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My CTO quit with no runeway left with Glenn Tan · Founder F**K ups

• Ben Bagg: Today's guest is Glenn Tan, co-founder and CEO of Xavier, the Singaporean Regtech startup using AI to get teams Glenn Tan: Yeah. Ben Bagg: work ready on PDPA, ISO, and everything else. He is also CISO at Aona AI and came up through Antler, Tesserat, and TMB Ventures. Glenn is a sales and partnerships founder. He would tell you that himself. So he did what almost every non-technical founder does. He left building to the person who builds a CTO. And then the product took too long to ship. It was hard to scale, VC money was gone, and then so was his VTO. Glenn was left holding a company, a market, nobody to write the code to finish the product. Two options left: get the product out fast or kill it. So he took the tech on himself while still running the sales and partnership, and they managed to ship every feature they had wanted to since day one. Today we're talking about what it really costs to outsource the thing your company is made of and what you actually find out about yourself when the floor goes under you. Glenn, welcome to the pod. Glenn Tan: Thanks, Ben. Thanks for having me. Ben Bagg: Yeah, yeah. So before your CTO quit, before that you know all that happened, where where was Xavier at that point? Like how late was your product, what had you promised to customers or investors, like where were you at that point? Glenn Tan: Well, great question to set the to the context, right? I think we as a as a company we we had a few clients already, right? we could deliver some of the work. But then the challenge was that I mean we h we had about maybe f four to five clients already. But the challenge was again trying to get the product to make ourselves more efficient, make the client more happy, right? So I think that was kind of the the the part where we were stuck as it we could solve the problem. It took a lot longer than it should. And we we We basically couldn't met some of our like even investors or partners requirements, right? Whereas we were taking too long to build maybe part one of the product. Ben Bagg: Okay. time out guys. Lots of you are watching, lots of you are learning from the founder fuckups that we've all gone through, but please do me one little teeny favour and subscribe so that we can keep growing the channel and get more great founders on. Back to the episode. time out guys. Lots of you are watching, lots of you are learning from the founder fuckups that we've all gone through, but please do me one little teeny favour and subscribe so that we can keep growing the channel and get more great founders on. Back to the episode. Glenn Tan: Right. I think that's kinda like the challenge or like the conundrum we were, yeah. Ben Bagg: Yeah, so we had promised, you know, X number of features or whatever it was to the customers and investors. We weren't meaning that. How late were you? How far behind? Like how how bad was this problem? Glenn Tan: I mean I guess in terms of like the product roadmap, right, we were quite far behind because Something about building has which is traditionally always been the case is that you you spent a lot of time building all the pipes, you know, to a home, right? So be f so I think the the vision I the the analogy I put out is that when you build a home, traditionally you will always sort of build out the piping and and the mechanical parts and everything first, right, before you start to build a home. So that's kinda the old way of building, which means that you have to like work on a lot of tough things like role based access control, you have to figure out all the logins, right? You have to figure out all these fundamental things which takes a lot of time, very important, but it doesn't really sometimes solve the problem. So I think a lot of time was spent on all those kind of building, right? And then what the client really need was actually like maybe a easy way to solve their problem, easy way to click through stuff. So I think that's kinda like the challenge we were facing, right? Is that how can we how can we quickly move away from the fundamentals of the basic, right? And then go to something that actually solves the client's problem or b or bring value or something that wows, right? So I think Ben Bagg: Yeah. Yeah. Glenn Tan: that that's where we were, yeah. Ben Bagg: And what was the delay doing to the runway, right? 