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Joel Leong: Serial Founder Lessons, Relational Mindfulness & Making The Call

· Podcast Episodes,Founder,Singapore,Aspire,Fintech

The fluctuation doesn't change. I guess for me, definitely there's that question like you say "are co-founders family or friends or colleagues?" There's that level dynamic but I think as I've transitioned and maybe speaking now from my experience, that's freshest in my head at Aspire I think that fluctuation occurs even as your organization skills, its not just at a co-founder level but even as your rapid scaling. Its literally, you're on this ship, you're trying to plug the holes, the leaks but you need that rocket to take off at the same time. Those are the fluctuations. You have people coming in, coming out. You're trying to manage that but still make the thing launch. - Joel Leong

Joel is the Co-Founder & Country Head at Aspire, the #1 all-in-one finance platform for growing businesses in South East Asia. Prior to starting Aspire, Joel was a multiple-time entrepreneur in the E-commerce space.

This episode is produced by Kyle Ong.

Jeremy Au (00:01): 

Hey Joel, I'm so excited to have you on the show because we have known each other supposedly since our junior collage days even though we hardly ran into each other. But we've had interesting parallel lives as serial founders and now you are the co-founder of Aspire, doing off amazing things. I think we've had some interesting stories, war stories along the way and so excited to share some of the war stories along the way. 

Joel Wong (00:31):Totally man, thanks for having me. 

Jeremy Au (00:34):Could you share about who you are professionally right now. 

Joel Wong (00:40): 

Currently I'm the co-founder at Aspire. Aspire in a nutshell is, lets say we are on a mission to re-invent business banking for the next generation of entrepreneurs. Founders like myself, yourself. Looking back, like you said, multiple time start-up founder, that's pretty much defined my professional life as it is today, much like yours and lots of learning along the way. 

Jeremy Au (01:12): 

What's interesting is that, we've got to understand how did you first enter entrepreneurship? Because you and I, you were doing rugby, you were in arts in JC. I was then doing judo, and biochem, econmaths, supposedly medicine faculty what ever the hell that was called in JC right? I wanted to do the mesh but university and. And then you eventually ended up working and becoming the founder of Haystack but how did you become an entrepreneur along the way? 

Joel Wong (01:55): 

It's funny when you look back, I don't know which side sort of defined me more as a person. There's definitely a very sporty go-getter side of me. There's also a very arts driven side of me, creative side and I guess I never saw them really as conflicting. I pursued a degree in Communication Studies actually. 

During which, at some point I actually got really into film, at some point, had this vision even of becoming a director. But eventually as I was thinking about what to do after university, it's actually a very naïve story. I choose naïve as a word because I think it was right about that time when I was actually quite a tech in that sense and I was still using a non-smart phone. I had just transitioned to my very first Iphone and I think there's just a couple of gens in so I'm definitely in that regard. But just using it kind of blew my mind. I felt that intuitively I could understand somehow the way the product was designed. 

Not so much in the hardware side but maybe in software side, certain decisions that I felt that I wasn't a pro but maybe on the higher end of pro-sumer, it was that naivety that kind of led me to say "no I should be in this world. I should be in the technology world. It's something that I think is going to change the way the entire world operates. I should be a part of it, I could see myself devoting the rest of my life to something like that." Not knowing any better, I decided to start something. 

Jeremy Au (04:05): 

Why did you decide to start Haystack because something could be so many things. Why Haystack out of all those things, all the way back in 2012, which was by the way super earlier. 2012 was pretty much also when I was also out of college, also starting something as well. And I remember seeing you building it around the same time as well. I was building Conjunct Consulting the same time as well. 

Joel Wong (04:33): 

I think Haystack was for me, sort of an expression maybe. I was definitely really young at the time, hopefully still young. There was a lot of creative energy that I had and was really drawn to that was occurring at the time. I think back then not knowing any better, I don't come from say, a management consulting background for example. It was a passion thing, on one hand I knew in the States you had Etsy that was democratizing commerce in its own way. Allowing everyone to creatively express and actually reap the rewards of that expression. I felt that it was something that wasn't in South East Asia. I felt at the same time there was a lot of people trying to do creative things here. I wanted to enable that, looking back obviously Haystack didn't work out, couple of learnings there would have been timing, I think if we did it today we could potentially have a very different outcome and also market, not sure if its something I would necessarily start in Singapore knowing what I know today. 

