Is community building really valuable to a fast-growing business? How do you ensure they contribute both to the company and the ecosystem’s bottom lines as well? Joel Leong, co-founder and CMO of Aspire, an all-in-one finance operating software for businesses, shares more about Entrepreneurs of SEA and CFO Connect, two community initiatives he has been leading, to answer these questions and share learnings on what it takes to bring value to communities as a B2B company. 

He also shares learnings from four years as a leader with the company, from its early days to now having raised a US$100 million Series C in a bear market, being one of the top 10 fastest growing companies in Singapore, ranking as one of the top 50 high growth companies in APAC, two-time LinkedIn Top Startups listee (2021 and 2022), and most importantly serving more than 15,000 businesses in the region.

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Timestamps and Highlights

(01:46) Building Startups in a Startup for Startups;

“What’s really interesting about a startup is that it can always be ground zero. It can always be day one. I think literally you’re just building many more startups along the way. If you think of startups as problem-solving, then that’s what you’re really doing. And I think the difference between starting a startup versus scaling a startup is just simply you’re building more startups…”

(07:18) B2B Community Case Study 1: Entrepreneurs of SEA;

“On the business side of it, you can say that maybe a North Star is community numbers, the organic growth of the community and it has to have value in order to continue to grow organically, with people wanting to join and creating content within that community…campaigns like that can bring your brand top line awareness, you can also use a community to be a group of super users or ambassadors for your business you can test new products with, get feedback from, and so on. It can be a win-win. But as I said, I think there are non-business gains from this as well, where I think in the larger picture, building a supportive community, knowing where Entrepreneurs of SEA started from, the ability to just let other founders know that they’re not alone. I think that’s building the ecosystem as a whole and I think that’s valuable.” 

(13:31) B2B Community Case Study 2: CFO Connect;

“Basically businesses have had to readjust themselves multiple times in these two years. And I feel like all of this kind of brings finance back to the driving seat of the business. Because there are a lot of financial decisions here…for all these you actually need data and you need the right analysis from your finance teams to actually guide you. With this community, what we felt we could do…one was to celebrate the role of finance in business and bring them back to the driving seat, bring finance leaders into the conversation with the business leaders as they should to drive the business forward…the other thing was also to provide an opportunity for finance leaders to learn from each other.” 

(18:29) Managing Community Initiatives;

“In terms of what else has changed in my worldview, maybe the topic of — not that I haven’t prioritized this or that the team has not prioritized this — but you really see the difference in an organization that’s aligned in terms of its mission, in terms of its culture and the impact that is multiplied when your numbers grow. I think it’s a problem that is a lot less visible when you’re a small organization, but as you grow, that becomes — it’s kind of the number one thing on my mind these days.”

(22:04) The Future of Aspire’s Communities;

“Our goal is to get it to an organic state and to a point where we don’t have to be as hands-on, and there’s a lot of value that the community’s getting from within.”

(23:00) #MinuteMasterclass: Building Communities for B2B;

“If you’re coming at it from a business perspective, I would ask two questions, right? Does it make sense for your business? And as a subset of that, which part of your business? Is it an awareness piece? Is it an engagement piece? And so on. You need to answer that for yourself. And secondly, can you provide value? Are you in a position to provide value?”

(24:08) #RapidFireRound;

About our guest

Joel Leong is a serial entrepreneur, having built an online marketplace for creators and group buying community in Singapore before joining Aspire, where he is co-founder and CMO.

Transcript

Building Startups in a Startup for Startups

Paulo: I want to talk first about Joel and let our listeners know more about you and how you crossed paths with this company. As I understand it, you have been starting companies even before you joined Aspire as co-founder. So maybe you can share a little bit about that and how one thing led to another, how you met Andrea, who’s CEO and Giovanni, the co-founders of Aspire, as well.

Joel L: Thanks again for having me. So prior to Aspire, I did run a couple of my own startups, mostly in the e-commerce space. We ran initially a marketplace and then it later also evolved into a crowdfunding slash group buying website. 

I would say they got to sort of decently successful stages, where they were, you could say, ramen profitable, but I kind of also got to a point personally where it wasn’t something that I was investing a lot of time in. It wasn’t something that I saw myself doing for the next five years. 

