Hey, I’m Philip Camilleri

Rome wasn’t built in a day; neither is a successful startup. Just ask Philip Camilleri. The three-time founder, who has raised a total $51 million dollars on his first venture-backed financial technology company SmartAsset, knows firsthand the long journey of bringing an idea from a concept to a thriving business. He knows, too, the pang of rejection, the hiss of naysay, and the whisper of self-encouragement that propels you forward, despite the doubters and the uncertainty ahead. 

Along with his business partner Michael Carvin, Philip co-founded SmartAsset in 2010 at the tail end of the 2008 subprime mortgage crisis that plummeted the world in a protracted economic recession. With Michael’s background in investment banking and Philip’s software development experience, they saw an opportunity to help consumers make better financial decisions, armed with the right information and assisted by technology. Although the economic crisis began through unethical and fraudulent predatory lending practices to consumers who largely neither had the credit nor the finances to take on the burden of homeownership, it was clear that there was some level of ignorance on the part of the homebuyers, a paucity of available financial planning information and no easy way to sort through it all. SmartAsset would be a valuable tool to make challenging financial consumer decisions more convenient and easier. Their addressable market would extend far beyond homebuying, including banking, investing, loans, refinancing, tax preparation, and retirement planning—all important financial decisions a savvy consumer must make.

The pair pooled their finances to create a minimally viable product that they could use to inspire investors to kickstart their business. Michael helmed the New York City-based company as CEO; Philip, its Chief Technology Officer. After 11 long months and countless rejections, including from three executives from a large fintech (financial technology) company who told them it was a terrible idea, they managed to convince Y Combinator and Quotidian Ventures, two venture capital (VC) firms, to give them a combined $900,000 in seed capital, according to Crunchbase. The first few months were rough, getting used to managing their own schedule and setting their own targets without the oversight of a boss. Even after four years, they weren’t seeing the traction in users and partnerships that they had hoped. Since SmartAsset didn’t have the common hockey stick-shaped growth trajectory VC’s expect from startups, one of their investors said, “If this were a West Coast company, we would have pulled the plug earlier on.” Instead, Philip and Michael were determined to forge ahead during that pivotal moment some 50 percent of startups falter and even belly up. Philip and Michael stumbled upon an idea that helped them increase their user base and another that allowed them to monetize and scale financially. They “widgetized” their interactive tools and partnered with large publishers like CNN, The Wall Street Journal and MarketWatch to increase traffic to the website. As well, they created a financial advisor platform to connect financial professionals to hundreds of thousands of new customers which gave them the economic lift they needed. Philip described their insights as a combination of luck and serendipity: 


“There’s no magic to it. Sometimes you get lucky and figure out something that helps you to pivot and scale up and sometimes it just doesn’t happen.” 

After four other rounds of funding over the past eight years, SmartAsset has since grown tremendously. The site gets over 100 million visitors every month and the company currently has a staff of over 150 employees. They were among the Top 100 Y Combinator Companies list in 2018 and a 2018 Benzinga Fintech Award Winner for Best Educational Tools & Services.

Without any background or familial history in business, Philip remembers selling herbs along with his brother from his family garden when the two could not attend elementary school one year because of a political crisis in Malta, the Mediterranean island nation where he grew up. A few years later, his father bought them an Atari 130XE, their first computer, which awakened an interest in Philip in understanding how computers and technology worked. He would spend every other waking hour disassembling electronics and teaching himself computer programming. Later in high school, he and two other friends started a theater company that would put on plays at regional theaters for a fee during the summer months over a four-year period in Swieqi, his home city. Then while at the University of Malta, he started a student newspaper called The Voice. Despite all his pre-adult entrepreneurial endeavors, he would not consider striking out on his own or leveraging his technical background, which he had since advanced in pursuing computer studies in college. Instead, like many of us, he took a 9 to 5 and worked for various telecommunications and banking companies as a software developer.

What lit a fire under him was recognizing he wanted more autonomy in his work life and becoming dissatisfied with the humdrum of its predictability. Creating something, although riskier, was more exhilarating. Creating something out of nothing felt nothing short of divine. However, the transition from being a worker to an employer: maybe a temporary kind of purgatory. He found it hard to let go of creative control until he learned to trust in the ideas and skills of others.

