In this episode of Money Tales, our guest is Mike Shannon. Picture this: On a Friday night, you’re 22 years old, standing in front of 8 million viewers on Shark Tank, shaking hands with Mark Cuban after closing a deal for your startup. The next morning? You’re back in the Chicago Bulls locker room, folding towels and doing laundry like nothing happened.

This is the extraordinary double life that our guest Mike Shannon lived while building his first company. By day, he was pitching investors and building a start-up. By night, he was mopping floors during Bulls games and running errands for NBA superstars. It’s a story that perfectly captures the wild contradictions of entrepreneurship—where dreams and reality collide in the most unexpected ways.

Mike Shannon is the CEO and co-founder of Impruve, an AI-native operating system built for financial advisors. Before launching Impruve, he co-founded Packback, an AIpowered education platform used by millions of students and recognized by TIME as a Top EdTech Company and by Fast Company as one of the 10 Most Innovative Companies.  Over 12 years, he scaled the business from scrappy startup to $20M ARR and a $50M+ acquisition. Earlier in his career, Mike appeared on Shark Tank and secured a deal with Mark Cuban.

His entrepreneurial journey began—uniquely—while living a double life as an NBA ball boy and evolved through years navigating the highs and lows of startup life. Those stories are captured in his upcoming book, Sweaty Equity: A Ball Boy, a Billionaire, and the Bonkers Startup Tale You’ve Never Heard.

Mike holds a B.S. in Finance from Illinois State University and sits on the board of directors for Future Founders, a nonprofit supporting thousands of aspiring young entrepreneurs nationwide. He lives in Chicago with his wife and two young boys.