Entrepreneurship Episodes

What if the place where you feel most successful has quietly become the place you go to avoid the parts of life you can't control? Kyle Holmes relentlessly climbed the golf industry, became a GM at just 25, worked 90-hour weeks preparing for a major championship, and eventually achieved a longtime dream of owning a golf course. But while Kyle kept winning professionally, work became the predictable place where he felt capable and in control—and staying there came at a cost: lost time with his ...

Jake Grosswiler spent years chasing what most ambitious people believe will finally make them happy: winning, money, business success, and achievement. From the outside, he had built a life others admired. But behind the victories was a painful reality—his identity had become inseparable from his performance, and every win only left him chasing the next one. In this conversation, Jake shares the hidden costs of building your life around achievement, what success actually cost him, and the iden...

What if the story you tell yourself—that you're working this hard for your family—is actually the very thing pulling you away from them? Dan Crabill spent years chasing money because he believed it would earn him respect, prove his worth, and eventually give him peace. He built and sold a successful company, accumulated the cars and houses he once dreamed about, and provided an incredible life for his family—but success also cost him his health, strained his marriage, and took away moments with...

From the outside, Kris was winning: an eight-figure business, more than 100 employees, a growing family, financial success, and people constantly telling him how well he was doing. Behind closed doors, he was battling crippling anxiety, depression, substance abuse, panic attacks, and a relentless belief that no matter how much he accomplished, he still wasn't enough. In this deeply vulnerable conversation, Kris shares how the same competitive operating system that helped him succeed nearly cos...