Debt Savings Automation Guides Student Loan Pay Offs with Bobby Matson

In this episode of The Modern Financial Podcast, Jake Hoffart features Bobby Matson, Founder and CEO of Payitoff. He shares how six-figure debt loans pushed him to create a solution in creating structure in the debt and financial decision space. Payitoff helps in these areas and automates debt savings which, in Bobby's own experience, was a game-changer in gaining control over his finances and creating a better experience for the borrowers he serves.


  • Student loans create a need for debt savings automation
  • Going to University of Michigan and founding his first company
  • Payitoff's vision is to create a better borrowing experience
  • Starting as a solo founder and taking on a founding team after


Creating structure in the debt and financial decision space Bobby: "What we've really uncovered is that automating debt guidance and automating that savings is really where there's a lot of opportunity and a lot of experiences that borrowers right now are managing on Reddit and spreadsheets. It's a really not good place to be and hard to manage yourself."

Founding Payitoff with a vision for a better experience for borrowers Bobby: "It's always been about finding savings for borrowers, and I think that using that same sort of vision of there should be a better way and there should just be a better experience across the board, I think that kind of consistency has informed out product."

Advice for aspiring entrepreneurs Bobby: "I was thinking too much about fundraising instead of thinking about okay, I just need 12 months to figure out this metric for myself and stay accountable to that. I eventually got there, but in the early days, I focused way too much tech stars and all this other stuff when really the focus should have been find one to two advisors in this space, go cold email all the people that you think could be customers, depending on your market, but just get feedback."

Find out more about Bobby by checking the following link: