Community Insurance for Runners

    Insurance for Runners


    Winston Cook is the president and CEO of Henley Financial & Wealth Management and he’s interested in working with runners. Cook, with 28 years of experience in the financial markets, is also the husband of a senior executive with Athletics Canada. He believes that when it comes to future planning and wealth management, runners make particularly savvy clients.     

    “The running community is the biggest bunch of planners that I know,” says Cook, a half marathon finisher who has watched his wife finish marathons in Boston, New York and Chicago. “If you want to run Boston, you have to have a plan in place; you have to train—that’s all goal-setting, and that’s essentially what my entire business is about.” 

    Cook’s business is a full-financial wealth management company that provides a wide spectrum of financial services—from investments, savings and living benefits to “death insurance,” which no one wants to talk about, but often times, at the exact worst moment, becomes the most important problem he solves.

    “You’ve done everything you can possibly do for your children, given them every opportunity and then the rug is pulled out from under everyone, and now your loved ones are told to figure it out,” says Cook, who thinks hard discussions are the best ones to have when dealing with something as important as financial planning. “If you plan for the inevitable, you can help your loved ones, not only in the future, but for generations to come.” 

    The planning aspect of one’s financial security isn’t the only area where being a runner dovetails with being financially astute. According to Cook, runners are adept at delaying gratification and used to both exerting discipline and planning for the long, slow run. Things we do as part of our hobby are also characteristics which will help us improve our retirements and live comfortably in our old age.

    “A runner would never show up at a race without preparing, you make a diligent plan and execute it because you know that’s the best way to cross the finish line,” says Cook, adding that the one time he didn’t follow his own advice, at the Seattle Half Marathon, it was such a brutal experience that he never ran that distance again. “Life, racing, training, saving and planning are all basically the same thing—you do everything you can to give yourself the best possible outcome.” 

    There are many types of insurance, beyond life insurance. And Cook says that insurance companies often rate their clients based on age and health. Since Cook’s Company is an unaffiliated brokerage—he spent a decade working with a major insurance company, but left because he felt his employer was more concerned with their own bonuses than with their customer’s health – he’s able to seek out the best plan for each individual client. He has no ulterior motive or parent company to serve.

    “All I do is listen to my clients and put the right financial needs in their hands,” says Cook. “I’ve been in the business long enough to know what works and what doesn’t, and, just like with training programs, there is no one way to reach your optimal performance—you need to make a plan, monitor it diligently, and keep adjusting as the unexpected inevitably occurs.” 

    Runners, of course, know that anything can happen on race day. And Winston Cook knows, as we all do, that only one thing in life is certain, and the best way to approach that is to be prepared. Speak to Cook for a detailed analysis of your finances. And prepare yourself for life, and death, as if it were race day. 

    For more information, and to schedule a consultation with Cook, please see

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