Ryan Chew on COO Skills, Order in Chaos for Blockchain and Army vs. Startup Leadership - E39

· Singapore,Founder,Executive,Podcast Episodes English

"… at the end of the day, even within the military, the better commanders are those who are very mindful about how they earn the respect of the team, and how they think through the boundaries of what is great performance, what is good performance, and what is poor performance, and then setting out the consequences in advance." - Ryan Chew

Ryan Chew is a second-generation serial entrepreneur and COO of Tribe, a deep technology innovation, talent & education platform supported by the Singapore government. Tribe’s ecosystem is supported by some of the world's leading organisations including AXA, BMW Group Asia, Citibank, Enterprise Singapore, EY, IBM, IMDA, Intel, MAS, Nielsen, PwC, R3, SGInnovate, Temasek, Ubisoft, WeBank and other partners to build up a neutral and hyperconnected innovation platform.

Prior to Tribe Accelerator, Ryan served as Managing Director [Asia Pacific] and member of the Board of Director of Verlocal, a Silicon Valley startup. In 12 months, he grew the company from inception to a team of 10, helping more than 100 SMEs and freelancers turn their passion into their profession.

Ryan also spent several years in the startup scene, having founded several startups ranging from gaming apps to utility apps including Fixir, an Uber for car repairs. His previous startup was accelerated by Plug and Play, Mercedes, Singapore Press Holdings, ideasinc. His first gaming mobile app was acquired when he was 21.

As a serial entrepreneur, he is on a mission to help build sustainable communities that will enable promising companies to leverage on new frontier technologies. Ryan is also a Commissioned Officer of the Singapore Armed Forces [Military] and recipient of the Commanding Officer Coin. Currently, he holds the rank of Captain in the Singapore Artillery.

You can find our community discussion on this episode at


Jeremy Au: [00:02:13] Hey Ryan, good to see you.

Ryan Chew: [00:02:14] Yeah, good to see you Jeremy.

Jeremy Au: [00:02:17] I'm so excited to share your journey, it's quite an incredible one. And yeah, times are good.

Ryan Chew: [00:02:24] Yeah. Congratulations on the new role again.

Jeremy Au: [00:02:29] Yeah, for those who don't know, I've recently joined Monk's Hill Ventures, the leading Series A VC and then we'll go from there. Meanwhile, the story is all about you, Ryan.

Ryan Chew: [00:02:42] Okay.

Jeremy Au: [00:02:43] On so many companies, you're now COO, you're on Blockchain. So, tell us more. How would you share your leadership journey with those who don't know you yet?

Ryan Chew: [00:02:53] Maybe let me just paint a picture about who am I in terms of my entrepreneurial journey so far. So, I started off a little bit I would say I founded my first app when I was about 20 years old, and this app is called SoCharades. It's kind of modeled after, if you can remember back then, there was this app called the Heads Up! app by Ellen DeGeneres. So, essentially one fine day, I was just playing this with my friends, and I realized ... for those who don't know, this app is a charades app where you have to kind of place your phone on your forehead with the screen facing your friends, and random celebrity names will pop up, and your friends have to kind of act it out, and you have to guess who exactly are they acting.

So, it's fun, but I found a problem in a sense, because as I was playing with my friends, I realized that a lot of the celebrity names that pops up, we don't recognize them because they are all American names, right? So, there was a lot of skip, skip, next, kind of thing, and when we do know, everybody knows it because it's very obvious. So, I thought, hey, this is a fun concept. Can I replicate this to localize it to include local celebrity names, and also in fact connect it to Facebook so that you can actually watch your friends mimic some of the people that you know.

So, that was the initial concept for SoCharades. So it got published, and I moved onto my next app, which is called Youtap. So that was riding on the trend of very challenging games like the Angry Bird back then, and stuff like that. So, it's actually a tap tap game, puzzle game, and we got lucky with that, so I managed to sell it off. I made a little bit of money from that application itself, and that motivated me to keep diving into the tech space to learn more and more about how we can make effective or meaningful applications that can interact with people.