'Cause you said VC money sort of got spent Glenn Tan: I think well, it's a very interesting thing. now on hindsight after le you know, after after my fa co founder left, I think what I realized was that sometimes, you know, a technical founder, right, so Backstory is I used to be an engineer co almost fifteen years ago, right? But I was an electrical engineer, right? So nothing to do with code, right? But we but we did do some like C plus plus. And I think I now understand the psyche of of or at least finally embrace myself as well, right? that if you're in the technical space, you you always know that things are difficult. Because Ben Bagg: Mm-hmm. Glenn Tan: The simple human analogy is this, right? if I tell you, Ben, go and climb Mount Everest, right? You know how hard it is. And if you're familiar with it, you have to go to base cam first, right? So you Yeah, you Ben Bagg: Yeah, which is already hot. Glenn Tan: know the the journey, right? But then what happens is in another context, someone goes like, hey, I want to go to Mount Everest, let's do it tomorrow. So what does that guy do, right? He flies a helicopter. Ben Bagg: Ha ha ha ha. Glenn Tan: Right. So as a technical person you are always assessing how far, how difficult, you know, you're covering all the corners of that journey to Mount Everest, right? But then you realize that sometimes you just need that that that spark within yourself to say, look I I don't need to do it the same way. I don't need to do it wh like how it used to be, right? So I think look looking back on hindsight, that's some of the things that we felt that, you know, like even between ourselves and myself now, yeah, I should've done that a lot earlier, right? Just fly that freaking Ben Bagg: Yeah. Glenn Tan: helicopter to Mount Everest and, you know, we could just get to the peak faster, right? So I think those those things were something that really you know, you know, with time to reflect I realized like those were some of Ben Bagg: Yeah. Glenn Tan: the challenges, right, we faced, yeah. Ben Bagg: And with your co-founder, obviously at the beginning you had you'd split your roles, right? Your co-founder would be building, you would be selling. when when did you start to see things going a bit wrong? Like where he was not being able to keep up with perhaps what you were selling or the promises that were being made, or he wasn't keeping up with his own promises. Like what w when did you first start to see that? Glenn Tan: I mean, I think there I guess for us there was signs that I think among us personally we were always saying like we're almost there, right? I think the word is always we're almost there, right? And that yeah, right. And then Ben Bagg: Every founder loves that. Glenn Tan: what kinda happens as well when we say we're almost there is that we're going through the motions of like, hey, if we completed like these few things, we could now build another few more things to g Ben Bagg: Yeah. Glenn Tan: ship ship it to certain clients, certain partners, right? but I think the challenge we faced was that, I mean the symptoms were Or related to every time the almost there came, right, there was another expectation that there was two more things to do for every almost there, right? So I think that's kinda like the the tough part to differentiate when you build, right? Is that you mean it when you say almost there, but you know that after that's done there's actually two more things to do. So sometimes we don't Ben Bagg: Yeah. Glenn Tan: anticipate that. you know, further on. And after a while the almost there pac piles up, right? And then you realize that hey that I think the the the the mountain is now pe like piling up, right? So I think that's that's Ben Bagg: Yeah. Glenn Tan: some of the signs that we realise that, you know, like like we can't keep going that way, right? 'Cause Ben Bagg: Yeah. Glenn Tan: we keep promising, we're excited, 'cause when we go out there we're actually also pitching things that is in progress, right? So I think yeah, I think Ben Bagg: And you're probably pitching it you're probably pitching the in progress like it's no longer in progress. Live. Glenn Tan: Yeah, yeah, you know. It's it's part of life, right? You you always wanna be better than who you are today, right? So especially as a founder, right? So I think that's kinda like the the real challenge we face, yeah. Ben Bagg: So obviously he quit. He he decided to call it a day and and we all have our various reasons. did you see it coming? Glenn Tan: I mean I think I would like to say that I didn't see it coming, right? But I think what we did was amount among ourselves we're trying our best to to push through the product, right? But the challenge is that when it's at the last stage, you know, where you don't have enough money or like sometimes you don't have enough time and sometimes there's too many promises, right? no matter what you do to sort of even double down, you can't because it it's it's just things that plays on your mind, right? So as a founder I wonder when you're at that stage, like like you're also in this position of like, do I find another opportunity now? Right? Do I work with other people now? How do I you know, while you're in that limbo. So your mind space also goes somewhere else, right? So I think even though you would think you wanna double up, but the truth is sometimes it plays on your mind, right? So that's that's the real reality of of running any business, right? Yeah. Ben Bagg: What felt the break what felt like the breaking point for your co founder? Was it the product or was it money? Glenn Tan: I think ultimately it's a very classic story of of of you know, we run our funds, we need