19 September 2022

Season 3, Episode 19. From Engineer to Founder with Bobby Matson

Welcome to Innovation Meets Leadership! I’m your host, Natalie Born. In this episode, Payitoff Founder and CEO Bobby Matson talks about turning a problem into a business possibility. Frustrated by his own student loans, he founded a debt infrastructure company to bring more transparency to the repayment process. He details how to dig deep into a personal pain point and discover the demand for a solution on a broader scale. Bobby also gives advice to people who are looking to begin their startup journey.

University of Michigan grad obsessed with building better infrastructure for all borrowers: Bobby led engineering teams at Carbon Five, where he built technology for Groupon, Fandango, and Stitchfix and shipped software to millions of users. After managing six-figure student debt in his own life, he's working on Payitoff to create better outcomes for every borrower.


[00:19] All Borrowers Want Clarity

  • Bobby on being in and out of student loan forbearance

  • Student loans are very hard to understand

    • There is a need to remove the complexity so borrowers can understand what the best steps are to pay off their debts

    • Realizing how little infrastructure there is to help borrowers was the starting point of his company

  • Why they focused on student loans in the early days

    • It’s important to go insanely deep into the problem and solve it better than anyone else

    • More use cases, more impact

[07:30] Driven by Customer Demand

  • How Bobby went from a non-technical founder to a technical founder

  • Doing direct customer testing and diving into the financial advisors' market

    • This experience allowed them to grow and gain their edge

  • Having the demand is a big advantage when it comes to fundraising

[12:51] Success Breeds Passion

  • When you get good feedback on the work you’re doing, it creates passion

  • Building a company vs. Solving a need

    • Be honest with yourself if you market and the customer before taking a leap into entrepreneurship

[15:29] Nailing Your Niche

  • Unlocking one opportunity opens more opportunities

    • It’s about discovering more variables around the problem and finding solutions for them

    • The complexity is the villain

  • A little pain point can be a deeper pain point for somebody else

    • This can be the push you need to move forward and start your own company

    • Eliminate the perceived risk and just go for it

[25:05]  Closing Segment

  • Connect with Bobby!

Key Quotes:

“Solve one problem and go unreasonably deep.” - Bobby Matson

“When I saw in the early days that I was helping us with something and everyone I knew with this debt, it was exciting. And I still reference and go back to those moments, the very real demonstrable impact of those days.” - Bobby Matson“I get very obsessed with the problem. If I really do want to see everybody have a better outcome, but with something this complex, with this many variables, it's all about how many profiles and variations you can throw at it.” - Bobby Matson

“There are a lot of moments in company building where you'll say to yourself, am I doing the right thing? Are we working on the right thing? Knowing the personal need that you had in the beginning is the anchor that helps you answer that question.” - Bobby Matson

Connect with Bobby 

Website: https://payitoff.io/ 

Email: bobby@payitoff.io 

Twitter: https://twitter.com/bomatson 

LinkedIn: https://www.linkedin.com/in/bobbymatson  

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