Jeremy Au (06:13): 

Is it just because you mentioned earlier that also you have an arts streak in you, you're also building up this market place as business thing and you're letting all these things, but also wrapping things up, because that must have been tough. You spent two years building this thing from scratch. What was that like? Especially coming out of university. 

Joel Wong (06:42): 

We didn't really see it as a full wrap up in that sense because I think one of the things that we manged to do was to really learn along the way and my only thing that I wish I would have done differently was to learn a little faster and I think if I had more experience that's what I would have been able to do. I don't think I would have necessarily been able to make better decisions right from the get go, but I think I would have been able to learn faster and move faster and end up making the right, getting the right mix together faster or at least figuring out that it wasn't going to work. Haystack actually formed the basis of what we built next. Maybe I can take you a little bit through that journey. 

Think of Haystack as the Etsy of South East Asia, open market place model, unfortunately not executed well but that was what we were trying to achieve. And when we realized that we had a real challenge to on-board a lot of merchants at the time we realized that we needed to solve a bigger problem. That the problem wasn't access to these merchants because these merchants were able to build out their own user base, their own community, their own following. We actually center around the idea of helping them produce their next production, or production that they have always wanted to try or to produce but never had the validation enough to say "hey I'm going to take this gamble, I'm going to put 50, hundred K upfront to go through with production" 

That was the insight that we got and here you start seeing the parallels to kick starter, which is kind of what we ended up doing, serving that same group of users that we had acquired. And again with a little bit of naivety we took a twist on the crowd funding model. We had this grand idea at the time, that if you were to produce more units, your unit cost would drop. And therefor you should be able to pass that cost saving to the consumers who supported you in the first place. And in return that should drive some sort of virality, some sort of conversation that we should try to bring in a larger group and drive down the price together. Obviously looking back, lots of number one production costs are just one part of your costs and secondly, is that cost saving necessarily significant enough to really drive that virality. 

But for what it was back at the time, it was still actually fairly successful and that was the last that we had of Haystack. We actually ran quite a few successful campaigns for artists and makers and designers back then. But realized quickly one seem to work. We realized quickly that market science was just not going to be large enough. Unfortunately at that consumer level production, South East Asia just doesn't have a robust enough economy for that to take off. That was when we decided that Haystack wouldn't work. Definitely the topic of figuring out how you move on between the founders, so we did have a bit of, I think two guys had dropped off at that point. And then I was going to try to run it solo next but I took that learning and then said "okay, we have a model that kind of works but the market isn't right for it. Lets focus on the consumers instead of continuing to serve just the creators who we very passionately wanted to support. But business wise didn't really quite have that case for it. 

Jeremy Au (11:21):Thanks for sharing that. What was that like, obviously going through that learning, step by step, learning by learning, milestone by milestone. What was that feeling like? 

Joel Wong (11:40): 

I think now I look back and through and thick glasses. You're able to crystallize that learning rather than create a re-write. Back the when you're actually going through it, honestly I think I was probably a bit of an emotional train wreck. It was not clear at the time. We would take, I think 2, 3 months to come to some sort of clarity. Which, I think is really a long time when it comes to stand up time. I think when you are at YCAL every week you want to come off. Not knowing any better at the time, aside from the ups and downs and really trying to figure out what are we trying to learn at all, I think the early days were messy to say the least. 

Jeremy Au (12:39): 

It's always messy because there you are and you've giant iterations of these companies in that sense or these add on teams as well, and you mentioned as well the team is also fluctuating, the co-founders are moving around, the team is moving around. What's the dynamics of that, what's the emotions or dynamics of a fluctuating team? Because I know co-founders is always a tricky dynamic issue. Are they family? Are they friends? Are they colleagues? I struggle with that myself. 

