Cutting Data Migration Down to Size

Two-time founder Jimmy McDermott ’21 caught the entrepreneurial bug in high school. When other students were taking American history and English literature, he was learning how to build iPhone apps – a class that ignited the spark for his first venture.

A year later, he launched Transeo (later rebranded PATHWAYos) as a freshman at BC. And seven years later, he founded Rubie, which leverages the power of AI to help companies cut the super-sized challenges of data migration down to size. 

We sat down with the business-savvy and deeply philosophical BC alum to talk about what he’s managed to accomplish in just a quarter century on this Earth. He credits the Shea Center, a well-rounded BC education, and “the Jesuits” as some of the biggest contributors to his success. And he’s only begun to set the world on fire.

So Jimmy, you’re a two-time founder. And your first startup was called Transeo and then PATHWAYos, right?

Right, we rebranded Transeo in the last year of its existence as PATHWAYos, so it’s basically the same thing.

And you created Transeo when you were in high school?

It was actually right after high school, and then I ran it through BC. So, it was about seven years front to back for that experience.

Was the inspiration from your own experience as a high school student going for an internship, trying to get into colleges, and deciding on the right school?

Yeah, that was part of it. I was in a very oddly innovative high school district in the suburbs of Chicago, and it was one of the first in the world to pilot an iOS development class for high school students. This was 2012, when iPhone apps were still new. And at the time, it seemed like kind of a crazy idea to bring in people to teach kids how to build apps. But thankfully, it put me in a position to learn those skills early. So, that was the original spark of the idea alongside my high school superintendent, who had brought the program into the school district. And with his knowledge of the school district and my knowledge building applications, we co-founded Transeo.

So, kind of an aggregator? 

We started as a community service tracking application, but what became our bread and butter was work-based learning within school districts and helping students find those same types of opportunities that my district had for me. We were the software to power the experience – the timesheets, job board, geolocation tracking, reflections – and all of that flowed back into the work that school districts had to do to meet grant funding requirements. So, we helped create a self-sustaining flywheel that would help them get grant-funding, and then they would use some of that funding to pay for Transeo. 

That must have been a pretty transformative experience. And did that lead to your interest in going to BC and being part of the business school? 

I picked BC before I started Transeo. It wasn’t for that specific reason, but I knew that I wanted to be on the East Coast. Funny enough, we went out to visit BU and I almost missed the BC tour. And then I got lucky, because I didn’t love BU as much.

And BC got lucky too. So, let’s talk about Rubie, and the inspiration for that.

I think to understand Rubie, you have to understand the problem we experienced at Transeo. So, as we scaled, we got up to over a million students on the platform from a couple of hundred school districts, and with that came a ton of implementation challenges. We would sign a customer, and they’d be super excited and ready to go, but we would have a bunch of data problems and challenges around migrating their data into our platform on an ongoing basis to make it valuable for them. That was a perennially difficult ops challenge that we never fully figured out. And after we sold Transeo, I couldn’t get that problem out of my head. I had spent seven years banging my head against this data migration process. So, the first thing I started exploring afterwards was how many other companies have this challenge. And it turns out a lot of them do.

What types of companies have signed on and what are the most common pain points this technology is addressing?

So, what we do at Rubie is help companies with AI-powered data migration. Often that means helping companies that need to move customers from their competitors into their software. We’ll help them build these very powerful data playbooks that can go and get customer data from the former company, clean it up, transform it, map it all together, and move it into this new system. Our best case studies move from days spent on data cleaning to minutes. The types of companies using it are largely high-growth startups, because that's usually the kind of company that faces this issue before they try to throw humans at it. The ones who get it viscerally are the ones growing quickly and trying to fix this problem through humans, and usually failing at that.

What sectors are these companies in?

Mainly healthcare, finance, education, and construction. And it ranges from early-stage startups to scale-ups that have raised $50 million+ and are scaling to larger customer bases. I’d say our biggest customer will probably do about 5,000 customer migrations on top of Rubie this year.

That’s amazing. So, they really need this. 

Yeah, you can’t do that with humans, or at least not in a cost-efficient way.

Who’s your competition?

We don’t really have any direct competition that can do everything we do. We have some competitors that can do pieces of it, and our customers will often deploy us alongside some of them while they wait to transition all of their operations on top of Rubie. Honestly, our biggest competitor these days is human time and status quo, which was our biggest competitor at Transeo too. Change management is the hardest part.

You also developed the BC Web Apps Crash Course with Branick Weix. How did that come about, and how many students have taken it?

The inspiration for it was a noticeable gap between what traditional CS education teaches and the skills you need to start up and build your first products. Foundational education is important, but it’s not usually enough to get you to the point where you can build something for actual users. We ran the course in college and kept it super informal – at night, no credit, about 30 students. Then this year, we were approached by a student who had heard about us doing this years ago when we were in school and wanted to run a version of it again. So Branick and I returned to do it virtually this year. And that was a very fun experience, because AI has really changed the dynamic. You don’t need nearly as much foundational experience as you did before to get to something you can build for users. So, it was a lot more fun to do one or two classes on the basics and then jump right into building things that you can show your friends and give to people.

And speaking of foundational education, you wrote a piece called “25 Lessons at 25,” in which #16 is “Pour your time into something that sets the world on fire.” You said you have the Jesuits and BC to thank for that. Can you elaborate?

Set the world on fire is a BC motto, and it’s always been a very important part of how I try to live my life. I think it's a great encapsulation of what it means to go out into the world and do something the world needs. There’s the Japanese concept of Ikigai that’s the intersection of what you’re good at, what you love, what the world needs, and what you can be paid for. Set the world on aflame is a version of that. And I have BC to thank for introducing me to that concept and trying to live every day like that.

So, Jimmy, what drives you and in what formative ways did your experience at the Shea Center shape your destiny as a founder?

The most valuable thing about the Shea Center was the other founders who were there at the same time as me. They’re all still running the same businesses they started in college, and a few of them have moved on to second-time businesses. So having that network as we’ve gone through post-college life has been super impactful, because everybody’s been at various stages together and been able to lean on each other. That was the true magic of the Shea Center, bringing together people who’ve now become lifelong friends. And part of that was also the speakers they brought in. I met lots of alumni and BC entrepreneurs who’ve invested in my companies and who are mentors and advisors. So that kind of self-sustaining flywheel is pretty impactful.

And once you get involved in that, it just sort of takes on a life of its own, right?

Definitely. It's an interesting environment, where BC isn’t known for one singular thing, like all entrepreneurship or all computer science. And I actually love that about BC. I think it creates a very well-rounded experience that shows itself in the Shea Center as well. I think that’s a unique strength of it, that the people who go through that program tend to be well-rounded individuals. So, I’m just very grateful it exists and glad that it continues to rise in stature and funding and possibilities. I think the students deserve it, and I’m grateful to have been a part of it in a small way.