Host Ian Fisher begins this episode with Josh Tobias, former professional baseball player and current scout, for an inside look at the path to competing at the highest levels of college and professional sports. Josh describes the work it took to reach his goals and what it was like playing at the University of Florida while balancing the demands of athletics and academics. He also discusses the increasing pressure college athletes face due to the rising business side of college sports and highlights the wide range of career opportunities within athletic organizations.

In the second segment, Ian is joined by finance expert Russell Seidelman as part of the May‑day series with a focus on finding scholarships beyond the first year of college. Russell explains why students need to carve out time to continue applying for scholarships even while managing college responsibilities, and how to identify opportunities for current students on financial aid websites.