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‘We’re really glad you made all these mistakes.’ This financial planner uses his five near-bankruptcies to help clients manage risk.

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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 bankrupt, he came close. All the while, he continued to build his financial planning practice.

By 2010, he decided to focus full-time on his financial planning firm. Now he owns Kahler Financial Group in Rapid City, S.D. A certified financial planner, he oversees six employees and says his firm has about $180 million in assets under management. 

Learning from experience

It may seem odd that an entrepreneur with such a rocky past could thrive as a financial planner. But for Kahler, his near-bankruptcies serve a valuable purpose.

“I’m quite open with clients about it,” he says. “They take comfort in what I’ve been through. I tell them about all my warts and they trust me more.” He recalls one client who told him, “Rick, we’re really glad you made all these mistakes so that you can tell us what not to do.”

Given his penchant for risk-taking, Kahler is careful to advise clients to calibrate their own risk-reward ratio. He cautions them to plan carefully before banking on a big potential payoff.

“I’ve learned that risk has to be done with a lot of intentionality, awareness and education,” he says. That’s better than impulsively throwing money at a get-rich-quick idea. For example, Kahler is not a fan of cryptocurrency. “It’s obviously super-fraught with risk,” he says.

In recent years, Kahler became a certified financial therapist (CFT-I). Developed by the Financial Therapy Association, this designation enhances his ability to help clients create healthy financial relationships and strategies to address problematic financial behaviors, usually driven by past traumas, so they can adopt healthy money habits and make sound financial decisions.

Pursuing training in financial life planning and financial therapy has enabled Kahler to work on his own relationship with money and gain a deeper understanding of the motivations and money scripts that underscored his entrepreneurial ventures. “I was so highly leveraged,” he says. “I had huge anxiety around money. Today, I almost have a kind of PTSD about taking on too much debt.”

Kahler is also more self-aware of triggers that can stoke money-related stress. “I carried a lot of anxiety in my body,” he says. “I was never really aware of that until I started learning more. I’ve done a lot of therapy and mindfulness meditation work.”

Also read: ‘It still shocks me when I look at my account.’ How financial advisers are coping with the bear market.

Plus: ‘This is what I believe and what I stand for.’ Financial advisers consider dumping clients who spout offensive political views

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