Koh Shiyan is the Co-Founder and Managing Partner at Hustle Fund, a venture capital fund that invests in pre-seed software startups in the US, 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$1 million to US$150 million in revenue.
Knowing how to learn is incredibly important because there’s just so much in the world you’re not going to know. You just have to have a prepared mind to go figure it out. In startup land, people want to index on credentials or experience, but the fact of the matter is that a startup is either inventing a new market or having a different approach. The team that learns and implements the fastest will win, not the team that started off with the most experience or the most capital.
Jeremy Au: How would you describe your personal journey?
Koh Shiyan: If we start from college, I had the opportunity to go to Stanford for undergrad. In many ways, that was a dream come true. My parents were Asian parents that really wanted me to go to Harvard, 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.
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 realise, “These people are super different.” The first year of college is just figuring out what was going on and being blown away by the quality, and the ambition of the people, but also feeling, “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.” Just tells you how old I am.
I majored in economics and, a little bit unusually, biomechanical engineering. If I had been smart, I should’ve majored in computer science. I really loved building things. I had always played sports 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 when I get older and retire from all my physical activities.
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Fate has many funny twists and turns. I wound up doing an internship in college for JP Morgan, at the investment bank arm. I didn’t really know what an investment bank was. I had a friend who had interned for Credit Suisse the year before and said, “I think you would like this. It’ll be good for you, and it’s only for 10 weeks. You can do anything for 10 weeks.” I replied, “I guess that’s true.” I read a bunch of books and it seemed like you had to learn how to create discounted cashflow models and do math or whatever. I was like, “Okay, I think I can do these things.”
They didn’t want to do any of these things that I had practiced for. Twenty years later, 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, “Yeah, I play.” And he’s like, “Oh, I played soccer in college.” We literally 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.” He’s like, “That’s so amazing!” There’s more reminiscing about trips. Then I get on the bus and all my teammates were like, “Did you get the job?” 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.”
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 in the run-up to the first boom and crash. It was intoxicating to be 21 and working on transactions at companies that you heard of, 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. 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. What I learned was a lot about how businesses get financed, because I worked on IPOs, followons, converts, high-yield, investment-grade. I also learned that I didn’t want to be an investment banker.
I just caught up with my old boss from that period. He’s now a vice chairman at JP Morgan, a long-time guy. When I told him I was leaving, he said, “You don’t want to grow up to be like me?” I said, “No. I’ve seen how you live your life. You’re on a plane 15 days a month.” He had a six or seven-year-old daughter, he had a stay-at-home wife. 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 is interesting because it’s actually built from the old Hambrecht & Quist teams, which were part of the four horsemen of those boutique investment banks that took a lot of the startups public.
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The practice on the West Coast was much more growth company-focused than the East Coast. They covered a lot more like the IBMs of the world. What I found was, I really like that part of it. I don’t need to go sell another revolver or credit facility. That’s 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 all these enterprise software companies that you’ve probably never heard of. That was a fantastic education because you evaluate thousands of deals a year. You end up making six to 10 investments a year. It’s a very thorough process to whittle that down.
After a couple years there, I wound up going to Harvard Business School. For women, business school is like an insurance policy, a place to mark your career in case you ever do take time out or work for smaller companies that people hadn’t heard of. I realised that I had no formal business training. I’d learned a lot from the financing side but I hadn’t really thought about businesses all that much. I didn’t really know anything about marketing, sales, or all these functions. I knew a lot about financial statements.
I go to business school, and this is a great reminder of how narrow my view was. I remember very clearly the practice case. HBS teaches lessons through the case method, so every case has this expository essay about the founder and the problems they were considering in their head.
At the end, there’s always financial statements. This 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, “Two per cent net margin? 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.
Business school was a great widening of my field of view, both in terms of types of businesses and also types of people. You meet people from all over the world who you never would have met in any more standard professional capacity – people who had served in the military, people who worked in more traditional industries, you name it, someone had done it.
There was a girl in my section. She was Polish. She had trained to be a professional musician, came from a family of professional musicians, and then decided she was bored. She became a professional competitive ballroom dancer, and then consultant. Super crazy bundles of skills and experiences. That was just fascinating. Of course, you go for the network and whatnot.
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The fun fact about business school is, I wound up living off-campus and my apartment wound up being super startup-y and entrepreneurial. The first year, one of my roommates was Kat Lake, the founder of StitchFix. 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 funny to think about. It’s crazy to think about where StitchFix and Hinge started, and how those businesses have grown.
