Boring Money

Stanley Henry ran hotels for 12 years. Eleven jobs in twelve years, because he was the guy they sent in to fix the one that wasn't working. New Zealand, Australia, the UK, a stint in Japan. In his last year he was running a hotel in Melbourne that did more profit in one January than it had ever done in revenue in a January, and his boss still didn't think he should be on vacation. He turned to his wife and said it out loud: as long as I work for someone else, they're always going to want more...

Jay Peterson got out of Boston College in 1991 into no jobs, went home to Kankakee, Illinois, and sold industrial real estate for a broker who gave him the listing nobody wanted: a hundred acres next to a dynamite plant. Two years later some friends set him up as a Canteen distributor with one route truck and two vending machines. He and his wife Myra were the first two employees. They canceled their honeymoon to take on a Sears distribution center. That vending company got to about $10 mil...

Ian Dahlberg got out of the Coast Guard and was trying to figure out what he was doing next. He picked up a security guard license on a whim while going to college on the GI Bill, and it got him hired at the Waldorf Astoria in 2012 as a security manager trainee. He says he's got more stories from that one year than from six years in the military. Seven incident reports a day was the average. Then he did the thing I keep telling people to do. He went back to being a guard. Night shift, shipp...

Ron Butler spent eight years at one residential electrical company and didn't want to leave. He asked them to match a $100K offer he'd gotten elsewhere. They couldn't. He pitched them on starting a service department instead, four guys, he'd out-earn the whole shop. They didn't bite. So he took the other job. Day one he walked into a branch running on chaos. Day two he called his CPA and asked whether $60 or $70K working for himself, after the tax treatment, would match the $100K. She said ...

Justin Campbell got fired from a management job at TGI Fridays, moved back home into the room down the hall from his grandmother, and started taking $50-a-day temp shifts. The job site was far enough that he slept in his car outside it rather than risk the morning drive. One evening a guy from the commercial floor care company next door knocked on his window and asked what he was doing out there. He offered him steady evening hours. That knock is the whole origin story. Four years later Jus...