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

19 September 2022