it to fund ourselves now, right? I think I Ben Bagg: Okay. Glenn Tan: think the money was was the easy one to put on, right? But I guess beyond the money as well is that I mean the readiness required a lot more. So then you go like, Hey, I have to actually spend way more to even cover these gaps that we have. So I think that's you know, it's it's a double thing. Ben Bagg: And in the first sort of ten seconds of your co founder going, Hey, I quit like what did you think? Like what was going through your mind when you're like your co founder, your CTO is quitting, we're out of money, like what's going through your mind? Glenn Tan: I I I don't think it's that dramatic in that sense where, you know, I think for mutual for I think for people who have relationships 'cause I have a great relationship with my co founder as well, right? I think it wasn't as dramatic as that. It's more of like, you know, you felt that hey, like this is not going right. this trajectory is not right. and then since you know we were engineers before so we go like, you know, trajectory's not going right. And I think that's why we say that look, I think it's time to reshape this thing, right? and then for his own good also find other opportunities that would help, right? And I I was looking out for him as well. so I think in that sense it wasn't as dramatic but I guess that's the real talk sometimes we have to have with our teams, right? And especially our our senior teams as well. Ben Bagg: Yeah. Glenn Tan: So I think that that that was kind of how it transpired, right? so Ben Bagg: Yeah. Well glad the relationship stayed stayed tight, obviously. It wasn't a relationship problem, right? It was just Yeah. Glenn Tan: Yeah, yeah, yeah. Ben Bagg: And you kind of had you felt like you had a binary choice, right? Ship fast or shut down. Like how long did you sit with that choice? Like did you spend a week going fuck what should I do? Or was it like immediate I'm just gonna ship like that? How long did you sit with that? Glenn Tan: Well so I think if you ask about what happened after we decided that, you know, it's time to sort of slow down or like like kill it in a way, right? I think what happens is also that for some of us Who are the like I think for me I had the burden of the brand, I had the burden of of starting it as well. so I then felt maybe like I I could let down let down a little bit more people, right? So so the path is like, okay, let's see what I could do myself to cover like the other promises that we make, right? there's some things we could say no to, but there's also a lot of things that we could say yes to, right? And Ben Bagg: Yeah. Glenn Tan: and in in a traditional way. is if you if you work in a business if you were to be a tailor, right? If you were to you know, doing clothes and everything and the shop decides to close down, the natural way is you go to some of your competitors and say, Look, I've got these great clients, you know, but I can't serve them anymore. Can you take them over, right? So it's you're kinda moving then to another ship and another house. So I think that was something that was playing in my head, right? On how to actually work through those things, right? I think yeah Ben Bagg: Okay. So it was like maybe go and join a competitor and bring my client book perhaps was like actually a not option. Glenn Tan: Or even pass them on, right? I mean in the simplistic way, just pass them on. Yes. Yeah. Ben Bagg: Just to just to do your customers the right thing. 'Cause you felt that obligation, hey, we've promised this, we've sold this, we've spent the money, we need to look after them. Glenn Tan: Correct, correct. Yeah. So I think that's the toughest part actually after that happened, right? Is is Ben Bagg: How long were you how long were you sitting in that form? 'Cause that's the big this is this is a big fork. Glenn Tan: to be fair it wasn't that long in a sense of like time, right? I mean in my head it was long but but I think Yeah. Yeah. But I think but I think Ben Bagg: In your head it was years, but in in reality it was like a day. Glenn Tan: couple of things that were that were working maybe for me was that like I had a good partner, right? My spouse, my wife was a amazing in the process. You know, I mean this is something that founders also have to know that i i your spouse or your other half is very much involved, right? And and this decision Ben Bagg: Yeah. They are, yeah. Glenn Tan: making process or even the to go, not to go and and how to go, right? So I think I had the privilege of having like a good support with my spouse and and Ben Bagg: I guess she become she became like one of my next questions was who did you speak to? Obviously you spoke to your spouse. Glenn Tan: Yeah, yeah. Ben Bagg: Hey wife, what shall I do? Glenn Tan: I mean the I think that's kinda like I think in that phase it didn't last long because it was just a decision we had to make, right? So either like I had to go and like serve the clients or I have to move the clients to another home, right? But I guess in a in a nutshell what happened is that like we decided I decided that okay, like I can still serve the clients, right? I can still work on this. and I still wanna see what can we do from what we've already built, right? 