#34 | Wyatt Smith: 50 Trucks in the Field, One Laptop to Run It

Wyatt Smith spent his last day at Uber turning off the lights on Uber Elevate, the flying-car division he helped build and sell to Joby Aviation.More on Wyatt Smith and this episode: thedealtablepodcast.com/episodes/wyatt-smithHe now runs UpSmith, an AI company for the skilled trades, and his argument is that the technology everyone is worried about is the only lever big enough to move America's builder shortage. That shortage across manufacturing and construction peaked near 1.5 million people in 2021 and still runs around a million. The stated goal: a contractor with 50 trucks in the field doing $25 million a year, run from a laptop.The technical distinction he draws is between deterministic and probabilistic software. Bounded if-then automation could never solve booking a job, updating a record or chasing an open quote, but an agent whose marginal time cost is zero changes what is even worth solving. That is also the private equity thesis: roughly 50 percent gross margin, 30 to 35 percent operating margin, and what happens when you add $1 million of top line without one more person answering the phone.The Uber Elevate section is worth it on its own. Global helicopter production runs about 1,000 units a year against projected demand closer to 20,000, and FAA type certification is still the blocker. He also traces the path from a farm in Alabama to Teach for America to Silicon Valley, including the terms scrawled on a paper lunch bag at the sale barn that financed his father's first chicken houses.Wyatt Smith is the founder and CEO of UpSmith, an agentic AI company built for skilled trades businesses. He previously helped build and spin out Uber Elevate, Uber's aviation division, and worked at McKinsey and Teach for America.KEY MOMENTS00:00 A shortage of about a million people02:07 A pathway to 50x the productivity07:21 His dad, a lunch bag, and a credit line11:29 1,000 helicopters against 20,00018:49 Why value sits in the application layer23:42 Deterministic against probabilistic32:13 Why PE is buying every service business37:51 $1M of top line, nobody hired41:05 120 NDAs on a single trades deal01:04:32 A $50 million business from a laptopNewsletter: thedealtablepodcast.com/connectLane Carrick on selling a business, The Optima Advantage: amzn.to/48nLElWFollow The Deal Table: YouTube, LinkedIn, Instagram, Facebook, TikTok, XThe Deal Table is hosted by Ryan Harper and Lane Carrick, filmed in Dallas, and produced by Harper Belmont Media.Sponsored by Capital Southwest.