And also, that got me some traction in some so far building a brand for myself among my peers as the person who is able to bring an idea to life from scratch. I think back then, I was one of the first few people that was able to do that. So that's my second app. And then the third app, I co-founded a mobile application called Fixer with a bunch of my army mates in university at that time. So, we had this idea of allowing people to easily find trusted workshops, car workshops, car mechanics wherever they are.

So, I think this problem started off where one of my friends scratched his car, and then he panicked, because he couldn't call his dad. At that time, we were all young, and then it's going to be very expensive to fix. He didn't know exactly what to do, and he was extremely afraid of getting scammed by this industry. It's a little bit of a tricky industry to navigate, especially for a first-timer or a first time car driver. So, this app primarily allows people to snap a picture, and they will get quotations from curated workshops around you.

And so, that was actually, we participated in many accelerators with that particular startup, like SPH, Plug and Play back then, and then we have the Mercedes Autobahn. We did the NTU ideasinc and many, many more. And we also got lucky with that. We were invested by SPH, Plug and Play, and then back then it was called IDA. So, that was Fixer. And after Fixer, I actually moved onto join a San Francisco-based startup called Verlocal, where I was the Managing Director for Southeast Asia. So, I helped to build the team from scratch in Singapore.

So, within a year, we managed to build the team up to about 10, and we had served and supported over 100 SMEs and freelancers in Singapore. So, what Verlocal is, is actually a booking management software and a marketplace that allows your home bakers and stuff, and dancers, yoga instructors, to have a booking system to manage their classes. At the same time, it allows them to have a wider audience through the marketplace.

So, that was what I did for a while, and after that, the entrepreneurial bug came in to bite me again, and I went to sort of co-found Tribe Accelerator with my longtime friend as well as my partner, Yi Ming. So, we built the accelerator from scratch, because both of us were founders, we went through many, many different accelerators. And we came together and we spoke about the industry. So, Tribe Accelerator is actually the first blockchain accelerator that is supported by the Singapore government.

So, why we actually wanted to start that, because we saw that there was a lot of mistrust and scams in the blockchain industry at that point of time, and with our collective experience as founders and having been through so many accelerator programs, we thought that hey, let's do something here to help some of these blockchain-based startups gain some legitimacy, stand out from all the crowd of the hype and so-called scams within the crypto space. So, that's how I end up here. That's kind of my journey.

Jeremy Au: [00:07:30] Amazing. You've really done quite a lot, and we're both Forbes 30 under 30, I guess that's a notch on the belt in that sense. But I think it just goes to show that you've done really quite a lot, especially with this recent Tribe Accelerator in terms of not just investing, but also accelerating a very important sector for Southeast Asia. So, obviously we want to get into that real soon, but I just wanted to hear that you've always been very entrepreneurial and very much a leader, and I'm curious about how that all first got started from your perspective?

Ryan Chew: [00:08:02] Right. I would have to trace the start of my leadership journey back to SAF, when I was at NSF serving my National Service full-time. So, this story started after I graduated from the Officer Cadet School as a very young second lieutenant in the Artillery Formation. I was what we called a forward observer, which means I would be tagged to a battalion of infantry of guards battalion to be the liaison officer for the artillery gunship. So, if you can imagine, usually the artillery gunship is very, very far away, but if you have watch enough war movies, you know that the first thing that people do to is call in the support fire, bomb the place out before you storm the ground.

So, I was the guy doing the calling, and there was a team of us attached to each battalion. And this team is actually led by a captain called the fire support officer. So, this man is usually very experienced artillery officer, as well as been in multiple vocations. So, my team leader was actually an amazing person. But unfortunately during one of the exercises, he fell ill, and he had to drop out of the exercise completely. And this was actually en route to our final test. For those Singaporeans listening, it's called ATEC, where we have our final test of our ability to fight.

He dropped out, and by some stroke of luck, actually they were looking for my senior, because I was a young, fresh second lieutenant. So they were looking for my senior to take over. But because of communication issue, for those of us, you know what I'm talking about, right? I was in touch with the commanding officer of the entire battalion first before the guy, so he was like, "Nevermind, you just come on." So he gave me a "battlefield promotion," and then I took over as the fire support officer, which is traditionally a captain [ And I was put in a very uncomfortable situation where I have to lead a bunch of my seniors. As a young, new officer, it's very difficult to be put in that situation where you have someone who is more experienced than you, but having to listen to you. You have to gain their respect and gain their trust within a short period of time. At the same time, I was directly reporting to the commanding officer of the entire battalion.

