Think Fast: Matt Dean, CEO

Building a career in financial technology is contingent on one's ability to roll with unexpected developments. With that in mind, I have set out to conduct a few "Ambush Interviews" with my co-workers. Participants don't know they're going to be interviewed, have no time to prepare, and their answers are captured via Zoom recording or text correspondence and reported here, by me, Jimmy Marks, in a new series I call Think Fast.

My subject for our first Think Fast interview: Matt Dean, CEO and founder of Trabian. I lured Matt in with a "I need some facetime with you when you have a few minutes" message via Slack, which Matt described afterwards as "anxiety-producing." Thankfully, the results are very insightful and much less likely to give one a stress headache. I got the lowdown on Matt's attraction to coding, his well-won lessons learned, and his appreciation for the basics of sandwich making.

 

Question 1

JIMMY: You wear a few hats these days (President of AFT, CEO of Trabian), and yet you still make time to get your hands dirty with code. Why is that? 

MATT: Because I am a maker and that’s what I enjoy doing and I feel like I’m good at it and it’s also how I express thoughts. For me, code is the only way to truly remove ambiguity. Every narrative description of something has ambiguity involved in it - every diagram, mockup or wireframe is ambiguous in some way. When you convert it to code, it becomes real. There have been times when I thought, “well, maybe I shouldn’t be coding, because of my role,” but first of all, I’m always drawn back to it. Second of all, there are priors. The CEO of Shopify, for example. He consistently has his laptop out, coding something. What he may be coding is more [...] tooling for the company, and they’re a product company, so he’s improving the product or he’s building tooling for the company itself. 

I found enough people who were successful in their roles as CEOs and coders where I was like, “You know what? I don’t need to investigate this further, I feel good about doing both.”

JIMMY: And it’s perfectly valid. You have that skill set, why not keep it sharp?

MATT: Yeah. If somebody is CEO of an accounting firm, they’re still going to apply their accounting knowledge to solve problems.

JIMMY: And if you stepped away from it for too long, especially with technology, that’s an impairment…

MATT: For sure. This industry changes so quickly, you have to be able to stay up-to-date on [technology] and actually use the tools. That’s how you understand if things are changing in a meaningful way.

 

Question 2

JIMMY: Do you think of FinTech as a passion of yours? 

MATT: Not FinTech specifically, so much as seeing it as an area that can benefit from our ability to bring our solutions to the problems at hand. What I’ve found is that it’s an industry we kinda stumbled into; as we stumbled into it, we really liked the people involved in it. The challenges that we were faced with were meaningful and rewarding to solve. Then, you kind of underlay that...financial matters are big stressors for individuals and couples and families. All these things converge to feel like it’s meaningful work in an industry that is bringing real positive change. It’s not necessarily passion for the industry per se, but it’s a passion for solving the types of problems that we’re solving.

 

Question 3

JIMMY: If you had to come up with a short list of “great advice for a new executive,” give me the top three bullet points. 

MATT:

1. Make sure you have a group of peers that you can talk to; being a CEO can be a lonely experience. Fortunately, I have a co-founder and a team that I have a high amount of trust in so we can talk fairly openly about matters. A lot of CEOs don’t have that and really need a group of peers to bounce ideas off of.
    
2. Understand YOUR strengths and weaknesses and, where possible, find people to help with your weaknesses. An example: I don’t have a great memory, Trey [Reeme, President of Trabian] does. He remembers things really well. That’s just a small part of it, but…fill the gaps.
    
3. If you’re building the team and/or evolving it, bring in people that you really enjoy working with. If you’re spending so much time in a business, make it something where…you actually want to be there and be with those folks.

 

Question 4

JIMMY: What’s your “go-to” sandwich? 

MATT: Toasted bread, lettuce, tomato, onion, mayo and whichever meat we have available…ham, turkey…plus salami, typically. Pretty “whitebread,” I guess, but it’s good.

JIMMY: You’re satisfying all the itches. I tend to focus first on protein and everything else is second, but you kind of flipped it, where you’re like, “I have the constituent pieces, I just need whatever protein is on hand…”

MATT: And I put cheese on there, of course.

JIMMY: Well, it goes without saying…

MATT: [Laughs] Now, am I gonna order that at a restaurant? No. But if I’m home and I’m hungry, that’s what I’m having.

 

And Finally...

JIMMY: What question do you want to ask [Project Manager] Morgan Schluttenhofer? 

MATT: "You recently started running. What's something you've learned about yourself through that training process?"

Note: This interview was edited for clarity and content.