The Human Side of Modern Sports Leadership with Andrew Siegel

In an industry being reshaped by NIL, the transfer portal, and private capital, one question is becoming unavoidable: how do leaders make principled decisions when everything feels up for grabs?

Investor Andrew Siegel breaks down what leaders in sports and tech often underestimate, like the emotional complexity of teams, the tension between performance and values, and how managing people becomes exponentially harder when competition, money, and public scrutiny intensify.

Drawing on his experience spanning venture investing, media, hospitality, and board leadership, alongside his academic background in philosophy and religion, Andrew shares why leadership ultimately comes down to “people peopling,” how he evaluates alignment versus raw talent, and what traits he believes matter most for navigating disruption in modern sports organizations.

In this episode, you’ll hear:

• How Andrew’s background in theology and philosophy helps executives make better “people decisions” during times of disruption
• The Trust–Loyalty–Integrity lens Andrew uses to decide which founders, boards, and companies to back 
• What NIL and the transfer portal reveal about the end of amateur hour in college sports, and why Andrew thinks private capital and commercial incentives are reshaping the system
• The repeatable investing behavior Andrew believes operators and executives need to focus on 

Resources and Links:

Connect with Andrew Siegel on LinkedIn.

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