Marathon Series: The Y Combinator Alum who returned to Singapore to build Saleswhale

Joining me is Gabriel Lim. He is an entrepreneur who went to Silicon Valley, who got funded by Y Combinator, and who of his own choice decided to come back to Singapore.

Gabriel Lim is the founder of Saleswhale, which uses AI to engage every lead over email, qualify them, and identify leads that are ready to buy.

I want to find out how he built up his business and why he decided to do it in Singapore instead of Silicon Valley.

Gabriel Lim

Gabriel Lim


Gabriel Lim is the founder of Saleswhale, which uses AI to engage every lead over email, qualify them, and identify leads that are ready to buy.


Full Interview Transcript

Andrew: Hey there, freedom fighters. I just startled you, didn’t I? I talk way too loud. I told you I grew up in New York. [Whitney 00:00:12] is here to help us out. Hey, there freedom fighters. My name is Andrew Warner. I am the founder of Mixergy where I interview entrepreneurs about how they built their businesses. I swear I try to tone down my energy. I really work on it so hard, and I can’t because I just love what I’m getting to do. I love entrepreneurship like the way that I did even as a 7-year old kid, 10-year-old kid, 15-year-old kid throughout my life dreaming one day of being an entrepreneur, reading endless books about entrepreneurship and actually being in it is more fun and also more heartbreaking and exhausting than I thought, you know?

So I try to tone down my energy level. I can’t. I can’t. I’m here in Singapore, which makes me super excited. I’ve gotten to meet so many people here and so many entrepreneurs and I didn’t realize how entrepreneurial this city, country is. Joining me is Gabriel Lim. He is an entrepreneur who went to Silicon Valley, who got funded by Y Combinator, who of his own choice decided to come back to Singapore. Could you have stayed in California if you wanted to?

Gabriel: Yeah, I think so.

Andrew: Our immigration policy is kind of tough but I know Y Combinator . . .

Gabriel: It is. It is.

Andrew: . . . has lawyers to help you out, right?

Gabriel: Yeah, yeah. The all want design stuff, stuff like that. Right?

Andrew: They’re there. They’ve got people there to help you. So you could’ve stayed. You decided to come back and I want to find out why he decided to come back. What was it about Singapore that drew him? He is the founder of a tool that I think many people that are listening are going to . . . I know they’re going to want to go try it and maybe they’re going to end up loving this. It’s called Saleswhale. It’s automated sales development assistance.

Here’s what it means. You know how you get all these email addresses of people who kind of signed up to your site, they’re experimenting by getting a white paper or doing a demo. They’re not sure about you and you want to follow up with them and get some of them on a call with a salesperson. But how many SDRs do you need? Sales development reps do you need to fire off messages to them, to respond to those people respond and eventually book the call with a salesperson? A lot, right?

So this guy Gabriel and his team decided, you know what, a lot of this could be automated. We can just use software to send out that first message saying, “Hey, I saw you signed up. Do you want to get on a call with a . . . ” you know? The whole. “Hey, you didn’t respond. Do you want to just check this out?”

He decided he was going to automate that. He did automate it. He got customers. He then went to Y Combinator and now he came back here. I want to find out how he built up his business. And I can do it thanks to two phenomenal companies. The first will host your website right, it’s called HostGator. And the second will help you hire a developer, it’s called Toptal. Gabriel, what message came through? Be open with me. I saw you reach for your phone.

Gabriel: No. Slack.

Andrew: Just Slack on the team contacting you.

Gabriel: Yeah.

Andrew: You’re maybe the first Singaporean I saw with only one cellphone. What’s going on?

Gabriel: Oh, wow. Really?

Andrew: A lot you people have two cellphones. I’m seeing some recognition here in the room. What’s the revenue?

Gabriel: So right now we’re north of a million in annual recurring revenue. That’s all I can say.

Andrew: Is it significantly north of a million?

Gabriel: No.

Andrew: No. Okay.

Gabriel: Yeah. We just raised our series A, right? So I think if you guys know the benchmark for series A companies, you probably can look back what . . . yeah.

Andrew: There’s a benchmark for how much revenue?

Gabriel: Yeah. Like there’s a million in ARR, at least in this part of the region. I know is probably higher in the Bay Area right now.

Andrew: I went back and I saw the time when you guys weren’t charging for anything, free software. I also went back and saw what you were doing before. You’re a guy who was working on something called Getting Real, right?

Gabriel: Yeah.

Andrew: What were you doing at Getting Real?

Gabriel: That’s a boutique mobile software development agency. So what we did was kind of like custom software for companies, building mobile applications, enterprise mobile apps, games, stuff like that.

Andrew: And you were a developer for them?

Gabriel: It’s my company.

Andrew: It’s your company?

Gabriel: Yeah.

Andrew: That’s why it closed up afterwards. It’s gone now, right?

Gabriel: Yeah, it’s gone.

Andrew: Because you left?

Gabriel: Yeah.

Andrew: So the thing that got me was, the reason I didn’t know it was yours, even though I saw that on your LinkedIn but I assumed I misread it. Here, I’ve got your LinkedIn right here. Principal, Getting Real. I assumed it wasn’t because that’s where you had the problem where you were apparently sending out what kind of email?

Gabriel: For us, we have a ton of inbound leads, right? So happens is we’re actually have to qualify them because a lot of people they’re just like tire kickers. They’re not really serious. But not just that but where we got inspiration for Saleswhale was also through working with our customers so we’re working at some previous large MMC

Andrew: What’s MMC?

Gabriel: I know it is [inaudible 00:04:49].

Andrew: What type of company is it?

Gabriel: Samsung, Epson, Rocket Internet, Hubert [inaudible 00:04:54].

Andrew: These were your clients?

Gabriel: These were our clients back in Getting Real Software.

Andrew: So you decided, I’m a developer . . . You’re a developer, right?

Gabriel: Yeah, I’m a software engineer.

Andrew: You wanted to get some clients. You created Getting Real. My sense is you called it Getting Real because you were buying into the whole . . .

Gabriel: David Heinemeier Hansson and the whole . . . yeah.

Andrew: How much was, cut out the extra features, the bloat ware, decide for you customers, keep it elegant. You bought into it and you said I’m calling my company Getting Real.

Gabriel: Yeah, actually, after the book. Yeah.

Andrew: I love that book. I think it’s still to this day a great book, it holds up, and it’s underrated. I bought it and I remember printing out the PDF of it for a friend. Did you get the digital version of it?

Gabriel: No, no. I didn’t. I had the physical copy. I have no idea where it is.

Andrew: I had no idea there was a physical copy of that book.

Gabriel: Nice.

Andrew: So you got that. You created this company. You got clients for yourself and you saw that they had a problem. Talk to me about the problem as they experienced it.

Gabriel: With regards to Saleswhale or regards to . . . ?

Andrew: The way that they were your clients going about getting their traffic to convert into sales by using people to develop the sale and turning those [inaudible 00:05:58].

Gabriel: Yeah, absolutely. So I didn’t fundamentally the problem, you know, that we noticed was that between sales and marketing. So basically sales and marketing alignment, right? So normally in a lot of large companies you see a very huge divide between the marketing team and the sales team. What essentially happens is you have a marketing team who has like, what, a quarter million dollar budget and they spend on events, you know, trade shows, you know, paid advertisements, where you generate a bunch of leads, and then they hand these leads over to their sales teams. Want to guess what happens after that?

Andrew: You know what, I bet what they do is they add it to an email list, probably some junky like MailChimp thing and then they hope that some of those are going to convert and it’s someone else’s problem.

Gabriel: Yeah. Absolutely, right? And it’s part of the sales team’s mandate to also manually follow up with these leads to emailing, following up, calling these people. But what you often notice is that the salespeople will cherry pick, you know, the top few mainly leads and they will just let the rest languish.

Andrew: Got it. Right.

Gabriel: So this was a huge problem that we see across, you know, many organizations, right? So that also kind of like formed part of the inspiration for Saleswhale in its current model right now.

Andrew: And so you were watching this. Why did you decide this is a problem I’m going to tackle? Why?

Gabriel: To be very honest I wish I had some kind of sexy story for you, but the truth is that Saleswhale started off as a side project. And I mean, it was not even the first iteration of . . . there’s many, many iterations of Saleswhale, right? We tried to build a mobile CRM. We tried to build a . . . what do you call it? Like a relationship intelligence tool. I was bought. I was commissioned to build software for large companies, right? So on my free time or nights and weekends I’d just be like working on the side projects and Saleswhale just happened to be one of the side projects.

