Sherry Jiang: Founder Poker Strategy, Navigating Product-Market Fit Pivots & Big Tech Career Advice- E475

Sherry Jiang, CEO & Cofounder of Peek, and Jeremy Au explored three key topics:

1. Navigating Product-Market Fit Pivots: Crypto winter forced Sherry to pivot from her original idea—an algorithmic stablecoin protocol for Southeast Asian currencies. This shift led to the creation of Peek, an AI-powered platform for managing net worth. She highlighted the challenges of gaining traction, facing ambiguous customer demand, and maintaining deep customer engagement. Sherry emphasized how adaptability is essential when an original business model fails to fit the market. She candidly discussed the emotional and logistical hurdles of steering a company through such changes, underscoring the need for transparent communication with both internal teams and external stakeholders, especially investors.

2. Founder Poker Strategy: Drawing on her poker experience, Sherry likened the entrepreneurial journey to poker, focusing on the importance of making informed decisions in the face of uncertainty. She discussed the psychological resilience required in both poker and startups, stressing that founders, like poker players, must manage risks and accept losses—even when decisions are strategically sound. The conversation tied this mindset to the essential founder skill of evaluating risks with the best available information and confidently making decisions amidst ambiguity.

3. Big Tech Career Advice: Sherry offered advice to tech professionals, particularly those considering a shift from stable corporate roles, such as Google, to startups. She encouraged them to assess their career paths in relation to their personal values, risk tolerance, and the volatility of startup life. Sherry urged introspection, advising individuals to reflect on what they truly value—be it autonomy, innovation, or stability—and how those values align with the inherent risks of entrepreneurship. For those contemplating the leap, she suggested carefully considering if their motivations and desire for autonomy align with the unpredictable nature of startup life.

Jeremy and Sherry also discussed the tactical challenges of communicating business pivots to stakeholders, the emotional toll of leaving secure corporate environments, and the importance of staying authentic when explaining business shifts to investors.

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(01:43) Jeremy Au:

Morning, Sherry.

(01:44) Sherry Jiang:

Good morning, Jeremy. How are you doing?

(01:47) Jeremy Au:

Good. Well, good to have you again as a sequel. I felt like this is about time. It's been quite some time since that first episode. So, I'd love for you to introduce yourself.

(01:56) Sherry Jiang:

Yeah. Hi everyone. I'm Sherry. I am the cofounder and CEO of a company called Peek. We're a AI-powered platform that helps you track and manage your net worth. I actually was on Jeremy's podcast, I think two years ago now. So it's been a really long time and been actually working on a few different things before Peek as well. But some of those learnings actually is what translated ultimately to some of the products, ideas that we started to put together. So I'm super excited to be here, talk about the journey, what we're doing with Peek and catch up in general.

(02:27) Jeremy Au:

Yeah, let's definitely talk about that, which is that, the last time around two years ago, you're still broadly the same person I know. You're still optimistic, entrepreneurial, still getting stuff done. You had, done that career in big tech and so forth. I think the big thing was that at a time you're working on a crypto kind of approach, and you've since pivoted since then. So could you share a little more about what you were doing back then, if that makes sense, and after we'll talk about change after that.

(02:50) Sherry Jiang:

Yeah. So, when we first had a conversation on the pod, we were building essentially a product called Bluejay. Bluejay was a stable coin protocol, protocol meaning it's a mechanism, economic mechanism built in decentralized coin slash crypto. So we're building the stable coin for Southeast Asian currencies, starting with the Singapore dollar. Our thesis back then was that there are all these inefficiencies in our current money system when it comes to cross border remittances, capital markets or borrowing lending across countries. And our belief was that, stable coins would be that next layer of that kind of monetary infrastructure, that will drive down costs and make things work better.