I was starting to see a lot of movement in other industries like fintech. At that point, I think a lot of e-commerce players had also entered the Southeast Asian space. Lazada and Amazon were really starting to kind of become mainstay names. So I started exploring other opportunities, and that was kind of how I stumbled upon Aspire. And I kind of remember going down to the office on a Friday evening.

Paulo J: What was your first impression of the office? 

Joel L: So back then we were in an office in Oxley BizHub. So it was in town, in the CBD. And there was a certain vibe to the office, I have to say. Like there was a certain energy that — it was scrappy, but you could tell that things were happening. There was a pace. There was movement. So that was my first impression. 

And it was interesting because I could actually observe it for a little while. Because I think Andrea was a little bit late to meet me, so I just sat in the office for a short while, looking around and that was the vibe I got. And I ended up having a three-hour chat with Andrea that evening. 

Paulo J: What convinced you? I mean like after that three-hour chat, was there anything that he said or was it more external things that influenced your decision?

Joel L: I think it was a couple of things, to be honest. I think that chat definitely had some influence. It gave me some confidence in having not just a reputation — at the time, I think Andrea, who also had his success at Lazada right before and Giovanni also obviously had his successes in his own startups before, so there was a certain reputation that these guys had as well. Being able to speak to them definitely helped validate that it was not just reputation, but there was stuff happening. 

But at the same time, as I said, FinTech was an overarching theme that was starting to really gain momentum at the time. So I was interested in the space. 

And lastly, as a business founder or startup founder myself, I could empathize with not just the immediate solution that they were providing at the time, which was credit — and that fit very nicely with the whole crowdfunding side of things that I could see a real need for people starting up to need credit — but I think also the larger mission of the company, which was that businesses are really underserved financially in, not just in credit, but even the basic stuff like your banking account or financial experience. There was a lot of opportunity in that space, that low-hanging fruit that could be plugged in and I think the mission of reinventing business finance spoke to me.

Paulo J: And now it’s been more than four years since the day you dropped by the office and felt that energy and had that three-hour chat with Andrea. And certainly, I would suppose you have grown as the company has grown. 

So maybe you can — this is a fun question that I’ve recently started to ask our guests — describe what your journey has been thus far in some numbers for us, three numbers specifically. How would you describe your journey so far? 

Joel L: That’s a good one. If I had to choose three numbers, the first is 2018. It’s the year when I think it was really ground zero. It’s interesting, that version of the company still remains very fresh in my mind. But you know, it’s that scrappy startup spirit, which is very different from today. So that definitely is one of them. 

The second number is probably 10,000, because I think the point where we hit 10,000 users was a real, internally very strong validating moment for us. So I remember that number off the top of my head.

The third number is maybe what’s to come, leaving it blank or a variable X or infinite. 

Paulo J: Infinite is a good way to put it as well. You mentioned 2018, you said that what you had encountered in your first days there in the company still remains with you to this day. Maybe you can describe a little bit more about what that is. What hasn’t changed in the more than four years you’ve been growing with the company? 

Joel L: I think so much has changed when I look at these four years. Maybe one thing that hasn’t changed is it hasn’t gotten any easier. 

But I think in all seriousness, I think what’s really interesting about a startup is that it can always be ground zero. It can always be day one. I think literally you’re just building many more startups along the way. If you think of startups as problem-solving, then that’s what you’re really doing. 

And I think the difference between starting a startup versus scaling a startup is just simply you’re building more startups, and then you maybe need to make sure that they all make sense and they’re cohesive and they fit together, [but that’s what you’re doing]. 

“What’s really interesting about a startup is that it can always be ground zero. It can always be day one. I think literally you’re just building many more startups along the way. If you think of startups as problem-solving, then that’s what you’re really doing. And I think the difference between starting a startup versus scaling a startup is just simply you’re building more startups…”

B2B Community Case Study 1: Entrepreneurs of SEA

Paulo J: That’s a great way to put it, sort of like a meta way to see the world. Bigger startups are just really like a combination of a lot of smaller problem-solving decisions that have been made. 