Andrew: Very similar to the 37signals guys who wrote . . .

Gabriel: Basecamp.

Andrew: . . . [inaudible 00:07:53] and then created Basecamp, which was a big hit.

Gabriel: Yeah.

Andrew: That’s what you were going through as you were doing it. Talk to me about one project that you poured your heart into that didn’t work out.

Gabriel: That’s a good one.

Andrew: Do you remember one?

Gabriel: Let me think.

Andrew: Was it a CRM?

Gabriel: Yeah, the mobile CRM. Right?

Andrew: Mobile CRM meaning like an address book essentially.

Gabriel: Yeah, address book . . . right. So basically what happens is we would . . . So have you heard of this thing called RelateIQ?

Andrew: No, no.

Gabriel: They got acquired by Salesforce for $390 million I think back in 2014. So what we essentially was building unbeknownst to us that RelateIQ was working on the same problem, we were trying to build a mobile version of that. So basically it’s a mobile app, right? We ingest the emails, right, of salespeople and then we actually sub-paste data and people usually following up to within this mobile application. I spent, wow, almost eight months of my life working on this idea. But ultimately, it didn’t really work out.

Andrew: Because? Let’s analyze it.

Gabriel: I think it’s because we sucked, right?

Andrew: Why do you think it sucked?

Gabriel: That’s a good question. So we tried to, you know, sell this to like our friends, who from other startups. We were selling for like what? $49 a month. And we kept getting kickback, oh, this is really expensive. We lowered it to $39 a month, to $19 a month and we couldn’t really find much traction. I think my maximum revenue with this product was like what? $1200 a month. Yeah, I guess in the end we just decided to kind of like shut it down and move onto the next product.

Andrew: Let’s analyze that a little further. I’m kind of curious because I think a lot of people in your position would have this idea that they don’t want to trade time for money. They want to build their own thing, they want it to be able to grow beyond them, but they can’t even find the time to do it because they have so much client work, right?

Gabriel: Mm-hmm.

Andrew: The fact that you did is big and I want to come back to that in a moment.

Gabriel: Absolutely.

Andrew: Let’s analyze why that first version didn’t work so we can learn from it. Why didn’t it work? Why that first product didn’t work.

Gabriel: To be honest, I think we were not intentional about solving problems. So it began with I’m going to build something cool, right, this new Gmail API that we could actually hack on something interesting. And we didn’t do a lot of customer development, or rather I did not. So I spent like, what, 99% of my time just like coding, right, on this application so kind of like there wasn’t much product market fit. You can sense it when you’re talking to people, they’re, “Yeah, it sounds interesting. Yeah, I’ll probably try it.” And when the rubber meets the road it’s like, “Nah.” Yeah. So there was kind like I guess the real reason was that we did not do customer development. We were not listening to what our customers wanted. We were just building whatever we wanted. We wanted to do something cool but it’s not necessarily something that people wanted.

Andrew: Okay. That makes sense. Was closing it hard?

Gabriel: Yeah, pretty . . .

Andrew: Yeah, I bet.

Gabriel: But I think the next day, 24 hours later I moved on to the next . . .

Andrew: It was just like that?

Gabriel: Yeah.

Andrew: Let’s go build something else.

Gabriel: Yeah.

Andrew: So how did you find the time? As somebody who was developing work for clients, how did you find the time to actually do it?

Gabriel: I enjoy programming a lot. I think I was working about 16 hours a day.

Andrew: 16?

Gabriel: Sixteen. Sixteen hour days, so like in the morning and the afternoons, you know, we would be coding for billing for like client work and then on nights and weekends I’d just be hacking away at side projects. And to me it wasn’t tiring, it was fun.

Andrew: You’d come home. You were working all the time. You did.

Gabriel: So we had our own business. So we had a small shop house, so it’s myself, my cofounder back then at Getting Real Software and I think five other software engineers. So in the morning and afternoon they’d just come in, we’re working on client work and at 6-7 p.m. I go out for some dinner, come back to office and finally I get to work on my own stuff.

Andrew: Again?

Gabriel: Yeah. And I was just like . . .

Andrew: This is something. [Ashwin 00:11:43], you’re here. You tell me if this is true or if I’m just imagining it. I feel like people work longer hours in Singapore than in the U.S.

Gabriel: Really.

Ashwin: I’ve lived in the U.S. 10 years, worked at consulting firms there and here, it is true.

Andrew: He’s saying he worked in consulting firms in the U.S. and here and it is true. Yeah. Even like look at the receptionist over here. She was here last night till 5:30 I saw and I said, “I’m surprised you’re here.” She said, “Yeah, I’m here till 6.” I said, “Didn’t I see you here at 8:30? I was one of the first people in the office.” “Yeah, 8:30 till 6:00.” Right? And this is a receptionist at a coworking Regus space. That’s just shocking for me because in the U.S. it’s I guess 9 to 5 and they’re done. How do you find time for relationships? I mean love. I see you’ve got a ring but also friends?

Gabriel: That is interesting. So my wife is actually my cofounder. So she was my cofounder . . .

Andrew: Venus?

Gabriel: Yeah, Venus. Getting Real Software and then now at Saleswhale.

Andrew: At the end of the day working for your clients the two of you would sit in the office and code?

Gabriel: Sometimes she would go back home first. Otherwise she’d just be in the office accompanying me.

Andrew: And you’d both sit there and code?

Gabriel: She would be doing design. But normally I’d work on my harebrained ideas alone. I try not to rope her in too much.

Andrew: Wow. All right.

Gabriel: So that’s hyper-optimized, right? Your cofounder is your wife so you have to spend too much time.

Andrew: No. Actually that makes a lot of sense because you don’t have to say I’m just hopping to work to go do this. Growing up were you like that too? Did you come from a family here in Singapore that pushed you to work longer hours, study more?

Gabriel: No really. So I’m born and bred in Singapore, so my parents were relaxed, which is very rare. Because like Singapore parents are crazy.

Andrew: Crazy. Give me a sense of how crazy they are.

Gabriel: So at the age of 3 or 4 years old they send you to like enrichment classes, right?

Ashwin: Not to interject here, but the school system here is really strange.

Andrew: What do you mean by strange? I wish they had a mic on you.

Ashwin: Olivia would just recoil at hearing this, because from what you’ve told if she’s as hippy as you say, school system here there’s something called an PSLE, which is like when you are around sixth grade . . .

Gabriel: They skim you.

Man: They basically tell you what you’re worth.

Andrew: At sixth grade they tell you what you’re worth.

Gabriel: Yes.

Andrew: This is it.

Man: And what your career path will be.

Andrew: What was your career going to be?

Gabriel: No. It’s literally what career path will be.

Andrew: What did they say about you were?

Gabriel: Basically they stratify you. So I did extremely well for my PSLE, so I went to the top school, like literally the top school in Singapore after my PSLE

Andrew: PSLE.

Gabriel: Yeah, primary school leaving examination. This is like a rite of passage for a lot of Singaporean parents.

Andrew: Studying hard to go through it?

Gabriel: It’s not a child that’s the one that suffers. It’s the parents.

Andrew: Why?

Gabriel: So when you see normally when children reach the sixth grade, right? Their parents will stop all of their vacation and their leave and like 6 months before this PSLE they will take leave to tutor their child to make sure that they ace the PSLE. I wish I was exaggerating, I’m not.

Andrew: Did your parents do that?

Gabriel: Am I wrong? Am I wrong?

Ashwin: People take a whole year off.

Andrew: Yeah, they take a whole year off sometimes.

Ashwin: So that they can be there with their child.

Andrew: Parents take a whole year off to go do that?

Gabriel: Yes, be there with their child. Right. To make sure that they don’t fuck up their PSLE. Sorry, am I allowed to swear?

Andrew: You can swear.

Gabriel: Okay. Perfect.

Andrew: [Ing Yee 00:14:55] who’s here with you from Saleswhale, she’s cracking up.

Gabriel: Am I wrong about the PSLE?

Andrew: Your parents too? Did they do that?

Ing: They were not that strict.

Andrew: They were not that strict. They only took six months off, not a year.

Ing: [inaudible 00:15:07].

Andrew: Is it helpful? Like honestly, if you look back, is it helpful to be pushed that hard? Don’t feel like you have to give me the stereotypical answer. I just want to get to know it. Do you feel like it’s helpful to get pushed that hard or not?

Gabriel: Not at all. Right.

