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Episode 2:
On today’s episode, Amanda speaks with Dexter Ligot-Gordon, the co-founder and CEO of Swarm, a community connecting founders with freelance tech builders. He was also the co-founder of Kalibrr, the first Southeast Asian and Philippine startup accepted into the global startup accelerator Y Combinator. Before his career as a founder, he spent almost ten years in public service, helping Filipino-Americans break through the glass ceiling.
What motivated him to pursue a career in public policy for nearly a decade? What was it like to build a startup in the early days of the Philippine startup ecosystem? How did it all lead to Swarm?
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✍🏼 TRANSCRIPT
[00:00:00] Dexter: It shaped three generations of my family, the trajectory our lives had taken. And I kind of care about just, well, connecting people with opportunity by removing the barriers of geography, of skills, of interest. I always had a day job, which, you know, was boring, and I always had night activities where I was moving and shaking. We felt that we're carrying the flag, so don't let this flag drop on your watch.
[00:00:40] Amanda: Hi, I'm Amanda Cua, and this is One More Scoop. Here we're sitting down with Southeast Asia's top founders, executives, and investors to have honest conversations about their personal journeys and find out what really happens behind the scenes.
[00:01:07] Amanda: Today, I'm speaking with Dexter Ligot-Gordon. Dexter is the co-founder and CEO of Swarm, a community connecting founders with freelance tech builders who want to solve problems and build impactful projects together. Before Swarm, he was also the co-founder of Kalibrr, the first Southeast Asian setup accepted into the American startup accelerator, Y Combinator, probably best known for companies like Airbnb, Stripe, Instacart, Reddit and Twitch. But before his life as a founder, he was actually in public policy for nearly a decade, working across projects in the US and breaking the glass ceiling for Filipino Americans.
[00:01:50] Amanda: Hi, Dexter. So great to be speaking with you today.
[00:01:54] Dexter: Awesome, Amanda. I'm super excited.
[00:01:57] Amanda: So I've done my own research before this. I've gotten to speak with you before, and I'm sure, as you know, many people have told me great things about you. But I think one thing I wanted to ask you the most was really about your life before you came to the Philippines. What was your early life like growing up, especially as somebody who was like Filipino-American in the US?
[00:02:23] Dexter: I recently gave a talk, and I made a very provocative statement, which was, "No one is qualified to be a founder." And I'll tell you why. Because my background did not align with a path that signaled I would be a tech founder.
[00:02:42] Dexter: I grew up in San Francisco, the mecca of all startups. I went to school because I thought I was going to be a social studies teacher. But then I got involved in government. For a time, I had actually held a pretty high office. I was in the Board of Regents for University of California. My whole career was geared towards… people thought I was going to run for office. And I was involved in a policy space called workforce development. It sounds boring, but it's actually kind of interesting.
[00:03:18] Dexter: I was trying to figure out how government could prepare people for jobs in high-growth industries so there's an education element and a job matching element. So my whole career has been building policies, government-focused programs. My last major project working was working for the mayor of San Francisco. I managed their workforce plan for the city and the strategic planning work with government, private sector, so on and so forth.
[00:04:16] Dexter: But what I did have was a personal North Star. I was always concerned about creating pathways for people to get work. Three generations of my family left the Philippines because there was not opportunity for the skills that they had. My grandfather left. He was a seaman. My mom became a realtor and moved to the United States. So this narrative about connecting people with work, it shaped three generations of my family, the trajectory our lives had taken. And I care about just while connecting people with opportunity by removing the barriers of geography, of skills, of interest. So that's how I was working through that core issue, connecting people with work by removing barriers.
[00:05:17] Dexter: And it (just) so happened that in 2012, there was a mayoral election in San Francisco, and I think that I actually was appointed to be the chief of staff for one of the viable candidates. And I came to the realization that I cared more about solving this work problem, connecting people with work, rather than the politics itself. And I had a crisis of identity because I came to the realization that if I pursued a career in politics, it would have destroyed my character. It would have destroyed my sense of well being, because I'm not a confrontational person. I'm not necessarily somebody who needs to win in order to succeed. I'm the person who loves solving problems.
[00:06:13] Dexter: So I decided to resign. I decided to move to the Philippines, my ancestral homeland, to just wait out the election and take time and space to figure things out. So I had literally no agenda in mind.
[00:06:31] Amanda: Yeah, you just wanted to come back after a tough time, I guess? Just a new place to get away from it all.
[00:06:38] Dexter: Yeah. And also, I was pretty good at what I did in the US. I built the reputation as a strategist and a problem solver and a system builder, both in terms of government and in politics. But my identity, the way in which people viewed me, and the career that I thought I would have would be one where I was an elected official. And when I decided that that was not the path for me, I was like, “Well, I don't know what's going to come next. That's why I ended up just taking time off.
[00:07:17] Amanda: I mean, how would you know? It was your life for a couple of years, and then you realize that, “Okay, surprise. The path I've been walking for a while is not what I want.”
[00:07:27] Dexter: I don't know. It's certainly something I didn't plan for. And it was more than a couple of years, it was like a decade. I was ten years, I'm dating myself, but I was 32 when I moved back to Manila.
