From bootstrapping to Transferwise to VC backed Startup - Chen Wang

If there's one lesson I learned, I have been a little bit too soft in terms of insisting on my opinion, but in autonomous organization, there's many, many strong leaders who sometimes have very competing views on things. My first year I've been very soft in terms of taking everybody's opinion on board, but then afterwards I realized that it's probably, you really need to be strong about your own opinion a little bit. And I try to push through things, which means you come to a product where nobody's quite happy about, but nobody's complaining too much, but that's probably not really where you want to be.

I've been in this game for, in the last 10, 15 years in the startup game but my journey is a little bit interesting because I started off with a SaaS company in the finance space, not necessarily as a company I'm running right now, but because the company I'm running right now is a regulated business. That's a lot more complex. Whereas the first business I helped created, it was very much a SaaS company, a trading simulator to help certain people in the financial demand, the traders in the financial demand to onboard people, to get the new blood in the company and then to trim people up. So I came in at the time as a technical expert, whereas my co-founder was a demand expert. So it's a very good match at the time.

Before I knew it, so it was very much of an accidental attempt. I didn't know at the time what it entails as a CTO of a company. And I'm actually looking back, I'm actually that we didn't, the company didn't get to a super big stage, because I wouldn't be able to cope it if we get to... Because I was very inexperienced. I'm very comfortable with my ability to deliver a product. I kind of have that ability that I had a confidence even before starting that business, but I didn't really know whether or not I have what it takes to be a good leader in terms of not only the technology, but the people side of things, because it's very easy in the big company to say, "I lead a team," because you get a lot of support from other functional units within that company and then you get lots of guidance. You get a lot of handholding if you're new. Or you get, you can pull in resources, you are experienced, whereas in a small company being a funding CTO is different.

You talk about technology, obviously there is a top priority for you to deliver, but also you get [inaudible 00:03:08] a lot more into the business side of things because at the end of the day, if the business doesn't exist, nothing exists, and then you have to deal with the in and out of hiring and in and out of keeping people happy, as I always say. So those are two things you do as a technology leader or even any leader in a company. The one thing is to keep the hiring strong, hire the best people you can find. The next thing is...

What scale did Volcube get to?

It's just very, very kind of a small team. And we used a lot of, so the contractors and interns at times. So it never really, the team size never really get very big. It's more like a small team setup. If I put in the equivalent, it's probably a small product team in a bigger company plus salespeople, and then that's the setup.

And also we're targeting the market where it's not changing very often. So a lot of the algorithm in that market, it has been there from the research paper 20, 30 years ago. And then it all derived from those research papers. And then all the models are not necessarily ever changing. It's not like a consumer tech company where you have to have a large amount of people chasing and then fine tuning your product. Once we have the product and we are quite confident our product does what it's supposed to do, it's more of a matter of selling to as many companies as possible. That really makes my job a lot easier. So I just need to make sure the operations side of things keep going tick, keep ticking along.

Also it's a bootstrapped company. So basically my co-founder funded the whole operation in the very beginning. Then it quickly becomes profitable. So it's an easy business. It's not a money spinning machine where you... Right now, there's a lot of venture funded business. It's operating in a slightly different model, whereas a bootstrapped business, you have to really look after your bottom line, which is making profit as early as possible. And then being in the survivor mode and then start developing into new market. So that's pretty much my first company

It can be very difficult if you are a bootstrap founder, because you naturally don't pull the network in to surround you, that you would, if you were going through the venture rounds, did you have a network to support your own learning at the time?

No, not at all. 10 years ago, especially in London at the time, London wasn't a place people talk about startups. That's the time when grads go to investment banks and grads... London considered be the finance center, not necessarily FinTech center, but not to mention the tech center. So it's very, very different picture compared to where we are now, where London is not only a FinTech center, but also there's a lots of strong technology companies and all different sort of companies setting up shops here. So that's very, very different.

Has that changed now you're the founder of a slightly different company?

It's an interesting story because I took the initiative because after a few years, the first company started just ticking along as we expected. So both myself and my co-founder, we both decided that it is quite good. And also we enter the joint venture with another company. That company will take over a lot of the operational side of things, plus the sales effort. And then that pretty much free up both of us from the day to day. So both of us decided that we should probably fund something else to do, which is also the freedom of a bootstrapped business, because we fully earn that business between two of us. And we know that it's profit making and then it's just ticking along nicely.

