in terms of often very much learning what you like and learning what you don't like, right? So you join a company, you're like, "Oh, I don't like FX," or, "I don't like this," or, "I like this kind of company." Is that how you think about life? When you think about a job, learning what you like versus learning what you don't like."

Koh Shiyan: [00:20:11] When I take a job, I think about optimizing for learning. I think about what I want to learn. I would think... in my first job, and I tell this to fresh grads, you don't really know how to be at a job, so your first job should be a place that maximizes teaching you, A, how to be a professional, and then, B, hopefully exposing you to a really wide range of things.

I thought things like... traditional paths, whether it's investment banking or consulting, they have that feature, where you can see lots of stuff, and then you're like, "Oh, wait. Do I like this or do I not like this? Which do I prefer to the other? What am I good at?" Because I think... I don't know, I'm sure kids today are much more sophisticated than we were back then, but I felt like, when I graduated college, I knew that I was good at school, and that's not actually the same at being good at life or good at work. I think, at least in your first role, finding an opportunity to be exposed to, A, what does high-quality professional work look like? And then, B, either different functions or different industries is super useful.

Then I think early on in your career, you're often primed to optimized for optionality, where you're like, "I could do anything!" But at some point, you only get compounding returns when you focus on something. So then you have to think about, "Okay, well, how do I pick that something?" And you can only get a better decision when you have more data, and the only way to get data is to do more stuff. So, yeah, I kind of think about it that way, right? Which is like, my early jobs were very intense, but I got to do more stuff in a smaller period of time, which then meant you could actually think about, really reflect, what are the things you're good at, what do you enjoy, what gives you energy, what doesn't feel like work, which, I don't know, sounds like a very privileged take on work. But yeah, that's how I think about it.

But I think with venture, I love the intellectual exercise of figuring out a business, and I think that's what I really like. I am a nerd about business and business models, and then what I learned in the start-up world with NerdWallet is that I also really like figuring out people and where they sit in an organization and how to make them do great work. How do you create the conditions to do great work, on one hand, and then how do you think about how that intersects with the actual business you're building, right? I think those are things that I'm very interested in and enjoy spending time on.

Jeremy Au: [00:22:28] One thing that is there as well is you were not only learning about optimizing for learning, but you're also learning about the business. And another thing that shocked me a lot was you kept mentioning the people you were working with, right? So you're learning about your boss, learning about the founder, learning about your boss's lifestyle, right? Which, by the way, I totally empathize with because I joined Bain as my first job, and then I looked at the Partner's life, and then straight away I was like, "Whoa, you don't see your wife as well and your kids for, like, four days a week, at least," right? So I was very much like, "Whoa, I just learned I don't want your job," which, of course, you never tell anyone else.

Koh Shiyan: [00:23:10] Yeah, we're good friends now, me and my old boss. But yeah, in the moment it probably was not the most politically correct thing to say to him.

Jeremy Au: [00:23:18] Yeah. How do you think about that? I think there's a big one, right, which is, how do you learn who's someone you want to work with? So you mention, obviously, the business side, right? Big market, early signs. You mentioned high integrity in the personal side, and you talk about it's only one year as a time gate. But talk about high integrity, talk about who you choose to work with.

Koh Shiyan: [00:23:41] I mean, I think of life, it's a repeated game, right? I often tell people, "Life is long but the world is small, so act accordingly." I think that governs how you want to operate with people and what kind of people you want to operate with. When you say high integrity, do they make the right decision even if it comes at personal cost to them? Do they have a sense of right or wrong?" That's important to me because I think life's too short to work with people that make you feel icky. And if you don't feel great about having them come over for dinner and meet your family, then that's not a good sign, I think, all the money in the world doesn't change that. Honestly, most people... I think if you went to college, you have a pretty decent life. Adding 10x more money doesn't make it that 10x better. Those are sort of personal values and trade-offs that you have to think about.