[00:07:43] Amanda: I think you mentioned that your family shaped a lot about how you care so much about matching people with the job opportunities. And then you said your grandfather was a seaman, your mom was a realtor, and she went to the US to find the job. But how did that shape you, as a young boy? Were there key moments that you remember were really impactful for you? Because I don't think you suddenly, just from a young age, tell yourself, “Yeah, I care a lot about jobs and job matching.” Right?
[00:08:15] Dexter: Yeah. No, it's one of those things. Well, education had always been a major theme in my family. The reason why my granddad became a seaman was so they could pay for a good education for his six children. And my mom, she wanted to earn enough independently so she could send me and my brother to good schools. And it was explicit that you have to prioritize your education, you have to do well in school, because our families are sacrificing so much for that.
[00:09:02] Dexter: So growing up, there was always this tie between work and education and education back to work. So people made sacrifices. People dislocated themselves such that they could earn enough to pay for education, and they wanted to provide an education. My parents, my grandparents wanted to provide an education to create social mobility for me and my parents' generation. So I think that it was something that actually was explicit. Maybe not the matching part, but getting a good education was always important, and getting a good job was always important. There were people who made sacrifices, so I could have both of those.
[00:09:52] Dexter: And I think just from how I connect that to my why, my broader sense of purpose, systems exist, or systems can be created to create those pathways and those opportunities for others. And initially, I focused on access to high quality education, like helping low income people get access to really good public schools, like UC Berkeley, where I went, and in later days, doing more radical things like re-envisioning how to connect people with work even if they don't have a college degree. What happens to the workforce? Can you create pathways for people who can just demonstrate their capabilities and that demonstration in and of itself is a credential, in and of itself qualifies you to get a project or to get long-term employment.
[00:10:50] Amanda: Were you able to make those pathways?
[00:10:53] Dexter: Definitely. I think Kalibrr was a really good example of that. And Swarm, my new company is also an example of that. Kalibrr was like nine ways to Sunday, this is what we lived and breathed. First, ourselves, we didn't require a college degree. We had college dropouts who did excellent work as engineers or designers at Kalibrr. Some of them were now leading companies. College dropouts, and to remove that stigma was really important. But it meant that we had to create tooling that allowed people to demonstrate what they could do.
[00:11:37] Dexter: So we actually built our own engineering assessments, and then, for product managers, our own case study exercises such that you can demonstrate, what you can do, what you can learn. So we, as a company, implemented these techniques for ourselves, creating alternatives to traditional signals like college degrees. And then we also turned those into products for our customers. So Kalibrr essentially used AI to personalize job search, but when you don't have certain signals like college degrees or past employment, you need alternative signals like skills assessments. So we productized skills assessments that can be used to match people with jobs, and that's what differentiated Kalibrr, what effectively gave us a stronger moat when we went to market.
[00:12:34] And companies like Gojek in Indonesia scaled up their engineering teams on the backs of those assessments, so we knew it made an impact on the clients that we had created. So hiring ourselves... one of the best engineers that we hired in 2017, she went to UP Los Banos. She majored in math and she coded. She was a self-taught engineer and did her engineering assessment using pen and paper. She was so intuitively smart, she could learn and she could compute, that just translated into learning new languages, solving novel problems and cracking through. So you don't need to have a college degree from a prestigious institution to be good. You just need the opportunity to demonstrate it. And that's how we connected people with opportunity.
[00:13:36] Amanda: So you're saying this math major was computing for the coding assessments, which people would typically do on a computer, right? But on paper.
[00:13:46] Dexter: That's right. And she cracked it. And that assessment had only 0.1% of the people who took the assessments scored perfect, and she was one of them.
[00:13:56] Amanda: And how many percent of people use pen and paper apart from her?
[00:14:02] Dexter: None. Well, none. She did pen and paper, and then she went to an Internet cafe and submitted the results. The year after, the best performing engineer that we hired was… he was a residential architect, so he designed houses and he taught himself how to be an engineer. Probably the best dressed engineer I've ever met.
[00:14:24] Amanda: But what does best dressed look like?
[00:14:26] Dexter: Like a hipster. He's one of my favorite people, so I can poke fun at him. He actually joined Swarm again, my new company. So I think that when... this actually sounds like outliers, right? These are exceptions to the rule. But mind you, my policy background is in workforce development. This is actually not exceptions to the rule. This is the opportunities you can create when you change the rules.
[00:15:03] Dexter: You can look for talent in places that you didn't know existed before, and that is how you can create opportunity for people that don't have access, and it's also how labor markets can grow, can get access to talent when all the obvious places run out. When you remove college degrees as a criteria or prestigious universities as a criteria, then your pool for available talent just blows wide open.
[00:15:37] Amanda: Yeah. And you're saying that these assessments are the filter that helps catch these people who typically wouldn't even be part of your talent pipeline.
[00:15:48] Dexter: Right, for ourselves, as a company. For Kalibrr as a company, for my company and for our clients.
[00:15:54] Amanda: So how do you find these people?
[00:15:56] Dexter: Well, Kalibrr had an unfair advantage in that, it was a talent platform so people were coming to us in spades to look for work. And Kalibrr in and of itself became one of the more desirable companies to work for. I think our Glassdoor ratings to 4.9. I was just like, "Okay, phenomenal. I think we did something right."