Now, the reason why we decided to change directions firstly was I would say, number one, I was probably more consumed with the concept of how this would all work out in principle, and it made sense. There's a lot of US dollar stable coins out there. The problem is a real problem, just that the steps in between that can get to that future, were just a lot harder to achieve at the stage that we're at and a lot muddier. And I think this is a lot of the challenges within crypto where a lot of things are quite promising, but then when it comes to like, what is the one user that you can identify with a hair on fire problem that wants to receive transfers and stable coins. It was just very, very difficult to identify exactly that. And I think this was a challenge that not only we struggled with, but I would say a lot of other companies within the crypto space that wanted to do something more real world.

We think we all struggled with it. And, it didn't help that at the time, crypto winter, essentially came upon us as well, right? So, not only was there murkiness around product market fit, but there was also not enough the typical kind of marketing drive that you would get from the space. So for all those reasons, we decided to actually do our first, kind of shift from the stable coin into something still within crypto, but I would say a bit more, a little bit more like a real world in nature.

And the way I describe that is we were looking at use cases for the stable coin, instead of looking at the building the stable coin itself. That was kind of a natural place that we were going. So we got into the space of tokenizing real world assets. Just to break down what this means in simple terms, it's, the idea that you can fractionalize into smaller pieces, certain assets in the real world, and facilitate those transfers on the blockchain.

A lot of projects have done this for things like real estate to make it a lot more accessible for people and people were starting to do it for private markets, right? So basically investments credit or hedge funds or alter other alternative assets where typically have a higher minimum check size. That's where we went first. So We were like, okay, we can allow for people to invest in private market assets in Asia using our stable coin. The need that is being solved is for people that are individual investors, either generally accredited, sitting in that kind of affluent range. They don't have generally like 10 million to invest in Blackstone credit. So that was the problem statement that we were gearing towards. So we went from like, okay, there's a solution that we have to like, there's might be a little bit more of a problem here than what we've seen before.

And, we did this for about nine months, actually. This was in 2023. And I would say that we had okay traction, but it was not the level that you would want to see at the earlier stage and actually, when people ask me, what do you look at in terms of numbers to decide what to do? I'm like, numbers are just one side of the story. It's better to be like 50% month over month growth versus 10% versus 20%. But actually the most telling thing for me is figuring out how much of a must-have versus a nice-to-have is your solution for your customers, right? And so, what actually convinced me of shifting directions from what we were working on before was when we actually went out and surveyed our existing customers. How would you feel if Bluejay did not exist tomorrow? So basically how disappointed would you be? And, there was not a single customer that said that we were a must-have, that they would be very disappointed. They said they will be somewhat disappointed, like a little bit disappointed, or they said they weren't disappointed at all. They had other solutions or this was not a essential thing to for them to invest in. They were just doing it out of curiosity. And so when that's the case, that signals to me that regardless of what you see in the numbers, you're not solving a fundamental problem.

But what's interesting as we still kept trying to understand what the problem is for customers. If this product is not the issue or this problem is not the issue, what are some of the issues? And actually then, listening to the customers, talking to dozens of people like these customers, actually led us to ultimately working on Peek. And so one of my learnings was just like, again, it's feels so obvious when you're maybe starting out and you're like, of course it's, that's, of course that's what you do. But after some of these, the experiences that I've gone through, it's become so clear to me that you have to let go of focusing too much on your product vision and making that happen and just be super, super close to the customer. Talk to so many of them. Find so many different ways to invalidate, try to invalidate what you think as well. And having that kind of airtight understanding is a must have before you get started with any other product. So I know that was a bit long, but I wanted to share a little bit of what's happened in the last two years and how we as a company navigated that as well.

(08:10) Jeremy Au:

Yeah. So having gone through the set, what have you learned about the pivot process? Because, I'm sure that each time you pivot, there's a certain set of like stakeholders, who have either invested in you or who are early customers or who are early employees of you. So how does that process work?

