THE $100K COLLEGE RISK

What happens when the cost of college keeps rising while AI makes knowledge available almost instantly? That question sits at the heart of this conversation with John Fees, founder of GradGuard, a company approaching $100 million in sales after a 15-year journey to help protect college students and their families from financial risks many don't realize they're taking. John explains something surprisingly few parents consider: if a student has to leave school because of a covered medical issue, the university may not refund tuition, housing, or academic fees. That hidden problem became the foundation for GradGuard and its tuition and renters insurance programs. But this episode goes well beyond insurance. John and Shahid explore whether college is still worth the investment, how families should evaluate the value of a degree, the potential impact of AI on higher education, and why John believes universities may become increasingly important for developing the distinctly human capabilities technology can't easily reproduce. John also opens up about the entrepreneurial journey behind GradGuard. He shares why stubbornness helped him persist for 15 years, why complementary business partners can dramatically expand a founder's capabilities, and why mission-driven companies need to create value for employees, customers, partners, and communities—not simply shareholders. One idea keeps resurfacing throughout the conversation: AI may increasingly know how, but humans still need to ask why. 🔔 Super Entrepreneurs Podcast To watch more videos and get new video updates please subscribe to our channel and stay with us:    / @superentrepreneurspod   ✅ Stay Connected With Us: 👉 Facebook:   / officialshahiddurrani   👉 SEP Facebook:   / superentrepreneurs   👉 Instagram:   / officialshahiddurrani   👉 SEP Instagram:   / superentrepreneurspod   👉 X:   / officialshahidd   👉 LinkedIn:   / shahid-durrani   👉 Website: https://shahiddurrani.com/ ============================= CHAPTER STAMPS 00:00 – Meet John Fees, Founder of GradGuard 00:59 – The Hidden Financial Risk of Going to College 03:50 – Building GradGuard Toward $100M in Sales 06:31 – Why Paying Claims Became a Measure of Success 07:15 – Why College Students Are More Financially Vulnerable Than Parents Realize 12:14 – When Does College Become a Bad Investment? 15:12 – Why Students Leave College Before Graduating 18:50 – Why Human Skills Still Matter in an AI World 20:45 – John Fees on the Importance of Your Inner Life 23:35 – Entrepreneurship as an Expression of Your Values 26:31 – Why John Believes Entrepreneurs Should Consider Business Partners 29:08 – Why Entrepreneurs May Solve the World’s Biggest Problems 36:46 – Is Education a Private Benefit or a Public Good? 39:10 – AI and the Changing Social Contract 41:25 – Education, Wages and the Responsibilities of Business Leaders 44:15 – Human Flourishing as an Entrepreneurial Legacy 44:55 – Five Things Parents Should Check Before Paying College Tuition 48:53 – How Families Can Evaluate Whether a Degree Is Worth the Money 49:36 – Using Strengths to Help Students Choose Their Future 53:11 – How to Find Your College’s Refund Policy 54:51 – How GradGuard Got Universities to Embrace Tuition Insurance 57:09 – The Partnership Strategy Behind GradGuard 58:56 – Why People Distrust Insurance 01:02:03 – Conversations Parents Should Have Before Their Child Chooses College 01:04:10 – Finding Work That Gives You Energy 01:06:46 – What Are We Going to College to Learn If AI Knows Everything? 01:07:10 – AI Knows “How”—Humans Still Need to Understand “Why” 01:10:00 – Why AI Could Make Human Skills More Important 01:11:33 – Final Thoughts: Observe Your Thoughts, Emotions and Behavior Pullout Quotes: “There are always those who know how, working for those who know why.” “If you don't have a strong why, it's very, very hard to persist and be able to achieve the results that you really see.” “If you can align on values and you have complementary skill sets, I actually think it increases your capacity to be successful.” “I think meaning comes through human connection.” Social: Website: https://gradguard.com/ LinkedIn:   / johntfees   Disclaimer Please be aware that the opinions and perspectives conveyed in this podcast are solely those of our guests and do not necessarily represent the views, ideologies, or principles of Super Entrepreneurs Podcast, its associated entities, or any organizations they represent or are affiliated with. We provide a platform for discussion and exploration, and the content of each episode is understood to be independent expressions from our guests, rather than a reflection of the beliefs held by the podcast or its hosts.