And specifically for this call, I wanted to zoom in into one of those, I would say “startups”, if I could call it that, [which are] the community building initiatives that you guys have been doing more recently. It’s something we normally see in a lot of D2C brands, B2C brands, and consumer platforms, but for a B2B, SaaS FinTech company like Aspire, it’s pretty interesting to see it done at this scale [with] a lot of different initiatives that you’re doing, and in particular, two of these initiatives are the Entrepreneurs of SEA (Southeast Asia) and CFO Connect.

Maybe you can start first with the Entrepreneurs of SEA. Maybe you can share with our listeners what that initiative is for those who haven’t heard of it yet and what the motivation was behind this. You can also frame it into the whole community-building ethos that Aspire has.

Joel L: So I think Entrepreneurs of SEA is really a community of founders in Southeast Asia. I think at the heart that’s what it is. But I think the root story behind this is what was really interesting and I think part of it was actually inspired by Humans of New York, this really great photography series. 

But I think, we, ourselves, as founders really identified a certain aspect of startups that I think is a little less known or seen by the public. So I think the public generally has a perception that startups are like glitter and gold. And that’s because the media feeds them success stories.

You hear these big companies, you hear this story of going from zero to hero, right? But the reality is that you and I know that — any startup founder or VC — knows the real numbers behind this sort of ecosystem. And the reality is that it’s just not quite as optimistic as the media puts it.

And I think when you’re really on this journey, there are so many ups and downs — the mental resilience, the level of fortitude that’s required to be a founder, whether you’re successful or not, is already an achievement on its own because it’s very often a very lonely journey. 

And I think when you contrast this with the perception that the public has created and social media has kind of created a world where people are only allowed to celebrate their wins. You have to shape things or you have to say things as if you’re successful. 

And I think that was really the genesis of this community where we wanted to provide a platform for human stories of entrepreneurship to be shared. And to say, “Yeah, we acknowledge that it’s not that easy. And that’s okay. And that there are other people just like you.” And that’s a proud badge to wear so that was how it came about.

Paulo J: So it’s a community and there’s a lot of content also being created around it to be able to share those stories that you mentioned. And I also wanted to frame it in the context of the business as well. Was there a North Star for the community that you were building? Like any specific kind of results, business results maybe that you wanted to see come out of this? 

Joel L: To be honest, I mean there is, right? At the end of the day, we’re a business. So there is, and when we first started, honestly, one of the interesting things though, be before I jump onto the business side of things, is that like a lot of these guys were actually our friends — they’re fellow founders and that was what was really special about creating this community, because all of us had somehow journeyed on this together for the past 2, 3, 4 years, doing various things and trying to make an impact in society with the businesses that we were creating. So that was very special. 

But on the business side of it, you can say that maybe a North Star is community numbers, the organic growth of the community and it has to have value in order to continue to grow organically, with people wanting to join and creating content within that community. 

Today we have a Telegram group that is vibrant. People are continuing to put stuff in a safe space. So that’s kind of the North Star for us today. If you want to measure it from a business perspective, obviously, campaigns like that can bring your brand top-line awareness, you can also use a community to be a group of super users or ambassadors for your business you can test new products with, get feedback from, and so on. It can be a win-win. 

But as I said, I think there are non-business gains from this as well, where I think in the larger picture, building a supportive community, knowing where Entrepreneurs of SEA started from, the ability to just let other founders know that they’re not alone. I think that’s building the ecosystem as a whole and I think that’s valuable. 

Paulo J: Was it easily embraced by the rest of the organization or was there some initial kind of pushback? 

Joel L: Not at all, actually. I think, to be honest, when we first started doing it, I don’t think there was too much thought or emphasis internally about it at the beginning. No one knew that it was going to resonate so strongly with folks. So, it was just kind of like another brand campaign we did and it really took off and had a life of its own. 

Paulo J: And since you started this campaign and this community, what has been the biggest learning so far? Specifically, how has this taught you to then run future communities like CFO Connect which we’ll talk about in a bit? 

Joel L: I think the biggest learning is about being genuine and being genuine about providing value to your community or your audience. I think that’s the only way it works and each community kind of values different things and you kind of need to figure out what that is for each community. But it’s definitely not one of those things where you should just do it for the sake of doing it.