[00:16:20] Dexter: And I actually think it's not just our analytical framework, it was embedded in our culture. We're a culture where we hire people for what they could do, not where they came from. And we had a culture that was centered on learning. So for those two reasons, I think people really wanted to work at Kalibrr. We paid a bit more than market, but not extraordinary.
[00:16:44] Dexter: Every company I started, well, with the two, I always had to fend off major tech companies who tried to swipe my staff. In Kalibrr, I was fending off Facebook and Google. Now I'm fending off other major companies who raise a lot of money in the Philippines and in the region. But I take it as a compliment.
[00:17:08] Amanda: How do you fend them off?
[00:17:10] Dexter: Well, ultimately, it comes down to the vision of the company, that's one. And the culture that defines how people can participate in bringing that vision to life. The core of Kalibrr and Swarm always centers very profoundly on learning. Nobody is qualified for a job in a startup because you will be forced to do things that you've never done before. So really the meta skill that you're looking for is people's ability to learn and adapt.
[00:17:49] Dexter: And the culture that you need to create needs to foster people to learn fast and to create a sense of safety, a sense of making time and space to experiment such that we can come to decisions faster by experimenting, learning, gathering data and iterating. This is the lifeblood of a startup, iterating and pivoting.
[00:18:14] Dexter: But many times where I think that because companies are under pressure to grow fast, they approach learning from an iteration from a growth and pivoting point of view, but not from a cultural point of view. They don't build in the systems of learning into the culture itself.
[00:18:35] Dexter: So to bring it back to your question, how do you fend off Google or other startups who've raised tens of millions of dollars. One, be the ground, the training ground, the place where people feel safe and can learn what they can't learn anywhere else. Then, secondly, just treat them fairly. The rest is, you know, it's straightforward and basic. Treat them fairly, pay them well.
[00:19:04] Amanda: Yeah. I have a few other questions about your early life. So you said that the young Dexter wanted to be a social studies teacher, right? So how did an aspiring social studies teacher become a politician and somebody involved in politics? When did that change?
[00:19:22] Dexter: Okay, so when I was a student at UC Berkeley, I ended up becoming the student regent.
[00:19:33] Amanda: What's a student regent for people who don't know.
[00:19:37] Dexter: So the University of California is probably one of the biggest and one of the most prestigious public university systems in the world. It's 10 campuses and it's a public university. So it was established by the Constitution of the state of California. It's chartered. And in the Constitution, in the middle of the 1960s student movements, the students in the 1960s had won the right to put a student on the Board of Regents. So the Board of Regents governs all 10 campuses. It's like the legislature that sets the admissions policy, that sets the budget, that hires and fires the senior administrators. And these are folks that are like... the governor sits on the Board of Regents. They're Nobel Laureates who are administrators that are responsible for hiring and firing. So this is a big deal.
[00:20:38] Dexter: I was a student. I was nominated by the students — all 360,000. So I represented 360,000 students. And the reason why I went for the position was because I, myself thought that the admissions criteria restricted access, especially restricted access to people who are disadvantaged. So that's why I went for the position. I happened to be it. And when I was on the Board of Regents, I actually passed a number of policies when I was there.
[00:21:16] Amanda: Okay, [overlapping] was in?
[00:21:18] Dexter: Well, imagine, I was like a 21-year old, sitting around the table with Nobel Laureates. The governor, the owner of Paramount Pictures was a regent. I don't know if you know the Power Rangers, but you know the Power Rangers?
[00:21:29] Amanda: Yeah. This is a lot of older experience and very well respected people, and there's you, right? In your eyes, you're like, "I'm just a 21-year old sitting here representing the students."
[00:21:42] Dexter: Yeah. These are the folks that politicians went to to get support.
[00:21:48] Amanda: Yeah. And you're on the same...
[00:21:50] Dexter: Yeah. I was at the same table. And there were several initiatives where actually, I was running point on getting a legislation passed, University of California one of them. The University of California was the first university system to adopt a green building policy and sustainability standard. And this is before the whole movement for sustainability became mainstream. So that was mine.
[00:22:23] Dexter: I worked on a campaign to instill or to institutionalize Filipino-American language and history studies on campuses.
[00:22:34] Amanda: Oh, wow. When I was applying to college, I saw something about Filipino-American Studies. I was really surprised to see that. Is that because of you then?
[00:22:46] Dexter: Well, I was the insider. So there was a multi-campus campaign at the UC system and I helped organize that. And it was funny, there was a demonstration in front of the Chancellor of UC Irvine, really good person. He ended up becoming the head of the National Science Foundation. But the Chancellor, there was a demonstration in front of his office, was poor Filipinos in support of Filipino-American Studies. And I happened to be meeting with a Chancellor on the inside at the same time. So I was in the office talking to the Chancellor about why Filipino-American Studies is important and there are demonstrators outside and we're all working together.
[00:23:31] Dexter: So I think that the goal there was to get just a handful of folks tenured, which would start to build broader programs and institutions. Because once you get people on the inside, once it gets them tenured track, once they can't get fired anymore, then you can build a critical mass. So, yeah, it was a lot of things like that.
[00:23:57] Dexter: So coming back to your original question, one of the administrators asked me, "So, hey, what are you going to do after your term is done?" I was like, "Well, I plan to become a teacher." He's like, "Dexter, if you become a teacher, you'll impact 30 students at a time." And he said, "But look at what you just did when you passed x, y, or z policy, you can affect society at a grand scale." And the UC system, it's a huge system in the most populous state, and it's like the fifth largest economy state. Think about the impact that you can make as in policy.