'Cause we did build something. It's just that it's not as wild as you want it to be, right? So Yeah, correct. Correct. So there's something to salvage still. Yeah. Ben Bagg: Yeah. It wasn't where you needed it to be at the time, but it was somewhere. And did you speak to Yeah. Did you speak to anybody else? Like did you get did you seek advice from anybody else, beyond the wife? Did you have to move close to speak to? Glenn Tan: Yeah. I mean of course we we speak to some of our teams, some of investors, we speak we speak to like even some clients as well, right? but I guess what also transpired is that Beyond speaking it's I I also realize it's our choice, right? It's our it's our own choice, right? We we can get Ben Bagg: Yeah. Glenn Tan: other points to emphasize the thing. sometimes I realize is that when we sometimes talk to too many people, we're also mentally delaying the decision. Right? Ben Bagg: Yeah. Glenn Tan: And and sometimes the the crux of it is we just have to d make the call, and and you Ben Bagg: Rick. Glenn Tan: know, pick up whatever we decide on, right? I think that's that's that's just the the truth, right? Ben Bagg: involved of it, right? Eventually you have to come to a decision. I'm Glenn Tan: Yeah. No one's gonna make it for you. Yeah. Ben Bagg: So what was the main why, like, rather than just to like 'cause I know you w had the obligation for your customers and that's one part of it, but was there anything else that was like, you know what, I'm not giving up. I'm gonna go and take this over. I'm gonna take over tech. Like Glenn Tan: I think I think one thing that was really amazing in that phase of time was that I think I think I mentioned, you know, a few times to some friends is that like like I was going through the code with my co founder, right? So we were looking at the stuff, we were looking at it being built, right? But then I sort of resisted like getting my hands into it because I felt that I was maybe overstepping or like you because we segregated the roles, right? But what Ben Bagg: Mm-hmm. Glenn Tan: then I realized is that when I was pushed to it, I just had to go pick it up and see okay. 'Cause the first thing I need to figure out is okay, where's the code? Where how do we do it? What's the back end stuff that that we set up? I have to go through that motions, right? and after that, I think we found I found a lot of opportunities, you know. Of course with AI, you have this ability now to to s to scale anything, right? So I think that gave a glimmer of hope that we could you know I could do it myself, right, in a sense. But by now I I I do have the domain ex expertise, I know what's happening. All I need to do is maybe brush up on my almost 20 year old like coding abilities, right? and and of course I was learning stuff in C plus plus, right? Which is Ben Bagg: Yeah. Glenn Tan: like the most old school stuff, but then like things are now in like, you know, the modern tech stack, right? With Next.js and stuff like that. So yeah. Ben Bagg: And what year what year was this c that you were doing this? Glenn Tan: I mean no, I started my career in that, like so we you know Ben Bagg: No, I no I mean like when you took over tech. Glenn Tan: We took over tech just about a year ago actually, so it's twenty Ben Bagg: So you had like chord code and all these different tools to help you as well, right? Versus what you would have had five years prior. Yeah. Glenn Tan: Yes. I mean we we we were we were early users of Cursor. We we even when you know when we had my f co founder we had Cursor already then. it was already amazing, right? But I think I take back to the analogy of Mount Everest climbing Ben Bagg: Yeah. Glenn Tan: and helicopter, right? Then what I realized was that we weren't pushing it because we were afraid of it. Right. We were afraid of like starting things that we know would take too much time traditionally. Right. So I think that's the face. And then when you push to shove and everything has left, right. Essentially you have no choice. You have no choice but to to now take risks, right? Ben Bagg: Yeah. Glenn Tan: I think after that the risks pay off, right? Because it was very clear that it was just a mental block for some of us, right? Ben Bagg: Yeah. Glenn Tan: that n that I could actually build some of these things almost overnight, right, or in in a couple of days, Ben Bagg: Yeah. Glenn Tan: right? So I think that that really changed the mindset as well. Ben Bagg: Yeah. What did your day to day start to look like when you became Glenn Tan: Ha ha. Ben Bagg: picked up the technical side, right? 