Sherry Jiang: Web3 Market Turbulence, Product-Market Iteration & Team Trust - E297

· Founder,Start-up,Web3,Fintech

“Trust makes teams efficient because you don't have to fact-check and feel anxious about what someone else is doing. Everyone knows what’s going on so the flow of information is hyper-fast. We’re not like separate brains trying to figure out what each other knows at certain points in time. We're operating with a hive mind and are all collectively in the same context. This is not always perfect, so it's something that we really strive for because execution is not just about yourself but the team as well.” - Sherry Jiang

“Most of the time, what you think is a brilliant idea for your company isn't what comes out. When you start executing it, meeting real potential users, and building the product, it evolves and changes to something that you may have not even imagined in the beginning. A startup should figure out a way to experiment and test what can work in the cheapest way possible. You should be hypotheses-driven and find a way to test and validate the idea. Once you have the inkling that you’re potentially right, narrow down your space, double down in that area, and soon, you will realize that there are a million more ideas related to what you're doing that you have to solve.” - Sherry Jiang

“The idea of things going well feels so foreign because we’re used to the bear market right now. You always have to manage risks. When cataclysmic events happen, you don’t want to be caught on the wrong end of things. We are a company born out of a market where being prudent and cautious is better than being aggressively growth-oriented. We are able to learn the lessons about risk management without suffering as many consequences.” - Sherry Jiang

In this engaging conversation between Jeremy Au and Sherry Jiang, the cofounder of Bluejay Finance, they delve into the world of cryptocurrency entrepreneurship and the challenges faced in the Web 3.0 era. Sherry shares her journey from tech leadership roles at Google and Amazon to founding her own crypto startup, providing practical lessons on risk management and asset diversification. She emphasizes the significance of execution and teamwork in the startup landscape, and how her company fosters efficient communication and builds trust within the team. Sherry's personal growth as a founder shines through as she discusses overcoming stage fright and embracing vulnerability to thrive in entrepreneurship.

Key Topics Discussed:

• The evolution of Sherry's career from tech giants to founding Bluejay Finance

• Challenges and lessons learned during the collapse of FTX and the importance of risk management and diversification

• The value of efficient execution and teamwork in startup success

• Balancing strategic planning with rapid execution in the fast-paced crypto space

• Sherry's personal journey and growth as a founder, embracing vulnerability and bravery

Supported by Pollen

 Pollen is a private B2B liquidation marketplace. The startup connects sellers carrying excess inventory with bulk buyers across the world. The platform incorporates pricing, algorithms, dashboard analytics and sustainability metrics to find great liquidation outcomes. Hundreds of tons of usable products that would've been incinerated or gone to landfill are now used by happy consumers instead. Manufacturers get more revenue, buyers get cheaper, and the world benefits Learn more at

Jeremy Au: (01:49)

Hey, Sherry, really excited to have you on the show. You are another school alumnus, go Bears, UC Berkeley, with me but also a great founder who is building in the Web3 space and wanted to hear a little bit about your story. So could you please introduce yourself real quick?

Sherry Jiang: (02:05)

Yeah, absolutely. So I'm Sherry. I'm the CEO and cofounder of Blue Jay Finance. We are a platform that actually connects investors to different private market investment opportunities like private credit in a way that is much more efficient and democratized compared to traditional finance.

So the way that we do it is actually through a platform that is on the blockchain. So it's actually done through stablecoin type of investments. I'm originally from the US and now I live in Singapore. I moved over here actually five years ago and worked in the payments team with Google, primarily focused on emerging markets like India. It was actually during my time working in FinTech that really opened my eyes to see how some of these technologies really can help accelerate financial inclusion, which is why two years ago I was really excited about exploring what that could look like in the new tech stack for finance, which at the time was all the innovation that was happening within crypto and defi. So that's really the story of how I got to Blue Jay.

Jeremy Au: (03:06)

So, you know, I've got to ask you, what were you like as a student? I know you were at the Berkeley Group, which is a club that you and I both share for undergraduate days, but we were doing pro bono consulting for social sector organizations. You came in a few years after me, but I'm so curious about what you were like as a student back then.