[00:24:35] Dexter: So that's how I went from trying to think about how to affect 30 students at a time and setting their personal trajectory to trying to affect systems through policy. And I guess that your extension is like "Well, how did it jumping into tech now?" I'm still actually working in the same problem, which is preparing people for work, but not at the public systems level. I'm looking at it from the market level. So private interventions to be able to create opportunities for people.
[00:25:13] Amanda: Yeah, but what is it like to work in politics? You said that at the end of it, you felt like politics will destroy your character, you're not really a confrontational person and all these other things. So what is it like to work as a politician, especially in the position that you were in?
[00:25:29] Dexter: I felt that I could be a strategist and an advocate, but I couldn't be a politician. I think, a politician, you have to fight and you have to win in order to be effective. I like building systems where multiple parties can win. So I think from when I see it would destroy my character. As a strategist, I probably could win. I helped other people win for public office, but I don't think it would have been very dissonant with who I was as a person.
[00:26:09] Dexter: So the role that I played in politics and it was actually really directly related to building communities and tech, which is we broke through glass ceilings for Filipino-Americans by creating, by connecting disconnected communities.
[00:26:34] Dexter: So in 2009, there was a local race in Alameda for somebody who was running, somebody who I knew was high integrity, really good. He's running for his first office, which was city council. And what I done was I created a coalition of supporters and volunteers from L.A., Washington, DC. New York, who are all focused on helping this person win for local office. It was a slam dunk collection. Then he ran for state office and broke the glass ceiling in California, and now he's the Attorney General of California. He's the one who replaced Kamala Harris after she became a vice president, then her successor became the cabinet secretary, and then Rob Bonta was appointed to be that…
[00:27:30] Amanda: Oh, got it.
[00:27:31] Dexter: So he's literally the top government official in the justice system in California, and I would bet money that he'll be the next California State Governor. Filipino, right? So breaking through these ceilings, this is a matter of strategy, looking for leverage points for people to get ahead. And in that instance, the way in which we were able to achieve it is we connected disparate communities and focused their energy to get this person in office.
[00:28:04] Dexter: And now that he's there and other folks that we helped get in, they're pulling up Filipino Americans behind them into government posts, helping them other folks run for office. So Filipinos are actually... We have several mayors in California that are Filipino-American, several board members, folks from all mostly center to center left or all left. I think there's just this groundswell of support when you focus energy.
[00:28:35] Dexter: So to come back to your question, I can apply strategy and build systems that can break through barriers like this, but I could never be the principal. I came to the realization I couldn't have been the person who would have run for office.
[00:28:50] Amanda: I mean, when you talk about it, it sounds easy like, "Hey, I'm going to bring groups of people, bring in support, and we're going to help this person get into office." By putting it into perspective, you were very young when you got into politics. You stayed there for ten years. So what were the real challenges or the most memorable moments of your career?
[00:29:11] Dexter: Yeah, I think, I always had a day job, which was boring, and I always had night activities where I was moving and shaking. So the biggest challenge was that I didn't know how to make a career out of solving the problems that I wanted to solve. So I always was looking to creating a community-based organization or helping volunteer for somebody who's running for office as a night job.
[00:29:46] Dexter: So the biggest challenge for me was I didn't know how to align what I wanted to do as an individual, solving the problems that I cared about solving with making a life out of it. And I think when I made the jump to become an entrepreneur, I saw for the first time that I can actually put those two things together. Being able to pursue problems that have an impact on society, ideally those that have well, in the case of startups, that can be profitable to solve. But I, as a person, can leverage my strategy skills, my community organizing skills, my ability to mobilize people towards a vision. And it's now just one integrated effort rather than a bifurcated night and day job type of scenario.
[00:30:46] Amanda: Like before, when you were working in politics, you had that division between night and day, but now, it's like the whole day is working.
[00:30:52] Dexter: Yeah, now I work night and day.
[00:30:56] Amanda: But for the same purpose at least, right?
[00:30:59] Dexter: Yeah. Just throwing in the same direction. A lot of folks ask Pia, my wife, like, "How's Dexter doing?" She nailed it. She knows exactly how I feel. "Dexter is ten times busier, but 100 times happier." Because the purpose, alignment and my ability to bring solutions to the world that affects people's lives, I think it's there, but I can also make a career out of it. In this case, a profitable business about it.
[00:31:35] Amanda: It's hard to not be true to yourself right. In the work that you do, and even just knowing that other people don't see it the way that you want to be seeing yourself. When did you feel that conflict the most?
[00:31:47] Dexter: Well, I think actually, I won't be judgmental. I think there are many folks who have careers and founders who want to make money. And that money represents stability. It represents being able to provide for folks that they care about. It means being able to do things that they really love doing.
[00:32:11] Dexter: For me, I think the money has always been a means, but not the goal. It's not the end that I was pursuing. And I think that the moments where I put money first are the moments where I feel the least happy and the least secure. When I put the problem first, when I put the goal first, creating access to employment, creating, connecting people with opportunities in ways that don't exist now. It brings both financial upside, but then also joy.