These days, already with a successful company under his belt, which he has since left, Philip has set his eyes on solving a different challenge, one he could have personally benefited from in his first venture. FoundersList, his new idea, started as a hobby but has since progressed into being a bit of an obsession. Its goal is to connect the founder community and provide the resources and information that entrepreneurs need throughout the life cycle of a startup: from finding a business partner and early-stage funding to hiring employees and accessing the networks and opportunities that will make the difference for a scaling business. The builder is dedicating his resources and his creativity to help others construct their own dreams. FoundersList helps budding business people reduce the time it takes to get an idea off the ground, one Philip still beats himself up over after spending years (pre-SmartAsset), thinking about ideas that consequently failed to launch due to inertia and a lack of information.

We sat down with the technologist and startup maven to discuss his experience and how it can help others at the cusp of their own entrepreneurial journey to gain a start.  


Who taught you how to code?

Nobody taught me to code, really. The way it happened was, as a kid, I always liked playing with things that you could build. My grandmother had this set—I don’t know what the brand was—but basically pieces where you are literally building blocks. We used to go to her house on Tuesday and Friday and I was just building whatever: houses and things. And then from there graduated to Lego, robots, and from there airplanes. I was kind of interested in how things work. Then my father, at like 10 or something, got us our first computer, which was an Atari 130XE. You could basically play video games on it or write code in Basic. But there was no manual, no internet as well, so you basically had to just start and figure things out. Then I think I remember going to a library and there was a program in Basic and then I thought this is it. Basic is a very simple programming language—like if you want to print something, you print with a certain code, a color comes up. You basically have to find out everything through experimentation because there was no manual. That’s really how it got started. Just trying to do things on this Atari without knowing if it was happening and trying to figure it out as I went along.

What is it like coding on an Atari 130XE?

To me, it was an experience because it was a lot of trial and error. You don’t really know how things work. For instance, there was a joystick. The only way to figure out what happens when you press the button was, at a certain point back there I can see where the signal comes and that’s when you press the button. When you see something change, I’m like, alright, that’s how I know when someone pushes the button to fire with the joystick. Same as moving left and right. It’s all about really just experimenting without really knowing what you are doing. And I think that’s the way I code, I tend to just try to figure things out. One thing I learned is that everything is logical. There is nothing magical in a computer. Everything works for a very specific reason and follows very specific rules. As long as you’re able to identify those and see what’s happening, then things will make sense. It’s an inexact style of programming where you try things, you figure it out, you see what other people are doing, and somehow try to copy that till you make it.

Did growing up gay have any influence in these early years?

Could be. Maybe just not fitting in with the stereotype of people wanting to play soccer and whatever. In coding you’re very much in isolation and you do it yourself. So, I don’t know if it’s directly related or not. Superficially I’d say maybe not but deep down there is some connection.


What is AIESEC? How did you learn about it and what kind of internship or volunteering service were you doing in Ohio?

AEISEC was the International Association of Students in Economic and Commercial Sciences. It’s a one-year internship when you graduate. You can spend six months or a year somewhere and I applied and got the one in code in a very small town outside of Columbus, Ohio. I ended up spending like nine months over there at a software firm, doing what I enjoy doing writing code, but it was a whole different experience living in Middle America.

Why were you interested in becoming an entrepreneur when you were already successful working as a developer?

Having a family business wasn’t something we did in my family. It wasn’t something I saw very often. It was just something I wanted to do. When I was maybe 16 living in Malta, before I even went to high school, two friends and I got together, and we created a theater company. We put up a show over the summer. Looking back now, I think it was pretty crazy. That became a small business. We did that every year for about four or five years. When I was in university, I started the university newspaper as well. I don’t know why I got into these things. Honestly, I really can’t figure it out, but I think it was also the fun, the adventure. But I started to find myself gravitating towards a regular job. After the internship in Ohio, I went back to Malta. I worked for Vodafone. Then I worked at a software company working with banks. I spent seven years doing that. Then after seven years I had nothing interesting to do and managed to start another company.

What was your first start up?

The theatre company would probably be my first startup, if you want to call it that. We raised money for it. The play made a profit. We used that money the next year and kept doing it for quite a while.


What is PickandGive? Was it successful? If not, why not?