So at the time what I decided is, I've done this sort of a thing from taking a company, a product from zero to profit making, but I have never really had the opportunity to say, "I want to witness a high growth company from, and I'm taking venture money and then see how they operate." So I've done the first bit, but I never really witnessed the second bit. That's when I started looking. That's probably about, actually four years ago. I joined a company called TransferWise and then that's where I think that opened a different door to me as to witnessing a company at the time is less than a thousand people. And then getting a lot of traction as a direct to consumer company, but then they still have a very small London base. And then when I joined the London office, which is the headquarter, there's 120 people, 130 people in London, even as a headquarter. And then there's only 150 engineers in the company.

So when I left three years after I joined, it's more of a pre-IPO because they have gone IPO July last year. And it's about 350 engineer and then more than 2000 people. So within that three year period while I was there, there's a lot of learning through that stage. But I guess if there's one thing I'm very proud of, is to take my initiative, to pick the company at that stage to join. If I say I knew exactly what I'm doing at the time, that's clearly not true, but looking back, that was probably the best decision I have ever made, is to get myself from a bootstrap funder mindset into working for a company, which is not a decision lot of people would make at the time, but just bend down, take your knee and then go look at how that company works and then learn along the way.

I did learn and a lot. And a lot of those are directly transferable to my current company because the purpose at the time, and also I realized that is if I'm only have done the funding company kind of stuff from zero to a certain size, I would never know what's waiting for me down the line, which would affect a lot of my decisions at the time because if I knew this is what we are going to anticipate three, five year down the line, before we IPO, a lot of decision I made at the time would be very, very different.

And I would still do a very lean startup approach, but still, there's a lot of subtle difference as to if I make this decision, do I have a view in terms of what if we survive? What if we strive in the next 12 months, in the next 18 months, in the next three years? I know the end game looks like, I know what we are going to be at the time but then I need to be prepared, not in my decision making process to say, "Okay, so I've seen this before, but even if we are not there yet, I need to be prepared. Maybe 10%, 20% of my decision needs to be prepared to just in case that we get there."

Even if that is the case, it takes a huge amount of character and a humility to do specifically what you did and go from being a company founder, to working for another company. What was the hardest part of that?

It never really occurred to me at the time, but I get where you come from, Ben, because let me just ask myself a similar question, is that, let's say that's exactly actually what you just asked, is that if I get to my current company to a certain stage and I'm quite happy about, would I still have made the same decision of join a much bigger company at a later stage? I would probably say no if that opportunity arises again. It's probably a few things that tick the box at the time. So A is, I'm aware that what I've started is a bootstrapped business. I never get exposure for a venture backed business.

So that's one thing that's very, very important because I definitely want to see how the VC money plays a role in a company at that certain size. And then B, I think it's also because I never really understand how much of a effort in this company that kind of size, a 1000, 2000 people pre-IPO with such a strong autonomous culture, how much of a struggle I have gone through. I mean as a very positive experience, but you only learn if you struggle.

So it's a such autonomous environment where you are on your own and you have to find your way, navigate your own way. A lot of my learnings, a lot of my reflection on my previous few years of experience as a bootstrap funder, fund the place just so well because without having a strong character in your personality, you would not even survive in that environment. It actually help you a lot. It cannot be said probably for another company. It just happened that that's the type of company that really pushed you to do a lot of those things, take your initiative. You have your full view on the things on your play. So whoever [inaudible 00:14:09] is only going to give you the more visibility that you probably don't have, but at the end of the day, it's your work and it's your team, it's your product, you really have to take initiative.

So I think at the company level, that's what's being encouraged. That's the type of people work there who can strive. So I happen to step in that kind of company, without even knowing that's what's expected of me and then I just learned my way. And then I'm now starting to apply a lot of that approach to my current company.

What lessons are you applying?

Good question. I still think that autonomous culture is very, very important. I do think that a lot of the companies say they hire the best people, they trust them to do things, but they're not necessarily doing that. So I have seen so many company that there's a manager who like to micromanage. There are, so the leaders who just don't give people enough responsibility and trust. And then there are also people who just question whenever there is a different approach to tackle a problem. They would just question because that has never been a proven, that has never been done in the company in the past. So all of those are basically a symptom of not giving people the autonomy they need to do things.