[00:32:53] Dexter: I think with Swarm, we're in a space right now. The reason why I found it, Swarm, co-founded Swarm with my co-founders, I just started to realize after having interviewed a number of professionals, people were getting jaded with their jobs. They were getting jaded, leveraging their skills and time to create value for someone else, for somebody else's vision, for somebody else's profit. And people were increasingly turning to doing side projects or many of whom already have left their jobs to be able to pursue something that is aligned with what they wanted to do or to become fully independent.
[00:33:38] Dexter: So narrowing in into the space where I'm familiar with like building software, design, development, product management, I thought this is a really interesting problem to solve because jobs no longer are full time, they're no longer exclusive, it's no longer binary working for one company or another, it's a range of commitment. And I believe that we can enable people to work flexibly without having to work alone. Oftentimes when people make that jump to want to work on their own, work independently or work flexibly, oftentimes, it means having to leave their company. Or even if they take a side project, it means that they don't have people to give them feedback because they don't have a team anymore.
[00:34:37] Dexter: So I think, ultimately, anchoring on providing people that option to work on what they want to work on, when they want to work, with whom they want to work without having to do that on their own. That's the space where Swarm is right now and I think it's fascinating.
[00:34:57] Amanda: Yeah, I think it's really interesting, too, like your first venture with Kalibrr, which matched people with jobs and now, you're also still in the same space but instead of matching people with jobs, you're helping people not get tied to a full time job and have freelance gigs.
[00:35:16] Amanda: I think, personally, for me, when I left my job and then I started BackScoop on my own, it's sort of similar to being like a freelancer because I'm still working on my own. Especially in the early days, I could tell I was really lonely. And I think especially if you're somebody who is doing multiple side projects, it's also very hard to manage a lot of other things added to feeling lonely, added to not getting a lot of feedback or help. You also want to have peers around you who are doing the same thing. And I think personally that's something I lacked.
[00:35:38] Amanda: I just came from high school and then I took a job, then I started my own company. I didn't have anyone my age who is also starting a company. And I just started to manage that cycle or even just like I didn't have anybody that I was close to who was also starting a company at the same time. But I guess being a freelancer, one, you already don't have the security of a full time job. You're already having that super tough time, then you don't get feedback, you're looking for more gigs. It's just a really difficult time, too.
[00:36:23] Dexter: That's the curse of working on your own. But there are also a lot of folks are trying to do the same, right?
[00:36:31] Amanda: Yeah.
[00:36:32] Dexter: And I think that it sounds so simple, but creating a space, holding a space where they could do that, it's like parallel play. Do that with each other, help each other on each other's projects, to open up opportunities for each other. Really, that's all we're just doing is enabling people who are working independently to be next to each other, to support each other, to create incentives and systems to sustain that and make that easy.
[00:37:06] Dexter: When you look at it, it's a very simple solution that the world just, I don't know, has a blind spot. And I think being able to essentially collectivize people, bring people together, create a context for them to share revenue, to share opportunities with each other, and to share support and feedback is that's what we're building right now.
[00:37:33] Dexter: And it's interesting, I think, Amanda, when you started, but it's phenomenal what you've been able to do with BackScoop, because when you reached out to folks for support, people rallied around you. And I think that especially, when you're looking at folks who are trying to build companies, founders and even investors, people want to support, can support, and all you really need is initiative and a moment to catalyze that and people rally around it.
[00:38:05] Amanda: And I think even beyond that, it doesn't have to be someone directly giving you help. But I think just knowing a community is there and the community is there around you is actually just very helpful. Just having a space that, you know, because people like you, people who can't support you if you want, might actually be more, I think, meaningful than even having their direct support. I don't know if you see that with your communities, but that's how I personally felt.
[00:38:30] Dexter: That's a good point, because it's like insurance. It's not that being able to make the leap and doing work into independent work, it makes that decision easier knowing that if and when you need help, it's available. And it's that if and when that takes some orchestration, that takes some like, "Who do you go to? How do you incentivize or at least reciprocate with the people who actually answer your call for help?" That if and when, it's not constant, but you want the security that there are folks who have similar values to you or are like minded, they can rally around you when you actually put out the call for help.
[00:39:17] Amanda: Exactly. And I think we glossed over it a bit, but I think what you did after your political career when you came back to the Philippines with Kalibrr is actually really special. It's also a lot of firsts, not just for the Philippines, but for the general startup [Southeast Asian] ecosystem.
[00:39:17] Amanda: But thinking about it, you came back [from the US] and started building Kalibrr in 2012. I was already telling people when I started BackScoop that in 2020, the Philippine startup ecosystem was still very, very early. But we're talking about 2012, that's extra, extra early. What were the challenges of not just building a startup in Southeast Asia in 2012, but in the Philippines? I've come across people who don't even know where the Philippines is.
[00:40:01] Dexter: Yeah, and try asking those people to invest. And that was our daily existential thing. So my co-founder, founder actually, Paul Rivera, was the one who convinced me to move back to the Philippines to co-found Kalibrr with him. Now, the dream was... in the back of our minds, I had always advocated for and worked in the Filipino-American community and Paul as well.
[00:40:32] Dexter: So in the back of our minds, we made the commitment to take on the risks that come along with being a pioneer. So we knew that going into this, it's going to be hard because we would be the first. And we weren't the first tech company. Sulit was actually who we looked up to. Yahoo was operating here at the time. There was some e-commerce that was happening. So we weren't the first tech company per se, but we were the first natively founded tech company that raised foreign VC funding to our knowledge.