Andrew: It’s not helpful

Gabriel: No. It’s not helpful. Right. So if you look at Singapore, traditionally, at least till recent years, we are not known for being very entrepreneurial. Right. People here they want to follow the cut and dot path be a doctor, lawyer, banker, right? These are the stereotypical like Singapore paths. Like I said, I was lucky. My parents didn’t push me that hard. They were kind of, “Just do whatever you do.” Yeah. So that worked out for me, I guess.

Andrew: So what did you do then instead?

Gabriel: Like after school or . . . ?

Andrew: No, instead. If you didn’t have work that hard on the traditional path of studying, acing these tests and so on. What did you do with your time instead?

Gabriel: So I played a ton of sports back in school like rugby and I actually . . . so in my secondary school we actually had computer lessons so I was actually spending a ton of time in the lab as well like hacking away at stupid Flash games, building those super ugly websites.

Andrew: So it was working out for you then. The fact that you were working on these stupid ugly websites and called it actually did lead to this life. And your parent they were right to tell you don’t sweat it too much.

Gabriel: Yeah, I think so.

Andrew: Did you feel like a loser at the time? Like look at all these people who were doing so much better than me?

Gabriel: I think so. I come from a family of overachievers so I have like cousins. Like half of my family tree are like doctors and the other half are like lawyers. So their parents pushed them extremely hard so I’m kind of like the slacker of the family.

Andrew: Did you feel like a slacker? Did you feel like you were wasting your life?

Gabriel: I did. Right. So my parents were telling . . . Sorry, my relatives [inaudible 00:17:01] they would be comparing grades like, “Oh, my child popped the class. Got second in cohort. Gabriel what do you do?” I got like 30, last in my class of like 33 people. Yeah, so yeah.

Andrew: All right. Fair enough. I can’t believe this worked out. So you start this company at that point?

Gabriel: No, no. That was like way earlier. That was like 13, 14.

Andrew: Later now. Getting Real, were your parents proud at that point?

Gabriel: No. So my parents wanted me to . . . I’m not sure if I shared with you but I actually did not go to college.

Andrew: No, I didn’t know that.

Gabriel: Yeah, my parents actually wanted me to go to college, right? So my original plan was like I want to be a doctor, not doctor. My grades were not great enough for that. Maybe like, I don’t know, banking, or like, you know, be a lawyer. So that was what I thought I would do with my life like when I was like 15 years old. In Singapore we have this thing called military service where you have to go through the years, compulsory years. So when I was in the army, I was just doing some self-reflection and so the thing is I didn’t come from a very well to do family. So I didn’t know what I wanted to do with life. I’m not sure if I want to burden all my parents money or like studying a course I’m not very sure about.

So I just decided that I would kind of bum around for a year to figure out what I wanted to do. And in that year . . . after I finished military service and I was like 19 or 20 at the time, I started a discount coupon website. I become a semi-professional poker player. I did a bunch of weird stuff. So my parents were like, “Dude, I know we told you to do whatever makes you happy, but what the hell are you doing?” right. So yeah, that one year was kind of an interesting period when I was trying to figure out what I wanted to do and I only started Getting Real Software, I think, 2011, 2012.

Andrew: Okay. Did you feel like a loser at that point? Were you doubting yourself a lot? Or were you out . . . ? I imagine, I’m looking at you, you’re in the I’ll show them mindset. Am I right?

Gabriel: Yeah.

Andrew: I’m going to show them. Poker will make sense because I know the math. I’ll show them because I’m willing to put in the time.

Gabriel: Yeah.

Andrew: You did? That’s who you were.

Gabriel: Yeah.

Andrew: I see that by you saying that. And then the discount coupon site, why didn’t that do well? That seems like a good idea at a time when some sites did well.

Gabriel: So I think that lasted for like, what, less than a half a year. So when we started we were . . . Groupon was like, I think they were doing extremely well. So when I started I didn’t realize how much cold calling I would need to do. Like calling up SMBs. Right. Hey, this is Gabriel calling from [inaudible 00:19:36]. Yeah. It was tough. Right? I’m an engineer, right? That was painful to me but we did well. So I think our very first deal we sold like a 150 coupons for like I think $75 per coupon. And then our second deal we sold like 1500 coupons at $32 a pop. So yeah,

Andrew: It’s great.

Gabriel: I think it was pretty good. And then afterwards we realized that the market started to get very crowded, right? It started to get very saturated from charging 25%, you know, per coupon. We were getting like 20%, 15%, 10%, 5% and I was like, you’re not making much money. So like okay, I’ll just move on to the next thing.

Andrew: I want to come back to that and move on. I see that a lot.

Gabriel: You see that, right?

Andrew: Yeah. I’m hearing your story and I want to know whether it’s intentional or not. For somebody who’s listening to us, I want to tell you guys about someone who’s listening to us who’s creative too, I want to tell you about HostGator. HostGator has this . . . you know HostGator?

Gabriel: No.

Andrew: It’s a hosting company that I like that they’re inexpensive but that medium, that middle size plan that they have gives you unlimited domains so that means if somebody you have a bunch of ideas, all they have to do is go back to their HostGator account, fire up another WordPress install, now they got a coupon site. It doesn’t work out, don’t like it, close it up. What’s next? Well, you know Wirecutter is doing well. Why does nobody make Wirecutter for camera equipment, camera enthusiasts always want as much data as possible and they’re likely to click the link and go to Amazon. I’m going to come up with that. Great. They go again to their HostGator account, hit another button, they get a whole website to just to do that. Try, try, try, try. You know Groupon, Andrew Mason told me that he created it on WordPress.

Gabriel: Oh, wow.

Andrew: First version on WordPress. Same thing here. Take your ideas, whatever they are to You’ll get an unbelievably low price, you’ll get good service from them and if you pick that middle option, it costs maybe a buck or two more. Let’s find out more it costs.

Man: Two bucks.

Andrew: Two bucks. No, here, look at this. The small plan comes out to $2.64 a month. The bigger or second plan is $3.98. I get no extra money if you pick the middle plan. But here’s what you get when you do that, unlimited domains and that is the power to just keep experimenting. Do you feel like you didn’t stick with ideas long enough?

Gabriel: Absolutely. I think that was the theme of the first 24, 23 years of my life, right? I would just bounce . . .

Andrew: The first 23 years?

Gabriel: Yeah, like bouncing around from stuff to stuff. Like trying things out, trying to get experience. Not experience, I wasn’t really conscious [inaudible 00:22:17] when it’s stops getting fun, that’s when I’ll move on.

Andrew: Is it that it stops getting fun or that you didn’t . . . that if it doesn’t produce, you start to doubt it? That you are someone who I see you, a lot of who you are comes naturally, right?

Gabriel: Yeah.

Andrew: And so when it comes naturally that means you do well. When you end up with an obstacle, it means this isn’t the right vehicle.

Gabriel: And then suddenly you have to put in the work and then you realize, oh, shit, it’s not as fun. There’s diminishing returns.

Andrew: Right, exactly. Especially where if you were someone who was crap at first, you’d have to prove yourself, prove yourself and every little bit of success would feel like all right, I’m making some momentum. But if you do well right away, your first deal, I did the math was about $11,000. Right?

Gabriel: Yeah.

Andrew: Second deal about $32,000 from the coupon site.

Gabriel: Yeah.

Andrew: Suddenly if you were to hit an obstacle, I’m not dealing well. What’s wrong? As opposed to saying, nothing’s wrong. This is life. I have to make calls.

Gabriel: So this was the lesson that I learned after in the later part.

Andrew: Okay. When did you finally get that lesson?

Gabriel: Getting Real Software, so we started for four years, four and a half years so there were many, many times I just wanted to throw in the towel. But I guess I was sick of bumming around from idea to idea with very limited substance. I wanted to have something that I have a solid footprint, solid win [inaudible 00:23:30] and I think we did that with . . .

Andrew: It’s like this is the time that I’m finally going to stick with it and I’m not going to give up until the world gives me what I need. Something like that.

Gabriel: Unfortunately, we did give it up in the end, right?

Andrew: What do you mean?

Gabriel: Getting Real Software.

Andrew: Oh, with Getting Real. Oh, you’re saying Getting Real Software was where you were going to stick with it. Got it. I thought you meant Saleswhale. Okay. Give me an example of time when you were going to not keep going with Getting Real, but because you pushed through, the business got better.