I thought I was going 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, “there will be more finance jobs in Singapore.” I wound up working for a hedge fund in Connecticut called Bridgewater, one of the world’s largest hedge funds. The founder & CEO, Ray Dalio, is pretty well known for his writing. First, many asset managers read Bridgewater’s daily notes. Ray has written a lot about his management philosophy, which was encapsulated in the book Principles. I was there for a year. I was on the investment team. I worked on FX trade strategy.
What I learned was I didn’t like public markets 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. Katharine, my now-wife, was working at a startup, so I was like, “Okay, I’m going to find a startup 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 realised, “I don’t really care about fashion. I don’t really care about jewellery. 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 with an old friend. He had been in New York ever since college. I said, “You’ve been here for a while, tell me some interesting startups that you recommend that I go reach out to?” He said, “I don’t really pay attention to anybody else’s company. I’m too busy working on my own business. You should come work with me.” I was like, “What do you do?” We were social friends. He said, “Well, let me show you.”
This was Tim Chen of NerdWallet, which at that point was him and Jake Gibson, 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 build and scale it. They’d been running it, just the two of them, for a while. I’m like, “Okay, well, tell me more. That’s interesting. Show me the books. Show me what you guys have been doing.”
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I don’t really know how to explain it. As he was talking, and walking me through the business, and explaining how it worked, I just had this feeling, “There’s something there. I don’t really know what it is, but there’s something 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, being the idiot MBA, 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. Whatever. 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, “I can commute.” Katharine’s like, “We just got here. We just moved to New York a year ago. I like it here. I’m not moving.”
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 startup? What’s in your framework? What metrics?” I was like, “Look, it was pretty basic. The way I thought about it was, this is a big market. Tim is a high-integrity person. I believe the thesis, because there’s early signs, but it’s super early. I’m going to give it a year. If it works, I’m a genius. If it doesn’t work, I’ll get another job. If it doesn’t work, it won’t be because someone screwed me or there wasn’t a market. 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. I’m betting on myself and this team.”
The first year I was at NerdWallet, 2012, I commuted 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 one 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 included Russ Heddleston, the founder of DocSend, that just got bought by Dropbox. I paid them US$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 US$2,800 per month, and we were already paying rent in New York. I wasn’t going to be paying rent in two expensive cities on a startup salary.
I did this for a whole year. Later, that spring, my mom flies in for the engagement party, which is in Sonoma at Katharine’s aunt’s house. She lands at the airport 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.” 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 we moved full-time to San Francisco.
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I was at NerdWallet 2012 through 2018. 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 US$69 million series A, so it was a pretty big series A. At that point we were probably doing about US$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 outsourced teams because as a bootstrap business, we couldn’t really afford Bay Area engineers. After we raised, we really pushed hard to bring engineering in-house, so I ran a couple product teams. My last
couple years there, I ran business operations and corporate development. We acquired a couple businesses, integrated those.
As most people in startup 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 almost every job at the business. When I left, NerdWallet was over 400 people. I think I knew the first 300 employees all by name. Then I had maternity leave, so there was a four-month period where people arrived and I never met them. When I came back from maternity leave, there was a big catch-up to try to learn all those new names.
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.
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.
We decided we were going to move back to Singapore in 2018 and I had to figure out what to do. 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. Where I landed 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 wanted to work 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 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 tried to hire me the startup before. We’ve always tried to do stuff, and this was our chance to work together.
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I feel like with Hustle Fund, I get the best things. I get to start something. Emerging management funds are just like startups. You are constantly raising money and constantly figuring things out. I get to give back to a nascent ecosystem, share some experiences, and build an institution that endures. If you really think about the great funds of Silicon Valley, they’re institutions. They survived generational transition. That’s something we aspire towards.
Jeremy Au: You talk about your career journey in terms of learning what you like and learning what you don’t like. Is that how you think about life?
Koh Shiyan: When I take a job, I think about optimising for learning. I think about what I want to learn. I tell fresh grads: you don’t really know how to be at a job, so your first job should be a place that maximises teaching you how to be a professional and then exposing you to a wide range of things.