I look for people who make me better. Ideally they're good at things that I'm not good at. They are sort of self-aware human beings. This is a hard one because everyone thinks they're self-aware, obviously, but they are emotionally mature enough to have hard conversations. They are not passive-aggressive. Because it's like, life's too short. If you think about most human drama, it's because Person A wants to tell Person B something but can't find the way to say it. Person B senses something is wrong with Person A, but Person A says nothing is wrong. So Person B makes up stories in their head about what could possibly be wrong. Meanwhile, no work is getting done. You know? You just kind of want to work with people who are like, “Hey, it's the classic formulation, when you do X, it makes me feel Y." Pause. "I would prefer if you did Z." And then you kind of just get over it and you move on, right?

So I think this sort of emotional maturity, self-awareness piece has become increasingly important as I get older because I just don't have the energy to deal with that anymore. I also think that in this remote world, strong communication, strong communicators are really important to high-quality work situations. It's not just tooling, although tooling matters. It's not just process. People actually need to understand and value high-quality communication. And that can be written, it can be spoken, but I think when I look for people to work with, that's kind of what I index on. And I like people who are a little bit weird, who don't take themselves too seriously, because I think for this business, you have to be a little bit weird.

Jeremy Au: [00:26:15] Yeah. That's really interesting, right? Because what's interesting is that you become more sophisticated. In other words, you've learned more about learning over time, right? That's something that I've suddenly picked up from this conversation, right? I mean, obviously you learned about bosses, you've learned about companies, you've learned about different industries, you've learned about yourself. But it also sounds like you think quite a bit about learning, you think a lot about learning, which shows me that you've been learning about learning, which is quite meta, I guess, but I'm just kind of curious: do you have any interesting thoughts about that?

Koh Shiyan: [00:26:46] Yeah. I mean, that's why I think it's so funny when people are like, "Oh, what should somebody major in?" It's like, "Well, I don't know." Influencer is a job now. That was not a job when I was in college, right? And how could you ever have majored in that? You wouldn't have, right? But if you are good at learning, you would've figured it out.

I think knowing how to learn is incredibly important because there's just so much in the world you're not going to know. You can't. There's no way you can prepare for it, right? So then you just have to have a prepared mind to go figure it out. And in start-up land, a lot of people want to index on credentials or experience, but the fact of the matter is if it's a start-up, either you're inventing a new market, or you have a different approach. It's not knowable, so you're going to have to figure it out. The team that learns and implements the fastest will win, not the team that started off with the most experience or the most capital, necessarily.

I think when we look at entrepreneurs as well, we think about: what is this person's pace of learning? What is the ramp, right? And you can see it, right? I have this company, they send us an update every week and it is incredible because, literally, you can see the progress. Every week, they're like, "Here's how many people we talked to. Here's what we learned. Here's what we implemented into the product. We shipped this feature." And then the next week, they're like, "From the feature we shipped last week, here's what happened. Rinse and repeat, rinse and repeat, rinse and repeat." You can see the business taking shape that way.

Conversely, there are people who never send you updates. You have to call them or text them, be like, "Hey, let's catch up. Tell me what's happening. Da-da-da-da-da-da." And they'll be like, "Well, we're thinking about these things." And I was like, "Okay. So what would make you do something? What would change your mind?" Right? And I think in the early stage, at least for software, I'm a big believer that good plans violently executed now, better than perfect plans executed later. That is all about pace of learning. How do you teach yourself that?

I think it's really hard because the most experience you accumulate, the more the tendency is to be like, "Well, in my day this was how we did things."  Sometimes that works, and then sometimes it makes you miss the big things. So how do you stay kind of constantly open to that, tune that balance between what matters, and what is new information that really is a paradigm shift and how do you prepare yourself for that?

Jeremy Au: [00:29:02] Wow, you just dropped a ton of knowledge with that, right? You said start-ups learning faster win faster than those with experience. It's a really good phrase and I totally agree with you about that. But I think you actually said a very interesting phase as well, which was: you asked people and said, "What would change your mind?" That's a really interesting question, right? Have you seen that question be effective? Does it actually wake people up and just be like, "Oh, I'm going to start thinking more rigorously about this?" How have you used that phrase?

Koh Shiyan: [00:29:33] I think it sometimes accelerates conversations where you can kind of feel like everyone's kind of going around in a circle, and you're like, "Okay..."you kind of just have to make a call. Right? It's like, talking more doesn't actually give you more information, right? So either it is, "Okay, I'm not having more information, but I think this is a reasonable hypothesis. I will try."Or, " I don't have more information therefore I don't feel comfortable acting." But at least when you ask the question, what would I have to see to act, then you know, "Okay, well, we don't need to talk about this anymore. Move on. But when I do see this thing, whatever it is, then I'll know, okay, I'm going to go do this," right?