I sat in most of these high level meetings and stuff like that, and that also how I got my first experience understanding why SAF does certain things, how this leadership and how this information permeates through the entire battalion, to make sure that every single soul in the battalion is motivated to complete one single objective, and how everything is orchestrated, and planned, and organized to the tee. Although, at the ground level, we more often than not cannot understand why certain things are done, I was in a position where I could. So, I really appreciated that, and I learned a lot from these commanders and these leaders, and that was what I would attribute a lot of my leadership skill set to this particular situation.

Jeremy Au: [00:10:51] That's so similar to so many Singaporean guys, myself included, where our very first true leadership experience in managing a group of people to tackle a mission very much came out from National Service. I'm just curious, I have my own thoughts on this, but first off, what things did you think translated well from National Service and being a military commander, to the entrepreneurial journey that you would do later? What skills translated well?

Ryan Chew: [00:11:21] I have kind of five high level points that maybe I would like to share on that. For the first thing, as a leader in the SAF, you must be an effective communicator for sure. Especially so if you have to give orders clearly in the fog of war, or in the middle of the battle, the clearer you can give your instructions the better. And I realized that actually being an effective communicator myself is not the end of being a strong communicator. It's also extremely important as a leader to build communication processes whereby your team can communicate within itself effectively.

So, you kind of need to build this communication process and translate into the startup scene, because more often than not you are managing multiple projects, your team is managing multiple projects, and it's extremely important for the team to be able to communicate within themselves and not have you being the one doing all the communication all the time. And this is extremely, extremely important in this time, right, where we are working mostly remotely, and communication and overcommunicating becomes even more important.

Actually, it was one of the things that translated well, being able to be an effective delegator. So, being an effective delegator is also extremely important. But more often than not in delegation, people have this perception that it's very simple. You just give someone else the task, just offload your task, you say, "You do this, you do this." In army it might work because you can scare them with pushups, confinement, and stuff like that. But in the real world, it's not the case.

So, being an effective delegator in my perspective also means you have to have the ability to break down complicated tasks into bite-sized ones, with very clear and specific goals, yet leave room for the team to exercise their own discretion in decision-making. So, the ability to assign tasks to the team, not just based on their strength and weaknesses, but also based on their current capacity. So, that is what it means to be an effective delegator, not simply just, "Okay, you do this, you do this."

And also, the ability to prioritize, that's number three. How do you identify the interdependencies within each task to be able to prioritize which is more important and which is not, the importance and impact of each task. So I always say to my team, if everything is urgent then nothing is urgent. So, it's important for you as a leader to be able to help with prioritization. Number four is very straightforward. Know your staff. As a leader, you have to know your staff. You have to know what you are talking about.

If you're not marketing trained, and you have to lead as a COO, I have to lead the marketing team as well, I have to learn, read up in my own time, and understand truly what exactly am I talking about. Because I'm sure many of you hearing or listening in to this podcast, you can also empathize, there are situations in your current role in your current company where you say, "Huh? Why the boss say this? He doesn't even know what he's talking about." And then that leads to mistrust within the leadership and whoever is supposed to lead. But it's also important to recognize that as a leader, you don't always know what you are talking about. You're never always the subject matter expert.

So, in this scenario, I would recommend you to just be honest, and say, explain and ask for patience within the team, when you ask more questions and take the time to learn, and don't try to act smart. And last but not least, as a leader, you must have incredible stamina. Because in the army, whenever after a mission, your bag is off, your helmet is off, and then you just plunk down. Who does the next planning for the next mission? As a leader, if you fail to do that, then your next mission is going to be horrible.

So, when everybody's bag is off, helmet is off, and resting wherever they are, the leader has to find the extra 10, 20% in himself to, okay, no, I need to start planning about my next mission. I need to start to see what are the things I can do to improve the current situation of my team. So, you will have to have that stamina, and same for entrepreneurial journey. Whenever someone finishes a particular project and you'll be like, "Whew! I'm done, I'm going to take leave." As the leader, you have to say, okay, now what's next? I need to pipeline this, I need to keep having the stamina to lead my team. So, these are five things that I thought translated quite well.