Traditional paths, whether it’s investment banking or consulting, have that feature where you can see lots of stuff. Then you’re like, “Oh, wait. Do I like this or do I not like this? Which do I prefer? What am I good at?” I’m sure kids today are much more sophisticated than we were back then. When I graduated college, I knew that I was good at school, and that’s not actually the same as being good at life or good at work. At least in your first role, finding an opportunity to be exposed to what high-quality professional work looks like and then either different functions or different industries, is super useful.
Early on in your career, you’re often primed to optimise for optionality, where you’re like, “I could do anything!” At some point, you only get compounding returns when you focus on something. Then you have to think about, “How do I pick that something?” You can only get a better decision when you have more data. The only way to get data is to do more stuff. I think about it that way, which is, 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, really reflect on what are the things you’re good at, what do you enjoy, what gives you energy, what doesn’t feel like work, which sounds like a very privileged take on work. That’s how I think about it.
With venture, I love the intellectual exercise of figuring out a business. That’s what I really like. I am a nerd about business and business models. What I learned in the startup world with NerdWallet is that I also really like figuring out people and where they sit in an organisation and how to make them do great work. How to create the conditions to do great work, on one hand, and then how to think about how that intersects with the actual business you’re building. Those are things that I’m very interested in and enjoy spending time on.
Jeremy Au: You were not only learning about optimising for learning. You’re also learning about the business. You kept mentioning the people you were working with. You’re learning about your boss, learning about the founder, learning about your boss’s lifestyle. How do you learn who’s someone you want to work with? You mention big market and early signs on the business side. You mentioned high integrity on the personal side. You talk about one year as a time gate.
Koh Shiyan: I think of life as a repeated game. I often tell people, “Life is long but the world is small, so act accordingly.” 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 life’s too short to work with people that make you feel icky. If you don’t feel great about having them come over for dinner and meet your family, that’s not a good sign. All the money in the world doesn’t change that. If you went to college, you have a pretty decent life. Adding 10x more money doesn’t make it 10x better. Those are personal values and trade-offs that you have to think about.
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I look for people who make me better. Ideally, they’re good at things that I’m not good at. They are self-aware human beings. This is a hard one, because everyone thinks they’re self-aware, but they are not emotionally mature enough to have hard conversations. They are passive-aggressive. 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 want to work with people who are like, “Hey, it’s the classic formulation, when you do X, it makes me feel Y. I would prefer if you did Z.” Then you get over it, and you move on.
This sort of emotional maturity, self-awareness, has become increasingly important as I get older because I just don’t have the energy to deal with that anymore. In this remote world, strong communications and 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. That can be written, it can be spoken. When I look for people to work with, that’s what I index on. I like people who are a little bit weird, who don’t take themselves too seriously, because for this business, you have to be a little bit weird.
Jeremy Au: What’s interesting is that you became more sophisticated. You’ve learned more about learning over time. You learned about bosses, you learned about companies, you learned about different industries, you learned about yourself. You think quite a bit about learning, which shows that you’ve been learning about learning. Do you have thoughts about that?
Koh Shiyan: That’s why 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. How could you ever have majored in that? You wouldn’t have. If you are good at learning, you would’ve figured it out.
Knowing how to learn is incredibly important because there’s so much in the world you’re not going to know. There’s no way you can prepare for it. You just have to have a prepared mind to go figure it out. In startup land, people want to index on credentials or experience. The fact is, a startup is either inventing a new market or taking 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.
When we look at entrepreneurs, we think about, “What is this person’s pace of learning? What is the ramp?” You can see it. I have this company. They send us an update every week and it is incredible because 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.” 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.
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.” They’ll be like, “Well, we’re thinking about these things.” I was like, “What would make you do something? What would change your mind?” 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? It’s really hard, because the more experience you accumulate, the more the tendency is to be like, “In my day, this was how we did things.”
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Sometimes that works, and then sometimes it makes you miss the big things. How do you stay constantly open to that, tune that balance between what matters and what is new information that really is a paradigm shift? How do you prepare yourself for that?
Jeremy Au: You asked people and said, “What would change your mind?” That’s a really interesting question. Have you seen that question be effective? Does it actually wake people up? How have you used that phrase?
Koh Shiyan: It sometimes accelerates conversations, where you can feel like everyone’s going around in a circle and you just have to make a call. Talking more doesn’t actually give you more information. Either it’s, “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.” At least when you ask the question, what you have to see to act, then you know. “Okay, we don’t need to talk about this anymore. Move on.” When I do see this thing, whatever it is, I’ll know I’m going to go do this. I think about meetings. 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. 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.
