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Reflecting on 45 Years in Wealth Management

Sep 17, 2024 | Steve Ross


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Remembering with gratitude the wonderful mentors who helped shape my career in the wealth management industry.

It’s a bit unbelievable that today marks my 45th anniversary in the wealth management industry. I began my career on September 19, 1979, as a George Washington University college intern (despite having the intention of following three Ross generations at our family business, Ross Plumbing & Heating.) Everything in life is serendipitous, and it was fate that motivated me to apply for an internship at my original firm, Ferris & Company – subsequently called Ferris, Baker Watts and eventually acquired by RBC Wealth Management in 2008. 

It didn’t take me long to realize that I could make a career in this business, partly because I was blessed to have incredible mentors such as George Ferris, Sr., George Ferris, Jr., and Gail Winslow. These three individuals took a chance on me with their selfless devotion to help me prosper in my business development. I can vividly recall many of their “fireside chats” where they discussed how markets and various events during “the old days” impacted stock or bond prices. 

I enjoyed seven years of carpool rides with Mr. Ferris Sr. (1893-1992) where we discussed his experiences over an illustrious 70+-year career in the securities industry (as it was called back then). My first encounter to a real bear market swoon occurred on Black Monday, October 19, 1987 when the Dow Jones Industrial Average plummeted 509 points or 21% in one day. I tried my best to assuage my clients’ worries and concerns about their portfolios, and this was during a time where one did not have the internet to get instantaneous values on portfolios. 

During our carpool ride home that evening, I blurted out, “Mr. Ferris, you must have lost millions today.” His immediate response: “Steve, what time is the World Series game on tonight?” He was deliberate in his retort in order to teach me that perspective and time would win out over “short-termism.” He further said to me, “Stay in the game with quality. Cream will rise to the top.” Indeed, Mr. Ferris was prescient because the stock market did recover quite nicely. 

I owe a debt of gratitude to George Ferris Jr. because he was the one who offered me the opportunity to be his father’s carpool mate. It didn’t take me long to accept because Mr. Ferris’s parking spot was private and free, whereas I was paying $6.25/day plus a $.25 tip at the nearby parking garage, and that outlay added up to about $1,500/year of savings in my pocket! 

Gail Winslow was my immediate boss during my early years at the firm, and she made an indelible mark on me in so many ways. I observed how this magnanimous woman could capture an audience with her depth of knowledge and storytelling. She had many fine traits, and one was to develop impeccable trust with her clients and their extended family members. Moreover, she spent a lot of time working with and empowering women as investors, during a time when the industry was very male dominated as was the investment decision makers in a family. Gail was a trailblazer who broke down barriers to help people of all backgrounds succeed as investors. 

These three individuals all had some common traits which they conveyed through their actions. One was, “Your word or handshake is your bond.” Another was, “Never take a short cut to get to the finish line because your name or reputation is all you have in life.” Moreover, akin to what I have heard for years from the mouths of Warren Buffett and Charlie Munger, these mentors would use times of market disarray to their advantage. They would go against the herd during difficult times to find values in the marketplace, despite the objections of the stock market fortune tellers. 

I am indebted to my mentors. I’ve used their sage wisdom as a guide when we experience many cycles of greed or fear in the marketplace. Time and history are the beacon for successful investing.