He closed the biggest deal of his life in October 2008. Ten days later it was worth nothing. Michael Dermer left Willkie Farr, one of the most prestigious law firms in the world, to build the first company in America that paid people to be healthy. Everyone told him it would never work. He built it anyway, to nearly 900 employees, and closed the private equity investment that was supposed to be the reward for a decade of work. His 3 biggest clients were Washington Mutual, Countrywide Financial, and General Motors. Within a month, two of them no longer existed. What followed was three years of 20-hour days with no finish line. Nobody tells you it'll be over in 700 days. What he learned in those three years became The Lonely Entrepreneur. Here’s what we got into: • The offer he turned down in 2007, and the 30 days it took him to stop replaying it • The only two rules he gave his team once the math stopped working • What his dad said to him on the steps of the New York Public Library when he put his odds at 1 in 10 • Why he insists he never felt lonely, and what he thinks loneliness actually comes from • Why he believes AI is this generation's October 2008 Thanks to Michael for going there with me. New episode of Through the Valley is live now. Links below.

"One of the best things that ever happened to me was getting pushed out of the CEO role." At 28, Jordan F. was the founder and CEO of CoachUp, Inc, roughly $15M raised, 30 employees, living across the street from the office. His board wanted to fund the next round and replace him. They also offered him a president title and asked him to help pick his own successor. He walked me through the math of why that happened, and it had almost nothing to do with him. Preferred stock, fund returns, the gap between a good outcome and a grand slam. He experienced an economic decision as a verdict on his worth. Most founders do. What he learned in that valley: • Why the seed and the very late rounds align, and why the middle is where founders get replaced • What he did with the year he spent as a title with no job • The two words he now says to himself whenever bad news lands • Why he came back years later and reversed all of it • Where CoachUp sits today, fourteen years in Thanks to Jordan for going there with me! NEW episode of Through the Valley, live now. Links below.

"I would not trade cancer for anything." Brandon Aversano knows how that sounds and he said it anyway.

“I would not trade cancer for anything…” Every guest on my show is proof of the same thing: the chapter people skip in public is usually the chapter that made them. Brandon Aversano is one of the clearest examples I've seen up close. At 30 he had the résumé everyone wants and a trajectory nobody would question. Then testicular cancer, disability leave, and medical debt his father's voice in his head told him he should never carry. To create cash he sold his grandmother's jewelry, and the industry treated him like a mark. 4 years later he runs one of the fastest-growing precious metals platforms in the country, built entirely around the idea that nobody should stand at that counter alone. He told me something I haven't stopped thinking about. Cancer created space for him. He'd been at JPMorgan for years with no room to ask whether he was on the right path at all, and the diagnosis handed him the first real pause of his adult life. What you'll take away in this conversation: - The difference between a valley that stops you and a valley that equips you - Why he says the achiever version of him "came back with a vengeance," and what changed underneath - How a bad experience at a jewelry counter became a company thesis - What he'd say to himself on the worst night, which is the answer I ask every guest for New episode of ‘Through the Valley’ with Brandon Aversano is out everywhere.

"There's a lot of shame in getting sober. Why is there none in the damage?" Justin Gurland, (founder @ The Maze) asked me that and I didn't have a good answer. I'm not sure anyone does.

He walked into rehab at 25, thousands of miles from everyone he knew, certain his life was over. The next morning was Super Bowl Sunday, 2008. He watched the Giants beat the undefeated Patriots. Then the staff turned off the game, walked everyone into a group room, and asked what each of them believed in. Justin Gurland, LMSW had no answer. No community or sober person anywhere in his life to point at. What he said was that the Giants had just won and he could hold onto that for now. 18 years later he's the founder of The Maze NYC, NYC's first alcohol-free members club, where a few hundred New Yorkers pay to belong to a building with no alcohol in it. My biggest takeaways from this powerful conversation with Justin: • Why the thing you survive on can be almost meaningless and still be enough • What his sister said to him the week before rehab, and what happens to people who never get that conversation • The Godfather scene he read a month before everything came apart • Why he says the amends isn't a conversation, it's how you live • What his father wrote about Justin's lowest moment, read out loud for the first time on camera So grateful to Justin for sitting down with me. This episode of ‘Through the Valley’ is live everywhere you get your shows. Links below.