(08:25) Sherry Jiang:

Yeah. Yeah. I mean, I think that trying to communicate a pivot should be treated the same way as like you pitching your company or talking about your company the first time. And you need to have the same data points, evidence, right? To back up why you want to go a certain way because you're fundamentally creating a disruption. And again, it's not to say that disruption is bad, but you need to have good explanations why. With a team, I would say that it's, not usually a huge surprise because I don't tend to come out of the corner, unexpectedly say, Hey, guys, we're changing directions. I bring my team in with it, right? We all share the same thoughts around some of the users because we're talking to the same users. So it is a gradual process to work with the team on bringing them along to come to the same conclusions that I would, but then what my job is as a CEO is to solidify what is the plan now? Now that we know this, are we going to now test by having some prototype or beta program out in the market? How are we going to do that? What is the business model of the product? What's the timeline? It's more like clarifying the specifics with the team.

I say publicly or with investors, right? With investors, I mean, as soon as I have a sense that there's a shift in the direction. I go and talk to them. I'll present similar numbers around why we're doing this. The funny thing is, you do have to go back to that seed stage mindset of, okay, you don't really have traction in a new idea because you haven't done it yet, but you show some user insights, right? So we'll be like, Hey, these are the customers we had at Bluejay here, quotes of what they have talked about. And so linking these together lead us to believe that this is a better product direction. So again, I'm trying to be very, very evidence based.

And then publicly, I'm very open about this kind of stuff. I think initially, maybe the first time we changed directions, I felt a little bit like, Oh, I don't really want to tell people like as open, as comfortably about it because I didn't like the shame that can come with it. Every founder, the first time they do it, they feel like it's a failure or a letdown. It's a very strange feeling. But the second time around, I was like, it's just part of the startup journey. You are doing your users, your company and yourself a disservice if you want to continue stubbornly down a direction that you do not think has as high of a chance to work out. I'm trying my best utilizing my own resource, which is my time, and the people's time around me, to create the biggest impact in the world that we think has a likelihood of succeeding. And so I'm going to put myself behind this new thing that I think has a higher likelihood of success. And I'm just going to go for it a hundred percent. And I find that when, I'm very genuine about it and like, I stopped working for a company like Google where I had a very comfortable life.

So people kind of think, okay, there must be something behind this conviction if this person's giving up so much. So, in a way, I don't feel like the second time around when I've communicated us moving in this direction, there's been as much of a concern on my side. And in fact, sometimes it's actually quite encouraging when people come around and say, actually, I really like what you're doing now. It's a problem that I have. So, really interesting. Let's talk more. So yeah, it's definitely not easy all the time, but I think, I learned just being over communicator, but also be really evidence based about how you communicate the decisions that you make.

(11:25) Jeremy Au:

You know, on a previous guest of Brave called Rob Snyder, he was talking about, he also had to go through multiple pivots. He was just sharing that the tactical side of doing a pivot, like you said, is relatively straightforward, but it's the psychological side of actually being okay with a pivot, overcoming confirmation bias, and some lock in based on your prior statements and your prior promises to stakeholders and teammates, that tends to be one of the harder things to overcome. What are your thoughts about that statement?

(11:51) Sherry Jiang:

I think it's absolutely true. First of all, you feel, I'm just going to share the emotions that you feel. You feel like you're letting people down in a way because you're going on one path and you're basically stopping it. And then, you don't have any data to support that the new product has traction because the product isn't there. So how do you prove something that doesn't exist when you're stopping something that already exists and has numbers. I think the second emotion that you go through is you feel like, dishonest is not the right word, but you feel like, you are so excited about something you're working on. And, you have a lot of conviction for it. And then change that conviction. Again, like if somebody isn't very empathetic to the founder journey or haven't been a founder themselves or surrounded themselves by founders, like there's a lot of judgment that can come with that, right?