Gabriel: Wow. I’d say probably in the early days, right. In the early days of Getting Real Software, we were just building like crappy websites, ecommerce, you know, applications for people. So we were charging like $3000, $5000, $10,000. And afterwards it’s just like, this is like a grind. And we were not like the only play in town. So we were not differentiated. I think it was around that time the mobile boom started to really take off and I was like, hey, you know, it seems like there is a lot of demand for iOS apps and there are not many iOS programmers around. So I went to the library, got my hands on all the iOS development books, you know, finished them in like one or two weeks and then started to offer iOS services to clients and that’s where kind of our business took off.

Andrew: Just to be clear for people who are listening, because you talk fast like me, iOS, right?

Gabriel: iOS.

Andrew: Apple’s platform. That’s when things took off and you started to specialize. You also started to increase your prices?

Gabriel: Yes, that’s right. So we pivoted, right? We changed from kind of like general software development house to we only do mobile apps right now.

Andrew: But it was more than just mobile. I couldn’t grab the fricken screenshot off of Archive. It said Getting Real is a Singapore mobile app . . . it was something else you . . .

Gabriel: I have it . . .

Andrew: Wait, artificial . . . No, no. What is it called?

Gabriel: Augmented reality?

Andrew: Yeah. You started focusing on that even?

Gabriel: Yeah, yeah.

Andrew: So it wasn’t just iOS, it was iOS augment reality. Was that your specialty?

Gabriel: No. So just iOS mobile.

Andrew: I tried so hard to find that phrase . . . okay.

Gabriel: That very interesting project we did one of our clients, right? Hubert Burda Media right? So there’s this magazine like they have like different like . . . So back then they had this mobile application that we were building for them so if you were to kind of open the ad and put over the magazine, you can see 3D visualization of like a car, right, or a watch, and you can literally play around with it. So we built that on top [inaudible 00:25:53] and it took me like one week to learn that and then my cofounder was building 3D models for that so that was a pretty fun project to work on.

Andrew: You are like a fast learner. Okay. So then Saleswhale starts to take off. Why did that take off? Did you start talking to customers? What was it that allowed that business to take off?

Gabriel: I don’t think Saleswhale actually took off then, right? So we went through a time in December 2015, right? So that’s where me, my cofounder, and my CTO said, a third cofounder came about fulltime. Back then we were like . . . we only had a handful of beta customers, right? And we’re building out initial version of Saleswhale, so it wasn’t a breakout success by any means.

Andrew: How did you get the first beta customer . . . so you built the idea with the first customer?

Gabriel: Talking to my friends. So my friends in the startup industry like, hey, you know this product. Do you want to use it? So yeah.

Andrew: Was the original artificial intelligence from the start?

Gabriel: Yes.

Andrew: There are tools that do what you do without the artificial intelligence. The tools will do things like you put a list of email addresses, you create a template for your first message, you create a template for your second, third, fourth, etc., and as soon as somebody hits reply, the sequence stops, right?

Gabriel: So this was the initial iteration of Saleswhale.

Andrew: It did that.

Gabriel: Yeah.

Andrew: No artificial intelligence. It was just . . .

Gabriel: No, it was with artificial intelligence. So basically what we do is we go through the email messages and then we tell you how to improve these email messages. We have this like API system that coaches you on how to send better emails.

Andrew: But it wasn’t potential client’s email and responding.

Gabriel: No.

Andrew: It was reading my message to them saying, “Andrew, this is stupid.” Like, I’ve got an example here and I found one. Give me a second here. Okay, here’s one. The person says, Justine Wong, this is a sample, subject line, “How can we improve . . . ” Wait. “How we can improve your website performance.” Right? So your software looks at that and says . . .

Gabriel: I know it’s a shitty subject title and this is how to do it better.

Andrew: It says our system flagged this as subject that is likely to misconstrued as spam marketing email. What has worked surprisingly well based on our data is super simple subjects like, “Hi, first name,” and that’s what you did. Automatically recommend based on what people did. And did you also fire off the second message if they respond to that?

Gabriel: Yeah, that’s it. So basically it’s very similar to the tools that you mention like Yesware, [inaudible 00:28:15] app, it’s just this layer of artificial intelligence that honestly wasn’t so compelling, but hey, we did get into Y Combinator with this idea.

Andrew: With that idea?

Gabriel: With this idea.

Andrew: Did you have customers when you had that?

Gabriel: Just a couple, just a handful of customers.

Andrew: Paying customers?

Gabriel: Paying customers.

Andrew: So I had a note here to say, why did Y Combinator . . . ? Why did Y Combinator let them in?

Gabriel: I have no fricken idea.

Andrew: You have no idea. There’s something about you. What do you think it is? No track record of sticking you in stuff. Track record of development, which they love, right? You don’t know what it is. Do you remember the question that they asked you?

Gabriel: Okay. Let me share the story because it’s very good story. I remember it was around early February so me and my cofounders were at like startups recording away, you know, building away at this application, this iteration of idea. And one day I was studying Hacker News and I saw the bottom of the screen like, hey, you know, applications for Y Combinator summer ’16 batch are open. So hey, guys, look, Y Combinator open. “Gabriel, fuck, can you focus on your work? Can you stop doing random bullshit?”

It’s like okay. No worries. Let me do it. I’ll just bang out the application. You guys don’t have to do anything, so I’ll just bang out the application and then after that I’ll take a one minute video of whatever we built and they’ll get a one minute video of us, right? So come on, you don’t have to say anything else. I turned on the webcam, I start talking, like, “Hey, I’m Gabriel. This is what we are building.” And I sent it over to YC. I didn’t expect anything. Like no one . . . we barely have any Singaporean or Southeast Asia Y Combinator startups. Not many, right? So one minute later I received an email from YC saying, “Hey, we love your . . . you know, we love you guys, we love what you’re building, you know, we’d love to fly you down to Mountain View for an interview all expenses paid.”

Andrew: Wow. Okay.

Gabriel: Well, guys, let’s go on a holiday. Let’s go to vacation.

Andrew: That’s it. You weren’t thinking we’re going to get in.

Gabriel: No.

Andrew: People practice the interview questions, the practice . . . You don’t do any of that?

Gabriel: No. So what I did I went through all of the interview slots and I told my cofounders, look there are x number of interview slots and they’re probably going to accept x number of people, right? We have a 19% chance of getting in. So let’s just go there and like have fun. Right? We’re probably not going to get in, like 19% chance even after getting . . .

Andrew: 19% . . .

Gabriel: 19.1% chance of getting in there even at the interview stage.

Andrew: So you go in, by the way . . .

Gabriel: We go in and . . .

Andrew: Actually, Mountain View is not a good vacation spot.

Gabriel: We took a ride up to San Francisco after the [inaudible 00:30:36].

Andrew: Okay. I still say not a good vacation spot, but okay, fine. All right. So you go in there. You have the meeting.

Gabriel: Yeah. So when I went in there, who was it? Seven of us in a room, was in our interview. Justin Kan was there, [inaudible 00:30:46]. Yeah, it was pretty nerve-wracking I have to be honest, right?

Andrew: You have what? Five, six minutes?

Gabriel: 10 minutes.

Andrew: 10 minutes.

Gabriel: 10 minutes. So before we even sit down, before our butts even hit the chair, they’re like bombarding us with questions, and like, oh, shit, they’re like . . . I was expecting these and they’re like you’re just kind of rolling with it. And at the end of the interview when we step out the room, we’re like, oh, shit, I think we did really badly. We didn’t cover any points that we wanted to cover. Okay, that’s it. End of the dream. Let’s go back to our apartment.

Andrew: And you’re not somebody who stresses about this? You don’t go back and you go damn, why didn’t I work harder?

Gabriel: It was a long shot from the very beginning.

Andrew: You were always good with it being a long shot?

Gabriel: It was, right?

Andrew: Okay. That’s got to be a benefit of being the slacker of the family. I was the only one in my family who went to college so everything has to be great. No? Right?

Gabriel: So we went back to our apartment. We rented an Airbnb. My two cofounder went to take a nap. I’m so tired, they went to take a nap. I went for a run. And I think 400 meter off from the house my phone started ringing like, oh, this is a U.S. number. I wonder who it is. Oh, picked up the phone Justin Kan’s on the line.

Andrew: Justin Kan?

Gabriel: Yeah, like, hey, you know who I am? Yeah, like, Justin. You know where I’m calling? Wait, wait, wait, hold on. Don’t say anything. I started sprinting back to our apartment and he was like, “Hey, dude, relax.” Ran to my apartment, woke my cofounders up, put him on loudspeaker, like Justin go. Like, “Hey, you know, we really like you, like to offer you a slot in YC, 7% for $130,000 U.S.” Yeah, of course, we’re . . . that’s how we got into Y Combinator.

