Nick Rogers, Co-Founder, Robin

A few weeks ago, I met with Nick Rogers to chat about his story leading up to founding Robin. We talked his time working with the Minnesota Twins, what his experience with Neo was like, and what has him excited with AI.

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Who is Nick? 

I grew up as a curious kid, I always loved reading and exploring things. I started playing with computers at a pretty young age, around 12 or 13. Computers didn’t really exist before that point. I always loved building stuff. I remember original technologies like CSS being invented and I just geeked out about that for a lot of my life. I studied math in school, afterwards I had a series of cool jobs - one of the cooler ones was working for the Minnesota Twins for a while, doing baseball analytics there. 

I think I’m just a curious, lifelong learner at my core, with my most recent adventure being founding Robin.

Was there a tie in with studying math and computers through school? Was working in code something on your mind at the time?

When I was getting ready for university, I applied for five different programs at five different schools, which my guidance counselor said was a really, really terrible idea. I applied for Math at one school, Theoretical Physics at another, political science in Ottawa, Zoology at Western. I applied for all these random things, but math I thought was something that would be hard to teach myself and it seemed like a good challenge. That's what attracted me to it.

I always like messing with computers on my own, but didn't really look at being a software developer professionally until after school. Though I had a little website building business when I was in high school.

I did my PhD in Applied Mathematics. I was working on modeling physical systems in waves. It was technical, and I was like in the weeds consistently. It was the hardest thing I've ever done, it was incredibly lonely. I worked at it for four years before leaving without finishing. I think of it as a turning point in my life, or like the origin story for Nick the Software Developer.

I think that the payoff at the end of something like that is not the piece of paper or the outcome you get. It's the things you overcome and the challenges that you go through. You still pick up some stuff, so leaving before completing my PhD wasn’t a total loss, you know? 

I always wanted to be a teacher, but the more time I spent in school it just felt like that wasn't the place to have the kind of influence that I wanted to. 

After school, how did you get into working in software?

I worked for a semester or so in a research lab just doing some data analysis, heavy lifting of big data sets for people that didn't want to get their hands dirty with code. That lasted for a bit and then eventually just kind of dried up. 

I was then looking for software jobs, but in the interim there, I was just looking for work - anything available. I took a job selling duct-cleaning over the phone on cold, outbound calls. The computers at the office were on lockdown, you couldn't use a web browser even though there's this computer sitting in front of you. I just thought of it as a challenge to overcome; I would bring containerized versions of software with me in a USB drive in my pocket that I could plug in and run my software on the computer. 

I would bring ebooks in and I would just read when I had the time, one being Tim Ferriss's Four Hour Work Week. He sets out this framework of five steps to kinda achieve automation success in your life. I started applying the framework to the call center job, taking repeatable processes, systematizing them, and applying them. I built a custom plugin that would extract the customer data from an app we used, and append a clickable link that would autofill the info in the second app.

And then one day, the manager saw over my shoulder and was upset I was using non-approved software. My manager sent me to the owner, he puts his feet up on the desk and he goes, “I hear you're having trouble with the Internet policy.” And I just thought ‘aw man, it's over.’ I told him what I did and he said “this sounds great, not a bad idea. Why doesn't everyone use this?”. Instead of firing me or writing me up, he then pulled me off the phones and hired me as a software consultant. I implemented the software on every one of the computers, we distributed it among like three different call centers, and he paid me to maintain that software for like a year. And that was my first software job. 

Then onto working with the Minnesota Twins as a software developer - was it like Moneyball or something?

It was exactly like Moneyball.

When I got hired there, a new GM had just come in. The General Manager of a baseball team makes the player decisions, some strategy stuff, manages the scouting departments and the minor league teams.