(12:29) Sherry Jiang:

They're like, you spoke on stage about this, you had this thesis, and then all of a sudden you're not doing it anymore. There's a lot of negative connotations that can come with that. So I definitely agree that the emotions are real, but I kind of just push them aside. And if anybody anybody who knows me or knows other founders understand that pivoting is just part of it. It's just how you handle the pivot. That's more important. And if anybody is ever judging any founder out there for a pivot, I'll just be like, you have no idea what it's like and what these people have been through. And so whenever I talk to founders and they share their story about pivots or change in direction, I will never, ever, ever make them feel like they did something bad or make them feel bad about themselves. Cause I know it's hard. And I've thanked them for basically taking a bet and trying to create something for the world that makes it a better place.

(13:17) Jeremy Au:

When you think about being a founder and everything, I also know that you're a poker player as well. I'm sure there must be like poker metaphors or analogies that you're thinking about in relation to the founder life. Any thoughts about that?

(13:29) Sherry Jiang:

Oh yeah, absolutely. So two things that you have to get over with in poker are, at least for me, these are the two that can be challenging when you do everything that you should have done with the information that you had, but you still lost a hand. Let me give you an example. Let's say you and an opponent are in a hand together and you happen to flop a set of Kings or have pocket Kings and there's a King on the flop and that's a really good hand but let's just say, for whatever reason by the river, which is the last card, your opponent hits a flush and there are more combinations of hands that you would have beat with your set of Kings.

But of course it's going to be combination of hands that beat you too, which is like, possibly a flush, right? So mathematically, there are a lot of times where, if somebody goes all in, you're supposed to call, right? Like it doesn't make sense to fold, but they flip over a flush and you lose all your money. And so for somebody who is new to poker or doesn't do any kind of risk based decision making will be like, Oh man, like that person should have folded the set of Kings. And I'm like, no, if you play that hand, thousands of thousands of simulations, like you should always call them that spot. But that's just going to happen in life where you will do everything you can in terms of inputs, trying to gather data, like, try to whatever asymmetric information there is, you try to lower that gap as much as possible but you're still going to fail sometimes. And you just have to live with it.

You pick up more chips and you pick up another hand. That's what it is in poker. You don't have time to mentally or emotionally digest that hand. You just move on and you're onto the next, right? And you do that enough times where you become desensitized to it where you're like, I've got to, I just got to know what I can control, what I can't control. And I do my best to make the best decisions within what I can control, but then there's a whole space of things I can't control and just knowing what that difference is huge thing. It's very similar to the serenity prayer that a lot of people use but I think it's very much a mantra that every founder should think about in the morning, right? So I think that's one lesson from poker.

The second lesson of poker is on the marginal calls and folds. This is basically where, if you're facing a really good opponent, they put you in what they call tough spots, right? It's a marginal call or fold, meaning you're kind of at that exact 50%, right? You're almost like, it doesn't feel great to call. It doesn't feel great to fold. I'm not quite sure what to do. And you end up going with gut. You're like, you know what? I can see a case for either direction, but I can't sit there and make these guys wait for me for one hour to make this decision. I got to go. Right. And you just make a call. And half the time you feel like, I don't know if I made the right call or not. It feels like there was some guesswork and intuition involved. And that's also something that happens in the founder. These very marginal calls, where, you would like, again, I would like to say that I make decisions where I'm like, 60, 70 percent equity. right? There's some percentage of the chance that wasn't the right decision, but I feel fairly confident that, there's at least something that tips in the favor of me making that call, but you're going to be confronted with some marginal decisions on what to do. And you just have to, I guess, find a way to, pick a direction and stick to your guns about it.

(16:25) Jeremy Au:

So, when you're thinking about this, obviously these are very powerful metaphors as well. I think the part that also resonates with me is that, there are stakes, right? When you're playing poker, you're betting with money, similarly in the founder life, you're also betting and it may not also be money in terms of invested money and so forth. But also there's a lot of time, right? You can play a poker game in one hour with your friends or two hours or three hours, but I think the big part, I guess, what you're really investing in is also your time as a founder in exploring A or B or C. How do you think about that time and process?