Jeremy Au: [00:15:26] That's amazing. That's probably one of the best categorizations of the learnings I've ever heard from military service. And I think what is very true is that it's not just translatable for the Singapore military, but I also see many veterans from other countries with military service who bring the same set of skills and attitude to their entrepreneur journey. I'm kind of curious, what would you say did not translate so well from the military to startup life? What would you say are the things that if you recently left the military as a veteran or as a conscript from Singapore, or you spent a longer stint there, what things would translate less, and they should be mindful about how to be aware of it as well as to improve on it?

Ryan Chew: [00:16:14] Right. One thing the military is known for is their rigidity as well as their preference of using the stick over the carrot. So, these are two things that really doesn't translate well. Like I said, I think I alluded to this a little bit earlier. You can't just bring the stick to someone in the real world, and say, "What are you going to do to that guy if he doesn't listen to what you do?" You have to empathize with him, you have to really sit down and understand what's the problem, and you can't just use threats.

You can't just use punishments and sanctions to govern your team in the real world, because it doesn't work, and it doesn't lead to effective leadership. It might lead to resentment, it might lead to hatred and poor motivation within the team to complete the task. That is one thing that we have to be aware of as leaders, that yes, there might be times where you have to use the stick instead of the carrot, but you have to be extremely mindful. And before you even go down that route, you must empathize. You must understand what exactly is the problem with your employee, whether he has some family issue, money issue, personal issue, whatever, before you jump in try to make threats and stuff like that.

So, that is the part that I feel that doesn't translate well. And second thing and very obviously the rigidity of the military, all of these structures, and stuff like that. In a startup, you obviously can't have that, because there are a lot of times where there are changes that bring about your goal. You have to maintain the flexibility to edit or change the structure fast, so that you can accommodate the new changes, the new growth. As your team grows, there must be new processes in place, and you must have that flexibility to change that. Having a very rigid structure to the point that all of our field packs are packed exactly the same, is just not going to translate very well.

Jeremy Au: [00:17:54] That is really spot on, because I think the rigidity of the hierarchy is because in the military, I always tell people, it's because in war, there's attrition. And when there's attrition, people die. So the chain of command is built in a way to create resilience, because if someone dies or is incapacitated, it's very clear who the next person to take over that person is. And if that person also falls, someone else can take over, because they will train exactly the same way. And so, every person is in some way modular. Every soldier can replace the other soldier if the person is killed in action.

And so, that's why the military is designed for that 500-layer resilience, where as long as you were trained as a rifleman, it doesn't really matter from a chain of command's perspective which rifleman is there. You're expected to perform the same way. But that doesn't happen in a startup, because you're the opposite. You're so resource-constrained that everybody has to do multiple work streams, so it's almost an inverted pyramid around that. And so, I'm not saying that the military is bad for being rigid. In some ways, I think it's a shadow of having that very resilient bench of people who are standardized and can cross-train to replace each other, but that's not true for startups where we just have to do everything.

And I think the second thing to be mindful about how you said in militaries, but conscript and professional, obviously people have made a multi-year commitment to the organization. And I think that what we see is that at the end of the day, even within the military, the better commanders are those who are very mindful about how they earn the respect of the team, and how they think through the boundaries of what is great performance, what is good performance, and what is poor performance, and then setting out the consequences in advance.

So, I always say to people, it's not that armies have bad performance, it's just that they also have a spectrum. We see that as well. But definitely I think that's amplified in the startup war, where anybody can walk out anytime. They can walk out tomorrow because they don't like what you just said. There's so many startups that are going to fight for that person's talent. Your great graphic designer, your great engineer. So, I think just being mindful about that is really important.

And I think one thing I want for you to kind of articulate a bit more of course is, you started sharing about how you take all these lessons, and you've not only translated them as a founder in your businesses, but also now as a COO at Tribe. And I think first of all, I just want to articulate, how do you articulate the COO role, and what defines success for that role? And maybe not just for yourself, but what that role entails for someone who's thinking about that role?

