Colonel Conn had heavily invested money in other businesses. One of his disappointments was his involvement with early electrical generating systems. In 1904 he constructed a powerhouse and provided electrical service as a competitor to the Indiana and Michigan Electric Company. They later bought out Conn's service at a great sacrifice to himself. The turning point to Conn's financial affairs and public life took place in April 1911 when he and his wife executed a trust deed for $200,000 covering all their possessions for the purposes of bonding the Conn indebtedness and securing working capital, the longest bond to mature in ten years. Conn's money problems stemmed partly from failed ventures like his entry into the utilities business, the building of his third factory, and its loss to fire, and his loss of a costly lawsuit filed against him by a former company manager. The deed included in addition to the horn factory and what was then known as the Angledile Scale Company, and The Elkhart Truth, some sixty descriptions of real estate in Elkhart and vicinity, various real estate mortgages, 125 shares of stock in the Simplex Motor Car Company of Mishawaka, Indiana, a seagoing yacht, a lake motor launch, and much valuable personal property. Conn also lost considerable face when he was ordered by a judge to publicly apologize for publishing inflammatory comments about J. W. Pepper. The Musical Courier picked up on the legal problems and reported about how Conn was knowingly making false statements about Pepper. In his published apology, Conn attributed his aberrant behavior on an addiction to tobacco.