(16:58) Sherry Jiang:

Yeah. I mean, I guess, okay, if you think about like our life three year chunks, right? It's not like we have a lot of time in our lives, in our careers. Let's say we work from like the ages of 20 to like, 60. So, that's like 40 years in there. So we do have time. It's not like we, have very, very small amount of time, but it's a lot more finite than the number of hands or tables that you play in poker. So, maybe I'll simplify it and call it two year chunks for the math, but basically you have maybe 20 bets you can take, right? If you have this 40 year time frame that you're working, right? and actually I really do think that's how people should think about their careers. Like I told some friends before, like every two years, if you're on Google, you should think about quitting. You don't have to quit, but think about what it's like to quit, right? Because you should be rethinking this stuff. So how this applies would be, okay, I can still play quite a few hands, but it's going to be a lot less hands than what I can play in poker. I think that also means the emotional weight of some of these is a lot more. There's a lot more ways that you probably would need to insure against certain things happening, than maybe in poker, where you can just pick up another hand and go. You can run this spot a thousand times and if you play enough poker, it kind of evens out, you don't really get that benefit in your own life as much, so there's a lot more variance, that's why I think, insurance policies are, figurative insurance policies are good ones to think about.

And I'll talk about some of the ones that, I've thought about, I didn't start a company in my early twenties. And I think again, nothing wrong with people doing that, but I was like, you know what, I don't mind being a corporate person for a couple of years and building some savings. So I have some safety net for myself. So in case I need to utilize any of that, if in case some of my two year segments of bets don't work out, I do have some fallback. There's some insurance where I'm not completely putting myself in a situation where I don't have anything left. I think that's how I would think about it. It's like, you still are playing poker. You still have more than one shot, but the number of shots you would have are a lot fewer in the real world than simulated within poker.

(18:52) Jeremy Au:

And, there you are, having made a decision and now it's multiple years out since you left Google, and so there's a lot of people who are at Google or big tech or, big companies. So what advice would you have for people who are thinking through their career, maybe frustrated at work, maybe they're okay with work, maybe they're bored at work, maybe they suddenly get laid off at work, but how would you think about that?

(19:13) Sherry Jiang:

Yeah. I actually think a lot of these questions are not so much just about work, but about what you value in life and whether or not the work that you're doing, which is, encompassing a large part of the hours of your day, like, are those lining up with your values, right? So, like I'll give an example. Some people, their biggest value is stability and they want to start a family and, they're happy with a job that gives them economic stability aspect, but they're maybe not as risk taking, right? Because they're like, okay, I want to make sure that I don't want to stomach that uncertainty. In that case, I would probably not really suggest that person to go and leap into a startup because you might think, yeah, I don't have to do things for my boss. Startups sound amazing, but trust me, you'll be doing things you don't want to for a lot more people than your boss when you do a startup. You have to really honestly ask yourself, is it for me?

If your values are like, look, I want autonomy, build my own brand or do things that best encapsulate who I am as a person? I don't feel I can manifest that working at a big company, because again, you're just one of many people then I'd say, maybe you can explore doing a startup, right? But I think that exercise needs to come before deciding whether or not you leave. What is it that you want? So if your gut is telling you that something is missing, but you don't know what that is yet, then you should introspect and then figure out, where there are misalignments the values that you care about and then the values being experienced in your current job. So yeah, that's kind of how I would say. I would never really tell everybody like, Oh yeah, you should all go do a startup, quit your job and just bet on an idea that has a 99% chance of failing. I probably wouldn't tell everybody to do that, but if they belong in the camp where they want to take the risk and they're kind of dragging their feet and they're like worried about if they're good enough or have that experience. I'll probably push them over the edge and you know, just go. So that's my thinking on that.

(20:57) Jeremy Au:

Would you say that your advice has changed over the years? Because, when you first left, obviously, you're early in the founder journey, and then now several years out since then, has your advice changed over time, you think?