[00:41:15] And we did so to solve this problem of connecting people with work. And we used AI to personalize job search and to add to the layer of things that were really hard to do. We had to build an AI team in an area. There were no AI off the shelf tools. There were no graduate programs that taught AI research or machine learning. And we were building a SaaS platform in a market that was still buying software on disks. So the market conditions were just very early. We were committed to solving this problem, personalizing job search, and we were willing to break the ice for everyone else.
[00:42:15] Dexter: So we ended up... this was Paul's initiative. We applied for Y Combinator. It happened to be the first time they allowed international startups in. So we're the first everything. First from Southeast Asia, first from the Philippines because it was the first [time they opened batches to global applicants]. The immediate challenge was it was really hard to raise money abroad. At the time, US market was just massive, and most investors felt that they didn't want to export their capital because they could make enough just focusing on the US.
[00:42:50] Dexter: Secondly, traditional DC didn't really have a footprint in the Philippines, they couldn't really help.
[00:42:58] Amanda: They can't connect you with talent, or they can't connect you with some friends here who can help you with your business, which are things that are very common among value add investors now. But before, that's non-existent.
[00:43:11] Dexter: So we ended up raising money from Kickstart, who has founded the same that we were. So we actually shared an office for a time. It was real pioneer days. 55 Paseo. So we're like building this thing together, building the ecosystem together, building our company together.
[00:43:31] Dexter: So right off the bat, it was extremely difficult to hire people with. There were no companies who were using the tech stack that we committed to. Back then, Angular was new, Python was our back end, and PostgreSQL was in our database. We couldn't hire data scientists. We couldn't hire AI. So the reason why we started to alleviate for ourselves all these requirements for college degrees is because quite literally, nobody was training those skills. And we threw out the window the requirement for years of experience because no other company in the Philippines were using the technologies that we were using to build software.
[00:44:15] Amanda: Let's say somebody had a four year degree in the computer science. You know, that's not really useful for you, because whatever they taught there is not really what you need. And at the same time, let's say they work for five years as a software engineer somewhere. Whatever they're using there is also not useful for that Kalibrr at the time which is why you eliminated those.
[00:44:33] Dexter: Correct. And we built our own assessments to test out. We hired super smart folks who are passionate about what we're doing. So essentially, the way in which we solved our own problem is we hired for people who can learn.
[00:44:47] Dexter: And the second problem that I faced is that I needed to find how to get those skill sets into my team. So we ended up taking money from Omidyar Network. So they were one of our seed investors. The people who worked at Omidyar Network were very well connected to the PayPal and eBay mafia. So I started to leverage those networks to identify operating mentors, to train my team members.
[00:45:19] Dexter: So I had Susan Phillips, who headed marketing for eBay Motors. She trained my whole team on persona driven customer journey management. Then I got Dean Howard, who was head of design for one of the eBay divisions, to train, literally on a weekly basis for two years. He sat down with my design and product management team to do design reviews. So we got very intense on seeking external capacity capability, and I just focused on constant training for my team members and for myself as well.
[00:46:03] Dexter: Many of those folks who went through that period of training, have gone on to co-found their own companies. Joanne, she joined us as an intern. She ended up... after she left Kalibrr, they assigned her to build the video product, and she led the GTM. And now she is the group product manager that oversees Canva's video product.
[00:46:31] Dexter: So I think, it was being able to intensively focus on problem solving and learning, really produced, really excellent thinking, really excellent engineers, product managers, and designers. And that's how we built our employer brand and how we're able to attract a lot of talent.
[00:46:53] Dexter: So raising capital is a challenge right off the bat. Hiring was a challenge right off the bat. And then just the market was not digitized in the way that it is now. This is before smartphones became saturated in the market. I remember Joanne pitched launching a mobile app and why we needed to do that, because the android phone prices were dropping at the time and more people could afford them.
[00:47:27] Dexter: So things so it was very different. It was very early for tech in the region. So I think for us, we wanted to just prove that it could be done. We wanted to genuinely solve this problem. And we kind of socialize, okay, there is talent here, there is a market here and demonstrated that it is possible to build a tech company in the Philippines.
[00:47:53] Amanda: I think, honestly, listening to that, it just sounds so tough. The founder journey is also tough. Now you add on to the fact that you're trying to fundraise for a country that most of your investors don't know about. And the second thing is, you can't even hire a team because nobody has the skills. So you have to train them yourselves and find ways to get them trained. It doesn't sound easy at all. And I think that even hiring nowadays is already a challenge. So imagine back then, I'm already stressed for you.
[00:48:30] Amanda: But I think my question is, how did you bridge that gap as a founder? Because what you did was you trained up the ecosystem for your team, but at the end of the day, training up your system, I mean, your team helps the feature tech ecosystem. So you sort of planting the seeds. It's like doing what all the other tech founders should be doing, but probably can't do because they're busy trying to build a business and they find other ways to hire. But then how did you bridge the personal gap for yourself also? Because how did you learn how to fundraise better? How did you learn how to solve the problem this way instead of maybe you could just give up, right? Or you could just complain and say that, "Hey, the market was too early and we shut down."