I think about meetings... or anything, right? It's like, it's like trying to score a goal in soccer. I'm not a big soccer fan. The thing that irritates me most about soccer is that you can play to a draw, right? But even more irritating is when you watch people just pass the ball back and forth, back and forth, and it doesn't move down the field. So I think every conversation, you want it to go somewhere. You want it to move down the field, right? And it's the same thing with these decision-making things. It's like, "Okay, either we're going to score the goal or we're going to stop playing, but we're not going to run around in the middle of the field and do nothing. That seems like not a great use of time."

Jeremy Au: [00:30:34] I think one thing that is interesting, as I keep hearing this, is what would change your mind. So it's a function of learning, and it's also a function of communication, right? Those are two sides of the same coin, right? Which is you can be learning eternally but if you're not communicating it well, you can't work as a team, right, and therefore you can't learn as a group."So I think that's something that I'm starting to hear from you, right? There's two sides of it. There's a learning loop and there's a communication loop, right? Because when you were talking about your start-ups... well, you're talking about teams debating, you're talking about you working with that person, or founder, or your teammate, communicating, and you're also talking about the investor updates that start-ups are giving to you, right? How important is communication as part of that learning loop?

Koh Shiyan: [00:31:17] It's huge, right? I mean, I've been thinking about this a lot because I think in the remote world, if you don't deliberately make an effort to communicate, then there isn't that serendipity of running into someone in the pantry and being like, "Oh, hey, how's that thing going?" Right? Or, "Oh, you look excited," or, "You look down. What's happening?" You have to initiate effort to communicate this thing out, right?

If you think about it, we all operate with each other based on our prior experience with the person. You emit a series of dots, like data points, over time, and I in my mind am like, "Oh, Jeremy. He has this pattern of dots." When I first meet you, I have no dots, right? I only have this first impression.

Then  imagine that we didn't hang out for, like, five more years. I have no intermediate dots except random things that I saw on social media. And then Jeremy's like, "Shiyan, I'm raising $10 million. Will you back me?" And it's like, "Oh, well..." It's almost like having no dots, right? I would just evaluate it separately.

I think that's like that with companies, but it's also with people, right?  If you don't emit dots at a regular cadence that kind of lets people update their picture in their mind of what you are or how your business is then they kind of have to cast back their minds to that last dot they had about you and be like, "Oh, I seem to remember the business was struggling with X, Y, Z thing."

but then the founder's just like, " Oh, but we fixed all those things and that's why we're raising money," or, "That's why we need you to bridge us," or whatever the case may be. It's just way more work to get there than, "Oh, I've been receiving steady reports on progress. I understand how they're thinking about this problem. It makes total sense to me. Okay, maybe the data's not that great, but because I've seen all this progress, I trust the process." And that's ultimately what you're trying to build with people, right? Whether it's human beings, one-to-one, we're trying to build trust with each other, companies to investors, companies to their own employees, you're trying to build trust with each other?

I mean, that's something we haven't touched on, which is, as companies grow, I think one thing they systematically under-invest in is employee communication. Everyone is so used to the, like, "Okay, I got 10 people, I stuff them all in a room, and we're jamming!" And then suddenly, "Oh, the business is doing great." Now we're at 25 people or 30 people. You can't stuff 30 people in a room, and in a remote world, you definitely can't do that. Okay, well, how does everybody know what's going on, and what is the cadence by which they are constantly reminded, this is where the business is going, here's how we're going to get there, this is your role in getting us there. And it feels like you're on this totally, just repeating yourself over and over. You're like, "How can no one know my strategy by now? I say it all the time!" But basically, the bigger your company gets, the more you have to repeat it. And so, yes, I think that communication, high-quality communication is such a super power. I think it is systematically under-invested in.

Jeremy Au: [00:33:59] Well, yeah, that's so true. It's so much under-investment. I think a lot about what you said about trusting the process. What's interesting as well when you talk about all this is that you're not only absorbing all this information, you also do practice what you preach, right? Because you do regular writing and you work very hard to communicate with your teammates and your founders from what I've noticed and absorbed over time. How have you improved your communication practice over time? I guess you didn't grow up in university writing updates and emails.

