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What to look for in a tech cofounder? With Philip Camilleri of FoundersList and SmartAsset.

Summary: Chris talks with second-time founder Philip Camilleri about how to find a tech cofounder, what makes a tech cofounder successful, how business cofounders can appeal to their tech counterparts, and the right mindset and communication skills needed to forge a strong cofounding team.

[00:01:02] Philip Camilleri background.
[00:02:34] Being a startup cofounder differs from a regular job.
[00:03:22] What to look for in a tech cofounder.
[00:06:43] Minding the budget and picking the right tools.
[00:08:14] Tech Skills.
[00:09:45] Pitching investors.
[00:13:27] Pick someone with a strong belief in your mission.
[00:14:59] Cofounder communication.
[00:17:01] Transition from sole coder to CTO.
[00:19:05] Second time founder.
[00:20:57] How to appeal to tech people as a business cofounder.

Intro: [00:00:00] Welcome to the FoundersList podcast, the official podcast of FoundersList.com, a place for founders and entrepreneurs to connect, find potential co-founders, relevant events, business partners, and search vetted service providers to help build their businesses.  And now here's your host, Christopher Kim. 

[00:00:27] Chris Kim: Welcome to episode three of the FoundersList Podcast. I'm here this week with Philip Camilleri. Philip is the founder of FoundersList, but besides that he was the cofounder and CTO of SmartAsset, one of the biggest consumer-facing FinTech portals out there. 

[00:00:44] And he's here today to share his wisdom about finding a technical cofounder and what it takes to do the job. Now Philip is from the island of Malta. Something we share in common is that we're both from islands, me from Hawaii and Phillip from Malta. We’ve both been all over the world, but I'll let Philip fill you in on the rest.  

[00:01:02] Philip Camilleri: Sure. Well firstly, Chris, thanks for taking the time to do this. Just a quick background into myself. I've been tinkering around with tech and computers since as long as I can remember.

[00:01:13] But on the entrepreneur side, I remember as a kid, we were for some reason locked out of school, a bit of a long story, but my brother and I ended up selling herbs from our garden just to keep busy during the day. Sometime in high school or university, I started a small theater company with some friends and moved on to create the university newspaper.

[00:01:36] So I guess I'd say, I've always had an interest in entrepreneurship essentially, though after university, I joined a company called iWorld, which was a business incubator. And I think there, I got a bit more of a grounding in building startups. But after that I moved off to the UK and I think at that point I moved into the corporate world, started working for the investment banks.

[00:01:56] But then I guess sometime around 2008 or so I started getting the itch to start something again. And thankfully in 2010, I met Michael who ended up being my cofounder at my most recent startup, SmartAsset, and we grew that essentially from zero to basically where it is today, which is a pretty successful company.

[00:02:15] Probably one of the best known FinTech consumer information portals around.

[00:02:21] Chris Kim: So before starting SmartAsset you were basically working as an employee in an investment bank. And Cofounding a startup is a lot different from working as an employee isn't it?

[00:02:34] Philip Camilleri: To be honest, I would say cofounding a startup is anything but like a normal job. I mean, just being in a place where essentially you don't really have a boss, you are the boss, you and your cofounder or cofounders are running things, setting deadlines, setting targets.

[00:02:51] At least to me, I would honestly say the first few months of running a startup were probably the most shocking and unusual time of my life.  

[00:03:00] Chris Kim: So in that early startup phase, everything is kind of chaotic and ephemeral. It's very important that your cofounder and yourself are on the same page and working toward the same goal. And I think personality-fit probably plays into that quite a bit. Can you tell me a little bit about how personality affects decisions in finding a cofounder?

[00:03:22] Philip Camilleri: So this is probably a really interesting question, but lots of folks starting businesses or startups are saying that finding a tech co-founder is  I guess, one of the hardest things to do. Many folks say it's like dating.

[00:03:37] So I would generally advise people looking for tech cofounders to look for individuals, obviously who they connect with. They should definitely believe in the same idea and be  very enthusiastic about the project. All right. So your tech co-founder needs to be one of your biggest advocate, your top promoters.  If they don't believe 101% in what you have been building, then it's going to be very hard for them to really be a valuable cofounder.

[00:04:04] Other than that, though, I'd say a tech cofounder needs to have the skills to really work independently. As a tech cofounder, as CTO of a startup, there's nobody overseeing their work. There's nobody managing what they're doing. They are ultimately responsible for everything. So you need to be able well, firstly, to trust that they know what they're doing and believe that, or understand that they can get things done to completion.