[00:49:23] Dexter: I think that we felt that we're carrying the flag, so don't let this flag drop on your watch. I think that's what gave us the motivation to keep pushing in spite of being tired, exhausted, frustrated, being criticized for being slow, being criticized for not having a big enough market. I think the market was just undefined when we decided to make the jump. But again, we felt that, I don't want to say that we planned to be the godfathers, but we just wanted to prove that the ceiling could be broken.
[00:50:02] Amanda: So the same thing you did in your political career. You've been a pioneer before, you broke the glass ceiling before. So maybe this to you was sort of natural already, even though it was hard, definitely.
[00:50:13] Dexter: Definitely. Because it's ecosystem and there's so many people involved, and so many people contributed to that, I could certainly not take the credit. My job was to say that it can be done. And to show bits and pieces that if we work together in certain ways, that we can crack it. And a lot of the fruit of that strategy worked, whether it was when I was a student regent, we didn't have Filipino studies. It didn't really take hold until 10 years after I'd stepped down.
[00:50:49] Dexter: You know, Rob Bonta didn't break the glass ceiling until after I had moved to the Philippines five years that I left. So a lot of that work was seed planting and just convincing people that if we work together towards this vision, for strategic, if we contribute a little bit to this part or that part of a broader strategy can happen. And I think if I only had one scope doing that is identifying what is the division, the strategy, and the bits, the parts of that strategy that people can contribute to from where they are. And over time, it orchestrates onto itself.
[00:51:36] Dexter: So, yeah, I think that's perhaps what I learned, being a 21-year old trying to influence Nobel Laureates and governors and politicians and how to mobilize and change, probably that skill set has carried forward into doing other things.
[00:51:52] Dexter: But again, I refuse to take credit for actually the glass ceiling being broken. Yesterday, I was on a panel with Roland Ros. He probably raised one of the largest rounds for a venture startup in the Philippines. And it's really that scale of a company that can actually reach scale. Kalibrr broke the ice but it's the Kumus, the Sarisukis, the Great Deals, even the PDAXes, that are going to actually scale up the ecosystem.
[00:52:37] Dexter: The cool thing is Kalibrr broke the ice, but then my second company, I think, can participate in that scaling. It's so much easier the second time around.
[00:52:47] Amanda: To find talent, you mean? And to build talent.
[00:52:52] Dexter: Yeah, to find talent. People believe in the Philippines. It's a great place to be a founder right now because it's a new frontier market for a lot of VC and for tech companies. So I don't have to prove anything anymore. It's there so I can actually build my company faster. We can be as nimble as the market will allow us to be.
[00:53:10] Amanda: Yeah. What was the personal toll on you? During the times of building Kalibrr, especially in that market as a founder on your personal life? Or let's say after you switch off your laptop or you get home from the office?
[00:53:26] Dexter: That's a really great question. Well, I measured it. Empirically, I gained 10 pounds (of weight) for every million dollars. Correlation, causation, I'll leave it to people to judge.
[00:53:40] Amanda: Maybe we should measure after you raise your next round. Let's see.
[00:53:45] Dexter: Hope the Swarm is to lose 10 pounds for every million. So maybe that's my self challenge, lose 10 pound for every million. I think that it's a really great question. I didn't have... like you, mentors or people who are doing what I was doing [overlapping] were in it, right? But---
[00:54:08] Amanda: You didn't have anyone to look up to in the ecosystem.
[00:54:13] Dexter: So everything always felt like nobody was there to reassure us that we were not going to fail. And the cortisol, the stress level, even when I would go to get a relaxing spa day, I couldn't just stop thinking about how do I keep from not feeling, how do I not.. You know, it was just this existential thing and it was not healthy. It was just really hard to have assurance.
[00:54:50] Dexter: Having gone through that. Now, I'm working on my second company. I know that where to embrace uncertainty. I know how to expedite learning loops and I know what failure really looks like. So the strain, the eco chamber of doubt, I think it doesn't exist the way it did when I was building Kalibrr, but it was really tough.
[00:55:25] Dexter: I lived in a backpacker hostel for the first eight months, working at Kalibrr.
[00:55:30] Amanda: No way.
[00:55:33] Dexter: Yeah. Before we raised the seed round, I wanted to keep my personal overhead low. So I lived in a six post, six bedroom in a backpacker hostel in Poblacion.
[00:55:43] Amanda: Was it Paul and other people you knew or strangers?
[00:55:49] Dexter: Well, Paul was a part of... no, Paul, his family had a condo in Rockwell, so a lot of the other folks but I needed my space. I just wanted to... I felt like I became a monk just to get no space.
[00:56:06] Dexter: And it was just hilarious. In San Francisco, when you're in your 20s, you save enough money to go backpacking in Southeast Asia, that's the cool thing to do. So here I was, living in a backpacker hostel and ended up being eight months.
[00:56:26] Dexter: So at first, it was really exciting. The hostel is in Poblacion, right? The heart of the red light district. And back then, there were no cafes, there were just red lights.
[00:56:39] Amanda: Yeah, it's not the exciting place it is now.
[00:56:46] Dexter: Yeah. It was just exciting for nefarious reasons. It was the only cheap place to get a backpacker place. So when I was in the backpacker hostel, the only time I felt sorry for myself was… I happened to get bronchitis. And a doctor friend of mine said that, just wait it out and if you can get some salt and hot water and gargle it to irrigate the infection.