Joel Wong (13:18): 

I think that fluctuation, the only thing I can say about that is that maybe that the fluctuation doesn't change. I guess for me, definitely there's that question like you say "are co-founders family or friends or colleagues?" There's that level dynamic but I think as I've transitioned and maybe speaking now from my experience, that's freshest in my head at Aspire I think that fluctuation occurs even as your organization skills, its not just at a co-founder level but even as your rapid scaling. I had this chat with a team mate today and its literally, you're on this ship, you're trying to plug the holes, the leaks but you need that rocket to take off at the same time. Those are the fluctuations. You have people coming in, coming out. You're trying to manage that but still make the thing launch. 

Jeremy Au (14:38): 

tough outright for everybody. Tell us more about that, there you are at Haystack and you're there at Grouphunt and you're just looking at this different dynamics and you say you're going to push on to be a sole founder and you're learning all these different things but at some point you make a decision, you say "okay" you decide to close that chapter, so what was going through on that said decisions there? 

Joel Wong (15:00): 

Grouphunt was by its own measure of success, it was a boot-strapped self sustaining business. We had built it to that level. I think we eventually had a small team of about seven. We managed to find a really solid growth loop, it was largely a CO loop that was working for us. For me, maybe the biggest decision came when I, along the way I ran that for about three years, after that, Grouphunt, to get it to that scale and during that time, got married, had a kid. Big life changes and then asked myself "hey, do I really see myself continuing to do this for the next five years?" And that was out the blue. One day you just ask yourself that question. And when I realized it that was when I started taking steps to exit and think about what to do next. But by all measures I think Grouphunt actually reached ramen profitability, I'd say. 

Jeremy Au (16:31):Go on, there you are and you're wrapping up and then you making some sad decisions. How did that go from there to Aspire? 

Joel Wong (16:42): 

There was definitely a short period of soul searching that followed. I didn't really know what I wanted to do. I knew that I wanted to find something that had real impact. I think that was what I was searching for. Honestly, I think I had a good six months there just trying to think of what to do next and in the meantime took a couple of consulting gigs, a couple of start-ups. I was maybe even living the 4-Hour Tim Ferris life for a while. And then I got bored of that very quickly. I realized that was not for me. My passion for impact only grew because of that. I started having a couple of conversation with folks, I think the scene is very small so you get linked up quite easily. 

And the one day somehow got linked up and ended up chatting with Andrea who's now my co- founder and Joe as well. And I still remember quite vividly it was a Friday evening. I went in thinking we'd have a one hour chat, ended up being four hours. I missed my dinner appointment. And then on Monday I was at the office. 

Joel Wong (18:25): 

I guess just chatting about the opportunity, and frankly I knew that fintech was a high potential space at the time. But I knew nothing about it. But I guess my short experience before that, building up these funding campaigns, the whole idea of crowd funding and the impact that brings to a business and business cashflow. That gave me a real insight into what Aspire was doing at the time. It made fintech somehow relatable to me as a entrepreneur or as a potential consumer. 

And that, I think was really why I decided to, that this fintech world made sense. It was more about how the problem became real to me. I think a lot of times when, as an outsider at the point in time when I listen to people talk about fintech, it tended to be quite on a technical level, couldn't for the life of me, make out what it was. Obviously not being from finance, not being from banking. But the idea of business cashflow was something that was for the first time the fintech, very real to me. And I could understand that, and I think that's what attracted me to the space. 

Jeremy Au (19:52): 

What's interesting is that you've obviously met a lot of founders along the way, amongst your peers, amongst the other founders you have worked with up to that day. Was there anything special about this care that made you say "this conversation is worth me bailing on my dinner dates, a few more hours and being very rude." 

Joel Wong (20:19): 

What was interesting was, there was a certain drive that really appealed to me so at this time this was probably three years ago now, Andrea had quit his position at Lazada where he was CMO. And obviously that, itself says quite a bit. He definitely saw something. From him I definitely got that drive and then Joel who is our CTO, he was someone who was very real. He had his fair share of start-ups and war stories so he had done one at the tour and he wasn't coming from an angle of "oh I've been so successful, x number of axis" kind of thing. He was more like "these are kind of the failures and lessons that I've learnt along the way." It was very refreshing. Somehow their combination, together with the fact that the subject matter was so relatable, made me feel that I think this is going to be, this is how fintech should have impact. 