At the end of the day, as I said earlier, if you hire somebody, if you trust they have the judgment, they have the right judgment, right experience level to tackle the responsibility you give them, you should let them do it. If that means they make a mistake, they make a mistake. They learn from that. And a lot of us are learning through our mistakes. So if there's a choice between giving them a safety net, and then saying that whenever they, what they are about to make a mistake, even if you know it, you can pull them back versus letting them make the mistake. Next time they learn from that mistake. I would always choose the latter, which is I will let them make the mistake. I can give them visibility. I can tell them, "We tried this last time, didn't work," but there's so many variables, so many factor that you can't really say it wouldn't work this time or it will go exactly the same outcome.

So I don't know it and I trust that person who has the judgment and the ability to make the right call. So let them do it. And then they try their best. You trust their ability. Then if the outcome is such, I mean, accept it. And then we can do better next time if that's a negative outcome.

What's a lesson that you have learned along your journey that you wanted to input at Bon Smith, that you haven't?

I will give you a answer which you may not like, which is, I'm also aware of the different stages of a company. A lot of the lessons I learned, they all come with a context. So you only do certain things, making certain decisions within a context, that context is very much associated with the scale of the problem, the size of the team, et cetera, and where we are in terms of the company growth stage. So I'm not the type of people who say, come from the big company, just always going to apply the lessons I learned from that big company. A lot of those, they are not really applicable to a small company at our size.

So it probably means that you need to tolerate a lot of the chaos at the end of the day, because in a small company, there is a lot of stuff that's not... You don't really need to have a lot of processes because you just let people flourish and then you let people do their own thing. And as long as at the end of the day you know that's the productivity, that's the output we are going for and that's fine. And then you sometimes have to refrain yourself from going a lot more explicit on things. And sometimes also you have to be conscious about a lot of your learning from a very different context. They not really applicable to where we are right now. So I hope that answer your question because it's not very specific, but I guess that's kind of... A lot of the time, I just have to remind myself, we are here doing this right now. That's absolutely fine.

And what's been the lowest point for you on your journey over the full 10, 15 years?

It's probably my first year at TransferWise. That was a very big struggle as well as the biggest learning. So I always maintain my viewpoint, which is if you don't go through the struggle, you're never going to learn. So that was my biggest learning the first year, because companies fast growing and a lot of people joined the company and everybody need to find their own way. And I'm also trying to find my own way. And then that's the dorm before you realize, before everything clicks, if you like. So there is a point I think towards my second and third year, it's just everything clicks and I can operate at the level that I wanted to operate and pulling in 300 or so engineers that I have my influence and I have my kind of... I can push things. I can push through things even if that's difficult, I can still do it.

Whereas your first year, you don't know many people, you don't have the network and then you don't even know how to operate things. There's a certain things, certain approaches that work, certain approaches doesn't work. For example, one of the senior leader in the company always says, "Whenever I do something, there's a certain thing I want to try." And then he always says, "Don't try to herling the cats, because they're not going to listen to you because that's how an autonomous organization works." But I still sometimes make those mistakes. And it's all part of the learning for the first year. I'm glad that I had that kind of environment where I must have made lots of mistakes, but still, I survived. And then I get a lot better in my second and third year. I really appreciate if I look back, the people who are around me, even as high up, the senior people in the company, really just tolerated a lot of [inaudible 00:21:17] try and errors. So that was both a low point as well as a very, very interesting fun period to me.

And where have you learned the most from? There are certainly sounds like at the very beginning, it was tricky to find that network of people who could help you figure out how to manage things internally, not just ship products. Who did you end up learning from the most?

I think it's very clear once you start working in an organization. There's a few key people who have either the power to make things happen, or have the ability or have the network to make things happen. It's very clear to me. So I talk to all of those people, very, very frankly. This is what I wanted to do, and I just want to get your opinion on things and it just comes very natural to me.

And if there's one lesson I learned, obviously I'm off topic a little bit, is that I have been a little bit too soft in terms of insisting on my opinion than just kind of... What I have done is actually taking a lot of opinions but in autonomous organization, there's many, many strong leaders who sometimes have a very competing views on things. I still tried in my first year to try to make a very good compromise out of a lot... It happens to be that the product I'm developing at the time, that end to end product requires touching pretty much every single team, every single functional unit of the company in the product development area. So I had to talk to a lot of the people who were in charge of different parts of the company to get agreement, to get alignment.