[00:57:15] Dexter: And I scrounged through the pantry in the backpacker hostel and all I managed to find… I had hot water. All I managed to find was two packets of Toyo.
[00:57:27] Amanda: Oh, soy sauce.
[00:57:15] Dexter: Soy sauce, right. So the only time I felt sorry for myself was pouring those two packets of soy sauce and hot water and gargling it. And I was like, "Man, what the heck did I get myself into?"
[00:57:43] Amanda: This is when you're starting Kalibrr, not the school searching part before.
[00:57:48] Dexter: Right. It was actually when I actually committed to living in the Philippines full time.
[00:57:55] Amanda: To build Kalibrr, yeah.
[00:57:56] Dexter: Build Kalibrr, that's right. It was just funny. There was somebody, I think he was Thai. He walked in because as I was gurgling and coughing, I spit the soy sauce into the sink in the shared bathroom, and he looked at the sink. He looked at me coughing, saw the black stuff, and he was like, "Oh, my gosh, this guy has tuberculosis or something."
[00:58:18] Amanda: He was your other roommate? Sorry. Quote, end quote, "roommate."
[00:58:22] Dexter: Yeah, he was my roommate. He was my roommate at that time.
[00:58:23] Amanda: Got it.
[00:58:27] Dexter: The moment that we had raised, closed our seed round, I put everything into my backpack, walked down the street to the Gramercy, and I was like, "Can I see condos?" And moved in the same day. And I'm still in Gramercy now.
[00:58:42] Amanda: Oh, okay. The same unit or a different unit?
[00:58:47] Dexter: I moved twice in different units, so I just upgraded to a bigger unit when I got married and had a kid. It's also, I think, the origin story for... the dirty secret is that I was in charge of finding the office, so I ended up putting the office walking distance from where I lived. That's like Kalibrr's office on Poblacion and then apparently, other startups started to put in their offices in Poblacion. I don't know if it was because of Kalibrr or they had the same idea as we did. I don't know. But yeah, now there's some talk of it being called 'Sinigang Valley'.
[00:59:35] Amanda: All right, the Filipino version of Silicon Valley. And I guess to wrap up, I have one last question for you. Outside of work, what's one thing you want to accomplish in your personal life? Whether that's something this year, this month, or something way beyond, but what's something that you want to accomplish with your personal life? Just one thing.
[01:00:01] Dexter: Well, I'm also a dad, so seeing my son excel, getting him in school grounded, he comes to all of our meetings. Our community members were called Swarmies, so he's Swarmy number one. So being able to get him enrolled in classes and get a good start post- pandemic, that's personal.
[01:00:30] Dexter: And then also, I design my own Barongs just for myself. And I want to design a collection for myself this year. This is my one creative outlet.
[01:00:45] Amanda: How would you define Barongs to people who aren't Filipino?
[01:00:49] Dexter: Okay. They are Philippine business wear or formal wear? It's a shirt that is... Yeah, it can be long sleeves and short sleeves. They're considered not traditional and Filipinoesque, but, yeah, essentially, I designed my own shirts, and I want to do another collection this year.
[01:01:17] Amanda: How do you design them?
[01:01:22] Dexter: Wherever I go, whenever I travel, I always collect fabric. So initially, I collected a lot of fabric here in the Philippines, from different indigenous communities. Embroidered fabric, woven fabrics. When we launched Kalibrr in Indonesia, I started to collect Batik.
[01:01:45] Dexter: My philosophy is beach to boardroom. So it's something that you can wear on a resort and then just put on a pair of slacks and walk into a formal business meeting. So I dress for comfort, for style, and, yeah, it's my one public form of creative expression.
[01:02:12] Amanda: Did you design the barong for your wedding? I saw the photo, I think.
[01:02:16] Dexter: Yeah, I did. And there are small, little tweaks in a more traditional Barong. So I'll do things like I'll wear different under shirts to put color in. I'll put hidden pockets into places, like jacket pockets. I could put a place for myself. So I'm the person who likes comfort and practicality. I wore a cardigan every day in San Francisco. So now, because it's too hot to wear sweaters here. The reason why I like cardigans is because I like putting my hands in pockets. So I ended up putting pockets into my Barongs, so I have a place to put my hands in a pocket.
[01:03:11] Amanda: Are you wearing a Barong today?
[01:03:14] Dexter: I was, but since this is not video recorded, I opted not to
[01:03:20] Amanda: Hahaha! Okay.
[01:03:22] Dexter: Well, I really enjoyed talking too, Amanda. I think that being a founder requires people to put their mind, their soul, their heart, their pocketbook to making something that doesn't exist real. And I appreciate how BackScoop has been telling the story behind the valuation, telling the story behind the round size or the traction. I think that really, it's people that take problems and create solutions.
[01:03:57] Dexter: And I hope that for those that are thinking about starting a company, both the downside, the scary parts, are maybe a dose of reality, but then also the joy, the excitement, the opportunity to work with amazing people on hard problems together is a source of encouragement as well.
[01:04:21] Amanda: Thank you so much for joining me today, Dexter. See you soon.
[01:04:26] Dexter: Awesome, Amanda. Cool.
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