There were two developers and one analyst on the team already, and this new GM wanted to make an Analytics Department because it was trendy in baseball after Moneyball came out. Around that time Statcast was becoming a thing - we ingested a lot of data from the MLB. I built a tool that the scouts would use to submit their reports, data pipelines to support model building, which led to an app where you could view the outputs of all the models, and it basically stated the value of a player, like this guy’s a $10 million player or whatever. It would drive decisions for all trades the team would consider and for the draft. 

The draft was the most fun. Every year during it, we would set up a big TV on the wall and put our app in it. My first year there, we had the first pick overall. 

We worked at Target Field, the stadium. On game days, we would just walk out to the balcony and watch baseball. I even got to go to Spring Training in Florida one year. 

What ended up bringing you to Calgary? 

I came to Calgary for a girl, to be honest. My wife got a job here, so I started looking for a job too to come with her. That job ended up being at Neo Financial. I was there for just over four years. When I started, the whole team could all fit in one room. Year two, we hit the billion dollar valuation. 

It felt special and still does. I really enjoyed my time at Neo. I learned more there than maybe anything else that I've ever done. It was a crazy time, long days and late nights.

Why do you think there seems to be quite a few ex-Neo founders?

I think that people developed faster there than maybe anywhere I've ever seen. There was a core of like 10 fantastic devs - the best devs they could find, like the smartest people you've ever met. And that core team mentored everybody. The upskilling among the team was crazy. It was almost intimidating just to work with these guys. The  junior devs among the team, I looked at them at the end of four years, they're not the same person at all. We would talk about some of the team like ‘what's this guy's second job gonna be?’ thinking how can these guys possibly work any normal job after this.  

We would have internal leaderboards and it would get real competitive, fighting over who merged the most code during the week. And with no AI at the time, we just hand wrote every little scrap of code. It's incredible how much was produced there. Some incredible builders came out of it.

What was next for you after 4 or 5 years of just going at it at Neo?

My wife and I ended up travelling for a year. She had the opportunity for a sabbatical year where she didn't have to physically be in Calgary to work, and she wanted to travel. I hate traveling,  I would rather, like, sit in my room and build code, work on hackathon projects - that's why I'm with someone that likes to travel.

We spent the first six months driving from Calgary down to Tucson, and then all through the southern United States. We camped under the stars, saw a ton of national parks, went on the road where Forrest Gump runs in the movie, went to Disney World. It was really something. Then we drove up the East Coast to Nova Scotia, and back to Calgary.

After the road trip, we flew into Dublin, and spent some time out there and in Scotland and England for about six months - my first time overseas.

During all the travels, I was also just fully immersed in AI, getting up to speed with everything that had happened and been happening - it was an extreme vertical moment for AI. I was working on a project called Marv, a fun, personal project during travelling.

I was working on Marv throughout that year while I was traveling and every city we were in, I would go talk to local people and get them set up using it just for fun. I think maybe 50 people have used it, it's still live - check out textmarv.com.

When I got back, my friend - Ian Sutherland - mentioned that a couple of buddies of his were building something very similar to Marv for businesses. I chatted with them about it, and ended up being a really good fit, personality wise and ideas wise. Around February 2024, we founded Robin - Ian, Ben, Ty, and myself. 

Ben had built some prototypes and actually had sold them to a couple events in Winnipeg and Saskatoon. Right away, we felt like there's some demand, or at least there exists people who might pay us for it, and we built it out. I came on to help out with the tech, to build it out so that we could sell it to more than one person at a time.

Having known you for a while now, what I find really interesting about you is that it almost seems you're always following what is just genuinely interesting to you. It’s like code and building is what gets you most excited and that’s what you do everyday.

I appreciate good code when I see it, but to me, it's always like what is the thing that it achieves? What does code achieve that you couldn't do otherwise? 

