I spent 24hrs with a blue collar millionaire

Sam Parr found Mark O'Brien on Instagram — a 63-year-old who buys wrecked New York brownstones, restores them and sells them — and talked his way into a day on site to find out whether he'd trade places with him. They start at 94 Bank Street in the West Village, a 180-year-old house O'Brien bought for $5.5 million and is living in while he waits out permits. He'll be closer to $6 million in and thinks it sells for $17 million, but the project has sat for two and a half years on landmark approvals alone: architects, engineers, soil bearing tests, working out where the neighbour's footing sits relative to his. Parr, who admits on camera he's 'cosplaying' in Red Wing boots, draws the parallel to selling products online — the build is the easy part, the permitting is the business.

The second site, a 4,500-square-foot house in Fort Greene around the corner from Spike Lee, is where the economics get uncomfortable. O'Brien paid $2.8 million, is putting in what has crept from $1.8 million toward $2 million, and expects $6.2 million — roughly $500,000 a year over a three-year hold, with every subcontractor and every regulator able to eat into it. He shows off the parts he actually cares about: a 140-year-old floor he found under vinyl and took a grinder to, exposed original brick where plaster had cracked away, a rubble-and-horsehair cellar he'll finish because floor area ratio doesn't count below grade, so it's effectively free square footage.

O'Brien's origin story is leverage and desperation. He got into real estate over-leveraged with two and a half kids in a Greenwich house he couldn't fix himself, bought his first place for about $800,000, put about $800,000 in and sold in under a year; the next one made him a million and he started running four at a time, prospecting by jogging past old ladies' houses with a stroller and leaving his number in mailboxes. He also owns Broken Shed, a New Zealand vodka distilled from whey.

Back at the office Parr runs his scoring rubric. Business: money machine 3, can-it-run-without-him 3, moat 2 — eight out of thirty, a lot of work and real downside risk for the money. Lifestyle: pride 9, people 7, freedom 5 — twenty-one out of thirty, dragged down because in the thick of a project weekends are included. Total Sam score, 29.