“On the business side of it, you can say that maybe a North Star is community numbers, the organic growth of the community and it has to have value in order to continue to grow organically, with people wanting to join and creating content within that community…campaigns like that can bring your brand top line awareness, you can also use a community to be a group of super users or ambassadors for your business you can test new products with, get feedback from, and so on…there are non-business gains from this as well, where I think in the larger picture, building a supportive community…that’s building the ecosystem as a whole and I think that’s valuable.” 

B2B Community Case Study 2: CFO Connect

Paulo J: Moving on to CFO Connect, which started last year, a much more recent one, maybe you can share this time. What was the context for that one? Why CFOs in particular? I guess the reason must be obvious given what you guys do, but then maybe there’s some story behind that and what you have been looking to achieve with this particular community. 

Joel L: Again, to be very transparent, I think there’s, on one side, a business driving factor after the first Entrepreneurs of SEA took off. We realized, “Wow, this is actually a valuable tool for our customers and a valuable tool for the business, right?” As our product offerings evolved and started serving finance leaders around the region, we thought as well, could there be value in creating something community for finance leaders?

The idea was there. It wasn’t really quite clear what shape or form that would be and what value we would bring to that community. But I remember along the way as we were thinking about this, it was a very interesting time for the world of finance leaders.

If you think about it, for a long time, the background context is that finance or finance teams have literally been back office functions. They kind of are tucked away, hidden in a corner, literally in the back office, right in a corner.

But I think what has occurred in the world in the last two years is a very different time that perhaps might change this. So let me explain. So first there was COVID, which really caused businesses to execute massive changes in the way they operated overnight. And then that was followed with this macroclimate where your interest rates are soaring, then you have the tech winter, where it is not about like top line growth anymore, but sustainable unit economics foundation, and so on. 

Basically, businesses have had to readjust themselves multiple times in these two years. And I feel like all of this kind of brings finance back to the driving seat of the business. Because there are a lot of financial decisions here. You continue to operate overnight during COVID. What do you shut down? What do you change? And then like tech winter, okay, it’s no longer top line, it’s the bottom line, so what do you change? And for all these you actually need data and you need the right analysis from your finance teams to actually guide you. So that was the backdrop. 

With this community, what we felt we could do — was we wanted to do two things. I think one was to celebrate the role of finance in business and bring them back to the driving seat, bring finance leaders into the conversation with the business leaders as they should to drive the business forward. 

But I think the other thing was also to provide an opportunity for finance leaders to learn from each other. A lot of times finance topics are for good reason kind of behind closed doors. And that’s why sometimes they are even kept in the back office. And therefore the opportunity for them to connect with one another, with other finance leaders with the right level of discretion but behind closed doors is an opportunity for them to grow and to bring the industry forward. 

Paulo J: I really find that point interesting because normally with CFOs obviously the information that they deal with and the scenarios that they deal with are very contextual and sometimes very secretive also to the company. It’s something that not many would be very upfront and transparent with.

So it’s interesting how you guys sort of try to balance that instead of providing a safe space for CFOs to interact. And in fact, my colleague Allen was at one of the events that you guys recently held and spoke on the panels. It’s been great to also see that Insignia has been a part of it in some way.

And I was wondering, you do all this content. You have these panels, which I mentioned earlier, to share insights with CFOs. But is there anything that you at Aspire have learned from the CFOs that are part of your community? 

Joel L: What we’ve learned in our conversations with CFOs and building up this community and we have all these closed-door events and the sharing is quite phenomenal. I think what I saw is that firstly, they should absolutely be in the driving seat. 

CFOs are extremely effective business leaders when they’re equipped with the right tools and the right data. The other funny thing is that they should be spending time on high-value analysis instead of chasing receipts, which is a pet peeve of theirs.

And then maybe the last one, I would say, that I’ve also learned is that they are also human and they operate just like any other team in a business. It seems like a black box but in reality, these guys enjoy playing golf. They have management challenges of their own, they’re always looking for better ways to do things and finding new tools and solutions just like any other team. 

