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Chairman’s Message: Your 'Hassle Map'

Tom McCullough

As we turn the corner to spring and nicer weather, my topic today is your 'hassle map'.

What is a hassle map? It is the combination of problems and frustrations consumers experience when they use a product or service. "Think about the last time you traveled by plane, challenged an incorrect cell phone bill, or dealt with any large and unresponsive bureaucracy. Think about each extra step, wasted moment, avoidable risk, needless complication, less-than-optimal solution, awkward compromise, and disappointing outcome" (from the book Demand detailed below). Some of these hassles you barely notice anymore because they're so familiar—but if someone were able to fix them, you would for sure take them up on the offer.

This idea comes from Adrian Slywotzky in his classic book Demand:

Creating What People Love Before They Know They Want It. I heard him speak at the Rotman School of Management years ago and have read his book. In it, he cites examples of numerous companies and products that have not only reduced consumer frustration with existing solutions, but also turned users into enthusiastic fans --iPad, Nespresso, Kindle, ZipCar, the Eurostar train (that runs under the English Channel) and Wegman's (a popular U.S. grocery store) -- just to mention a few.

It also has application in the financial and investment field. Since reading this book, I have been asking people I meet with to describe their own financial hassle map. In one such interaction with an affluent entrepreneur, I heard a pretty typical list of things that drive people crazy about the current options available for effectively managing their investments and personal financial affairs.

She said: "I have no effective 'bring forward' system to make sure important tasks get done, and this weighs me down. I have a long-term but unsatisfactory relationship with my broker and need to break away. My cash management is poor and I often find myself with large chunks of cash in various random accounts. And because I have multiple accounts, when I need cash or want to reduce an investment holding, I don't know which position to sell, nor what the tax implications to doing so are. I need monthly bookkeeping, but I am not organized enough. I am overwhelmed with the paper associated with numerous investment and banking accounts, with no overall summary or sense of how things are doing. I am behind on my corporate tax returns. My will is out of date. My aging mother’s affairs need attention. I find it all quite stressful, frustrating, and unsettling and I'm sure I am wasting money and time. I would like to have my personal affairs run properly, like a business. But I can't do it myself."

We hear this often from entrepreneurs we meet, and they are often happy to hear that as a family office, we specialize in fixing people's hassle maps and making their lives easier. Everyone's hassle map is different, depending on your personality and financial circumstances. But the common elements in an effective solution are clear goals, coordinated management, and proactivity -- just like how you would run a business. Imagine!

Enjoy the transition to nicer weather and I look forward to catching up if we haven’t had the chance to talk in the last while.


Tom McCullough

Tom McCullough is Chairman and CEO of Northwood Family Office. The combination of his background, along with his own family’s desire for a truly ‘comprehensive, customized and confidential service, led him on a search for a multi-family office. Tom is a frequent speaker on issues relevant to families of wealth and is the co-author of Wealth of Wisdom: The Top 50 Questions Wealthy Families Ask and Family Wealth Management: Imperatives for Successful Investing in the New World Order and the soon-to-be-released Wealth of Wisdom: Top Practices for Wealthy Families and Their Advisors. He is an adjunct professor and Executive-in-Residence at the University of Toronto’s Rotman School of Management MBA program. He is an Entrepreneur-in-Residence at Western University’s Ivey School of Business and a member of the Editorial Board of the Journal of Wealth Management. He was recently awarded ‘Best Individual Contribution to Thought Leadership in the Wealth Management Industry’ by the 2020 Family Wealth Report Awards.

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