(21:07) Sherry Jiang:

Yeah. I don't think my advice would have changed. I probably wouldn't be giving advice about it when I first left. Cause I was still trying to figure out if it was the right decision for myself. But no, I don't think I've changed on my views here. It's funny because, there are a lot of things that are different. I would say tactically around how I handled the startup journey. I've obviously learned a lot more three years. But, the reasons why I decided to do it and the reasons why I continue to do this have not changed at all. It does go down to values for me. I asked myself this question before I left Google. I was like, what is worse? Having to execute on a decision that I disagree with, but not having to take the accountability for when it goes wrong. So that's corporate, right? You do a lot of things that you don't always agree with your manager, your director wanting you to do something, but you're like, you know what? I still have a salary. That's fine. I'm just going to go ahead and do it. Does that bother you more than the uncertainty of having to take accountability for all of your decisions? You get full reign of everything, but if something goes wrong, it's completely on you. I decided that I didn't like the idea of having to constantly do things I didn't agree with.

And I'm like, I don't mind taking accountability for my decisions. I want to have the freedom to be like, this is the brand that I want to shape. These are the people that I want to hire. This is the problem space that I want to work on. And so that's where that value alignment came into play. And that's why I left. And it continues to be the reason why I don't want to go back to corporate either. I mean, never say never, but, I have nowhere near feeling like, Oh, this journey is not for me. So that advice still stands. I'm still kind of the same person, the reason why I'm doing this is still the same.

(22:39) Jeremy Au:

And any advice that you have for your younger self? Imagine you had a time travel machine, and then you could go back to your early days of being a founder, like day one of having left your job, any advice you give to your younger self?

(22:53) Sherry Jiang:

I would say number one is, stop worrying about what you do not know today. Understand what you do know and what you do not know and what backs up what you do know. Then wait for what you do not know, just figure out what the plan is to find the answer. The methodology is a lot more important than the answer. I feel like I'm able to build my confidence based off of that versus back then I felt like I needed to know things. If I didn't, that was much harder for me to psychologically stomach that kind of uncertainty. The second thing I would tell myself is just trust my gut a little bit more. I think there were times before I made the decision to pivot, I kind of felt it, but it took me months to really trust my intuition. Like high stakes decisions where, like, you're sitting there, you're tanking at the poker table, and then, you make a decision that you thought about making the first second that happened, but you take long time to make those decisions. I would tell myself just to trust my gut and go for things more.

I think that would have saved a lot more time. I probably could have saved like at least half a years of like work if I just trust my gut. So right now I do this exercise all the time. When people ask me, how do you know this is going to be working out this time? I'm like, what's that signal for you? I feel good in my gut, right? I feel like things are moving. I can feel the excitement from our customers. I can feel the excitement from the team. I can see the path. I feel good about it. And, when I was younger, I feel like I just like, I'm like, no, you need to be, you need to be a hundred percent certain about something that kind of just ignore what you feel inside.

So those are the two things that I would tell myself. Focus more on the process and the methodology of getting an answer than just the answer and then, yeah, second one is just trust your gut. That's, what's going to get you through the marginal decisions, by the way, because you're not going to be able to always have all the evidence for a 50-50 decision.

(24:30) Jeremy Au:

On that note, I'd love to summarize the three big takeaways from this conversation. First of all, thanks so much for sharing about the experience of pivoting several times in terms of how you went about the process, but also how you thought about working with your stakeholders, your customers and your team.

Secondly, thanks so much for sharing about, I think the poker analogy for founder life. And the advice that you would give, especially in terms of making the right decisions, with the best of the information you currently have and being comfortable and confident, about what that set of information has given you in terms of what to do.

And lastly, thanks for sharing the advice you would give, to some extent, your younger self, but also to the folks, at, big tech companies. who are thinking through what the next stage of their careers would be. And I do feel like he has some really good advice about thinking through about what that life meaning is and also what that career bet is going to be.

On that note, thank you so much Sherry for sharing.

(25:19) Sherry Jiang:

Yeah, for sure. Jeremy, thank you so much for having me on again. This was a fun conversation.