“Basically businesses have had to readjust themselves multiple times in these two years. And I feel like all of this kind of brings finance back to the driving seat of the business. Because there are a lot of financial decisions here…for all these you actually need data and you need the right analysis from your finance teams to actually guide you. With this community, what we felt we could do…one was to celebrate the role of finance in business and bring them back to the driving seat, bring finance leaders into the conversation with the business leaders as they should to drive the business forward…the other thing was also to provide an opportunity for finance leaders to learn from each other.” 

Managing Community Initiatives

Paulo J: I think like a thread that we’ve been sort of covering throughout the conversations about Entrepreneurs of SEA and CFO Connect is how this ties back to Aspire as a business.

And you’ve touched on that a bit, but maybe you can share, have there been any challenges in making that link and how you overcome those challenges and really tied things together? 

Joel L: I’m really surprised because one would think that initiatives like this may require certain buy-in from other teams to get the resources to conduct stuff like that.

But for us, the tie has been very natural, thankfully. We kind of think of it as we exist to provide value to customers we want to serve. And that can come in many forms, right? It can come from the knowledge that we share, the product that we build and consume, and all the communities that we create.

And I think at the end of the day, all of these things still push toward the mission, which is to empower these businesses. So somehow it’s been easy actually.

Paulo J: It seems like it’s very much a no-brainer for you guys to actually have embarked on these initiatives. So we’ll get back to community building in a bit, but I just wanted to shift gears also and talk about how your journey in Aspire has impacted your own worldview having been a leader yourself of other organizations prior to Aspire and also a founder. Is there anything that you’ve had to unlearn, let go of, biases, or things like that as you’ve grown as a leader in Aspire? 

Joel L: Almost everything, right? The learning doesn’t stop and I take comfort in the fact that the quality of the problems are getting higher.

In terms of what else has changed in my worldview, maybe the topic of — not that I haven’t prioritized this or that the team has not prioritized this — but you really see the difference in an organization that’s aligned in terms of its mission, in terms of its culture and the impact that is multiplied when your numbers grow. 

I think it’s a problem that is a lot less visible when you’re a small organization, but as you grow, that becomes — it’s kind of the number one thing on my mind these days. And I think also the nuances or the things that you learn in kind of trying to shape the alignment and the culture to have that impact.

Paulo J: I was actually curious, since you mentioned alignment and culture, what do you do like personally in yourself, like as a leader of a specific team within Aspire to actually like align and make sure that the people working with you are actually aligned with the direction of the — say for example, if you do an event for CFO Connect, how do you rally them and tell them that this matters to the bigger picture?

Joel L: I think a lot of it is communication. But I think it’s also about creating the available touchpoints for that communication. Like do you have kickoff calls that align everyone? Do you have weekly updates to relevant stakeholders so they’re not kept in the dark? More and more, it’s looking for opportunities like that. How can you continue to make that alignment more robust?

Paulo J: Giving everybody the chance in the driver’s seat, in the passenger seat, not just leaving them in the back office, to borrow your visual.

Joel L: I think that’s the only way it works, right? One of our core values is ownership and that’s really how we operate. How else do you do things when you’re an organization that’s 400 large?

“In terms of what else has changed in my worldview, maybe the topic of — not that I haven’t prioritized this or that the team has not prioritized this — but you really see the difference in an organization that’s aligned in terms of its mission, in terms of its culture and the impact that is multiplied when your numbers grow. I think it’s a problem that is a lot less visible when you’re a small organization, but as you grow, that becomes — it’s kind of the number one thing on my mind these days.”

The Future of Aspire’s Communities

Paulo J: And finally I wanted to ask about the future. And specifically, I wanted to contextualize that within the communities that you currently run at Aspire. How do you see the future of these communities in the next five years? Are there any particular segments that you’re thinking about creating communities for in the future? Or how are you planning to deepen the communities that you already have with the CFOs and the  Entrepreneurs of SEA? 

Joel L: I think we plan to continue to invest in these communities. Our goal is to get it to an organic state and to a point where we don’t have to be as hands-on, and there’s a lot of value that the community’s getting from within. That’s kind of the goal. Obviously, playing the organizer role in this, we obviously have certain avenues or events that help everyone get together. But that’s kind of where we hope these communities can go on to.

“Our goal is to get it to an organic state and to a point where we don’t have to be as hands-on, and there’s a lot of value that the community’s getting from within.”