Jeremy Au (21:48):Wow. As you built all of that, how did you tell yourself, because you've built two companies by then. 

How did you tell yourself, "I have the energy to do a third one." 

Joel Wong (22:07): 

I think the couple of months that I had as a break, I think that really refueled the tank. Coming off the second one, I was tired man. It is no easy, I was tired, it was taking an emotional toll. I was asking myself why do I grind like that. I that that couple of months really helped and steadied the mind and at the same time I think earlier on we saw that traction. I think at the end of the day as a start-up winning matters, that energizes everyone and energizes the team. All the signs were there. 

Jeremy Au (23:10): 

That helps a lot, I can imagine. One interesting of course is that you also had a family right process, a kid, a partner. How was going along because its not easy to have a family and then be a supposed bread winner. That's what I always say. How was that, if you don't mind sharing. 

Joel Wong (23:38): 

Definitely my number one supporter is my wife, I think any founder probably holds their wife in that regard. It's a conversation that you guys have to have, set the right expectations and manage that relationship and conversation depending on what happens. My wife has really been a tremendous source of support for me. That said, obviously there's still challenging times. I still remember when we had our kid, I think about a year, a year half in both of us didn't realize how completely sleep deprived we were. It's not something that we expected. 

To this day I often joke about how I ask my friends why no one ever told me about the amount of sleep that I would wreck up. But on the other hand I found myself actually also being more efficient, cause I was also driven by the desire to spend more time with the family and to manage my life better as a whole. I'm a firm believer in mindfulness and trying to create that mindful environment for myself. Still a student here, still got long ways to go. Sometimes I still get completely consumed by work. But mindfulness is something that I constantly try to remind myself to try to reach. 

Jeremy Au (25:16): 

Recently I went for a good walk with another founder and he was reminding me about a challenge that I had, cause we were discussing it and he was just like, the question about financial security. That conversation between the two partners of the household especially in the context of family. He was struggling and it reminded me of my conversation with my partner. Do you think you have any advice on how a founder should talk with their husband or wife about the context of, the building something which may or may not work. It's like 90% chance of failure especially in the early stage. How do you have that conversation? 

Joel Wong (26:02): 

For me, I think it's really about truth and objectiveness. When I was thinking about the topic, read up about the topic at the time. Cause it's something that every founder goes through I think. A couple of tips that I had learned along the way was being clear about what are the goal lines, what are the time lines, what that means and committing to that. And assessing that in periodic checks. I think those were maybe some of the more practical useful tips that I gathered. 

Jeremy Au (26:44): 

Lets talk about time lines, because there's a lot of promises, I feel like as a founder I was always making promises to my wife. If I do this, ship out this product, get my we'll break even and then things will turn around. "oh okay it didn't work out so we just got to ship it out one more time." I don't know, at least that's my recollection. Eventually things did turn around but I think it was touch and go a few times. rubbery with my time line, I got to say. Rubber- bandy about my time line. 

Joel Wong (27:29): 

That's definitely a tough one, I can identify with that for sure. I think I felt it a few times, the rubber band was there. But my wife, like you said, I really look at her as partner, partner at home. I involve her in a lot of the big decisions that I have to make. She's a completely different field but we both are able to and thats been really helpful. 

Jeremy Au (28:09): 

Definitely. I think similar for my wife also, being in different field and being able to be a good independent fair partner, to talk to her, just talk about people stuff and be able to get a independent point of view has been nice. But also now “Jeremy stop bringing work back home, don't want to talk about your company anymore. Can we just talk about TV or movies or the news." 

Joel Wong (28:45): 

That's something I've also learnt over time. But these days I see the upside in that as well. The whole thing about mindfulness that I shared earlier. I think its something that I've really realized to benefit off. If you're stuck in something 24 seven, you don't, I think its really important to be able to do that, obviously to be able to say that is even larger step in itself. 