So my first year, I've been very soft in terms of taking everybody's opinion on board, but then afterwards, I realized that it's probably, you really need to be strong about your own opinion a little bit, and then try to push through things. That's why I said the second year, the third year, I really feel quite comfortable. It just suddenly clicks to me that's the time when not only you have to taking people's opinion, but at the end of day, it's your product, go for it and people will understand. I think that actually earned a lot more respect for people than just trying to make a lot of compromise, which means you come to a product where nobody's quite happy about, but nobody's complaining too much, but that's probably not really where you want be. You want to be, create a product that's great for your customer. And then some people will have a strong opinion. They're always going to have a strong opinion, but just go with it.

It sounds like a contradiction to say that an autonomous working environment should have very strong leaders.

I actually think that you will have, because at the... That's what I put down at the grass root level, strong leaders. They're not necessarily the senior leaders. I actually think the senior leaders are a lot more tolerant, a lot more switched on in terms of letting people doing their stuff, because in my opinion, so I will be there very, very soon. Is that the higher you go, the more senior position you hold, you actually lose the operational visibility a little bit. So what you have, what you gained is the higher level where the company's going kind of visibility, not necessarily the operational visibility at the product level.

So we have a lot of strong leaders for products. And that's very, very important, to drive each individual functional area, product area to go forward. But I happen to be in developing a product that has to touch on different products and then it just, I have to get their alignment to say, "Okay, this is how it could work, and I'm quite happy for you to go for it." And then that's the reason why I don't have full visibility. So I have to take their opinion on board. However, sometimes I have to make course to say, "Even if I don't have the full visibility as you guys have, but because I'm developing this product, I have my visibility to, this is how this would work with our customer. I just have to make a decision. If that upsets you, I guess you guys just have to work with me on that."

If you were doing it all again, what would you do differently?

Be a lot more stronger. If I knew earlier... So I've been very, very strong towards the latter part of my journey there, and to have influence on people by truly being the person you are, because a lot of the time in organization, the position is one thing, but also whether or not you have that influence to talk to people, to really present your ideas, et cetera. In autonomous organization, that's even more so because you are pushing through your ideas and there's going to be a lot of roadblocks and your influence actually plays a very important role. It's the trust people have on you and it's also their reading on your ability to deliver. A lot of those things, it's pretty much people's judgment on your character.

And then if you are a strong character, it actually is a plus point, but I also see, I would also say that there is a line that you may not want to cross, which is the strong leader can very much transition naturally into a very opinionated leader. And lot of the time when you're in a growing company, if you had created a lot of successful product in the past, it's very easy for you to take all the credits and then say, "Because of my past success, my opinions are pretty spot on." And that doesn't really help. If you want to be strong, but also you still want to have a grounded view to look at your surroundings to say, "Right, so I did have a few success, but there's a lot of luck involved. There's also the other people's effort in the mix." So be a strong leader, but also sort of granted because you never know, because there's so many factors. Your past success doesn't, it's not an indicator of your future success.

Strikes me that is top of mind for you, as you transfer from TransferWise to starting Bon Smith. What practical things are you doing day-to-day to enable that transition?

If I look back 10 months ago, when we just started, it was really the excitement of starting something fresh and building the company from the ground up. And there's both the technical and the people side of things. So I've just written a blog post, it's not published yet, about our technical decisions. That's very interesting because I build a lot of products in the last 10, 15 years, but we're talking about 2021, 2022, building something from ground up. There's a lot of excitement as to what technology you pick and how you approach the problem. And if you build, let's say, just take a very inappropriate example, if you're building Monzo bank or Starling bank now in 2021, the tactical decisions you're going to make going to be very, very different when they started. And there's going to be very different when TransferWise started, which is a lot earlier than those companies.

So that's the excitement that I kind of went through as a first few months. Then it's about the people side. I know very well that just myself, it's not going to build a company to the size that we expect that to be. So it's a lot of the hiring, get the best people in the company and as I said, get the most out of them. So that's definitely a journey. So at TransferWise I hired, I get heavily involved in the whole engineering in the London office, in the headquarter. So I know I have a taste of having a few engineers every week, so they're coming through the door, but that's basically a 100, 200 a year, as a base. So they quickly absorbed in the bigger teams and so that's fine, but for us onboarding from zero to where we are with eight or nine engineers, and then there's also a little bit of turnover in terms of the people. So it's very, very different.

It sounds like it comes from a place of your own personal learning and throughout your journey and I've loved hearing it and thank you for sharing it.