[00:04:30] I would say another thing as a tech cofounder is you need to have a personality, That's probably a bit crazy. Being able to work through the highs and lows of a startup. if we talk about Paul Graham’s “startup curve,” there's many highs, but many, many more lows building a startup. And if you don't really believe in what you're building, or the potential success of that product, those lows can really bring you down and hamper your work.

[00:04:54] So your tech cofounder needs to be somebody who either can work through those or can work with you to kind of power through those lows. Another important thing of the tech cofounder, is finding someone who is collaborative building a startup.

[00:05:11] It's a strange situation. You don't have lots of folks around you, don't have lots of supporting team members. So both you and your cofounder need to be able to really be on the same page, understand what you're building and work collaboratively to get things done.

[00:05:27] Chris Kim: Getting things done is important. Skills are important, but it's not really just about the coding and the skills though. Is it?

[00:05:33] Philip Camilleri: Yeah, Chris. Far from it. I would honestly say your tech cofounder needs to be Jack or Jane of all trades. You've got one person,  essentially your tech cofounder needs to be able to do, if not everything, almost everything, on the tech side, and that might be picking the right tools, the right technologies,

[00:05:57] planning for the future, of course. But also bearing in mind that you've got to be extremely frugal and efficient when you're in your very early days, because otherwise, you know, startups are out of money. So case in point, one of the companies I'm advising right now is in their pre-seed stage.

[00:06:15] And they're planning to bring on, I think it was two devOps and a DBA. And my big piece of advice was that's going to massively increase your burn rate. Is it something you really need right now? Or is it something your tech co-founder can take on? It is a lot of stuff to take on, but that is the role of a tech cofounder.

[00:06:32] Being able to get things done with as little budget, as quickly as possible, in order to get the company moving forward.

[00:06:43] Chris Kim: I think that's an interesting point right there because a lot of things can be done really cheaply, but also if you're not looking at things like the budget —tools, developers, all kinds of outsourced projects, could really add up really fast.

[00:06:57] Philip Camilleri: Yeah, for sure.  When we started SmartAsset back in 2010, I guess I came from a background where I always try to be as frugal as possible.

[00:07:05] So using things that are either free, open source, or had very low costs for early stage startups. To me, that was always a bit of a key focus. In fact, I used to find it a bit funny back then when I saw startups using things like Microsoft tools that had pretty high licensing costs at the time.

[00:07:25] To me, one of the big things, the tech cofounder is that person that needs to build things, but also needs to select the right tools, within obviously budgeting constraints. If you're an early stage startup, most of the time, you don't have the massive budgets to spend  on tools and technologies. So being frugal, being efficient, I think would be a good skill to have as a tech cofounder. 

[00:07:48]. When my cofounder and I raised our first round, we allowed ourselves a little luxury of, an espresso coffee machine.

[00:07:54] And I'm proud to say 10 years on what, nine years on, that little Nespresso machine is still in the office. 

[00:08:01] Chris Kim: All right. So frugality, watching your burn rate, all very important things. When it comes to actual tech skills, though, what should I be looking for when I'm evaluating a tech cofounder?

[00:08:14] Philip Camilleri: So I'd say this obviously varies a lot based on the type of product and the business you're building.

[00:08:19] At a high level, obviously one of the key skills is finding someone who has a broad set of technical skills, whether they can do backend, frontend, database, system administration, whatever it is, just because that person really has to be doing everything themselves. They should also be able to take very high level ideas, most often without any specs, and build out a product.

[00:08:40] And that I think is key. As in, you need somebody who I guess some folks would call a product engineer, someone who can take an idea, think about all of the ifs and buts and caveats, and build out a fully fleshed product. 

[00:08:54] Taking a concept and figuring out what questions need to be asked and putting it all together. I'd also say another thing is being able to work to completion. It kind of ties in with the highs and lows, like running the startup sometimes can be very depressing and de-motivating, if you're not getting the numbers you want, or the funding you hoped you would get.

[00:09:14] But despite all of that, if you really believe in the product and the company and the business, you need to keep powering through. So having that mental mindset, or just be able to focus on what needs to get done and shutting out all of the noise, I think that's a really important skill to have.

[00:09:29] Chris Kim: Okay. So what about when it comes to pitching investors? it can be an exhausting process, but often all hands kind of need to be on deck, including the tech cofounder’s, and that's not always within their comfort zone. So what do you have to share about that?  