Andrew: Wow-wee. How did they help shape your business?

Gabriel: It was tremendous. It was a fantastic experience.

Andrew: I saw a photo, by the way, of the three of you. Five different photos I think out there. Interview with the Y Combinator sign.

Gabriel: Yeah. We loved it. Like we had a blast of a time.

Andrew: Tell me, how did they help shape your business?

Gabriel: So I think number is YC is modeled around build something people want and I think it’s something all along in our life I’m exaggerating when I say that I probably created 145 side projects.

Andrew: 145 side projects.

Gabriel: 145 side in four years, right. And one thing that we didn’t take seriously was like customer development, talking to users, building something people wanted, just something that Y Combinator drills into you. So they force you to talk to your customers.

Andrew: How? What did you do when you talk to them?

Gabriel: [inaudible 00:33:06] too much. So basically every two weeks so YC is so huge now they shop you into different groups so they lock you in a room with your group partners and you have to go around in a circle to share what you’re working on, problems you’re facing, where you’re stuck and this is kind of like where you would get like the brutal treatment from your group partners like, hey, why are you guys doing this? Why are you doing that? Right? No. That’s stupid. So it was a very interesting experience.

Andrew: So you felt like you had to talk to your customers. One thing that I noticed about you was your early customers were from Asia. So did you have to make calls in the middle of the night?

Gabriel: Yeah, we did. So I was up . . . like I have some photos like 2 a.m., 3 a.m. in the night I’d be on Skype, you know, talking to . . .

Andrew: Talking to potential customers.

Gabriel: Talking to potential customers in Asia and like in the morning I’d be talking to customers in San Francisco. So yeah, but it was fun.

Andrew: So for once you were actually really talking to customers. The thing that’s always been a challenge for you?

Gabriel: Yeah.

Andrew: And how was it? Did you take to it as someone who likes to code and develop? Did you like it?

Gabriel: It was a grind at the start but after a while you realize that, oh, my god, like you’re learning so much like damn, why didn’t I do this earlier?

Andrew: Like what? What did you learn that you didn’t know before?

Gabriel: Specifically, with regards to the product or . . . ?

Andrew: Yeah, what did you learn about your customers that you didn’t know before that surprised you?

Gabriel: I think one interesting insight that we had was for this iteration of the product, so one thing that I learned was that this idea was dead on arrival.

Andrew: The one that you just described?

Gabriel: Yes.

Andrew: Why was it dead on arrival?

Gabriel: So because when you’re talking to customers you’re asking hey, how are you using the product? Walk me through what do you like about the product, what don’t you like about the product. You realize that we realized that a lot of them was not actually suing the AI component. They were just using us like a very cheap kind like Yesware [inaudible 00:34:59]. So they were using the sequencing module a lot but not so much of the AI portion.

Andrew: Paying attention to the advice that I just read.

Gabriel: Yes. So when we ask them, hey, why are you guys not leveraging all this advice? You are the sales manager. Why aren’t you enforcing this advice for your salespeople? You agree that this advice in order to us that, hey, we really love the suggestions that you give, but, look, it’s a little convoluted. Why if you guys can give suggestions on how to send better emails, on when to follow customers, you know, stuff like that, why can’t you cut the sales development reps out the loop all together? Why can’t you guys just do this instead of telling them what to do and you have to do it?

And this formed the foundation for the next iteration of Saleswhale which is the current iteration just iteration right now, they’re seeing a ton of success with, which is we took this, right, and then we went back and we discussed internally, me and my cofounders hey, you hear what they’re saying, right? I recorded calls. You are reading the memos. But this sounds like a fricken insane idea. I’m not even sure if it’s [trackable 00:36:00]. I’m not even sure if this . . . this can be solved with current technology. So we are just debating about this and we managed to find a pretty elegant want to solve, like, on the backend, right, to solve this problem. And this actually became the next iteration of Saleswhale. It’s this iteration we’ve been running for the last three years, right?

Andrew: You know what, that is something that only is obvious once you hear it. Here’s why what I’m thinking. I ignored the second message. I’m studying up on you. And even the first one, I felt like it was just so longwinded that it was like, okay, interesting. Why don’t you just do that as a subject line, yeah. But I didn’t think about it.

Gabriel: Here’s in hindsight. We didn’t realize. We were like [inaudible 00:36:40] court and I’m just wondering why people are not using it.

Andrew: I wonder if people can even understand it without seeing what I’m talking about because it does look really elegant, the advice is on the side, it’s super . . . like I agree, I’m nodding as I see it but I ignore it. Right?

Gabriel: Right.

Andrew: And so you went back and you had to figure out how to do it. What’s the elegant way that you created so your software would write it?

Gabriel: A bunch of technical hacks. So basically we had to go back to the drawing board and the first problem we had to solve is basically how to understand responses, right? The intent when . . . so that’s the only way we can run with our own advice.

Andrew: Because you could do the first message easy. It’s a templated thing. People can okay it or pick from your templates. Was it pick from your templates?

Gabriel: No. So think of it like composition [brunch 00:37:23] so they create like their composition brunch. I wish I brought my laptop so I could show you a demo of how the software was. So the insight we got was that when we receive any email, how do we kind of break it down into like, you know, like components, right, that we can actually like run kind of like protecting each component. Different level.

Andrew: This, then that. So you have a bunch of . . .

Gabriel: Not really.

Andrew: No?

Gabriel: Sort of like we provide a concept like, “Hey, thanks for sending me these. Unfortunately, now is not a good time. I’d love to receive more information.” Right? We break it down like sentence by like, what’s the intent of this response? What is the sentiment? What exactly is it acting? Is it topic classification? Are there any named entities in this email? And then from there we actually reconstruct. We have a picture of what this person’s email is trying to say, and then we are actually able to deploy the right response with the right collateral to this person.

Andrew: But who writes the response? Is it your client or you? You internally want to write it all.

Gabriel: We create like a whole conversation topic tree that has a bunch of messages snippets that we put together like creatively that look as if they come from a human being.

Andrew: And then how do you customize it for different types of businesses then?

Gabriel: So right now, today we have a customer success team that actually sits down with each customer to do unboarding and then they create this whole universe of responding . . .

Andrew: For the first time how did you do it?

Gabriel: The first version we were only able to handle like yes and no responses and like requests for more information. So if the conversation gets too complicated, we stop responding and then [inaudible 00:38:57] .

Andrew: Now that I think about it because ultimately if somebody is responding at all, they’re pretty decent.

Gabriel: Yeah, that’s right. So the first version sucked. But yeah, we kind of just evolved the product as we went along.

Andrew: And how did you start analyzing what people said? How did you do it?

Gabriel: Like what?

Andrew: Like what software? What did you do on the software end to do it? So one of the first companies that did something like this really well was You remember them?

Gabriel: Yeah.

Andrew: They blew up. Everyone talked about how they’ve got software that can understand you and book meetings for you.

Gabriel: I’m going to review our secret sauce. The way we do it at the back is similar to so what happens is we have a team. We call it human interloop. It’s not pure software. We have a bunch of human operators. So what happens when an email comes in, we break it down into maybe 14 right microtasks. So basically all operators would see it’s kind of like a dashboard with these various microtasks all the confidential and identifiable information stripped out. Like this sentence, is it positive or negative? Just indicate. This sentence what is the classification? What is the intent? Right? Are there any name entities? Annotate and highlight any name entities. And basically what we do is that we based on all this information we put them back together and then we . . . the computer now understands.

Andrew: So if a prospect hits reply, it’s not artificial intelligence software that’s doing it, it’s human beings who are asked to answer question tagged with different parts of the response.

Gabriel: It’s artificial intelligence software combined with humans.

Andrew: Was it humans at first?

Gabriel: Yeah. No, human and AI.

Andrew: From the very beginning.

Gabriel: Yeah.

Andrew: How much AI was this?

Gabriel: Very little, very, very little.

Andrew: One thing I forget who it was who I interviewed who has an artificial intelligence company who said, “Every good artificial intelligence has to start with human beings. If they tell you not, they’re lying to you.

Gabriel: Yes, absolutely. So very little. We started with very little, right? A lot of manual labeling, annotation, [inaudible 00:40:53]. I still have nightmares when I think back to those times.

Andrew: Because?

Gabriel: I was the one doing it.

Andrew: You were sitting down and typing.

