Alexi Lalas. Naomi Girma. Tim Howard. Landon Donovan. Richard Motzkin has been there representing each of them throughout their careers as their Sports Agent. In this conversation with Ryan, Rich recalls his journey of quitting big-firm law to become U.S. Soccer’s first in-house counsel, and how that leap led to his own agency which began before Major League Soccer even had a name. He explains how the early days of MLS felt like a startup, complete with fax machines and jersey swaps that exposed just how far U.S. soccer still had to go. Now a top executive at Wasserman, Richard reflects on what’s changed, what still holds the sport back, and why chasing happiness, not just trophies, remains his north star.