Every Business I Tried Before Making My First Million
Sam walks through roughly ten different companies and side projects he tried before making his first million at around age 31, sharing how much money each made and what he learned from them. The conversation covers early hustles like flipping sports equipment, running a hot dog stand, selling white whiskey online, organizing an Anti-MBA book club, building a roommate-matching app, launching niche products like poison ivy treatment, and eventually creating The Hustle and this podcast. Along the way, Sam and Sean discuss developing money-making skills, scrappiness, project selection, risk reduction, and how entrepreneurship is largely about enduring uncertainty and fear over many years.