Ryan Chew: [00:20:22] Right, so do not underestimate that question, because it's actually an extremely important and also very difficult question to answer, because there is no one size fits all definition of what a COO does if they look it up. So, I think the best, or at least what works for me and my partner Yi Ming is how we take on complementary roles. He as the CEO, because I strongly believe that the company must have one leader to break the stalemate, to make sure that the team is aligned.

You can't have multiple visions, you just have one, and I'm there to bring his vision to life. I think that is kind of my role. He talks to a lot of the external people, liaises very closely with the Singapore government, with all our stakeholders, and he has to maintain that big picture vision of what we are going to be as a company. And it's my job to back him up fully, 110%, and to make sure that his vision is brought to life. Together we manage the company this way.

There's no, oh okay, strict role restriction between the two of us, but that's how we operate, very complimentary. And I think among all my startups, and all the businesses, and all the projects that I've been on, he is actually one of the most incredible person to work with, and I am extremely impressed with his work rate, I'm extremely impressed with the way he thinks, the way he manages the stakeholders. This guy just continues to impress me all the time. So, it's quite exciting to be on this journey with him.

Jeremy Au: [00:21:57] And how did you first meet him? Everybody is always looking for a co-founder. Every week someone is pinging me like, "Hey, I'm looking for a business co-founder." "Hey, I'm looking for a technical co-founder." "Hey, I'm looking for an operations co-founder." So, how did you meet your co-founder in this case, and do you have any tips for people searching?

Ryan Chew: [00:22:16] Well, the way I met him is not going to be a tip for many people, because you wouldn't expect this. I actually met him in Poly long time ago through a mutual friend of ours, and we met up to go to Butter Factory. So, for those who know what Butter Factory is, Butter Factory is actually a club. Back then, it was very popular among the youth. I don't think it's around anymore. So, he had the prestigious black Amex card that allows us to skip the queue.

So that is my first encounter with this guy, and then after that we kind of kept in contact. We went to the same artillery unit in fact, and after that he went to LSE to further his studies, I went to NTU, and then we reconnected again in the startup space. So, I'm not saying that you should be looking for a co-founder in the clubs. I don't think that's a good tip. What the tip would be in this case, is to keep an open mind, because you don't know where your next co-founder is going to come from. He can come from the club, which is in my case.

Jeremy Au: [00:23:15] That's so funny. I definitely remember Butter Factory. I similarly met my co-founder in secondary school. We were just acquaintances. We were both in creative writing and poetry, so we knew of each other, we hung out a few times, but not very close. And similar to you actually, I actually met him and we were in the same command course together. I can't remember which operation it was, but we had to dig a fire trench together, and both of us just dug all night long, because the soil sucked. And so, we would dig, dig, dig, kind of fall asleep but keep digging.

But after I did that, of course all kinds of random stories there, I felt I could really trust him, and then we became really good friends after National Service in the military. And we stayed in touch from there, and then years after university, that's when we reconnected and built our first company together. So, I also concur about keeping an open mind, because when I first met him I was like, I don't like his poetry. Mine is better. And then, very much, time flies. So, that's life.

I think one thing that's interesting, I would love to hear more is, there's something that you say very true, is that you have that trust, you have that relationship, you start talking about roles and being complimentary. What would you say is something that you start out founding obviously with him, and then you've become the COO as the team has scaled. So, how has that role of that COO role changed from your perspective from a team of two, to now your larger team of you said about 16 to 20 people? I'm kind of curious, how has that role changed from your perspective of the COO for a startup?

Ryan Chew: [00:24:53] For starters, there is a lot more fires to fight, because now you have instead of two, it's relatively easier for us to align a team of two to a particular objective. We both agree that this is the way we're going to do it, have each other's back 100%, and then we just go ahead and do it. But as you expand your team, you realize that different people will always have different perspective.

And also, the element of the broken telephone comes into play, because when you pass down information, or when information gets passed down, sometimes they just translate into something completely different, and then when you see the end product you're like, what the hell is this? This is not something that I imagined. And that's why I think one of the things I said was not just you being a good communicator, but also to build a very strong and robust communication process within the team.

