After retiring, Pipp invested in the stock market, but lost his wealth in the Wall Street Crash of 1929. He authored a book, titled "Buying Cheap and Selling Dear". He worked as a broadcaster on a pregame baseball show for the Tigers, wrote radio scripts, and worked in publishing. He organized baseball programs around his community for the National Youth Administration. He also spent time unemployed during the Great Depression. In 1940, Pipp was on the verge of bankruptcy, but he managed to pay off his debts without going bankrupt.