[00:09:45] Philip Camilleri: Sure. There’s so much to unwrap on this. I guess one of the key points that you raised here is having the tech cofounder really be a partner in the business, a lot of time they're going to be with you at investor meetings, investor presentations.

[00:09:57] So they need to have the necessary skills to present to make a case, and really express their belief and their determination to build up the company in front of investors. Having said that again, doing a startup is, as one of my friends said,  you've got to learn to ride the waves and the highs and the lows, and being able to take rejection.

[00:10:17] Unfortunately, doing a startup means getting lots of rejections, whether it is from people you're trying to hire, or partners you're trying to work with. Or, as often as the case with investors, I guess the joke I used to say is, if you have a hundred investor meetings, you're going to probably get 95 “no”s, four absolutely “no”s and maybe one possible yes. And all of those nos take their toll. So just being able to power through those or ignore them and not take those rejections personally, but probably more importantly, being able to support your cofounders, or anybody on the team,  to have them support each other through the highs and the lows.

[00:10:56] So your tech cofounder needs to be someone you get along with, someone you enjoy working with, but somebody who you can rely on for support. 

[00:11:05] Chris Kim: When you're talking about getting 95 out of a hundred rejections, it's gotta be pretty demotivating sometimes. Did you ever, during that process, suffer from imposter syndrome? Where you felt like, well, maybe I'm not doing the right thing?

[00:11:18] Maybe I shouldn't be here? And if so, how did you overcome that and power through and get to where you eventually got to, which is a pretty successful startup. 

[00:11:26] Philip Camilleri: So that's an interesting question. I might've been a bit facetious about the 95 rejections, although it took us a good 11 months for us to raise our first seed round.

[00:11:37] So I think the numbers are pretty much up there. I think it's a bit of a weird situation. As in, I think with SmartAsset, we got lucky. We kind of powered through and kept on. We had this determination to build what we had in mind, and granted, yes, things changed and we got lucky and stumbled across twists or ideas on the product that really got us to where we are today.

[00:12:01] And sometimes I do keep looking back and wondering at what point might we have pulled the plug and there's just, and I think this is something one of our West Coast investors said that like after year, two or three, like SmartAsset’s growth wasn't the hockey stick that VCs look for,

[00:12:21] and I think he had said something like, “if this were a West Coast company, we would have pulled the plug earlier on.” I definitely think we got lucky and our focus and determination allowed us to stumble across ideas that made the company successful.

[00:12:36 ]I think the key thing is, one, really listen to your customers, to users. Secondly, believe in what you're building. If you believe it enough, then you can somehow make it a success, obviously without being too over-confident.

[00:12:52] But believing in your own talents.  Honestly, like when I look back, I think both my cofounder and I were crazy when we started this, but there's no, there's no certification or just having a Yale degree, or Stanford degree isn't enough to just say you're going to be a good cofounder, a good startup founder.

[00:13:10] Chris Kim:There’s no external validation, right? It's like, it doesn't matter what kind of paper you have, what kind of stamp of approval you have, if you're building something that doesn't exist, and bringing it into this world for the first time, you know, it takes a lot of personal fortitude to get that done when there's no real roadmap. 

[00:13:27] Philip Camilleri: Exactly. What made me, for instance, a tech cofounder build what we built at SmartAsset. I honestly don't know. I mean, I loved what we were doing. I believed in it. So it takes lots of hard work, but I look back now and I can see all of the mistakes we did in the past, and what I would make again, what I would repeat, wouldn't repeat. But I think that’s a key thing. That's an important thing of a tech co-founder. You need to find someone who obviously does pick the right whatever tools, technologies, what have you. But more importantly, that they really believe that what they are picking is what what they want and what they really believe in.

[00:14:02] As in, I've seen a few too many startups spec things, because they're the shiniest toy or the newest tool on the block, not to say that's a bad reason, but if you're going to have to sometimes stick with those technologies for two four, five years and beyond. Sometimes the newest shiniest tools don't last that long.

[00:14:23] So finding a cofounder who is confident enough to know what is right and what is not right, and what they believe will carry the company and the product forward, honestly, I think that is really extremely important because you can't afford to spend a year building something  and afterward you realize we have to go back and start from scratch and do it again. That's just not reality. 

[00:14:47] Chris Kim: A lot of what I'm hearing from you has to do with communication. Having been there yourself. What sort of tips do you have for tech cofounders especially, when they're communicating with nontechnical counterparts . 

