168 The Entrepreneurial Journey of NFL Athlete Turned Investor Chris Wilkerson

Chris Wilkerson’s career has taken him from the football field to building and exiting companies to investing in the future of sports.After earning two First Team All-American honors at Stephen F. Austin, Chris spent time in the NFL with the San Francisco 49ers and Tennessee Titans. But his entrepreneurial career actually started while he was still playing. He taught himself to code in college, built a software agency and eventually sold the business before pursuing the NFL.He later founded Sideline, a recruiting technology platform that grew to more than 800 universities before being acquired. That experience ultimately helped shape 51Ventures, his early-stage investment firm focused on sports, health, human performance, and the technologies connecting elite athletes with everyday consumers.In this episode, Chris shares his journey from athlete to entrepreneur and investor, what he looks for when backing founders, why access and relationships can be more valuable than capital in sports, and where he sees the next wave of opportunity as more institutional investment enters the industry.We also discuss what founders get wrong when selling to teams and leagues, the growing connection between sports performance and consumer health, and why Chris believes there is still significant room to build as more capital flows into sports.