Jeremy Au (29:24): 

You mentioned mindfulness a few times as something that you care about and you're thoughtful about. How did that get started for you? When did you realize that was something important to be intentional about? 

Joel Wong (29:37): 

I think it was probably sometime towards the end of my second start-up, Grouphunt. I was going through lots of emotional highs and lows. As a founder you can go through a couple of those troughs in a 24-hour cycle. It's really no joke. It was around the time when I realized this is not productive. I'm not making any better decisions. I'm stressing myself out unnecessarily. And thinking about things I potentially can't change for long periods of time. And often it's when you don't think about it where you find a solution. And that just started building up and its something that I've taken with me since and constantly remind myself about these days. And its something that I think even with COVID and the pandemic it's extremely important as well. 

Jeremy Au (30:47):How do you practice that mindfulness now in terns of maybe your aspirational verses like actual routine, 

I guess. What does a actual routine look like to you? 

Joel Wong (31:03): 

Couple of things I can think of, at Aspire we run a fully remote team right now ever since COVID hit. Doesn't matter where you work, what time zone you work, and we are huge on ownership as culture. The idea that you're the owner for that particular part of the business. We trust you'll get it done, however you get it done. When you need to take time for yourself, take time for yourself. Likewise, I'm like that. I run a fixed schedule each day. I make sure I spend time with my family, I make sure I carve time to exercise, something I didn't do before for a long time. I experience different things to break out of that monotony of COVID life. 

Actually like we were talking about earlier, picked up sailing, picked up sailing. I like that idea of, I'm so bad at it that it's a real challenge for me there. Another thing that we do that's maybe a bit more related to work or BAU, is that either every Friday or every Monday we ask everyone in the company to send out a simple email, there are three parts. You describe the highlights of the previous week, the low-lights, as well as the priorities for the coming week. I find the exercise, it really helps you to, number one, rationalize the fact that you have ups and down throughout, not just and entrepreneurship journey but working at a start-up or working anywhere. There are ups and downs. 

But number two, it also makes you reflect upon the week and ask yourself, has it been effective, have you been spending your time the right places? It helps you to think ahead and to prioritize for the next week. I personally find that really helpful, but the exercise is also two-fold. On the other hand now we are distributed, we have over 200 employees. It updates you on each department and what going on in the company. It provides a lot of sync. 

Jeremy Au (33:51): 

It's amazing to see how you've really had embedded not just the personal side of mindfulness but also the company level as well. On that note, I'd love to about, you telling us about a time that you have been brave. 

Joel Wong (34:07): 

I would say maybe it was the time when I decided to wrap up my second start-up Grouphunt. I think it was, like I shared, considerably successful but it was not an easy decision to say "lets transition out." We had a team of seven, we had to consider that. There was, lets say no real reason that we had to do it. But I think, looking back it was a very scary decision at the time. I didn't know what I was going to do next. I had no plans. I knew I wanted to figure somethings out. And obviously with the seven, we helped then transition et cetera. But looking back it was, I think that was a time when I was brave and looking back I'm glad to have been brave. 

Jeremy Au (35:04):What about it was brave from your perspective? What aspects of that decision was brave on reflection. 

Joel Wong (35:12): 

I think the fact that we could have continued going but the question at the back of that, not just in my mind but in the teams mind, what we were doing at the time, is what was the impact we were making? It was coming to terms with that and the fact that we didn't feel that it was as impactful as we wanted. And then making that call. Cause it would have been relatively easy to continue. And then making that call, not knowing what was next. 

Jeremy Au (35:54): 

What does it mean to make that call? When you say make that call, some people call it shut down, you can call it a failure, you can call it closure. What do you call it now? I guess in your words, how do you call it? 

Joel Wong (36:13): 

I think when I look at it, practically speaking the reality of it is a shut down. You decide to fulfill all outstandings and make good on customers and employees and shut it down. If you ask me to choose a word, its a learning. 

Jeremy Au (36:41):Why'd you choose that word? 