Gabriel: Me. Right. I was doing sales, I was writing the software, fricken like . . . recording like tasks as the tasks were coming out, I was annoting, I was clicking, like yes, no, positive, negative sentiment, requests for information, topic classification, annotating name entities. I think I did like . . .

Andrew: Why name entities?

Gabriel: Name entities example is like our potential competitors. So let’s say one of our customers they are Zendesk. So Zendesk is customer. If someone replies and say that hey, I’m really using FreshBooks. What the difference between you guys and them? FreshBooks is a name entity, is a competitor to Zendesk.

Andrew: So do you also tag it as a competitor for your client?

Gabriel: Yeah.

Andrew: You do. Got it. And so enough people do that and you realize, okay, from now on whenever we see a competitor, it’s tagged and we know how to handle it?

Gabriel: Absolutely.

Andrew: Let me talk about my second sponsor. Anyone who’s listening to this who says I need this in my business. We’ve actually been doing things in a very automated way. It’s time to add artificial intelligence. It’s actually not as scary as it seemed to be. I can see that Saleswhale did basically and improved. I need a framework for it. I know people who can do it. They do. All they have to do is go to Toptal, top as in the top of your head, tal as in talent. They can hire experts who’ve done this already before and this goes for anything that you need. You bring them in, they help set up the framework. If you like it, you keep working with them for as long as you want or you say to them , “Guys, now transfer this knowledge to our team. Our team will take over.” Oh you guys are thinking of writing this down? Good. If you need this, write this down, When you throw that /mixergy . . . Did I say that clearly? Because I talk very fast.

Ing: Yeah.

Andrew: Top as in top of your head, tal as in talent. When you use that you get 80 hours of Toptal developer credit when pay for your first 80 hours in additional to a no risk trial period. Really good company. I love them.

One of the things I saw that you did was . . . actually, well, was Y Combinator tell you to charge?

Gabriel: Yeah, they did but still do [inaudible 00:42:57]. So in the early days, even when while we were in YC we charged like $39 to $99 a month for the software. That didn’t work out. So today, our largest customer is paying now a quarter million dollars a year.

Andrew: I couldn’t find the prices on your site, and then I . . .

Gabriel: So we start at $1000 right now, $1000 U.S. per month.

Andrew: Per seat?

Gabriel: Not per seat. It’s kind of like per license, I guess, which multiple users can share. So depending on how they scale, I’m happy to [inaudible 00:43:25]. So our smaller customers are paying us like $1000 month and then our enterprise customers are paying us like six figures, quarter million dollars a year right now.

Andrew: That means that one client is taking up about a quarter of your sales, revenue?

Gabriel: Slightly less.

Andrew: Slightly, less. Here’s the thing that I saw in the early days. Somebody wrote a review on . . . where is this? Capterra. Look what he said. “Pretty buggy, duplicates records in Salesforce, multiple times, not easy to bulk send,” which he’s seeing the upside of it which is good because he needs to do customization. But here’s the thing that got me, by the way, three out of five stars features and functionality. Here’s the thing that got me. He likes the software. Four out of five stars overall, this person is actually net positive, very big fan of your software. Why do people and this is not just a random person, several people said very buggy and they still liked it. Why were so many people into it even though it was buggy?

Gabriel: I think I guess finally now we solved the real problem. It solved a real problem that I don’t think there’s any other software in the world that actually solves the problem quite the way that we do. And to be very honest, the software was buggy in the early days.

Andrew: It was buggy in the early days and the problem that it solved was what? It was they just want to load up their email addresses and have their salespeople have hot prospects, someone who’s possibly going to buy? That’s it.

Gabriel: It’s the whole two-way email conversation, right? Just imagine to be a sales rep you load up like maybe a 1000 prospects into your database, right? You’re probably going to get like 50 to 100 bounce emails and the leads may not be [inaudible 00:45:04]. You have to manage the process then. I think you’re probably going to get like 100 to 200 people saying I’m not interested. Some who say I’m not interested but contact me again in like the next quarter. And you have to manually process them.

Andrew: Manually create a task for yourself to . . . ?

Gabriel: Manually create a task for them. You have to reply to them and say, “Oh, I’m sorry to hear that.”

Andrew: Even in this buggy version you did that for them. You automatically would create a task?

Gabriel: Yes, yeah. Right.

Andrew: I see you when you get serious. It’s like we can laugh at all the bugs, but when I talk about the features you’re proud of, I see the seriousness in your face. This was [inaudible 00:45:33]. This is a feature you’re proud of.

Gabriel: Yeah. Right.

Andrew: And it was creating a task in what software?

Gabriel: We actually created a task back in Saleswhale, but actually had adoption to sync it back to Salesforce. Do it make sense?

Andrew: So in your software?

Gabriel: We’ll create a tag in the software, but for it to reach its full functionality, because who logs into Saleswhale? Like a sales rep does not log into Saleswhale to check . . .

Andrew: Into sales what?

Gabriel: Saleswhale, like my . . .

Andrew: Oh, into Saleswhale. Okay. Got it.

Gabriel: Right. So for it to see its full functionality, you have to sync this task back into Salesforce.

Andrew: Got it. Okay.

Gabriel: And it was buggy. The sync was buggy.

Andrew: How soon did [inaudible 00:46:06]. Multiple people said that it was buggy with the dukes. How soon did you incorporate Salesforce?

Gabriel: Salesforce, how soon? I think we did the first couple of months. A very rudimentary version.

Andrew: I wish I could find it. It seemed like one of the first messages that you sent, maybe this is before Y Combinator. It’s gone here in my notes.

Gabriel: One thing [inaudible 00:46:32] is that there are two versions of Saleswhale that’s on the internet right now. So I think for you to get a better picture . . . yeah, you probably should look at G2 Crowd.

Andrew: Yeah. They have a lot of views there.

Gabriel: The danger in some of the reviews are about Saleswhale is actually about the previous product, the old product, which is also called Saleswhale.

Andrew: Yeah, and I saw G2 Crowd way more reviews which made me think these guys are probably are asking their customers to go to G2 Crowd. That’s like, it is. Yeah, I get it. But what did I see in the beginning? I know what it was, a couple of things. One, you guys used to compared yourselves to MailChimp. It was like look at how a salesperson would do this in MailChimp. And look at how MailChimp makes you have that whole unsubscribe versus Saleswhale, it looks like a regular email. At some point you stop comparing yourself to MailChimp and you recognize that’s not what your customers are using. Right?

Okay. The other thing that I notice was back then you had a whole section for developers. You wanted developers to build on top.

Gabriel: It was misguided. We will come back to that maybe in the future. Again, we realized that we were really selling. Because in the early days we were selling to other startup founders, right? To other startup founders they are technical like you, they’re engineers. They’re like, hey, you know, I want to build on top of your [inaudible 00:47:50]. And you get down this path. But in the end we realize now, this version of Saleswhale we’re selling to the enterprise, you know, our key decision makers are not startup founders like who are also engineers. They are CMOs, VP of marketing, director of marketing. So what they want? They want Salesforce integration and robust Salesforce integration.

Andrew: This is what happens when you stop selling to your friends and start talking to your customers.

Gabriel: Customers, right. So yeah.

Andrew: Okay. What’s the difference between these two features? There’s the Engage and Prospect.

Gabriel: So Prospect was the original version of Saleswhale. We applied to Y Combinator with it.

Andrew: That’s a [bunch 00:48:25] prospecting. What does that mean?

Gabriel: It’s basically the one that you’re showing me. The one that you send sequencing and then there’s an AI assistant on the right-hand side. That was the [inaudible 00:48:35].

Andrew: That’s called Prospect, got it. Okay. And Engage is more our automation is going cost [inaudible 00:48:41].

Gabriel: Yeah. So what happened was we took the Prospect product so we took the Prospect product three years ago and then we doubled down on Engage and right now we only have one product. So very focused right now which is Engage.

Andrew: Engage and that’s it.

Gabriel: That’s kind of like the Saleswhale product.

Andrew: You stopped even calling it Engage it seems like because it’s just Saleswhale.

Gabriel: Just Saleswhale.

Andrew: Because I followed old articles to Engage . . .


Andrew: Yeah, it’s a 404. I go, wait a minute, what is this? They’re called Saleswhale and then they’re also trying to promote Engage and Engage is a hyper . . . this is a confusing.

Gabriel: Confusing. Right. Now you got it.

Andrew: Now I understand what you were working on. You still love this?

Gabriel: Yeah, I do.

Andrew: You do? It’s not tough to stick with it?