Some other guy wanted to do a startup like DonorsChoose but rather than teachers fundraising for their classes, any nonprofit organization can say what they need—like tables and chairs. You can specifically go and say I want to pay for two chairs or one table. We started building that and I guess interest waned and it died a slow death. He and I were doing it part-time and other things got in the way. Any startup you’re doing, any project, you need to be 110% otherwise it’s not going to work.

In all your ventures, what have you learned as a founder you did not anticipate?

Oh my god, where do I start? It looks prettier from the outside than it actually is on the inside. So that’s one of the big things; doing things takes work. Success doesn’t just happen magically and overnight. Hiring people has always been a big challenge for me, like figuring out the right people to work with, figuring the right expectations. That’s something that I thought was incredibly challenging. Raising money for a startup, that’s like one the worst things ever.

And there are positive things: when you start something from nothing and see it grow and see how it develops a life of its own or a personality on its own, it’s quite amazing. Going into the office and seeing everyone working (when we used to work in offices), that was one of the good things. But just getting there, some people say, “Never do it again,” and I understand why.

What’s the transition like from being an employee to an employer?

I think I’ve learned through making lots of mistakes. When you start a business or a company you are ultimately responsible for it. If it succeeds or fails, you are responsible. When you’re building codes, you need to know what’s going wrong because, if something’s wrong, it’s your responsibility at the end of the day. But the key thing I think is hiring the right people, getting to know them, trusting them that they know what they’re doing because as things keep growing and scaling you definitely can’t control everything. I think it’s just one of those things that as an individual contributor you know exactly what you’re doing and everything is in your control, but as you start building, things get to be different. I’ve always been amazed how companies with thousands of developers manage when things go wrong. Sometimes it takes a single line of code to break everything. It’s just the nature of the game unfortunately.


Are there other traits you had to unlearn in order to be a better entrepreneur?

When you’re managing a big team, your time is no longer your own. You can’t just spend eight to 10 hours a day just sitting down in front of a computer coding. You’ve got to do other things. So that was something I had to learn to adapt the way I do things or manage my own time. As well as patience, that things don’t happen overnight, that things take a long time, and managing your time.

What’s at the core of the business or market problems you take interest in solving?

PickandGive was set up as a non-profit. FoundersList is a bit of a mix. For me, it’s something fun. It’s something useful. It’s something that I hope will help other founders or other entrepreneurs. FoundersList is something I would have loved to have used seven or eight years ago. I wish it existed. The economy isn’t doing good, so it was a good time for me to go and build it. Hopefully it all works out as I planned.

So, you're not making a conscious decision to make things that help people?

I wouldn’t say it’s a conscious decision. It might be an unconscious decision. I know it’s helping people and I’m helping myself as well. I’m not trying to sound non-altruistic but it’s something I enjoy building and I hope people will find use in it. At the end of the day, I think any business or any product that you build, hopefully, somebody is going to use it and enjoy it. Unless you’re completely sociopathic or you’re doing this for your own personal benefit.


What separates a good idea from a great idea?

This is something that I was actually discussing with another founder literally a couple of days ago. I was in a talk with a founder and this founder is talking about how they’re trying something, and it wasn’t working. He said, “The universe was telling us this was not a good idea.” And I kind of got a problem with that because the answer is not clear cut, meaning when we started SmartAsset, at the very beginning, I remember at least three people clearly, who ran a very big fintech product in this space who told us this was a terrible idea. So, I don’t know if we were just hard-headed, crazy, whatever but somehow, we managed to figure out something that really worked and scaled. If you look up the story of Airbnb, they tried so many times. They tried, they failed. It was a big struggle for them to get to where they are but somehow, they really believed in the idea. They thought it was going to work and they actually made it work. So, I don’t know. I think what separates a good idea from a great idea is a bit of madness—madness and luck. You’ve got to be crazy and you have to not only have a vision, but you also have to be lucky. It’s got to be the right time and the right moment for it. I don’t think there’s a formula.

How important is it to be passionate about the idea you’re championing as a founder or co-founder?

Completely. You’ve got to be obsessed with it. And again, obsessed in a good way. Very often ideas change and pivot and get tweaked. You can’t be obsessed to the extent that you’ve got blinders on and you don’t see anything else. But you need to be passionate enough to say, “Somehow I’m going to make this succeed and, come what may, I’m going to figure out something.” It takes a lot of trial and error to get things moving, at least, in my opinion. So, being passionate and a bit obsessed with it to the extent that you want it to succeed.

