STOP PLAYING SMALL. So often we are afraid to go all in. Whether it’s in a relationship, in business, or in an investment, the fear of failure keeps us from fully committing. What a mistake. I’ve had to learn to love failure. I have to consciously tell my brain, “You’re going to fail. And it’s going to be ok.” Take the leap. Make the commitment. Dare to take a stand. If we’re not failing, we are staying too safe. And you won’t grow unless you are constantly making yourself uncomfortable. On today’s episode of The School of Greatness, I dive deep into the idea of going all in when the time is right with one of the most successful investors in the world: Matt Higgins. Matt Higgins is a proven operator, investor and business builder with a knack for helping founders at pivotal growth moments achieve breakout success. He serves as CEO of RSE Ventures, a private firm that incubates and invests in companies across sports and entertainment, food and lifestyle, media and marketing, and technology. Higgins co-founded RSE with Miami Dolphins owner, Stephen M. Ross, the most prominent private developer in the U.S. and a serial entrepreneur. Together Higgins and Ross have helped build enterprises from scratch, including the largest privately owned soccer tournament in the world (International Champions Cup) and leading brand strategy and communications agency Derris. Matt didn’t graduate from high school. He came from a humble beginning but never let that hold him back from getting where he is today. He says that when you do things your own way and you start with a blank page, it’s going to be a lonely journey. You have to trust yourself and be careful about the advice that you take. So get ready to learn what makes Matt a great investor and why certain businesses are winners on Episode 727. Some Questions I Ask: How did you start this business-building fund? (7:00) What are the characteristics of the people you invest in that made them stand out? (9:45) If the product is average but the person is incredible, can there be a massive business? (19:00) What’s the biggest lesson your mom taught you? (44:00) What’s your greatest fear? (46:00) What’s the thing you’re most proud of? (53:00) In This Episode You Will Learn: The two things you need to be a great business leader (10:00) The question Matt asks himself before he invests in a company (12:00) The story of Matt’s first investment (14:00) Matt’s advice for people who are playing small (22:00) Matt’s biggest regrets in business (23:00) What do you do when you go all in but then you fail? (24:00) About Matt’s surprising backstory (31:00) The one thing Matt thought about when he was diagnosed with cancer (51:00)