Money Moments

Managing the portfolios of wealthy investors taught me how to be a tougher negotiator

By: Kelley Keehn on January 10, 2020
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Money is a funny thing. It’s tangled up with just about every aspect of our lives — from where we live, to what we eat and the quality of our relationships — so it’s no wonder that all of us have opinions on what we should do with it. But what shaped our approach to money in the first place? What pivotal moment forever changed the way we think about our finances? To explore these questions, we’re introducing MONEY MOMENTS — a regular series where Canadians reflect on a moment in their lives that shaped their attitudes toward money. 


I began my financial career at one of Canada’s largest banks, working with clients who had significant investments of half-a-million dollars or more. As a Personal Investment Manager, I was in charge of 24 branches. 

I was also just 21 years old.

Those branches were regularly on the lookout for clients who had large amounts of dollars sitting around in their savings account or who they thought had investments at one of our competitors. These clients were what I like to call the “seemingly wealthy.” On the surface, they looked like a million bucks. Donning fancy cars and expensive clothes, they were the envy of their communities. Of course, appearances can be incredibly deceiving.

The first time I realized this was during an appointment with a very well-known businessman in the city I was living in at the time. He was super celebrated as a local success story, and so it was no surprise that one of the bank tellers booked me an appointment with him. When I opened his file at the bank and saw his net worth statement (all of his assets minus all of his debts), he was nearly one million dollars in the hole! This sort of thing happened on an almost-weekly basis. But what struck me most about these kinds of clients actually had nothing to do with their net worth: it had to do with their confidence.

When getting a business loan or renegotiating a mortgage on their rental property, house or cottage, almost all of my clients would ask for a reduced interest rate. And when locking in a GIC, every investor asked for a better deal or for a reduction in the investment fees they paid. To the average person, a quarter of a percentage increase on your investments or reduction on your mortgage might not seem significant, but my savvy clients knew otherwise. They were uber aware that these small numbers add up to hundreds, even thousands, of dollars per year. Some clients, when paying for our drinks or lunch, would scour their bill to ensure they weren’t overcharged for an item. And if they were, they were confident enough to call the server over to have it rectified. Watching the wealthy be so protective of their money and confident in negotiations taught me that when you really appreciate your money — no matter how much you might have — your money will appreciate, too.

What struck me most about these kinds of clients actually had nothing to do with their net worth: it had to do with their confidence

This realization didn’t come immediately, though. In my 20s and 30s, I struggled dearly with negotiating. It didn’t matter if it meant asking for more money when accepting a job, haggling over the price of a vehicle, or just asking for last week’s sale price on a new sweater. That was something that poor people did — or so I thought. I was raised, along with two older brothers, by a single mom living in poverty. She had to watch out for every cent she could. My clients, on the other hand, simply did it out of principle. 

My “poor kid syndrome” (as I like to call it) made me feel like I had to keep up with a certain air of wealth. Early on in my investment management job, for instance, I bought a luxury car I couldn’t afford, financed a lavish wardrobe on credit, and bought dinners for wealthy clients even though that left me eating peanut butter and jam sandwiches until my next pay cheque. It wasn’t until I witnessed my wealthiest clients guarding every penny of theirs that my attitude began to change. 

It took time, though, and I had to start small — like calling up my cell phone provider, for instance, and posing the simple question: “Can you give me a better deal?” But the more I flexed my negotiating skills, the more confident I became, and the better results I saw. I try to carry this same confidence with me today, whether it’s requesting an upgrade on my hotel room, walking away from not getting what I think is the best price on a new car, or even negotiating a book deal. I can’t say that now, at 44 years of age, I’m completely rid of my poor kid syndrome, or that negotiating is second nature to me. But I will say it’s a little addictive. And you know what? I get tremendously more “yes’s” than “no’s.”