Koh Shiyan: [00:34:34] It's a great question. I mean, I think there's some professional training around it, right? When you work on a project team on a bank or whatever, you're on a deal team, there's always people you have to keep appraised of what's happening because you're on a deal timeline. It's always like, "Hey, this is what's happening. This thing is in motion. We need this. Blah, blah, blah." And it's the same thing with venture, which is, like, you have this weekly meeting cadence, right? So you're always like, "What deals am I looking at? What am I evaluating? Who do I need introductions?" It's very regular.

I think Bridgewater took it to the next level. Bridgewater has this thing called the daily update, so everyone has to write a daily update and they have a whole internally-developed software system to do that. But I actually found it most when, at NerdWallet, I implemented it when probably we were, like, 10 or 15 people, because we were already starting to feel that strain where you have people running around and you have no idea what they're doing. It was just, end of the week, everyone writes an email that just says, "Here's what I did this week and here's what I learned, and here's where I need help." We actually did that... it evolved a little bit. Of course, at one point, the company got too big. You can't just send an email to, like, 50 people. No one's going to read 50 update emails, so it's just by team. You send it to your manager and then the manager rolls it up to the manager's manager, and then if you're the CEO or the management team, you can kind of see updates from every business unit on Sunday night. So when you head into the office Monday morning, you kind of know. "Okay, what fires do I need to go fight?"

Actually, it was Bridgewater plus Diane Greene from VMware talked about how she ran this at VMware, so I was like, "We need to do this." I have to check in with Tim, but when I left, we basically just did a version that was CEO's reflections that went out to the whole company, and we alternated between the CEO, the COO, the CFO. They would alternate reflections that went out to the company. I think that was incredibly useful, separate from our all-hands meetings or whatever it was because you basically could just see, "Oh, this is what's on Tim's mind," and it kind of just gave that intimacy and that communication channel.

So it's a lot of practice, it's a lot of fine-tuning, but some of it is just the forcing function. Last year I said I was going to write a note every week to the portfolio. I did, and that was just a forcing function. I still don't do it enough. My business partner Elizabeth is really good at it. In the spirit of learning from people who are better at things than you, I am constantly learning from her on how to get even higher-quality, higher-frequency.

Jeremy Au: [00:37:11] Awesome. Well, coming out of time here, but just kind of my last question here is: where were you 10 years ago? And if you could travel back in time, what advice would you give her?

Koh Shiyan: [00:37:25] Buy Bitcoin.

Jeremy Au: [00:37:29] Wait, wait, wait. We need to start first, where were you 10 years ago? What were you doing? What were you hanging out with?

Koh Shiyan: [00:37:35] This is... we're 2021, so 10 years ago I would be in my final semester at HBS. I had this job, I was starting at Bridgewater in the summer. What would I have told her? Oh, gosh. Exercise more. Yeah, I mean, I think it probably would've been do more self-care. I feel like in the first, like, three years at the start-up, and even at Bridgewater... Bridgewater I worked a lot. I didn't feel particularly healthy, and I think in the spirit of things that compound over time, sleep, exercise, good diet. All those things I think are useful things to invest in over time.

Jeremy Au: [00:38:09] So true. I always tell people, how did you balance two start-ups? And I'm always like, "Yeah," I tell them, "I gained 20 kilograms over those two start-ups, so self-care is important, I'll be upfront. Under-appreciated advice." Well, Shiyan, thank you so much for sharing your journey. I just love what you said about kind of learning what you like and what you don't like, start-ups learning faster, wins those with experience, what would change your mind as instigation topic, communication and learning, being both sides of the same coin. My favorite phrase actually, still, as well, is: you can do anything for 10 weeks.

Koh Shiyan: [00:38:51] I think that's true. I mean, the human body is incredibly adaptable.  It's good to push yourself early because then you know what you're capable of. It gives you more confidence for subsequent things

Jeremy Au: [00:39:06] for sure. Awesome. Thanks so much. I really have enjoyed having you on the show.

Koh Shiyan: [00:39:11] Thanks, Jeremy.

Produced by Adriel Yong