In the spring of 1998, I was six months into my first job out of college—a mutual fund and insurance salesman for MetLife. The people were kind, and my boss was supportive, but it was a terrible fit for a 22-year-old fresh out of school. Nobody wants financial advice from a kid who, not long before, was slinging pizzas and wings for barely more than minimum wage.
So when my father offered me a chance to move in with him in Tampa, Florida, and look for new opportunities, I glanced out the window at the grey Buffalo skies and didn’t hesitate. Sunshine and a fresh start sounded like the only logical move. Less than a week later, I was on the road.
The first job I landed in Tampa was with what could generously be described as a pseudo-boiler room. We weren’t cold-calling doctors and lawyers with high-pressure penny stock pitches, but we were dialing other stockbrokers and trying to convince them to pump those same junk names to their clients. One step removed from the end-sucker. I was young, naïve—or rather, stupid.
Three months in, barely making any money, it became clear the whole operation was a scam and we were being taken advantage of.
But that job gave me something priceless: I met Kenny.
Kenny was smart, clever, always smiling. He had this contagious laugh and an optimism that made every bad day a little more bearable. Like me, he was a recent transplant from the Northeast. We didn’t know anyone else in town, so we started carpooling. I lived 40 minutes from the office; he lived even further out, and since my apartment was on his route, it just made sense.
Those long drives became our daily ritual—talking about everything from the absurdity of our jobs to life, dreams, frustrations. We schemed. We supported each other. We laughed a lot.
One day, Kenny told me about a new “trading arcade” that had opened up nearby. I had read a bit about these places in Forbes and Fortune—stories about the so-called “SOES Bandits” exploiting market inefficiencies. I didn’t understand it all, but I was intrigued. So we checked it out during a lunch break.
We walked into a nondescript office building, found the right floor, and eventually stood in front of a blank door with no sign, no logo—just a suite number. Curious, we stepped in. No receptionist. No waiting area. Just rows of desks and people glued to screens. We stood awkwardly until someone looked up and asked, “Can I help you?”
That was the beginning of my trading career.
For the next four years, Kenny and I worked side-by-side at that prop firm. There was no training, no structure—just a bunch of 20-somethings with no Wall Street background, learning by trial and error. We struggled, made mistakes, got a little better. And every day, we still drove in and out together, trying to figure it out.
If not for Kenny, I never would’ve found this world. I wouldn’t have met the people I’ve met. I wouldn’t be doing what I’m doing today. He opened that door for me—literally and figuratively.
We kept in touch sporadically over the years—random texts, calls, usually about football. We had Tampa Bay Buccaneers season tickets together back in the day. We were at the 2003 NFC Championship Game, which the Bucs won. We celebrated that Super Bowl run like it was our own personal victory. So many good memories.
The last time we spoke—six, maybe eight months ago—Kenny didn’t sound like himself. He’d separated from his wife. He was living alone, away from his two daughters. He mentioned “health issues,” but didn’t go into detail.
We made tentative plans to get together soon. We'd been talking about it for years, but as of yet, have not made our long-overdue reunion a reality.
Sadly, it's never going to happen.
Kenny died this week.
Alone. In his apartment in St. Pete.
I learned from a mutual friend, he'd been battling alcoholism. His mother had recently passed away. A decade earlier, his father—healthy and active—died in a tragic fall off a ladder. It’s never just one thing. It’s usually a slow, toxic cocktail of pain, loss, and isolation.
The official cause of death hasn’t been released, but it’s believed to have been a heart attack or stroke, likely exacerbated by his drinking. His dead body wasn’t discovered for several days.
What guts me is that he was alone. That he suffered in silence. That he was hurting and, maybe, felt he had no one left to turn to. So he turned to alcohol.
This wasn’t the Kenny I knew. The Kenny I knew was light. Joy. Hope.
We all have our own battles. Our own demons. Our own dark nights.
So please: check in on your friends. Particularly the ones you haven't spoken to in a while. Especially the ones who seem to be pulling away. And definitely the ones your gut says might need it.
Your voice might be the one they needed to hear to turn things around.
I’ll miss you, Kenny. Thank you for everything, and tell your parents I say hello.
RIP.
Sean McLaughlin | Chief Options Strategist, All Star Charts
