INTERVIEW | Make Money by Building Relationships, Creating Impact, and Thinking Like a Sports Agent with Leigh Steinberg

Leigh Steinberg is one of the most influential sports agents in history, having represented more than 300 professional athletes and negotiated over $4 billion in contracts across multiple sports. Often recognized as the real-life inspiration behind Jerry Maguire, Leigh has built a legendary career at the intersection of sports, business, branding, and philanthropy. Beyond contract negotiations, he's helped athletes create lasting impact through charitable initiatives, entrepreneurial ventures, and personal development. In this conversation, Leigh shares lessons from five decades in sports representation, entrepreneurship, resilience, and leadership. On this episode we talk about: How Leigh accidentally became a sports agent and negotiated the largest rookie contract in NFL history The evolution of athlete representation, branding, and business opportunities beyond contracts Why impact and relationships matter more than money in building a meaningful career Leigh involvement in the creation of Jerry Maguire and the real stories behind the film The future of college athletics, NIL deals, conference realignment, sports gambling, and fan engagement Top 3 Takeaways The most successful careers often emerge when you combine your passions, strengths, and opportunities rather than following a traditional path. Focusing on impact and serving others can ultimately create greater financial success than chasing money alone. Resilience is one of life's most valuable skills—every setback creates an opportunity for a meaningful comeback. Notable Quotes "I tried to figure out what I loved to do in life and turn that into a practice." "The high points really are watching lives be changed." "If it impacts just one person out there who's struggling, then it's been a success." Connect with Lee Steinberg: LinkedIn: https://www.linkedin.com/in/lesteinberg/ Instagram: https://www.instagram.com/leighsteinberg/ Website: https://www.steinbergsports.com/ Book: The Comeback Other: https://leighsteinbergfoundation.org/ A Word from Our Sponsors: Today's episode is brought to you by our amazing sponsors. Their support allows us to continue bringing you conversations with world-class entrepreneurs, athletes, investors, and industry leaders. Be sure to check out the sponsors featured below and support the brands that help make this show possible. - Are you ready to start your own creatorjourney and make it big? Visitwww.fanvue.com today and launch yourcareer! - To learn more about Mode Mobile and its investor community, go to https://invest.modemobile.com/travismakesmoney -Travis Makes Money is made possible by High Level – the All-In-One Sales & Marketing Platform built for agencies, by an agency.Capture leads, nurture them, and close more deals—all from one powerful platform.Get an extended free trial at gohighlevel.com/travis Learn more about your ad choices. Visit megaphone.fm/adchoices