[00:14:59] Philip Camilleri: So obviously I think, well I'm coming up this from the technical side, so I might be a little bit biased. I’d say one of the key things is managing  skills and expectations. Sometimes tech folks believe or expect that everybody understands or speaks the same language, and often that's not the case. So having a tech cofounder who can explain things in simple straightforward terms is obviously important.

At the same time, there has to be, a very high level of trust. That if you're a non tech cofounder, your role isn't to keep questioning your tech cofounder about what they're doing, why they're doing certain things, why they picked certain tools or whatnot.

[00:15:40] You essentially need to trust that you are partners in this business and your tech cofounder knows what he or she is doing. And you need to allow them to get things done. I think  there's also different ways of working. I guess, just to give you a quick story. My cofounder came from investment banking, so his working day was pretty much 5:00 AM to 11:00 PM, versus in the tech world where it's a bit different when you're sitting in front of the computer coding all day.

[00:16:06] So it took us a while to get to a balance of what our work day should look like, and what productivity on the tech side really looks like. So it's important for again, for tech and non-tech cofounders to understand that folks work differently. For me personally, I like to put on my headphones and get couple of hours of straightforward coding time.

[00:16:27] And I think this is pretty much what developers or coders would agree, every time you're interrupted — You don't just lose a few minutes for that conversation. Sometimes you have to go back to figure out what you were doing and unwind a couple of things. So different working skills, different time management, that's something that both tech and non tech cofounders need to understand about each other.

[00:16:47] Chris Kim:  The skills for an early stage founder, when you're the only one coding, the skill sets required, the strategy, the tactics, are completely different than when you're hiring teams and you're managing people. What are the challenges and how did you make that transition?

[00:17:01] Philip Camilleri: So that, Chris, is probably one of the most, the toughest question. And I have to admit, I had a very tough time. Growing from basically an individual contributor, building a product to hiring a team, leading a team, and growing the product…

[00:17:21] … don't think there's any natural progression. You don't just go from a coder/developer, to a great leader. And in fact, I mean, speaking for myself, it took lots of help from my team, from my cofounder, and even external help. I kinda like to sometimes joke I had what I used to call my “organizational therapist” who really helped formulate the way I treated certain things.

[00:17:46] But I think that's actually really important because you need a tech cofounder at the beginning who really kind of get things done, right? So who can build stuff. Who can choose the tools, but who’s focused a lot on building the product for the business. But over time that same person needs to start hiring people and training them and bringing them on board and motivating them and being a leader to that team and interacting with other teams as well with sales or product, whatever.

[00:18:13] So. Those skills or those personality skills are extremely important, but they're probably not the things you might look for day one. They’re things for down the road. So I think that co-founders will need to be aware of this, if that's the kind of role, but you know, some tech cofounders might prefer to just focus on building stuff, on coding.

[00:18:33] And as the team grows, they might, the team might decide to hire, whatever, a CTO or a team lead who brings a different set of skills to the table. 

[00:18:41] Chris Kim: So you've expressed the challenges you had going from being the sole contributor of the tech side, to having a team and all that, but now you've started all over again with FoundersList. How are you finding being the main individual contributor now?  Has it been easy to go back? Do you find it refreshing, or  is it difficult to not have a team? 

[00:19:05] Philip Camilleri: That's interesting. So for founder's list, I guess this started off as a bit of a project that I wanted to build because I enjoyed coding.

[00:19:13] So. I wanted to do this because I wanted to keep my skills up to date and build stuff, but it's very different. Again, early days you're focused on just building things, being as efficient as possible. Sometimes that means cutting corners. So it might mean well, I'm ashamed to admit… like when we started off SmartAsset, I doubt we had a single unit test or a test in there.

[00:19:38] But when I look back, our priority was we had to get a prototype out by a certain date because otherwise, well, we would run out of money. A company can’t survive without money. So there's certainly things that you do very different. They have different stages when it's just you yourself coding. You know exactly how the code works.

[00:19:55] You know where everything is. You don't need to explain everything to anybody else, but as you're building a startup, you know, over time, that product is going to be modified or other people are going to be contributing to the code base, so you do need to plan a bit for that event.

[00:20:12] Again, it's a fine balance. I think tech founders need to be very aware of that, because spending too much time initially building unit tests and building massive infrastructure for something that just needs to essentially be an MVP, can bring down a company.

[00:20:26] I've seen too many startups spend too much time and money on building really complex systems when all they need is they need to prove the product X number of users. And once we prove the product, then we can move on. There's no straightforward answer. Unfortunately, it's a fine line to have to walk.