How can the VC community improve upon their track record of marginalizing underrepresented groups like women, the LGBTQ and minority founders?

Investors tend to invest in people who reflect their values, that check the boxes that they are familiar with, such as people who went to certain schools or people who have a certain background. They’re making bets often on unknown individuals. You need to try to risk averse in a certain way. But the problem with that obviously is the people who go to Stanford or MIT fit a certain persona or personality. I think it’s very good that VCs broaden who they invest in and what sort of founders they invest in. But honestly, it’s easier to talk about these things. It’s a very different thing to change them in practice. I think changing that aspect of it doesn’t really solve the problem. It’s just solving one of literally several thousand of issues. It’s definitely a good start but there’s a longer way to go. I think the VCs and entrepreneurs pat themselves on the back and say, “Great, great. We’ve done a really good job. We invested in so many minority founders. Job done.” I think that that’s just the beginning.

Have you thought of a way to tie FoundersList into creating that solution?

I started SmartAsset in 2010, I really had no idea of how things worked in the investor space. The idea behind FoundersList is just making that information easily available and allowing anybody on the platform to ask questions and can get support from others. So, there is that aspect of democratizing access to the startup world. But there’s also an aspect of creating groups; you might have a career as an LGBT founder group. You might have an immigrant founder group. And the idea is for those groups to organically support each other. I dislike groups that by their very nature exclude others, but the idea is that immigrant founders deal with certain issues that they’re intimately familiar with that others aren’t. So, if we’re talking about visas, immigration issues, how to start a company as an immigrant those are topics that that group is aware and may want to discuss and others don’t. Likewise, an LGBT founder group has a whole series of other questions that they probably want to discuss or cover. The point of FoundersList to me is just making things more broadly available.

What would you tell the 12-year-old you who taught himself to code, given his experiences all these many years later?

Stop thinking about ideas and just do them. I enjoy thinking about what I could build or what might happen rather than just saying, “Ok, let me go ahead and do this.” I’m a master at procrastination. I would definitely tell my 12-year-old self just get off your ass, do something and do it to completion. Don’t just try it and then change your mind or focus on something else two weeks later. Just get something done and get it done right.

What advice would you give to a young queer person who hasn’t yet had their ‘aha moment’ or know how to recognize it?

I forget who said this, “If you do something you love, you won’t work a day in your life.” If you think you enjoy working on something, try your very best to work at it. As well, keep pushing. The first few months of a startup, the first few years, are a struggle. People are going to be ignoring it, thinking it’s a poor idea. Success definitely doesn’t happen overnight. If you really believe something’s going to work, just keep pushing, ignore the noise around you or the naysayers. It might take a while; it might take a lot of work, but it will work out.

What’s the best piece of advice you never got?

I’ve been thinking about doing things like FoundersList for many years and just never really got off my ass to do it. Just getting it done was a good first start. At SmartAsset, we were struggling a lot for the first few years and there were so many times I thought this isn’t going anywhere and we should give up. Thankfully, my co-founder and I started supporting each other and somehow managed to keep pushing. Sometimes you don’t realize that some form of success is just around the corner. If you really believe in it, just keep pushing forward. Obviously, listen to the signals around you. So many people thought SmartAsset was a bad idea. If we had just listened to them, we would never have done anything.

If you didn’t have to worry about being successful, what would you do with your life?

I think I enjoy doing what I do. After taking a bit of a break after SmartAsset and being in a bit of a different space where I could choose, I quickly got frustrated. I’m like “My God, I need to do something, to build something, talk or meet people.” It really motivates certain parts of my brain. Having said that, I really enjoy helping other founders, discussing things, trying to figure things out, introducing them or helping them get things done. But I think just building something with my own hands, I think I would miss it if I stopped doing it. I think no matter what it’s probably something I’m going to be doing for a while.


Disclaimer: Philip is Freshfruit‘s technical advisor.

Know a Freshfruit of the Week, send us your nominations and reasons why they should be selected to contact [at] freshfruitinc [dot] com with “FFOW Nominee” in the subject line.

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