Bobby Matson of on Navigating the Complex World of Student Loan Repayment (EP.224)


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I’m excited to have Bobby Matson, founder and CEO of, back on the podcast. The last time he was on the show was in April of 2020, less than a month into the global COVID panic. Since then, 45 million plus Americans with student debt have kicked the can down the road. Until now.

Bobby is a self-taught coder. He and his wife had student loan debt to deal with, so they built a product called to help sort it out. Their API allows financial apps to empower borrowers with ways to assess and address their student debt while freeing up cash to invest or spend.

And while there’s been a “pause” in repayment, student debt did not go away. The problem was just brushed aside for a couple of years. During those few years, Bobby and his team went and built other debt API products. But as repayments are starting up again, the “phones have been ringing off the hook” as everybody tries to catch up. Bobby and his team stayed in the game, didn’t overspend their VC money, and kept things under control. Full disclosure – Social Leverage is an investor in

Guest - Bobby Matson, Founder and CEO of,

Twitter: @howardlindzon, @bomatson, @payitoffapp, @PanicwFriends, @knutjensen

#fintech #invest #investment #venturecapital #stockmarket #finance

Show Notes:

  • Introduction (00:44)
  • Welcome Bobby (08:08)
  • What is Payitoff? (08:36)
  • COVID hits (10:35)
  • Demonstrating category leadership (13:34)
  • A good type of panic (15:36)
  • Product & Execution (16:34)
  • Domain experience & problem solving (17:36)
  • Debt relief options (19:26)
  • Use case solutions (20:09)
  • Expanding beyond student loans (24:44)
  • Self-taught coder (25:48)
  • Learning to build companies (27:09)
  • Trapped with debt (29:48)
  • Navigating student loan relief (31:33)
  • Avoiding channel conflict (37:31)
  • Building the Enterprise (40:56)
  • Tailwinds come full circle (43:17)
  • Rising interest rates & consolidation (43:31)
  • Wrapping up (43:49)
  • Closing thoughts (44:33)

268 episodes