Sherry Jiang: (03:23)

I think I was extremely busy as a student. You know, I think during college I wanted to get the best experience I can out of the four years, and so that meant trying to meet as many interesting people as possible, cram as many courses as possible, but also like engage in meaningful extracurricular activities.

So, unfortunately, that meant that my sleep wasn't really great, which I think I've now worked on correcting since, you know, becoming a working adult, but I, I felt like Berkeley just gave so many opportunities for you to explore different things. So I was actually very lucky to have been part of the Berkeley Group which you and I both kind of share as experiences, but a few years apart, cause it was really a cool opportunity to really combine skills within business strategy and social impact, which, it has always been a bit of a North star that I use when looking at opportunities that I want to do in my job most of the time.

Jeremy Au: (04:21)

Yeah. And after that, you know, you went on to work at Google and Amazon, so can you explain how you made that career decision from your perspective?

Sherry Jiang: (04:29)

Yeah, for sure. So, when I graduated from university, at the time, most people went into what we called the ABCs. So I was also in the high school of business, which I think you were also a graduate of, and so ABC stands for accounting, banking, or consulting. And so that was where I think 90% or a good number, 80-90% of people went into for their first jobs. I did actually a summer internship in IB and decided that it really wasn't for me just based on my work style and my personality. And so it was quite interesting actually to see tech companies start to recruit for non-technical roles in universities.

So, I actually first landed a job at Amazon, moved up to Seattle, and worked there for a year in the marketplace business, and it was quite exciting because you know, Amazon at the time was in this hyper-growth stage. It was before Prime Now was announced and launched. It was before Alexa even came out.

So I got to work at Amazon when those products were all being launched, which is really, really exciting. And then I moved over to Google within a year, not because I didn't think the opportunities at Amazon weren't interesting. I just felt like the heart part of the job just wasn't there for me as much and the building products for everyone, part of Google really did appeal to me, right? If you think about what Google's really trying to do, it's really trying to bring internet access to billions and billions of people around the world so they can access information and do things to make their lives better. So, that's what really made me switch over, and while I was at Google, I was super fortunate to have worked on quite early-stage teams, right? So it wasn't like working on Maps or Search where it was already a multi-billion user kind of product. I joined this team called the Next Billion Users where products were basically being incubated. So imagine if Google was a VC and then these little products were like portfolio companies, and the thesis of this team was building for the next billion users coming online from Brazil, India, from Indonesia, require a completely different set of assumptions than looking at building products in the US or in Europe.

So at the time, most of the time when people were thinking about searching or finding information, let's say in Asia, it was actually done socially through Facebook, through those kinds of channels versus through the search bar on the Google homepage, to other kinds of differences where at the time, at least, cash was the major medium of exchange in most developing or emerging economies. So, you didn't really have credit cards, so you had to build payments or think about payments in a very different way. So it was actually that experience that brought me to Singapore. So I was part of the team that started building what was called Tez at the time and later rebranded to G-Pay which was the payments product for India.

So it was really exciting. I remember at that time, we had to really convince folks in Mountainview that payments, that the feature of payments was really going to be in places like India when less than 30 million people, across the board were even using non-cash payments, like digital. But over time, that became hundreds of millions of users just because of how much it was really kind of, leapfrogging and improving over the existing experience of using cash.

Jeremy Au: (08:03)

And what's interesting is that there you are building, building, building, and then you made the decision to become a founder, right? So could you share a little bit more about how you started thinking about this?

Sherry Jiang: (08:13)

Yeah, so. None of these decisions, becoming a founder, doing a startup in the space that I'm in right now happened overnight. It had been underneath the surface for a really long time. So actually, what's funny is back in 2019 was the first time I thought about quitting Google to do my own company with my younger brother actually. We wanted to democratize software engineering education for smaller, mid-tier cities across the US where it's not as easy for a parent to be able to send their kid to a school where there's an AP, CS education curriculum, and getting private tutors in CS would be like exorbitantly expensive plus like very low supply in certain places if you don't have somebody who has that. So, we were actually thinking about some of those ideas but I think what ultimately happened for me at that time was I didn't want to move back to the US. I felt this kind of calling to work on the problem spaces within Asia.