Gabriel: I wake up every morning very grateful to, yeah, to be where I am now and to work with the team I work with.

Andrew: The first customers I saw were . . . where is it? It’s like this has got to be an American writing about this because it says, “Grab is one your customers and then they explain it by writing more about Uber.” I didn’t realize how big Grab was. I owned years ago. So I’ve been following the company, the domain.

Gabriel: No way. You owned . . . how much did you sell?

Andrew: You know what, believe or not it was for like a dollar or something. It was part of a bigger deal to sell the previous company.

Gabriel: Oh my god.

Andrew: It’s a great domain, isn’t it?

Gabriel: Yeah. Wow.

Andrew: The asking price on that domain was $100,000 is said, great, let’s do it. And then the guy on my team Michael [Silberg 00:50:08] said, no, no. we’re going to negotiate. He negotiated down, I forget the number, $75,000 or something. It was worth it. He did a whole other thing with it. It was like a billion dollar contest. Warren Buffett backed it. So I’ve been following the business a lot. The fact that when I went downstairs to get chips, they’re not big on accepting credit cards in places, but they did have this big poster for QR code so I could pay with a Grab payment.

Gabriel: They actually going to build a super app right now in Asia, right? Kind of like the WeChat in China.

Andrew: You know, the founder of [Glints 00:50:37] asked me why is it that here these super apps are existing and there’s a possibility but in the U.S. there isn’t. I had such I don’t know.

Gabriel: I have no idea. Why do you think that?

Andrew: Here’s why I think. I think because the internet, the mobile internet developed in the U.S. first. And if you look back on the old phones, like when Uber launched, what did the phone look like? When Facebook launched, it was a tiny phone, very pixelated, right, because it didn’t even have retina display. If you even included one message, it was too much to say we are Uber and we do rides and we do food and so on, overcomplicate that stupid little app and so they all disambiguated or they all broke up. In Asia the phones were bigger and clearer when they took off and your could put more functionality in and so why force somebody if you could add more functionality, you go back to the home page and then come back to the next app when you could . . . that’s my theory. I’ve been thinking about it a lot.

Gabriel: Interesting. Cool.

Andrew: Anyway, Grab was a customer. How the hell did you get Grab as a customer?

Gabriel: Cold email.

Andrew: Cold email?

Gabriel: Cold email.

Andrew: Using your software?

Gabriel: Yeah., using my own software. I created, hey, this is what we’re building, do you think your sales team will find something like this interesting?

Andrew: Because they’re calling out a lot of restaurants.

Gabriel: I think so. Not just restaurants, but like Grab for business, so we’re seeing like for corporate rides.

Andrew: Corporate rides, got it.

Gabriel: So how they became an early beta user. They were paying us like next to nothing, like $50 a month.

Andrew: But they would’ve paid. They had money.

Gabriel: Yeah. They paid.

Andrew: They paid next to nothing because you were too afraid to charge?

Gabriel: Not that was the very first iteration of the product, like we didn’t know how much we could charge, right?

Andrew: Did it help that you were from Singapore?

Gabriel: Yeah. I think so.

Andrew: It did? You worked that angle.

Gabriel: Yeah.

Andrew: Okay. What about getting other customers? Does it help that you’re here?

Gabriel: No. That’s an interesting point you brought up. So we actually opening a U.S. office next month. So we just hired our first U.S. employee who’s going to be U.S. employee number one. So we’re going to place him in San Francisco, in a WeWork in San Francisco, sorry. And we’re just going seat our face with him and basically expand from there.

Andrew: For sales?

Gabriel: So it’s interesting that we are from Silicon Valley. We came back to Singapore and then now we’re opening a forward sales and marketing face back in Silicon Valley again.

Andrew: I asked you why you left and you said, do you know how much engineers cost in San Francisco, which I do. By the way, the hard thing is I still go to all these kindergarten things. I talk to other parents. Engineers are making $300, 400, 500 easy way more and they still bitch about not being able to find a house.

Gabriel: You are kidding me.

Andrew: I swear. It just is endlessly about that. I get it. That’s why you moved here for developers. When you got here were you selling internationally too? You had a sales team?

Gabriel: Yes. On day one we were global. We have customers in the U.S., right in Hong Kong, Australia, in the UK, from day one.

Andrew: For sales calls were you the one at first who would get on a call?

Gabriel: I’d be at 2 a.m. in the office, you know, doing like Zoom calls with people in the U.S..

Andrew: 2 a.m.?

Gabriel: 2 a.m.

Andrew: Get up and do it. Relationships [inaudible 00:53:28].

Gabriel: And like 7 a.m. would be like my next call with like someone on the East Coast or sorry, on the West Coast.

Andrew: Did you sleep in the office?

Gabriel: Yeah, in the early days. Yeah.

Andrew: You did? On the mattress or on the floor?

Gabriel: On the couch, we had await couch that was pretty nasty but . . .

Andrew: But you do it?

Gabriel: Yeah.

Andrew: Venus, your wife worth . . .

Gabriel: She’s used to it.

Andrew: She’s used to it?

Gabriel: Yeah, she’s used to it.

Andrew: To this day? Is she kind of proud that you’re doing this?

Gabriel: I’m much more relaxed these days. Yeah, I don’t sleep in the office anymore.

Andrew: But when you were, I’m trying to understand culturally, was she proud . . were you proud that you were working late? Or is there an embarrassment and a stigma about working late?

Gabriel: I think neither. I think it is what it is.

Andrew: That’s it.

Gabriel: Yeah, so if I have issues of understanding, so 7 p.m. she’ll just go back, she’ll do her student, and I’m just here. I’ll just stay a bit more to wrap up my work. Hey, you know, I think it’s getting quite late. I have a call tomorrow at 7. I’ll probably just sleep over here. Yeah, it’s just feels pretty chill.

Andrew: That’s just the way life is.

Gabriel: Yeah, just the way life is.

Andrew: You take vacations together?

Gabriel: Yeah, we do.

Andrew: Where do you go?

Gabriel: My last vacation was two years ago, I think. Japan, Tokyo, it was nice.

Ashwin: When did you start dating her?

Andrew: Let me repeat the question. Ashwin is asking. This is for people who are listening to the recording. If wish I could mic you. When did you start dating her? Yeah, good question in the timeline.

Gabriel: Very long ago. I think like almost . . .

Ashwin: This is the reason. Because in Singapore you will often find that many of them will date for nearly high school or junior in college and date through the rest of their life. So they already built the foundation for coming where she knows him real well.

Andrew: Just to be clear, he’s saying that, Ashwin’s saying that because you guys dated and many people date from high school on. Got it. And then you have that established relationship, this is a phase in your life . . .

Gabriel: So from day one when we started Getting Real Software, we were already dating. So kind of like she knew what . . .

Andrew: Do you ever feel like what else is out there? Like I didn’t get to date enough?

Gabriel: Not so much.

Andrew: Sometimes.

Gabriel: Not really.

Andrew: No? Not at all?

Gabriel: Not really. Yeah, I think maybe because my brain is like fixated on work all of the time.

Andrew: That’s it. There’s no sense of I’ve got to party. I’m earning something here. I missed out. No?

Gabriel: No, not really.

Andrew: That’s a ridiculous thought.

Gabriel: I still lead a pretty austere life now.

Andrew: All right. And your parents, are they still living austere lives?

Gabriel: So that’s the interesting thing. Yeah, my parents are still . . . I come from a humble background, right? So my parents are still living austere . . .

Andrew: What do you mean by humble? Give me a sense of how humble.

Gabriel: My dad is not working due to health reasons and my mom is the sole breadwinner. She’s a clerk, right?

Andrew: She’s a what?

Gabriel: Clerk.

Andrew: Oh, clerk. Okay.

Gabriel: Clerk, that’s right.

Andrew: And when you say poor or not well off as a kid, give me an example of what you missed out on.

Gabriel: I wouldn’t say that we are like . . .

Andrew: Not poor. What’s the word?

Gabriel: I don’t know, lower middle income.

Andrew: So what did you miss out on growing up? What was the thing that felt awkward?

Gabriel: I guess it’s always like not being able to have the things that I want. Like everything that I want I need like a toy, I want to buy a Star Wars toys . . .

Andrew: You had to buy it with your own money?

Gabriel: Yeah. So actually a master of getting very high paid part time jobs. So when I was in secondary school, I was doing jobs that paid like 40 to 70 an hour.

Andrew: Okay. How?