So, communication is definitely one of the biggest challenge, and also one of the biggest change, because as your team expands, you can expect this to be a bigger, and bigger, and bigger problem. So, beyond that, it's also to really align everybody's core values, and what they believe in, and how they work, so that you're starting to see a culture being formed. I think this is something that is relatively new even today for me, so I'm very excited to actually see how this team grows. My role has changed. I have to become a much better communicator. I have to fight more fires. I have to do a lot more coaching and mentoring as well, so you can help to bring the team up to speed. I think primarily, this is one of the biggest change as the team grows.

Jeremy Au: [00:26:21] What's interesting of course is that you as a COO are standardizing processes, leading the operational side, very much in some ways nuts and bolts, but also being very practical about you said transforming vision of reality, and you're also doing that in a very fast emerging field called blockchain, which is new in and of itself as a vertical, and is even more new in Southeast Asia. So, it's a little bit of a contrast, this stabilizing force in a very fast-moving, turbulent, vertical geography. So, how do you feel about that? Is it like we are bringing order to chaos? What is that feeling like? What do you think to yourself?

Ryan Chew: [00:26:58] You are absolutely spot on with that characteristic of bringing order to chaos. So, I think for the majority of my new hire, I do warn them and say, "You are stepping into a very organized mess for us," because things change so fast, and the structures that we have in place, the processes that we have in place as we scale, they are bound to be broken, they are bound to have to be improved. So, we have to update our processes almost every week, like for example, just from the tools that we use.

We started off using this Slack, and maybe Google Drive, very standard easy stuff, and then we incorporated Notion, we tried out Monday, and now we have Discord in the mix, and so many different things. What is the best way? How do we optimize this? Every two, three months, we kind of sit down and review, and how do we improve our internal processes from bidding for a particular project, all the way to executing it. How do we hand it over? The very nitty-gritty nuts and bolts, and stuff like that.

And this is even more so in the environment that changes every two, three months in the blockchain space. When new blockchain emerges, we need to study that. Okay, what's happening there? And new projects come in because of these changes, government projects like where we designed the Singapore Landscape Map. So, that was in itself very challenging, because we have to create categories that were non-existent, and then we have to categorize completely new and innovative startups, like creating categories.

Like for example, let's talk about Ethereum. How do you categorize that from an industry perspective, because it cuts across industries. You can't just say it's fintech, because you know it can be applied to supply chain. It can be applied to medical tech as well. So, this inherently was very challenging for us. Somehow, we managed to move through it. So, you are right in describing it as an organized mess. Even as I am saying it, I realize that it's kind of like an organized mess.

Jeremy Au: [00:28:45] Yeah, it feels like artillery (arty) mission, right? One last question before we wrap up is, one thing you said earlier was, you're very much about, a leader has to know their stuff. So how did you learn stuff? How do you stay on top of it? How do you upgrade yourself in terms of skills and industry knowledge? What's that process or flows that you are looking at to improve yourself and keep on top of it in order to know your stuff for the team?

Ryan Chew: [00:29:11] So, in the past how I acquire knowledge is through reading, and I read a lot. I have an entire bookshelf behind me. But as a progress and as we grow, it's just very impractical for me to digest knowledge through books, because I just don't have the time. I know it sounds like an excuse, it might be an excuse, but I have transited into a leveraging of podcasts, listening into podcasts like yours, just to acquire knowledge really quickly.

And also, I find it easy for me to learn new stuff by talking to people, so I constantly try to speak to people at the forefront of technology. So if you guys are listening in and think that something interesting that you'd like to speak to me about, feel free to reach out. But yeah, so I enjoy talking to people, and from these conversations, I'm able to string knowledge between different individuals, what they are saying, and kind of build a perspective of what's happening out there in the market, or what is happening in the street.

Jeremy Au: [00:30:01] Awesome. Thank you so much, Ryan, I just really appreciate you taking the time to share not just your knowledge, but also I think your thoughtfulness on what it means to be a strong leader and have that journey.

Ryan Chew: [00:30:13] Thank you so much for having me, Jeremy. I wish you all the best in your new role as well.

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