So building this company, what it meant, going back to the US so it didn't feel right to continue with that, but really during the pandemic was when I had a lot of time for reflection, a lot of time for reflection. I considered a whole gamut of different things to do and ultimately, doing my own company came out as the ideal choice at the time because I think number one, I was feeling the most risk-seeking in my life at the time. As in I don't have a family to feed at the moment. It's really just myself independently. I don't have to make this decision with somebody else.

So I felt like, strike when the iron's hot, when you have that risk appetite, just go for it, and then I also felt, towards the end of my time at Google, despite it being like an amazing experience working there, I felt like the bureaucracy or the slowness of execution in a large organization was really catching up.

The payments team itself was moving beyond just this small couple of hundred-person team to a couple thousand-person team, which becomes very different. So, it was a bit of a push and a pull factor for myself that made me ultimately take the jump summer of 2021 and it wasn't an easy one. I talked to a lot of people about it, just bouncing ideas off and ultimately, I realize that it's a decision you have to make for yourself and what feels right. You can rationalize and have all these logical reasonings for any kind of decision, but you had to go with what felt right. So I was pretty fortunate to have an avenue to be able to meet other founders or other potential founders through a program called Entrepreneur First, which Jeremy, I think you also did at a certain point in time and see. So maybe what I am doing in life is basically following behind you for just a couple of years. Right? So maybe one day have my own podcast.

Jeremy Au: (10:56)

Just don't become a VC.

Sherry Jiang: (10:57)

Oh, I was, I was just about to say maybe one day I'll have a podcast like yours. But yeah, I did EF. I was like, look being a founder, I know, is going to be lonely. I had this Google family, this Google community, and all of a sudden I was by myself, so, going through EF actually felt quite appealing for that, and with EF just so folks understand the program and the context, it's a little bit different than a Y Combinator, or a YC, or if you some of these other accelerator programs that everyone's heard of in that you don't join when you have a team or a product or prototype. You sort of join as yourself and the idea of the program is for you to actually match with somebody who compliments your skillset or edge or domain area and within a very short amount of time, figure out if, whether or not you can actually build a VC-backable company together.

So that's what happened, and there's a lot of stories around, teaming together and breaking up, teaming together, breaking up because they actually even encourage it. You should definitely think very, very, very hard about the right kind of person you should co-found a company with, but I was actually pretty lucky in that I actually met my co-founder in the first week, or I teamed up with my co-founder in the first week and we have been together ever since, and it's been two years. So, yeah, that's a little bit of the journey from, realizing that I wanted to do it and why, and to actually taking that leap and doing it for real.

Jeremy Au: (12:24)

Yeah, and I think that's an incredible journey that you made that transition. And what's interesting is that you chose Web3 and FinTech as that category, and these past two years have obviously seen a lot of change as well. I remember discussing this review in the first 30 days and then after that, lots of things have unfolded with FTX and Binance, with the global economy, and the Ukraine war. There are all kinds of things happening. So I want to hear a little bit about your perspective.

Sherry Jiang: (12:49)

Yeah, for sure. Running a Web3 company through 2022 had to be one of the most difficult things, especially in comparison to the euphoria that the bull market brought in 2021. It was just crazy. You were hearing people that were raising insane valuations for their companies with just a white paper, basically, a document that describes what your project protocol is doing, and then, funding would just kind of materialize. So that , funny enough, was a conversation that we had, I think when we got Thai food where you're like, this historically low-interest rate environment is going to change and this entire landscape is going to basically turn on itself. And that has actually eerily played out exactly like you described from the time we had that conversation. So, we saw basically this slowly crashing plane across all industries, but especially crypto in 2022. So instead of going through macroeconomic explanations for all this, I'll talk to you about my own personal experience as a founder. It was actually quite difficult, but a blessing in the end, and I'll kind of break that down.

So what was really difficult was that we were fundraising for our seed round, I would say during the, the beginning of the end, the beginning of things kind of getting worse. And it was midway through our fundraising round that Luna, the terra ecosystem crashed, right? And so, there was this frenzy where everybody was just so scared of anything that had stablecoin in it. And so, that involved going back to the dozens of investors that we're raising from and actually explaining in more detail our mechanism as a stablecoin at the time. Why and why we're different and why the concerns of Terra Luna wouldn't apply to us as much. But you know, of course, you have people that were assured and convinced, and you had people that weren't right. So there was actually a little bit of turmoil in bringing everything together for the round.

