In 2007, Mike Brenny's tax return said $530,000. In 2008 it said $17,000. He spent the next two years mowing lawns and reselling Air Force base auction finds on eBay, trying to keep his family in their house.

He didn't stay because he was made of something rare. He stayed because nobody offered him a way out — and he says so plainly. If someone had put an insurance job in front of him in 2008, he'd have taken it.

Mike is a Minnesota kid who moved to Hawaii after college, met a girl from Sandy on the beach, and followed her to Utah twenty-five years and four daughters ago. At 22 he bought a condo two blocks from the water, then bought a trashed one nearby for reasons he still can't explain, and spent his evenings fixing it up with paint from Home Depot. When he sold it he made a year's salary in one go. This was 1999, before house flipping was a thing anyone had named.

Utah in the early 2000s had no tech industry and no job he wanted, so he opened a Curves franchise in Sugar House, was projected a hundred members in week one, signed eleven, and had to go get a job to pay for the business he'd just started. That job was mortgages — an industry he knew nothing about and was setting company records in within six months. Spec houses followed. Things got bigger. He decided he was a genius. Then 2007 arrived.

What came after the crash is the shape of the whole conversation. Two months of his parents covering his mortgage, then a month of his mother-in-law covering it, which he describes without any softening. Years later, a short sale finally cleared and he pulled the repayment out of the bank in cash, because he knew his father wouldn't accept it any other way. Then a $200,000 raise turned into a $2 million line of credit, and for five straight years he was at the courthouse auction every single day — roughly 300 houses.

He's equally direct about what happened next: a million dollars lost on his first big Park City deal, another million on his first development. Today he's building ski-in ski-out at Powder Mountain and has just taken on High Star Ranch, and he's honest that the reason he can do it is a single narrow skill. He values real estate better than the people bidding against him. That's the whole superpower, and he can point to exactly what it's been worth.

Running underneath all of it is a question he keeps circling: how much of this was him, and how much was timing. He'll tell you the only common denominator across successful people isn't intelligence or hustle — it's the ones who don't quit — and then immediately admit he was one phone call from being someone who did.

It's also a conversation about four daughters. A farmer, a nurse, a self-declared golf mom, and a fifteen-year-old just signed by an LA agency. About a wife who told him at nineteen exactly what she wanted to do with her life. And about the low-grade dread every parent of grown kids carries — that one day someone new walks in and the thing you built at home changes shape.

At 8:30 one morning Brett Chell was the CEO of a company he'd spent thirteen years and $53 million building. By 9 he'd been told not to go back to his house, not to speak to a single employee, phone off, computer off. They towed his Escalade. His visa was attached to the job. He walked out of downtown Houston with a backpack.

Brett dropped out of high school and spent eight years on oil rigs. What he also saw was a problem nobody was solving: operators running hundred-million-dollar sites from headquarters half a country away, getting their data emailed to them piecemeal by a dozen service companies who had no interest in talking to each other. He figured software couldn't be that hard. Thirteen years and $53 million later, he had his answer. The company he built is still running, doing $50–60 million a year with 250 employees. He was removed from it right as it hit escape velocity.

What followed was sixty days of Domino's and Netflix with his phone off, then a year of trying to work out who he was without a company name to lead with. His lawyer told him he'd win the fight for his equity — two years, half a million in fees, roughly $20 million in warrants on the table. He let all of it go, because taking it wasn't who he wanted to be on the other side.

Then he sat at a kitchen table and wrote down what he actually loved. Supercars. Art. Being around his friends. Marketing. He flew to Salt Lake, drove the city in a grid for two weeks writing down addresses of interesting buildings, walked into the first one, and met the man redeveloping the entire neighborhood. The warehouse he ended up with had gravel floors, smashed windows, rain coming through the roof, and people living inside it. He took it because it was the only one he could afford.

That's Bricks: a business club, a car club, and a media house in one building, built on the observation that most coworking spaces sell community and deliver a room full of strangers who never speak. His fix is curation plus actual services — pooled media production, distribution, and a network members can use.

This is a conversation about what happens when the thing you built stops being yours, and what you're left with. Brett is unusually honest about the role ego played in staying too long, about how much of his earlier success he now attributes to timing rather than talent, and about the difference between the CEO a small company needs and the one a large company needs — a distinction he understood about himself and ignored.

His line for anyone whose identity has quietly merged with their work: "I ask people, who are you? Not what you do."

One day from the summit of K2 — three weeks on the mountain, a teammate just killed in an avalanche — Jenn Drummond turned around and walked down.

"I don't want to teach my kids peaks over people." That decision cost her the entire climb: the money, the training, the window, all of it back to zero, on a mountain she says kills a quarter of the people who attempt it. She went back and finished it.

Jenn Drummond holds two world records and had never slept in a tent before any of this started. She's a mom of seven who moved to Utah at 35 with seven kids under the age of eight and two thousand miles between her and everyone she knew. What set the whole thing in motion was a car accident she says she shouldn't have survived — and the realization that came with it, that she'd been building a life on external validation instead of internal.

In this episode she and the guys get into what she's learned from mountains that transfers directly to building a business: why you climb a big peak multiple times before you ever summit it, why every step back down feels like failure and isn't, and why winning means coming home alive — which is also the question to ask before you launch anything. She explains the "grump dump," a journal where she writes down every failure and leaves blank lines underneath, then goes back months later to ask whether it was a failure or a pivot.

Plus: landing on a Denali glacier with five people, 650 pounds of gear, and no porters allowed. Getting stranded in Russia when a missile closed the airfield and no American card would work. And the "somedays" list she's building a company around — because her grandma died, her dad was diagnosed with Alzheimer's, and a friend got cancer with a mountain still on his list.