Even back when I was 10 or 11, friends and I would be experimenting with it. We got ahold of this software called a war dialer. The idea is you put in a few digits of a phone number and some wild cards, and it'll just dial all the existing numbers. So, you’d put in, like 587 *** ****, and it would go through one by one. We used it to call all the numbers specifically to identify the ones that are machines. When a machine would pick up the phone in the early 90s, it would make this handshake sound. We would make a list of all the phone numbers that were machines and then try to call them and log in to the systems. I remember we found a private branch extender, you could just call, press nine, wait a second, and then dial another phone number and get free long distance calls. We didn't abuse it or try to make money on it, that wasn't the culture then. It was purely just to see if you can. What can you make the computer do that is not the intended use? That's the kind of stuff I love. And that's part of why AI is so much fun right now, because it's just changed everything. 

Computers used to be these things with a very defined set of steps that software can do. Put your name in this field, put your phone number here, hit submit, it gets written to a database. Computers are a lot more noisy now, there's a lot more fuzziness in the actual design, delivery and implementation of software. That's the most fun thing for people that like building stuff.

It feels good to say that out loud, man. I feel seen

Does what you’re seeing now around what people are doing with code excite you?

Yeah, I'm always going to vibe code sessions and hackathons and all that. I think the exciting thing right now is that hackathons look a lot different than they did five or six years ago. Coming out to a hackathon now, there's a whole crowd of non-technical people that never would have done this before. To be able to create code with just English, like English as the programming language, natural language. Describe what you want. It’s opening up the field to lawyers or firefighters, people who don’t have backgrounds in coding. 

The leverage is very high. You talk to senior engineers and their multipliers are huge because it's like they have a team in their back pocket. You're only limited by your imagination and your capability to review their work, basically. You can probably manage somewhere between four and ten people, but if you swap in AI for that, then the velocity is off the charts because it can work all night for you. Maybe I respect it in that way because I love pulling All Nighters so much. 

We're a team of three at Robin right now and not everybody's writing code, but we're shipping features out with velocity that would have required five or six devs in the past.

And you’re doing it with newborn twins. You’ve built a really interesting schedule that allows you to build a sweet business and raise your kids.

Yes, I'm a recent father. You know that it'll change things when they’re born, but once they arrive, you really feel how much you just want to be there at home for them. Family is important to me. And it's scary to run a business. It's scary to try and found a business that might not work out when you have two little kids - the sensible thing to do is to have a steady job. But in addition to wanting to spend as much time with them as I can, I also want Robin to succeed to show them what's possible, I'm really motivated by that. 

I've gotten pretty creative with my schedule because I want to spend days at home with them. I’ll work longer days that are more concentrated, and usually one all nighter a week is my go-to move. I call it breaking the week. The week is so boring in its default configuration of ‘go home at night, work during the day’. Maybe you don't want to work during the day. I think what you have to do, if you want to succeed at both growing a company and starting a family, is you have to find intensity in a way that other people don't. 

One of the best devs I know at Neo worked exactly nine to five every day. He would check out at 5PM sharp, but during those eight hours he was more productive than people who stayed until 7 or 8 at night. It's not about finding more hours, it's about making the hours that you work count. 

I like the all-nighter because I think it's important to have it during a forbidden time, it has to break you out of your thinking. When I pull an all-nighter, it's one thing laser focused. One project, and it has to be done before the shift is over. And a lot of the time, I have to force myself to be done. Then I can take the rest of the day off and spend time with my kids afterwards because I knocked out all I needed to do before they woke up. I’m still trying to build the full framework for it.

I think I'm just inherently really experimental, and this is one way I’ve been experimenting in my life. 

What are you proud of? 

I take pride in being a good person, a good co-worker and friend. I'm proud of what we've built at Robin. I'm proud of a lot of the software that I've built throughout my life. And it would be silly to not say that I'm proud of my kids. It's still pretty early, they’re still young, but I think at this point in their life (6 months old) I can take some of the credit. As they get older, the credit will shift more to them.

Also, I want everyone to experiment with AI. If you’re not already, you should. Non-builders should go build some software. Now is the quickest and easiest time it’s ever been to make things come alive on computers. And build something you can show other people, that’s the beautiful thing.