My first Big Sale Was With a Wall Street Legend

Back in '95…

I had landed a gig at a company making glare reduction screens for those monstrous, old-school computer monitors. My luck turned around when a pal handed me the "Red Book"—basically a secret directory of every big shot in the securities biz. It felt like I'd gotten the keys to the coolest club in town, but only had sweatpants and hoodies in my wardrobe.

“My luck turned around when a pal handed me the "Red Book" -

basically a secret directory of every big shot in the securities biz.”

I decided to skip the usual suspects (IT folks, purchasing departments, and secretaries) and went straight for the head traders. Learned a few lessons quick: Don’t bother them at 9:30 AM, keep it short, and that this was either going to be incredibly exciting or incredibly confidence shattering.

My first big break was with a legend named Richard Chapdelaine at Chapedelaine & Co, near the Seaport. They called him Chappy (I had no idea who this guy was, I didn't know a Muni bond from a train ticket) . I was too green to be nervous, which probably worked in my favor. I got through to him not because I was a smooth talker but probably because he wanted me off the phone.

After a few minutes in reception, Chappy came out to get me. After a quick introduction and a puzzled look on his face after I reminded him of our meeting, he led me onto the trading floor.

Walking onto his trading floor was nothing like the movies. The place smelled of cigarettes and testosterone, guys were yelling across the room, and it was chaotic. Monitors everywhere (Quotrons, Bloomberg's, NEC's) flashed numbers I couldn’t make heads or tails of. Instead of the neat rows of screens I had seen on movie depictions of Wall Street, there were wires and empty coffee cups everywhere. But it was still my first view of a different world, and my jaw must have been on the floor.

Upon arriving at his position at the head of a long row of traders, he sat down and stared back at his screens. He must have been used to being pitched this way. I stood there for a minute then ditched my planned pitch. Instead, I spoke loudly and showed everyone the screen, pitching to the entire desk (my thought was why not increase my chances of someone being interested) "Look how it cuts the glare!" my pitch stated. It caught on—traders started calling me over, eager to see if it really worked. Suddenly, about half of them were into it, complaining about eye strain and wanting one.

Chappy, seeing the stir it caused (and realizing he had a dilemma), finally asked, "How much for these things?"

Here was my moment. I could either go all in for a sale or just offer a demo. I went for the sale. Told him we could outfit his 100 screens for $150 each, no strings attached —return them if they didn’t like them (the screens worked as advertised and rarely did they ever get returned). He bit.

With a quick handshake, I was out the door, feeling like I was floating down Water Street. That day stuck with me forever. Chappy turned into one of my best clients and even started calling me "kid", giving me shout-outs and referrals when he moved offices.

That first sale taught me everything I needed to know about hustling on Wall Street. Timing, guts, and knowing your audience are everything. I walked onto many other trading floors after that but your first big close, you never forget.