(Stock photo by Greenleaf123/Getty Images)
A central Iowa man convicted of defrauding an elderly women out of tens of thousands of dollars has been ordered to cease his business practices.
The order against Alan S. Kessler, 70, of Waukee comes three months after he indicated to a judge that he continues to have a relationship with the victim in the case.
State records show that Kessler, a self-described “business and life coach,” is the president of a business identified as Optimal Health Technologies, also known as Ask The Coach Inc.
According the Iowa Insurance Division, Ask The Coach has never been registered in Iowa as a broker-dealer authorized to sell securities and Kessler has never been registered as a securities agent or investment adviser.

In April 2022, a woman filed a complaint with the Iowa attorney general, alleging Kessler had defrauded her then-70-year-old mother, identified in court records as Jenny Eishen, by inducing her to invest $80,000 in Ask The Coach. The attorney general’s office referred the case to the Iowa Insurance Division, which initiated an investigation.
According to court records, Kessler met Eishen through the online dating site eHarmony in January 2022, and the two entered into a romantic relationship. Within a few weeks, prosecutors later alleged, Eishen sold her Toyota Highlander to Kessler for $3,000, although it had a Blue Book value of $20,000. A week later, Kessler allegedly sold the vehicle to a dealer for $16,100.
Soon thereafter, Eishen entered into a written financial arrangement with Kessler that indicated she had asked Kessler if she could become a director and business partner in his new business that involved the purchase of “red-light therapy technology” and the resale of that technology through Kessler’s Optimal Health Technologies.
The agreement allegedly described red-light therapy — often used to treat acne, but also used by some for purported benefits related to pain relief — as an incredible business opportunity to bring the technology to chiropractors and physical therapists. According to the division, the agreement described Eishen’s $80,000 investment as “one of the strategies (she) will use to make sure her retirement years are fruitful and allow her to enjoy her life to the fullest.”
In exchange for her $80,000, Eishen was to receive a 30% stake in Ask The Coach. As part of the deal, Kessler also made a personal guarantee to Eishen for the principal amount of the loan, according to the division.
Eishen then obtained a home equity loan on her Waukee condominium and gave $80,000 of the proceeds to Kessler. Kessler allegedly deposited the $80,000 in an Ask The Coach business account but within days transferred $70,000 to his personal checking account which previously had a balance of $49.
In June 2022, Kessler allegedly wrote a check to Eishen for $30,000 that was marked “pay off loan” in the memo line and told Eishen the remainder of her funds was in the stock market.
The division alleges that on Aug. 13, 2022, Kessler bought a Corvette for $52,000, and that he later told a division investigator Eishen told him to use the money she had invested to purchase the car. Kessler never invested the $80,000 into any red-light therapy business, the division alleges. To date, Kessler has allegedly paid back Eishen only $45,259.
‘I am simply trying to move on with my life’
Court records indicate that in 2023 Kessler agreed to plead guilty to charges of second-degree theft and securities fraud. He was given a suspended prison sentence of five years on both counts and was fined $1,025. He then agreed by consent order to “cease and desist from all future violations of the Iowa Business Opportunity Promotions Act.”
Last month, the division filed its cease-and-desist order, alleging Ask The Coach is still an active business that is engaging, or may engage, in fraudulent or deceptive practices.
“It is contrary to the public interest to permit (Kessler and his business) to continue to use fraudulent and deceptive practices in the state of Iowa,” the order states.
The order requires Kessler to “immediately cease and desist offering or selling a security in this state” unless that security is properly registered by the division, and that he pay restitution to Eishen in the amount of $34,741.
Kessler has the right to request, by Feb. 21, a hearing on the matter.
The Iowa Capital Dispatch was unable to reach Kessler for comment. However, in October 2024, Kessler discussed his view of the case when he petitioned the court to have his convictions expunged from the public record.
In his written request, Kessler argued that “as a 70-year-old man in the final stage of my life, this felony conviction will make it impossible for me to have any type of life without misery from making it impossible to live or work anywhere when a background check is performed … I only took a plea so all the parties pulled into this situation would not have to testify and the ridiculous cost and the delays that the state put me through.”
Kessler also told the court, “I am still with Mrs. Eischen (sic) and she will tell you that I have done nothing but try to make her life better and be there for her when her entire family walked away from her … I am simply trying to move on with my life without being a felon and the misery that goes with it.”
District Court Judge Charles S. Sinnard denied Kessler’s request for expungement.
Eishen told the Iowa Capital Dispatch on Thursday that she doesn’t feel victimized by Kessler. She said her daughter, with whom she’s now estranged, was “snooping” through her records and found evidence of the payment to Kessler.
“She ruined everything for us,” Eishen said. “Alan and I were going to do a business together and she interrupted it … He has been very good to me.”
She said she and Kessler recently bought a house and live together in Indianola. “I have supported him all the way,” she said, noting that the Corvette he purchased was “in the garage right now … We’re doing very well together now.”
She acknowledged that in 2019, long before she met Kessler, she was the victim of what prosecutors later called a “sweetheart scam” in which she turned over all of the money from her 401k plan, plus $20,000, to a man she had conversed with online and who claimed to need the money to come visit her. She “never met or spoke to” the man before she sent him the money, according to prosecutors.
“That was in Kansas City where I lived at the time,” Eishen said. “The man promised me a lot of things and it was all crooked … I lost, I would say, about $50,000. I don’t know for sure how much it was, but that’s what I am guessing.”