Joel Wong (36:45): 

I guess that's how I see it. I guess I use that word quite a lot but I really believe in that way, I think the combination of actions of what you've created, the learnings that you draw from each experience defines you and moves you to your next thing. Yet at the same time it's a very real part of you that you bring along. 

Jeremy Au (37:12): 

That's a tough one right, because there's the recent study which was saying one out of 40 companies that receive seed funding from a reputable company, however you want to call that, will become a unicorn and the rest will pretty much, effectively fail from that. get somewhere, get some revenue zombie-ish. And so it's going to be 39 out of 40 so I remember some friends are like, " wow one out of 40 is great odds." And I always tell people, "well you have better odds doing roulette", you're not. There are less numbers on a wheel than 40. There's actually a lot of founders who are going to be in that same position as you. They're going to be, you know limbo zone, the judgment zone of whether how to make that call. What advice would you give them in processing or structuring the process on how to make that call. On whether to push on or call it a day and start a new chapter and close this chapter. 

Joel Wong (38:38): 

That's a great question. You're a VC, you would know that. But it's true and I think maybe the only interesting point that I would say to that is I think there is also a firm belief that if you are a multiple time founder that that stat changes. And I think that really boils down to experience and learnings and when you do it again you don't do it the same way. I don't know if I have a great answer to how to think about when it's time to make that call. Because sometimes you don't know, sometimes its very clear in black and white. Those are the easy ones to make. Nothings working out, those are the easy ones to make. This particular decision was really hard because it wasn't so clear. 

I can only speak from personal point of view here, as to maybe quite a few of those reasons were person or decisions as a team came up with eventually and that was fine and right by us. But I think maybe the only silver lining to share or maybe what I would like to tell other founder is that it's not a wasted experience, for sure. That's the way I would love for everyone to look at it. I think failure whatever you want to call it is often not something that's celebrated or talked about much in this part of the world. A very different culture when you compare it to the States for example. 

Jeremy Au (40:34): 

I agree with you. I think the process is not easy for sure, on that note I think that like you said, clear cut is more, super clear cut. I think the between is super hard. Actually I think what you're right to say is, I think the most important process is to remember that its not a binary between, the only way of succeeding failure is equals zero because actually at the end of the failure of this thing is that you actually walk put with that experience and learning and the potential to build something new. That's actually quite a new chapter. That can actually restart the whole process all together. The chance to build something new. Success of this venture or the chance to succeed in something new. That's the choice at the end of the day. Awesome. Well, I don't know, I'd love to paraphrase by summarizing the three big themes I got from this discussion. 

The first of course is, thank you so much for sharing all the lessons you had as a serial founder all the way from, I guess, rugby artistic junior college days. To artistic market place days, to group buy market place days, to where you are at Aspire. To lots of learnings about what you learn, your rate of learning, but also I loved what you talked about which that dynamic between how in retrospect, everything is very crystallized, in terms of lessons versus at a time, very drawn out ways to learn those things. And I love that self-awareness because it helps remind people, you and I can boil it down into a one hour conversation and yes because we are looking at it backwards rather than living it at that time. thank you so much for sharing, what I call the relational mindfulness. I love all the advice you gave on how to discuss with your partner and how to be thinking about family commitments, and how to be thoughtful in conversations with founders in your own role. 

And also how to structure mindfulness into the company as well, as a form of practice in the workplace. As well as your own personal practice and mindfulness as well. Especially because you're aware of how, like you said, "there are multiple emotional troughs in the same hour as a founder." Which is, I think the most succinct and diplomatic way of describing the founder life. And thank you also for very sharing, what's it like to make that call to shut down a company, is the way of saying it but it's not necessarily a choice between choosing to fail, but actually a choice of choosing to push on versus the choice to choose to build something new. And Joel thank you so much for being brave and choosing to build something new twice. And being were you are today. I cannot help but continue to wish you much bravery and the best of luck in continuing to push this. I'm sure that you'll continue pushing your ventures and your into the future. And then you so much for sharing your journey Joel. 

Joel Wong (44:03):Thanks so much friend Jeremy, it's a pleasure catching up. 

 

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