In Part 1 of this special two-part episode, Matt sits down with College Aid Pro CEO Kevin “Degs” Degnan to unpack the personal journey that shaped his mission to reinvent how families pay for college. From growing up as one of eight kids in Massachusetts to facing the hard truths of the college application process, Degs shares the setbacks and pivots that ultimately led him from Stonehill College to the Peace Corps in Peru, and eventually to earning his MBA and building a remarkable career in finance and business management.

This is a candid look at what happens when your dream school says no—and how that moment can fuel a lifetime of purpose. If you’re navigating college admissions, financial aid, or wondering how rejection shapes resilience, this episode is for you!

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Chapters

1. Meet Our CEO (00:00)
2. Growing Up in a Big Family (02:53)
3. College Application Journey and Rejections (05:20)
4. Advice for College Applicants (08:16)
5. Transitioning to the Peace Corps (10:35)
6. Experiences in the Peace Corps (13:27)
7. Pursuing an MBA and Career Reflections (15:59)
8. Working with ExxonMobil in Iraq (18:33)
9. Career Path and Investment Banking (21:12)
10. The Evolution of College Aid Pro (24:09)
11. Understanding the College Funding Crisis (26:44)
12. The Historical Context of Student Loans (29:10)