We're very lucky that we ended up closing it with $3 million, but it certainly wasn't anything close to the euphoric fundraising rounds that people would talk about where things just closed in two weeks, and there was none of this market drama to deal with. So I think that's number one, but I think, maybe one lesson to take away from here is that you really do have to prepare for any situation when you're doing fundraising and always keep your options open, and never, I mean, until the money is in the bank, you're not done. I think I want to tell that to every single founder.

I don't care if term sheets are signed or verbal commitments are made. It's only done when the money is there and you need to assure your investors every step of the way. Hopefully without a six multi-billion dollar system crash happening at the same time, but, you always have to keep that in mind.

I think the other difficult point that every company had to go through was the events of FTX where basically, an exchange that people didn't really think would fail, would actually collapse, and have had been collapsing for a very, very long time, and, unfortunately, affected a lot of people I knew who had, for instance, part of their company treasury in FTX.

That is just, God knows when or if they're going to get that back. And the reason why a lot of people were doing that also is because there were all these yield opportunities that you can get on your treasury in FTX. And so you're like, why not? Take your idle cash and runway and put it in FTX. We were lucky that we didn't actually have exposure to FTX but after that instance, we actually made this concentrated effort, as part of our own treasury management to diversify our assets across multiple places, so bank account, like hard, just fiat, not crypto. We have a Multisig account on the chain, and then we have multiple different assets that we hold as well. So it's not just one single asset where if it goes down 80%, we'd lose everything, right?

So, you have to prepare for the worst, and I think a lot of people didn't think about that when things were great, or going great in 2021 because the idea of disaster just seems so foreign, kind of like the opposite right now where the idea of things going well feels so foreign because we're so used to things being in this bear market right now, but you always, always have to risk manage. You do not know when cataclysmic events happen, and you do not want to be caught on the wrong end of things there. So, we are a company born out of a crisis, basically, and born out of a market where being prudent and cautious is better than being very aggressively growth-oriented at the cost of best practices. So in that way, I also count this as a blessing where we were able to learn the lessons about risk management without actually suffering the consequences as much. And so, I would say, all in all, it was tough, but I would say that we ended up okay, which is good.

Jeremy Au: (17:51)

Amazing. And I think what's interesting about all of that is that you had both the macro-environmental changes, as you said. So there's Terra Luna, there's FTX, there's Binance, there's a global economy, and then there's that next layer about the company itself. So you mentioned your company, the company changes you had to enact in terms of compliance and to make sure that your treasury was safe and secure.

And now, of course, you talk a little bit about your own professional changes over this time period. So what would you say have been your own personal changes in your own outlook on being a founder today? You know,

Sherry Jiang: (18:24)


Jeremy Au: (18:24)

I mean, I feel like there are like three stages. One is, while at fang, it's a big tech company. Then there's like the early stages of the crypto, Web3 dynamic, and now where you are today. So could you share with me, how about that evolution or adaptation of yourself as a founder?

Sherry Jiang: (18:37)

Yeah, Jeremy, that's a really interesting question, and definitely, there are a lot of directions to go with this. I think two years ago, I really thought as a founder, the people with the best ideas are the ones that end up winning. It was all about, and I don't disagree with this anymore, but I would say, I have some edits around how I think about it, but it was all about, do you have differentiated insights about the market? Do you have an idea that's original? And how do you get the best idea out there? And where I'm at now, I would say, is that your idea is just the starting point, and most of the time, what you put down on a napkin as what you think is the brilliant idea for your company actually isn't at all really what comes out, because you actually start executing on it, meeting real potential users, really try building the product. And it just evolves and changes to something that you may have not even imagined in the beginning. And what I've learned is that execution is extremely important in this regard. And there are multiple kinds of layers to this.

