You Are the CEO of Your Own Life: Greg Scheinman on Midlife Male

Greg Scheinman is the founder and CEO of Midlife Male, the premiere digital publication and lifestyle brand for men over 40, with a newsletter that reaches more than 50,000 men every week. He's the author of the bestselling book The Midlife Male, a keynote speaker on transformation and redefining success, and a coach to midlife CEOs, executives, and founders, with two company exits behind him. The path there started with loss.

Greg lost his father to cancer at 17 and went off to college carrying it, then spent years numbing the grief instead of facing it. In his twenties he chased the film business in New York, got his start at Miramax, produced independent films, and made a movie dedicated to his dad. He built a sports children's video company out of the trunk of his car, landed licensing deals with the NFL, NBA, NHL, and NASCAR, brought in an investment from former Disney chief Michael Eisner, and sold it. Then he did the opposite of everything he had done and went into insurance, building a million dollar book of business, becoming a partner, and helping sell the firm in 2020. It was his biggest financial success and his least satisfying professional experience.

At 47, with resentment building and his wife telling him not to blow what they had built, he got his first coach and started writing what he now calls his Midlife Action Plan. It took thirty days to write and three years to follow, and from 47 to 50 his life changed in every category. The conversation moves through grief, entrepreneurship, fatherhood without a template, and what it actually takes to rebuild a life once you stop running from it, all of it grounded in the idea behind Midlife Male: most men plan the first half of their lives and have no plan at all for the second.