Dakota Live! Podcast: After the Exit - Teaching the Next Generation of Investors with Chris Cesare

In this episode of Dakota Live!, we sit down with Chris Ceasare, institutional investing veteran, teacher, and mentor—focused on turning theory into practice and helping students and managers communicate what truly matters.

From UPS’s pension desk to co-founding Rocaton and navigating the OCIO wave, Chris Cesare has seen how real decisions get made, and how great managers actually communicate.

Now a University of Connecticut adjunct professor, Chris shares practical lessons on integrity, “managing by commitment,” simplifying complex strategies, and why the analyst of the future will spend less time reporting and more time thinking.

With guest host Kiera Liesinger (UConn ’26), we dig into mentorship, boutiques vs. scale, and leaving the pitch book in the bag.

In this episode

 ✅ Plan-sponsor lessons from UPS: decision processes, culture, and humility
 ✅ Building Rocaton, the OCIO shift, and life inside GSAM post-acquisition
 ✅ Communicating without the crutch of a deck: clarity over complexity
 ✅ Boutique edge vs. big-firm scale—and fitting managers to clients
 ✅ The new analyst: less reporting, more analysis (and what that demands)
 ✅ Teaching investing at UConn: turning theory into practice
 ✅ AI as co-pilot (not autopilot) in the classroom and office
 ✅ Mentorship: how to ask, how to help, how to grow
 
Chris has sat on every side of the table—plan sponsor, consultant, OCIO, and now educator—and he turns that vantage point into usable rules: manage by commitment, simplify the pitch, fit managers to clients, and train analysts to analyze.

 You’ll get stories you can apply in your next IC, client meeting, or class, plus a sober take on boutiques vs. scale and AI’s real role in the craft. If you sell, allocate, or teach in this business, this episode will pay for itself.