Like many financial advisers, Rick Kahler runs a successful practice. But he may be the only one who has been on the verge of bankruptcy five times. Kahler started as a fee-only financial planner in 1981. It was then among his many business ventures. Beginning in the 1980s, he operated multiple businesses at once. He owned a real estate firm where he worked as a commercial real estate and business broker. He worked as a general certified appraiser. And he owned a company that bought and sold seller-financed mortgages.
“I had two or three businesses at any given time,” Kahler, now 67, recalls. A serial entrepreneur at heart, he kept seeing opportunities to expand into related enterprises that often revolved around real estate. Some of these opportunities soured. Kahler bought a mortgage on Iowa farmland that lost two-thirds of its value in a farmland real estate crash. He owned a commercial strip mall at Ellsworth Air Force Base in South Dakota that suffered a major drawdown of military personnel. He ran a factoring business in which an important client filed for bankruptcy. He even invested in a hardwood basketball court manufacturer where the managing partner had a nervous breakdown. While Kahler never went b …