#MinuteMasterclass: Building Communities for B2B

Paulo J: They become sort of their own sort of organism. And speaking of communities, that leads me into our minute masterclass corner, where we get to hear about specific advice on certain programs, initiatives or functions. 

If you were to do a masterclass on running community building initiatives, especially for B2B, maybe some founders out there are thinking why should they even maybe even consider this in the first place? Maybe they should not even invest, but even just think about whether this matters to their business or not. What key takeaway would you want for these entrepreneurs or founders to have when it comes to that?

Joel L: If you’re coming at it from a business perspective, I would ask two questions, right? Does it make sense for your business? And as a subset of that, which part of your business? Is it an awareness piece? Is it an engagement piece? And so on. You need to answer that for yourself. And secondly, can you provide value? Are you in a position to provide value? Because I think if these two ingredients are not there and they’re not aligned, then probably it’s not the best strategy for you. And there are a lot of other things you could do. But if these two make sense, then probably you could explore them.

“If you’re coming at it from a business perspective, I would ask two questions, right? Does it make sense for your business? And as a subset of that, which part of your business? Is it an awareness piece? Is it an engagement piece? And so on. You need to answer that for yourself. And secondly, can you provide value? Are you in a position to provide value?”

#RapidFireRound

What digital technology innovation excites you the most? 

Joel L: I guess the cop-out answer is AI. But I’m especially interested in the impact AI would have on humans 10, 20 years from now. Which part of the human mind does it accelerate? Which type of skill in the workforce does it accelerate versus which ones get replaced? I find that very interesting and I have had many debates about that.

If you were to produce a Netflix series, what would be the title of the show? 

Joel L: I saw something today that I thought was interesting. Maybe I’ll just use that. It was from actor Tom Hardy actually — passion produces results. 

Looking back now, what is a skill that could be a soft skill or a hard skill that you believe you should have learned back in your time as a student?

Joel L: Failing.

If there was something that you could automate in your job just by wishing for it, what aspect of your role would that be?

Joel L: I guess it’s kind of like Neurolink, right? I wish that, whatever I’m thinking, could be typed onto Slack instantly and like sent so that I just need to go through stuff and like think and reply and that’s it, without actually having to do any typing, screenshot-ing of stuff, and moving everything around. If my mind could be translated into an output, that would be great.

What’s your favorite go-to destination in Southeast Asia or any trip that you’re looking forward to taking in the region? In the region?

Joel L: Interestingly, I find Malaysia really interesting. Not anywhere specifically, because what I like about Malaysia, strangely enough, is that you can drive there and I enjoy the road trips. I’m not a speed driver, but I spent some time in the States and I enjoyed taking these road trips, and somehow from Singapore, you can do that in Malaysia. It’s a really rich country with lots of resources. They have amazing beaches, and amazing mountains. It’s an abundant place. 

What’s your favorite activity to de-stress these days? 

Joel L: Tennis. 

Anything you’ve read recently or taken up recently that you’d like to recommend to our listeners?

Joel L: I love to recommend taking up a new skill. So like during COVID, I took up sailing. I mean, it was completely new for me, but like that perspective of being at the age that you’re at and learning something completely new, it doesn’t happen quite that often anymore. You used to learn lots of new things when you were young, but to take on something completely new and I fell in love with it. So that was really refreshing.

Paulo J: Now that you’ve done sailing, is there anything on your checklist that you want to get to, if you have the chance?

Joel L: There are lots, maybe skiing. 

Paulo J: So definitely I still like moving from one point to another. I sense a theme here with the road trips and the sailing. 

Joel L: It’s a theme, right? Because I spend so much time seated where I am right now. I definitely believe a lot in balance and maintaining your health. Not doing the best job of it right now, but I can do better. 

Paulo J: On that note of finding balance, I’d like to thank Joel for coming on the show. It’s not that often that we really talk about community building here on the show, and especially how it relates to a company like Aspire, which is FinTech and B2B, which is pretty interesting. And hopefully, there are takeaways for any entrepreneurs out there listening who are thinking about what community means to their business. In the meantime, thanks so much for tuning in on this call, and thanks again for coming on Joel. 

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