The best thing a startup should do is actually figure out a way to experiment and test, in the cheapest way possible, what can work, because you have to go and be like, I do not know actually what would work. I only have hypotheses, so let me be hypotheses-driven and find a way to test and validate. And then once you are able to see an inkling of you being potentially right, then narrow down your space, double down in that area, and then you're soon going to realize that there are a million more ideas related to what you're doing that you have to solve for. So you start out with this universe of all these cool, interesting ideas and that's actually where I would say most people in bar conversations with their friends get stuck in when they're like, oh yeah, I want to do a startup. I thought about this idea. I thought about that idea. I'm like, all of your ideas sound probably plausible to some extent, especially when I was back at Google where there were a ton of smart people with great ideas most of them had plausible ideas that they would talk about, but when you're actually building a company, it becomes so different, and so, do not get married to your idea. Do not even get married to the thought that maybe you are the best at coming up with ideas in a certain place. Be good at figuring out whether or not ideas actually work by being ruthlessly good at executing, learning from them, implementing them, and making sure that you're able to do that at a team level too. Because it's not just about you, but it's about your team, be it five people, 10 people, or 20 people, being able to also move as in sync as a Dragon Boat team on it.

So, yeah, I would say that's one of my biggest learnings as a founder, and I'm continuously looking for ways to improve on this. And so, this is a topic that everybody talks about right now, which is AI, right? And I'm not going to pontificate on the generics here, but when it comes to go-to-market for our company right now, I want to get us very good at testing out content that works. And so there are so many things that we can now leverage to make. Our learning process for this goes from maybe two years all the way down to maybe two months or two days. And just like crunching the time that it used to take to get things right as a startup to a much smaller period in time and pretty, and just find a way to execute much, much better.

Jeremy Au: (21:54)

And as you think about that, why is execution hard? It feels like everyone's like, oh, we all know that. Yeah, you have strategy execution. It feels like, that's a no-brainer. But why do you think, from your perspective, why do you think that's important for founders to reflect on and be crisp?

Sherry Jiang: (22:11)

Yeah. Absolutely. And by the way, you need strategy and execution. Just to be clear, it's not just 99% execution, and 1% strategy, but the execution is incredibly important because I don't think people can learn in a vacuum in their heads. You cannot conceptualize things without actually going and getting and doing things and getting feedback. That kind of response, I think, is really important. And so, I think that's why it's incredibly important to get that execution piece right, because it is actually related to iterating it on your own strategy, and constantly looking for ways to test it to become more confident in et cetera. I think execution, it can sometimes be difficult to pinpoint what exactly is good or not, but it does come down to a couple of different layers.

I think number one is being good at the planning part of the execution. So one thing that we do with Bluejay, just to give it a bit more of an example, is we actually create these contingency maps. We're like, here are the scenarios of what could happen and what could go wrong. What if this deal doesn't go through? What are we doing in contingency plans B, C, and D, if this doesn't go through? Okay, then maybe we should start B and C as backups, right? So that we don't have to wait another five days. So in our case, we onboard different deals on our platform to be listed for investments. We might have been really excited about one deal, but we will have other conversations going on to make sure that we have other options in case you know, an agreement isn't reached or we do demand testing, and it's not really there for that particular deal. So, there's a lot of pre-planning and pre-pre-planning and just thinking about all the scenarios that can happen to make execution good. So by the time you're actually executing, you've done a lot of that work upfront. And so it's just going, just kind of using your muscle and going through without having to stop and think, oh shit, like this is not going through. What do I do? So I think that's one.

I think the second part that makes execution difficult is people often just think about their own IC or individual contributor-level execution. It's like, how many hours and how much input and output can I do myself at a computer? But actually, it's really about teamwork. And this is something that we've been really working on as our team has grown. We're at 13 people now, but we used to be five people last year. And so, you could imagine that there's some growing pains when you have people with different work styles and some people might be in flow stay, some people are not. And like, how do you bring everyone together? And so we have to create some norms that I think make working together a little bit easier.

Number one is that we have hybrid work, meaning people come into the office, and I may sound really old school for saying this and very non-Web3 because a lot of people are remote only, but it is so nice to be together in the same place because the amount of idea formation, the efficiency of just going to somebody and getting something done is just phenomenal when you're in the same office. Plus, I think trust is better or built easier when you actually see someone face to face, at least some of the time. So you don't have to, I think trust is one of the things that makes teams efficient because you don't have to fact-check and feel anxious about what someone else is doing. You trust them, right?

