Checking his LinkedIn, I discovered that he had a consulting company that ran concurrently with his most recent jobs. His most recent jobs were all less than 12 months of tenure, and the start/end dates didn’t match what he provided on his resume in some cases.
Curious, I started digging more. Through some LinkedIn friend-of-friend backchannel references I eventually deduced that he was trying to run his freelancing shop as his primary job while getting full-time employment at companies with flexible and/or remote employment where his real daily activities could go unnoticed (for a time). He collected a paycheck and benefits while running and building his freelance company. He would also try to recruit some of his coworkers to become part of his consulting company “on the side”. I suspect he was trying to outsource his own work to his freelancers as well.
Eventually each company would catch on and get sick of his behaviors, strange lack of availability and presence during the day, and work output that varied depending on how much contract work he was trying to do.
Then he’d move on to the next company to continue collecting benefits and a paycheck remotely while running his freelance shop.