Though I didn't know who he was at the time (mid 1960s) he did "remotes" at various businesses, like Drive In Ice Cream establishments. He had a Part 15 type transmitter, which got out several hundred feet, and called his station "WDAW 1200". If you google "WDAW 1200" in quotes, a few links will come up. Bob was 16 at the time I met him. A couple years later, he had shows on a couple stations which hired Co-Op High School students. He had a show that did an hour of Top 40, and he even had a printed Music Survey. Still didn't know who he was. My mother ran into and talked to him more than two decades later in Cheboygan at a Walmart Grand Opening, which connected all the dots. I think his new station, WFGE 94.3 Mackinaw City, called "Fudgie", after the resorters who go up to buy Mackinac Island Fudge, was doing a real remote there. Turns out he also went to my HS, graduating four years ahead of me.
He applied for quite a number of AM and FM stations, and at least five were granted and built, one of which was KVEG 840 Las Vegas, now Audacy's KXNT. Now he is mainly involved in putting Digital LPTVs on the air.
His other stories related negotiating interference or buying out mutually exclusive applications for the AMs, so they could be granted.