Finding the Path

“In every man, heredity and environment have combined to produce a creature of certain abilities and desires— including a deeply ingrained need to function in such a way that his life will be MEANINGFUL. A man has to BE something; he has to matter.”

-Hunter S. Thompson

For nearly two years, I’ve been wanting to tell this story. Something has held me back. Fear? Some degree of embarrassment, perhaps? Worried that the stigma associated with financial planning and wealth management would elicit eyerolls?

 For most of my career, I have been chasing something. I think we all are. And even when I found it, I still didn’t honestly believe it. Could I really find my place and my people, working in wealth management? Would anyone else believe it if I told them? More eyerolls? It took me a minute. But once I believed it, then embraced it, I came to see that my story might help others to find their own greater happiness. In fact, I wanted *everyone* to find that same happiness. That’s when I knew I had to share my experience.

For 17 years I worked in equities trading. I would often refer to what I did, in a word, as “sales”. And it never made me particularly proud to say that at parties. Despite a lot more intricacy than the term might suggest, I never thought anyone outside of the industry would find that intricacy particularly compelling. “Sales” became an easy way to perfunctorily answer the question while allowing the conversation to move towards other, more interesting topics.

In the early days, the work came down almost exclusively to how much of a good time you could show your clients: elaborate steak dinners, taking clients on ski trips or to the Super Bowl or the best concerts in town. And for those that wanted to “get ahead”, there were always opportunities to push the envelope into more provocative (or illegal) activities, as well.

The business was competitive, but it didn’t take a big brain to be successful. It often came down to who was the wildest. Or who joyfully (and drunkenly) made the biggest fool of themselves. I appreciated the fast-paced nature of the work, the camaraderie, the pressure of having so much money on the line every day. And yet, I recognized that I wouldn’t ever be the craziest guy on Wall Street. I would never separate myself by doing the wildest thing that made everybody laugh, cringe, or maybe both. And most importantly, I needed to be myself; I couldn’t pretend to be someone else, just to earn more business or make more money.

Thoughtful Guidance

As I searched for my place in this bizarre world, I soon found an opening. Luckily, I had great guidance from a few smart and thoughtful mentors. The industry was evolving rapidly, and these mentors showed me a different way to stand out, a way to solve problems by using creativity and intelligence. I could separate myself by doing what I did best – connecting with people. I wouldn’t compete on wild. I would compete on brains, responsiveness, and authenticity.

As our business changed, so did the people who ran it. People who excelled with jokes and drugs and entertainment — but no substance – were losing relevance. Computers began replacing humans. The nerds began winning. Wisdom trumped wild. More and more people, who had once made tons of money and had built themselves a high-roller lifestyle, were being fired — or “repriced.” 

Many found a second home in wealth management. Having spent their careers following and trading stocks, managing people’s money seemed like a natural pivot. I remember being wary of these guys, nervous that they’d be trying to sell me something or turn me into a client of theirs, just because I knew them from their previous life. I knew how most of those firms did it – the first 100 days was “make a list of everyone you know and try to get them to be a client”. Ewww. No, thank you.

 Yet there was also something I found appealing about it. I loved the idea of helping actual people, not just big corporations. It drew me in on a personal level. Growing up, I watched my parents struggle with their finances. Any conversation about money would quickly devolve into an argument that ultimately went nowhere. We spiraled into debt. I watched so many of my friends’ parents struggle, too. I wondered what they could’ve done if they had someone in their financial corner, helping them make hard decisions and have hard conversations. When I thought about a career in personal finance, those were the folks I wanted to help.

 But my aversion to sales — and how people might react when they discovered what I did for a living –kept me away. It was one thing to be selling to clients in the equity trading world; they expected it, they even enjoyed it much of the time (See: elaborate steak dinners, concerts, Super Bowls, etc). But having to sell to the guy you meet on the first tee box? Or even worse – your friends and family?

 I worried that people would avoid me, like I had avoided others before, because they feared I’d always be trying to turn them into a client. I wouldn’t get the best from people, I wouldn’t get their authentic selves, because they would always be just a little wary of my friendship or my intentions. Maybe it would even change the way I saw the world — would everyone I met become a “target” in my mind? I was worried.

Taking the Leap

I had expressed these reservations to my good friend, Brian. He was CEO of a wealth management company, and we had often danced with the idea of me joining him. He claimed that their approach was different, but all I really knew was that he was different. Brian wasn’t the “stereotypical” wealth-manager-guy. He truly cared about people and about forming connections. He was eminently trustworthy. I had known him half my life. As roommates in New York City in our mid-20’s, we shared a bathroom for two years — it doesn’t get much closer than that. But I assumed that he was the exception to the aggressive, over-promising, sales-driven culture that the wealth management industry had the reputation for.

But then, a funny thing happened: Brian was deciding to start his own company, just as I was coming to a crossroads in my own career. We talked about what this company would look like, how it would be managed, what its values would be. It finally began to click. I had seen enough examples of great leaders and bad leaders in my time that I knew what I would do if I had the chance to start from scratch. I knew the kind of culture I wanted to build and be a part of. We shared a vision for not just a company that would be good at what it did, but a company that could change the industry – by empowering people, by helping anyone who wanted it, and by eliminating “sales” from the mindset.

I came to see tremendous alignment, both in what we wanted from a business, but also what we wanted out of life. We would use our knowledge and skills to help people. Help them gain confidence and control in their financial lives. Help them remove the pressure and the overhang and the guilt, and all the other negative associations that people often have with money. Help them eliminate fear and uncertainty. Help them have hard but necessary conversations and come out the better for it. Help people achieve their full potential — through education, encouragement, and empowerment. If we did it this way, we wouldn’t have to “sell” anything. Because isn’t that really what we all want?

Two years later, here I am, loving the business I was once intrigued by and afraid of. I don’t ever want to do anything different. This small but mighty team is building a company I couldn’t be prouder of. The most amazing humans work here. I know it sounds corny, but I don’t care — we are a family, and I feel lucky to be a part of it. We practice daily gratitude, we celebrate breakthroughs and hugs, and we lift each other up when we need it. We “enter the danger”, committing to vulnerability and honesty as a path for building up stronger and truer. We bring our authentic selves to our work and our clients, every day. We’re all nerds about personal finance. We focus on solving problems and empowering people. We treat everyone with respect. We are fortunate to work with some incredible clients, whom we value as people and are also lucky to call friends. And we especially love the exponential power of bringing us all together, team and clients alike…the power of creating a community and enjoying what magic springs forth from the connections that are made!

 I feel so fortunate to be part of something much greater than just another “me too” company. And this is what I’ve been chasing, all along, I just didn’t know it. Until I finally caught on.