'Cause previously it's like sales and investor conversations Glenn Tan: Yeah. Ben Bagg: and partnerships and now you're like now you're building, like what what did the day to day look like suddenly? Glenn Tan: Well, I think it was still we were still doing a lot of delivery 'cause we had some clients. Ben Bagg: Yeah. Glenn Tan: and then we still did partnerships 'cause you know, partnerships take time to brew. but then a lot of time was spent like even day in, day out, just trying to cope, right? And and I think Like it was the first few times like like and I actually I used to have I used to work on a product where we had to do accounting migration that was kinda painful, right? so we walked through the night, we worked through when people are not working. So this kinda felt like that again, right? But I guess the the other feeling that was different now is that it was pretty liberating actually, right? Where we came to a position I came to a position that, you know, actually some of these things like why didn't I try this earlier? Why didn't I ask Ben Bagg: Yeah. Glenn Tan: for it earlier, right? You know, it it's like y y you sometimes have this small regret like like I we should have done this earlier, that we should've asked and and make it happen and then Ben Bagg: Yeah. Glenn Tan: we'll fix it, right, even faster. So I think those those were you know, the day to day was really for the I think Ben Bagg: Yeah. Glenn Tan: three to three to six months, right? Was really just like hammering out day in, day out, day in, day out, right? we Ben Bagg: Yeah. Glenn Tan: were maxing out our our credits, you know, like like but it's also a great time. I'll share that that was also a great time where where all the LLMs were trying to compete with each other. So they were introducing like new stuff and and we were we were maximizing every single Ben Bagg: Yeah. Glenn Tan: like like you know, discount that they had, right? So so that was a pretty amazing time as well. Ben Bagg: Yeah. And obviously before you when you had your CTO and again nothing against your co founder, your CTO, but when you were working with them we were we were behind, we weren't able to f ship the features we wanted to, we you know, we were struggling, we ran out of runway. But when you took over, you got all the features out, you got everything you planned. Why why was it possible then? What what what was different? Perhaps were you operating differently, like you had a first principal and he was operating from a previous way of developing? Like what shifted? Glenn Tan: Yeah. Ben Bagg: 'Cause that's a big Yeah. Glenn Tan: Yeah, it is, it is. It's it's so it's a it's a analogy I I tell to a lot of people. I said when I lost my CTO and and he was a friend as well, it felt like I lost a limb, right? Like a limb. But then Ben Bagg: Yeah. Yeah. Yeah. Glenn Tan: I felt as well because of the the sort of the pressure or like the the season that we have to be in, right, I found that I got like a rocket ship, right? Like so I lost a limb but I'm on a rocket ship right now, right? So Ben Bagg: Yeah. Glenn Tan: that's such a weird feeling to feel 'cause there's a sense of mourning and loss but then there There's also this Ben Bagg: Yeah. Glenn Tan: sense of like wow, like you know, we can actually do some of these things, right? So in that context, what really changed was that I think that's and that's also changing in the world right now whereby people who are from the domain, right, are actually the best people to build right now in the world. Because Nowadays, the the how is easily fixed, right, through AI. But if you know the domain, you know what the customer wants, you know what the client wants, you know what the partners want, you you know, like Ben Bagg: Yeah. Glenn Tan: what you just need to do is speak it right or like write it right in a sense. And that really changed the way you know we built from then on, right? So I was just basically trying to always imagine what what it felt like to be using the product, what it felt like to be in In in it, what it felt like to solve the problem. And from there, you just have to work through it. So there are days whereby I'll share that. There are days whereby we start a feature, right? And with the coding of AI, right, it's it's a bit crazy in the feeling is that you can't start a feature over a week. It doesn't work that way in this new age because you gotta have real these are real short sprints, right? Where you you put everything out there, then you spend more time testing than you spend time building. But Ben Bagg: Yeah, yeah, yeah. It's all fun. Glenn Tan: not spend more time building because if you spend too much time building, right, it it becomes something that that you know i it means that the problem was never important to begin with, right? So that's kind of what it felt like. So that's why it was kinda intense as well, right? Like you had to build features within days because you you kinda have the whole mindset of it, right? So I think that's that's a real shift of of way of building, right? And and I think that also affects how we work with our teams. That also affects how I work with some of the engineers I I we hired and we worked on. Right. So i it's really different, yeah, in that sense. Ben Bagg: Yeah, yeah. And then I guess for I you see a lot of this now with the forward deploy