So trust leads to efficiency. We also have strong communication norms as well. So after most external meetings that someone takes with a potential partner, potential customer, or whatever that is fresh in your head right now, write down the top takeaways from this meeting and send it out to Slack to everybody so that everyone knows what's going on. And so the flow of information is hyper-fast. That velocity of information sharing is there so that we're kind of not just like little separate brains and like having to figure out what each other knew at a certain point in time. It's like we're operating as a hive mind, right? We're all collectively in the same context. This is obviously not always perfect at all times. So it's something that we really strive for. So execution is not just about yourself, but it's about the team level as well.

And the last point I'll make about execution is that you need to manage your energies as a person. I think some people think if I really enjoy doing something, I'll work a hundred hours a week and just brute force it and that is not the right approach. You need to manage your time and energy because when your energy depletes, you cannot think critically as well. You cannot think creatively as well. You are irritable and that irritability erodes trust, which erodes collaboration, which creates inefficiency. So make sure that everything that you're doing ladders up to a goal, right? And that's why we have OKR planning, but also, take care of yourself as well. I think for myself, I'll speak for myself, maybe not for other folks, but I try to sleep. That's something I prioritize, I protect. I don't believe in sleeping three hours a night and just try to brag about how little you sleep and how efficient you are. I had times when I sleep three hours a night cause I'm jet lagged. And I'm telling you, I'm not more efficient. I am just tired and irritable and not great.

I also try to make sure that I bake in time to expose myself to things outside of my company, be it taking a dance class or volunteering, or doing something that's different than thinking about FinTech, crypto, or startups, right? I think that is really important for the brain to take some rest so it could come back fresh. So professional athletes usually have a rest day. They don't go hardcore at it every day cause they're going to injure themselves. It's the same thing with running a company, right? Their muscle is your brain. If you do it every single day, hardcore, a thousand percent it's going to, you're going to injure yourself in some way. You're going to burn out. You're not going to be as productive. So those are the different layers of execution that I think about a lot, but, it's not always easy to get entirely right.

Jeremy Au: (28:02)

And to wrap things up, could you share about a time that you personally have been brave?

Sherry Jiang: (28:06)

Yeah. So I actually get stage fright sometimes, which I think comes as surprising for some people because you know, I've done public speaking and done band performances, whatever. But I get get mad stage fright when I feel like I'm being very vulnerable. And so, for those who don't know, I'm actually a pretty avid musician.

Outside of work, I love to sing. I play piano. And so back at Google, actually, I joined the Google Band. So it was like a group of Googlers that perform music together. And We were going to do a performance at the Google Holiday party. And so it was in front of at least 3000 people, which is the largest audience I've really been in front of. And these are my bosses, my bosses' bosses. These are like colleagues, and when you're up there, singing, and music is a very vulnerable thing. It's not like you're going up there and talking about tokenization and crypto. You're up there, you have to feel the music. And so, I was so nervous, honestly. I didn't want people to see it, but I was so nervous. But I think what really helped was I just spent a lot of time giving eye contact to my bandmates and my fellow, other fellow singers and just interacting with them, and just pretending that no one else was out there.

But yeah, and it was actually really fun. I had a great time, but I think I was literally just so nervous when I first got up there. So I would say that's probably one of the bravest things I've done. I don't know when I'll ever do that again in front of thousands of people. I think sometimes, I do get kind of shy about music for some reason.

Jeremy Au: (29:39)

I feel like I got to come by for one of your performances.

Sherry Jiang: (29:46)

If it's in front of, if it's in front of friends, I don't know, like a couple of people, that's fine. But yeah, maybe it'll be a while before I'll be in front of an audience of that size.

Jeremy Au: (29:55)

On that note, I'd love to summarize the three big takeaways I got from this conversation. First of all, thank you so much for sharing about your early life as a student, but also how you chose to join Google and Amazon, and also what you learned from building Google Pay across emerging markets. And what eventually sparked your exploration of becoming an entrepreneur. So thank you for that.

Second, actually was really you sharing about your personal evolution as a founder, right? So in terms of the skill sets you had to learn in terms of managing, for example, your vulnerability, your stage fright, your conversations, the in-person trust building, I thought there was a lot of good advice you had about what you've learned as a founder.

And lastly, thank you so much for sharing about Web3, You know, what's it like to be a founder, just chugging along, heads down, building, pivoting, and iterating during this giant storm? So, thank you so much for coming to the show and sharing.

Sherry Jiang: (30:50)

For sure. Thanks, Jeremy for having me.