[00:20:42] Chris Kim: We've seen on FoundersList so far that the demand for tech cofounders is much higher than that for business development cofounders, at least in our early users. With that in mind, what can I do if I'm a business development cofounder, to attract the interest of highly capable tech people?

[00:20:57] Philip Camilleri: That, unfortunately, is definitely the case. I guess, as some people say, ideas are a dime a dozen, but finding somebody who can turn that idea into a product, who will bring it to fruition, are unfortunately in low supply. It's basically, of of the current environment. That said, I think from a tech cofounder point of view, what I would look for myself, is a business person, who's got real conviction around the idea of the business, right? So. I don't really want to speak with somebody who just thought of an idea yesterday morning in the shower, and now things are going to do the business.

[00:21:36] I'd like to speak to folks who have been thinking about the idea, digging, poking holes into it, trying to do some research, quick tests, get some data, but essentially a well fleshed out well-researched idea. Having some expertise in the field as well, would definitely help, or some hands-on experience with the industry, the market that we're talking about.

[00:21:59] So, my background is in tech, I wouldn't presume to be able to run the, I dunno, an aerospace startup. I don't understand the first thing about aerospace. I think same thing with business people are looking for technical founders. Of course there's a question about background and personality.

[00:22:15] So running a startup is I'd say, a very tough and very lonely job. So being able to bring real conviction, real, motivation and those leadership skills to be the CEO or the leader of the company. To me, that's something I definitely look for in potential cofounders. and finally, I think, if you're a nontechnical founder looking for a technical founder, my recommendation is, you know, you're looking for a partner.

[00:22:41] You're not looking for an employee. That's a big distinction. So when you're having these early conversations, like really, if you don't believe you're looking for a partner, then I'd probably say, you're looking at this the wrong way. A tech cofounder does not want to be an employee.

[00:22:55] They're not looking for. Okay. Speaking in generalities, I'm not looking for a high salary, but they're looking for high involvement in the company. So whatever, high equity stakes, but a strong voice at the table. So whenever somebody posts something that they're looking for a cofounder, a tech co-founder, but the posting seams to implicate that they're looking for an employee more than a real partner.

[00:23:21] …I tend to shy away from those sorts of things. But other than that, I think it is, to me, the person I see as the most important, right? The idea will change over time. But knowing that you found someone who is dependable, reliable, responsible, maybe knows or understands what they're going in for, like doing a startup is tough.

[00:23:38] Most startups do not end up as the next Facebook, or Slack, or Google. Most of them unfortunately, fail. So having somebody who is realistic as a cofounder, that's really important. 

[00:23:52] Chris Kim: It's hard to find that combo though, of both realistic and a super determined to have something work.

[00:23:58] Philip Camilleri: The realistic aspect is a bit important. So as an idea person, you need to be visionary —and I agree with that, but coming up with ideas that you want to build the next mailchimp, for instance, whatever email management system, it might not seem like a very complicated system, but it takes work.

[00:24:18] It's not something that somebody is going to build in a couple of weeks. Maybe you can build a quick prototype or something, but there's lots of things that go into building products. So I think that's actually important, that the ideas person needs to understand that things take time, and having a tech cofounder who can actually explain in realistic terms or simple terms, like what, what is doable today?

[00:24:40] What's doable next week? What's doable next month? And what might take a year to get done? Is important, because somehow there's going to be these early on negotiations about what we can launch with and is that going to be sufficient for these users? And when we test that out, what happens next?

[00:24:56] It's a very long process. Unfortunately, not unfortunately, it is part of the fun of doing a startup. 

[00:25:01] Chris Kim:  And working on a startup really is everything that you've said so far. It's got highs, it’s got lows, but it is at the end of the day, quite a lot of fun so far. So, thanks Philip for talking with me today and if people want to get ahold of you how can they do that?

[00:25:16] Philip Camilleri: Chris. Thank you. This was, I think my first podcast. It was a really nice to do this. If anybody wants to reach out, I'm always available. I can be reached at philip@founderslist.com. I love speaking to folks who are building things, especially early stage founders, so I’m happy to carry on the conversation with anybody.

[00:25:36] Chris Kim: Alright, that's a wrap for episode three of the FoundersList Podcast. If you want to get a hold of us, you can reach us at podcasts@founderslist.com. I do encourage everybody to subscribe, rate, review, let us know how you're feeling about the podcast so far, what you want to see on the future. And thank you so much for tuning in.