engineer kind of move because I guess if you're hiring I I I completely understand, like if you're an engineer building a product and you've been an engineer for a long time, you're gonna build it with your habits and and and ways of thinking. But you as a subject matter expert are actually you're just building what you think is right. Rather than thinking it from an engineering lens, you're just thinking about the user lens. Glenn Tan: Correct. Ben Bagg: I guess this is why product managers are are are gonna go well Glenn Tan: Yeah, yeah, yeah, yeah. Ben Bagg: a good product manager's gonna be worth their weight in gold. so do you think pre Glenn Tan: Yeah. Ben Bagg: do you think the blockers previously then were were the way we built previously was from an engineering lens as opposed Glenn Tan: Yeah. Ben Bagg: to a user lens and when that's shifted you're actually able to make great headway in the product and actually release everything and and Xavier Xavier Glenn Tan: Yeah, I yeah, yeah, yeah, yeah. I think I'll I'll take it back to another analogy I made where traditionally we always build fundamentals first, right? We always build like every time you start a new startup, the first three to six months is painful to figure out authentication and all this kind of stuff, right? but What's the problem with that is that you're not solving the problem immediately, right? So now Ben Bagg: No, no, no. Glenn Tan: if you think of it like building a city, right? Instead of building piping and drainage first, what you're doing is you're building the image of the city. You're building the functionality of the city first. And when you get buy-in for that functionality of the city, then you simultaneously launch the other team, which is the backend team or or the other engineers that to to make the city function, right? You then do it simultaneously, right? It's kinda also literally the analogy of of you're you're building the plane while you're while you're flying, but now it's a bit more intense because you now see functionality as well, right? We used to have Figma that had no functionality. But now you have Figma with functionality, but you still have to do the back end So I think that's kinda what has changed in the world is that, you know, there's no longer value just to spend time on good infra. Although good Ben Bagg: Yeah. Glenn Tan: infra is very important to scale, but it's a priority, right? as well. Yeah. Ben Bagg: Agreed. Well, Diane, you went through an incredible situation where you had, you know, had to kind of basically take over the business, your your co-founders left, you're you're in that position where like what the fuck do we do? We keep going, do we stop? Like that's a a difficult question we all have. But for a founder who might be sort of one resignation away from this themselves, what do you think they should be thinking about? Glenn Tan: I think In this day and age we we have to ask ourselves what are we solving, right? Because it's even more evident because if you say I'm only solving my own problems, right, there are a ton of people who have that problem and there are ton of people that were built today, right? so I think you have to have a lot more conviction today in what you're trying to solve versus then because last time it was just sometimes hard work was enough, right? Nowadays hard work It's not enough, right? You have to figure out like Is this problem really worth solving? Is really is this problem really big enough for a lot of people? Right. And and I guess that's one aspect. And then and the other aspect of that is also like how do you want to solve it? Because now there's so many ways to do it, right? There's so many ways to to build solutions, build offerings. And and I think if you don't ask that questions enough, and I guess as a founder you have to ask it almost daily, right? Ben Bagg: Pretty much. Glenn Tan: Yeah, because basically the world changes even faster right now. So I think, you know, when the people are at the brink, right, I think it's not wrong to ask yourself these questions, right? it it's kinda like you're being tempted to deep, right? But sometimes that's good because when you when you think through that process And you decide to stay on, you're a lot more stronger than you were, right? Because you now made a actual decision to stay, right? Versus Ben Bagg: Yeah. Glenn Tan: a indecision to go on, right? Ben Bagg: Yeah. Glenn Tan: So I think that's what's really important, you know, for for anyone who's out there who who's going through this or or the or have been through it or might go through it, right? Just be clear that that that that's that's the foundation, right? Yeah. Ben Bagg: Yeah, I agree. I agree. Glenn, thank you so much for sharing your story and coming on the pod. I think it's it's people want, I'm sure that you will not be the last founder that has their co founder quick. Glenn Tan: Ha ha Ben Bagg: so thank you for sharing and I'm sure people can take a a lesson from you. Glenn Tan: All right, thanks so much, Ben. Ben Bagg: Coming on. Glenn Tan: Right.