The Business Game

Insurance With No Gotchas: How GradGuard Earned Trust at Scale | John Fees

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On today’s episode of The Business Game, we’re sitting down with John Fees, Co-Founder and CEO of GradGuard. After more than two decades as a serial entrepreneur, John has built and successfully exited multiple companies, including businesses acquired by Viacom and JPMorgan Chase, before founding GradGuard, a fintech company providing financial protection products for students and families navigating higher education.


Let’s dive in,
 With John Fees

  • Why John identified the financial risks facing students and families as a problem worth solving
  • How GradGuard was born from John's previous experience in university software and student lending
  • Why his earlier exits to Viacom and JPMorgan Chase changed the way he approached building GradGuard
  • Why John chose strategic partners over traditional venture capital for GradGuard
  • How GradGuard grew from its first university partnerships to more than 750
  • Why it took five years to reach the first 150 universities
  • How GradGuard built insurance products designed specifically around the realities of student life
  • How GradGuard redesigned tuition and renters insurance around students and families
  • How he designed his life around being a founder, husband and father of five
  • Why sleep, exercise and time in nature are essential to his performance
  • The biggest challenges facing higher education, including declining enrolment and AI
  • Why John believes AI could actually make education more affordable
  • The future of human skills, credentials and university education
  • Why John believes business leaders have a responsibility to think beyond shareholders
  • The role of values, ethics and stakeholder responsibility in modern business
  • Why long-term thinking matters in both business and life
  • The importance of mentors, fellowship and asking for help
  • The business systems John recommends for founders moving from Level 3 to Level 5
  • What John believes founders need to measure as they scale

If you're a founder, business owner, or leader navigating the high-stakes world of insurance, fintech, or higher education, or you're simply trying to build a values-driven company for the long haul, this episode is packed with practical lessons on partnerships, mission-driven growth, ethical business, and building trust one relationship at a time.

Connect with John Fees:
Website: https://gradguard.com/
LinkedIn: https://www.linkedin.com/in/johntfees

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