Gabriel: Basically there’s just like a theme park in Singapore, so we wear this like costumes like I dressed as a Power Ranger. I dressed up like a sumo . . .

Andrew: How did you get $40 doing that?

Gabriel: No, because it was shit . . . Well, like the costumes are hot and sweaty.

Andrew: So nobody would do it. It’s a $40 job and you would just take it.

Gabriel: And people would like throw shit on your head, but it paid well, right? So growing up I would do all these jobs to make, you know, pocket money and I just like blew on it on, you know, random rubbish.

Andrew: All the stuff that kids just got. And okay, you were saying something happened to your parents. I cut you off. You grew up from humble background, but now you parents are . . .

Gabriel: Still humble. Still humble.

Andrew: Still, okay. All right. And do you in the back of your mind like fantasize one day I’m going to take care of them. I’m going to give them things that . . . you do.

Gabriel: Yeah, absolutely.

Andrew: That’s part of the fire.

Gabriel: Yeah, absolutely.

Andrew: Wow-wee, man. All right.

Ashwin: So the junior college that he went to is very, very prestigious in Singapore, brings out some of the most elite people and the most [inaudible 00:57:36].

Andrew: Oh, yeah. He’s saying the junior college . . .

Ashwin: Correct. Raffles Institution. I was just doing the research.

Gabriel: Oh my god. Are you Singaporean?

Ashwin: I’m not.

Gabriel: No. Okay.

Ashwin: But I’m familiar enough. But obviously your peers, you didn’t go to university after that. Your peers obviously went to some of the three universities here and then got really good jobs.

Gabriel: And some of them went to Ivy league schools, so basically Raffles Institution is the feeder school to Ivy league schools.

Ashwin: Correct.

Andrew: Just to be clear. He’s saying that you went to . . . I don’t know how much people are picking up on the mic here. Ashwin and I were just chatting yesterday via email. He heard that I was going to be in Singapore. He said do you want to get together. I go, “Yeah.” He pops up and shows up. It’s great. He said hey, you’re five minutes away from me. Okay. So all of his friends were going to . . . he went to prestigious high school . . .

Ashwin: Junior college.

Andrew: And you’re saying that all of his friends went to prestigious colleges. So what’s the question?

Ashwin: That feeder school to the Harvard, Wharton, Stanford where you get a fully paid scholarship and then the government pays for you to come back and still care for the . . . [crosstalk 00:58:30].

Gabriel: The Singapore government is insane.

Andrew: You should’ve gotten a scholarship to go to something like Stanford and the Singapore government would pay money to bring you back. And you still didn’t do it. And what’s your question for him then?

Ashwin: My question is did you ever feel like an imposter when your friends were already doing this and you were not even pursuing an education. You did not have the qualification. You didn’t know how to sell. You knew a little bit of coding. Did you ever feel, “I’m not qualified enough to do this”?

Gabriel: Absolutely. Even up to today.

Andrew: You still feel like an imposter?

Gabriel: Absolutely. Some days I walk to the office, like, “Wow, this 6000 square foot office, like almost 40 employees and I’m the CEO, like, no you’ve got to be kidding me, right? Like up to today, yeah, absolutely. I don’t it’s something that ever goes away, this imposter syndrome.

Andrew: You know what, and then there’s some people who have . . . I don’t know. I do think eventually it does go away, I think. And then I also think there’s some people who have the opposite who have this like greatness syndrome where all they do is they think every little thing they do is great, which is . . .

Gabriel: Oh my god.

Andrew: I don’t know which one I would rather have. All right, what’s the best part of having done this, gotten to where you are?

Gabriel: The team, absolutely.

Andrew: Getting to work with the people who you work with.

Gabriel: The team, the team. Every day, you know, you get to choose the people that you work with. Everyone is like . . . I mean, not only are they like insanely talented at what they do, but they are great, very nice, you know, amazing people to . . . like friends.

Andrew: I keep referring to Ing here. She is sitting her at the corner. She’s a great supporter, right?

Gabriel: She smiled.

Andrew: What does she do at the company?

Gabriel: Marketing.

Andrew: Marketing.

Gabriel: Yeah.

Andrew: Okay, how did you pick her?

Gabriel: I did not pick her. My cofounder hired her. So my cofounder heads up marketing. She’s like the VP of product. In the early days she was hacking marketing. So she hire Ing.

Andrew: Okay. Why is she here with you now?

Gabriel: I have no idea. No. So okay. Ing kind of helps me organize all this marketing events, speaking events, so from time to time she just like comes along for like photo ops, taking notes . . .

Andrew: So she took a picture of you here. I think, did you hit me up and ask me what we were going to talk about?

Gabriel: I think so. No? Or was it me?

Ing: No.

Andrew: Okay. I was especially eager for this so I remember even sending you . . . didn’t I send you an email like was it to you or someone on my team where I sent you guys an email with a screenshot of the website.

Gabriel: It’s me, me, me. You sent it to me. Yeah.

Andrew: Look at what I’m finding about you. I’m so excited to do this. So I was a little worried you were emailing me to say I’m not showing up. I go, look at what I’m finding. Get over here. I got to ask you about all this. All right.

Ashwin: Before we wrap up, I have one more question.

Andrew: Yeah, one more question. Yes.

Ashwin: You finished Y Combinator 2016.

Gabriel: Yeah.

Ashwin: How long did you stay in San Francisco or the U.S. before moving here?

Andrew: Let me repeat the question. He’s saying you finished 2016 Y Combinator. How long did it take you to get back here?

Gabriel: One month.

Andrew: One month? Immediately.

Gabriel: Yeah. So we finished Y Combinator around like late August, early September. I was back in Singapore in the start of October.

Ashwin: Do you feel from 2016 through to now 2019 in the three years you’ve sacrificed growth by not being in the U.S.? Would you have been in a much bigger place there than moving here?

Andrew: I’ll repeat the question just because I’m not sure what the mic is picking up on. He’s saying did you feel like you sacrificed growth by not being in the U.S.? And it sounds like you’re thinking maybe a little bit.

Gabriel: Yeah. Potentially yes. I think potentially yes. But the truth is that we may not even be still around today if we stayed in the Bay Area. So we raised $1.2 million for our seed round, right. $1.2 million U.S.. That probably gets you like, what? Half an engineer in the Bay Area. But with $1.2 million we were able to build a team of 10 engineers within the first like, what, 9 to 10 months. And that really accelerated the product development. And now that we’ve raised our series A, $5.3 million U.S., we have a bunch of revenue, then we are going to open like a forward sales, right, and marketing office in the Bay Area and hopefully that makes up for like . . .

Ashwin: Lost time.

Gabriel: That lost time. Right.

Andrew: All right. The website for people who want to check it out is and for anyone who wants to come visit San Francisco and look around, there’s nothing to see. There’s nothing, right? You go see the Golden Gate Bridge, there’s nothing there. The best thing you can do for yourself is go meet people, right?

Gabriel: Absolutely.

Andrew: If you’re a developer, you could get to meet someone like Justin Kan, you could meet other people that are building phenomenal companies and those relationships are the ones you can draw on. The sites . . . there’s so much more to see here. Are there two buildings here? Maybe you would know, Ashwin. Two buildings with what looks like a boat on top of them?

Ashwin: Yeah.

Andrew: What is that?

Gabriel: It’s just nearby.

Ashwin: Marina Bay Sands.

Gabriel: Marina Bay Sands, casino.

Andrew: Can I just walk on top of that boat looking thing?

Ashwin: Yes, you can.

Andrew: Can I take the elevator and just go walk on there?

Gabriel: Yeah. The sky top.

Andrew: This city is freaking amazing.

Gabriel: Infinity pool, right. It’s a swimming pool that like . . yeah.

Andrew: I didn’t expect it. I didn’t expect to love this city. I didn’t expect to have any views. I just thought I’d see a bunch people who were working their butts off, and I definitely see that. I went down for lunch. I made a mistake at noon. Everybody comes down for like their 10 minutes, then they’re all gone. Code 12, 10 and everyone is back at their desk.

I want to thank the two sponsors who made this trip happen. The first HostGator, really, I’m grateful to them for sponsoring this and making possible for me to travel the world and interview entrepreneurs and bring them to you. HostGator and Toptal have been with me since the beginning of this tour. Go check them out at and if you want to hire a developer, go check out

All right. Ashwin and I are going to go out for a drink. I’m going to go talk to as many people as possible from Singapore. Bye, everyone.

Who should we feature on Mixergy? Let us know who you think would make a great interviewee.