Every conversation, you want it to go somewhere. You want it to move down the field. It’s the same thing with these decision-making things. 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: You can be learning eternally but if you’re not communicating it well, you can’t work as a team and therefore can’t learn as a group. When you were talking about your startups, you’re talking about teams debating. You’re talking about working with that person, founder or teammate. You’re also talking about the investor updates that startups are giving to you. How important is communication as part of that learning loop?
Koh Shiyan: It’s huge. I’ve been thinking about this a lot, because 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?” Or, “Oh, you look excited,” or, “You look down. What’s happening?” You have to initiate effort to communicate this thing.
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. In my mind, I am like, “Oh, Jeremy. He has this pattern of dots.” When I first meet you, I have no dots. I only have this first impression. Then, imagine that we didn’t hang out for five years. I have no intermediate dots except random things that I saw on social media. Then Jeremy’s like, “Shiyan, I’m raising US$10 million. Will you back me?” And
it’s like, “Oh, well…” It’s almost like having no dots. I would just evaluate it separately.
It’s also with people. If you or your company doesn’t emit dots at a regular cadence that lets people update their picture in their mind then they have to cast back their minds to that last dot they had about you and be like, “I seem to remember the business was struggling with X, Y, Z thing.” Then the founder’s just like, “Oh, 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 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.” That’s ultimately what you’re trying to build with people. 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.
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That’s something we haven’t touched on, which is, as companies grow, one thing they systematically under-invest in is employee communication. Everyone is so used to, “I’ve got 10 people, I stuff them all in a room, and we’re jamming.” Then suddenly, “The business is doing great.” Now we’re at 25 people or 30 people. You can’t stuff 30 people in a room. In a remote world, you definitely can’t do that. 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. It feels like you’re repeating yourself over and over. You’re like, “How can no one know my strategy by now? I say it all the time.” The bigger your company gets, the more you have to repeat it. High-quality communication is such a superpower. It is systematically under-invested in.
Jeremy Au: A lot about what you said is about trusting the process. You’re not only absorbing all this information. You also practice what you preach. You do regular writing, and you work very hard to communicate with your teammates and founders. How have you improved your communication practice over time?
Koh Shiyan: There’s some professional training around it. When you work on a project team in a bank, you’re on a deal team. There’s always people you have to keep apprised of what’s happening because you’re on a deal timeline. It’s always like, “This is what’s happening. This thing is in motion. We need this.” It’s the same thing with venture. You have this weekly meeting cadence. You’re always like, “What deals am I looking at? What am I evaluating? Who do I need introductions?” It’s very regular. Bridgewater took it to the next level. Bridgewater has this thing called the daily update. Everyone has to write a daily update and they have a whole internally-developed software system to do that. I actually found it most helpful when, at NerdWallet, I implemented it when we were 10 or 15 people. 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 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.
At one point, the company got too big. You can’t just send an email to 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 see updates from every business unit on Sunday night. When you head into the office Monday morning, you know, “What fires do I need to go fight?”
Actually, it was Bridgewater, plus Diane Greene from VMware who talked about how she ran this. I was like, “We need to do this.” I have to check in with Tim. When I left, we just did a version that was CEO’s reflections that went out to the whole company. We alternated between the CEO, the COO, the CFO. They would alternate reflections that went out to the company. That was incredibly useful, separate from our allhands meetings or whatever it was, because you basically could just see, “Oh, this is what’s on Tim’s mind.” It gave that intimacy and that communication channel.
It’s a lot of practice. It’s a lot of fine-tuning. Some of it is 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: Where were you 10 years ago? And if you could travel back in time, what advice would you give?
Koh Shiyan: Ten years ago, I would be in my final semester at HBS. I had this job. I was starting at Bridgewater in the summer. It probably would’ve been to do more self-care. In the first three years at the startup, and even at Bridgewater, I didn’t feel particularly healthy. In the spirit of things that compound over time, sleep, exercise, good diet. All those things are useful to invest in over time.
Jeremy Au: Thank you so much for sharing your journey. I love what you said, learning what you like and don’t like, startups learning faster, what would change your mind, communication and learning. My favourite phrase still, is, you can do anything for 10 weeks.
Koh Shiyan: That’s true. 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 period.
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This is an excerpt from the book BRAVE10: The Singapore Edition by Jeremy Au. You can buy it here.
Image Credit: © inspirestock, 123RF Free Images
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