Adolph Frederik Linden (aka prisoner #14851) did it all. He owned a bank, a hotel, a record label and a radio network. But a lot of it was luck. He married well and inherited most of it. He was born in 1889 in Iowa but moved to Seattle as a youth. In high school he worked at a lumber camp, at a deli, and eventually Puget Sound Savings & Loan bank. He married the bank presidents daughter and the rest is history.
It's a great leap from banking into media. He began in 1927 with two moves, the purchase of KJR from Vincent Craft and the founding of the Northwest radio Network. At KJR he expanded the station with a full orchestra and a load of live talent. It was good for ratings, but not at all profitable. In 1929 he'd taken on so many loans form his own bank it became unseemly. He stepped down as president of the bank and focused on radio. In quick succession he bought KEX in Portland, KYA in San Francisco, and KGA in Spokane. Around this time he also began calling the network ABC, the American Broadcasting Network. Strangely, this is of no relation to the ABC network of today. More here.
By the Fall of 1929 it was in free-fall. Linden owed almost 100 grand just to the phone company for the networked programming. At the last second Twentieth Century Fox sent him a note that they'd like to buy up the beleaguered ABC network. Linden piled the family in the car and headed off to New York City to do the deal. It was the rescue he desperately needed. If you remember your history, you know what's coming next. While he was literally in transit to NYC on Tuesday, October 29th the stock market collapsed. It was Black Tuesday. The bank he just left went bankrupt. By the time he got to Manhattan the deal was dead.
Linden was broke. He sold his car, and borrowed money from a friend to open a small restaurant. It flopped. His wife took a floor job at Macy's. He was arrested on a grand jury warrant on charges relating to the bankruptcy of the Puget Sound Savings & Loan bank. There woudl be three messy dramatic trials. In 1932 he was convicted of grand larceny. [I wish we still arrested bankers] He served 5 years at Walla Walla State Penitentiary making acetate recording discs on an assembly line. More here.He was paroled in 1938 whereupon he started a business in vanity and short-run recordings. This time the honest business took off. By 1943 he opened Western Recording studios to supplement the field recording he'd been doing. By 1946 they were issuing commercial recordings on 78s. He had a few hits and worked his way back into radio from the programming side. His label put out over 200 albums even lasting long enough to see vinyl pressings in the 1950s before he sold it off. More here.