How a farm kid cold-called his way onto Wall Street

In 2019 I was 25, selling house painting door to door and paying off $60,000 of credit card debt. My best friend and I were so broke we furnished our apartment with free couches from Facebook Marketplace. He'd been my archrival in the painting business, number one in Canada for College Pro while I was number one for Student Works, in the same territory. I drove the U-Haul, because growing up on the farm I'd learned to drive a 28-foot truck.

Around then I met a guy named Dave who told me to get into commercial real estate. I looked into it and learned the hardest firm to get into was Eastdil Secured. So that's the one I wanted.

Burning the boats

I quit my job and sold my house. I did a trip around America interviewing at real estate firms, JLL in Dallas and CBRE in San Francisco, living out of hotel rooms. Eastdil turned down my online application.

I was 27 and had never set foot in New York City, or anywhere in the Northeast. I booked a one-way flight anyway.

I lived out of a hotel in Times Square and spent my days cold calling and cold emailing managing directors at Blackstone and the big banks. I knew no one. No fraternity, no alumni network, no contacts. Eventually one of those calls turned into a referral, and the referral turned into an interview.

"We're full in New York"

They told me the New York office was full and offered me an interview for San Francisco instead. I told them I wanted New York.

Then came the Excel exam, and I was not good at Excel. So I asked the hiring managers for two hours, and I spent them watching YouTube videos on my phone, learning how to build a real estate cash flow model from scratch. I ended up doing an okay job.

Then they asked why I wanted it.

"Look, I may not be the blue blood that grew up with this and had 15 internships. I'm a kid from the sticks, but I will outwork the blue bloods, and I will earn my keep."

They were honest back. It would be 90-hour weeks, and I would hate my life.

I went back to the hotel to wait for a call at 3 p.m., and I missed it. When I finally got through, they asked how I was feeling. I told them I'd sold my house and quit my job. "Hernando Cortez burned my ships, and here I am."

"Congrats, you're in."

That was 2021. My dad happened to be in town from London, and I got to see how proud he was. A few weeks later my mom drove a diesel F-350 for 65 hours from our hometown in Western Canada, with my little sister, to bring my things to a 380-square-foot apartment in Manhattan.

What I got wrong

I thought outworking people was the same as being the best. It isn't.

On my first big deal, a $300 million building in SoHo, I got staffed at 9 a.m. on a Friday and worked until 4 a.m. Saturday, then all weekend, then until 2 a.m. Monday and Tuesday. I passed out at my desk at noon on Wednesday. Meanwhile, analysts five years younger than me, who'd been preparing for this since college, could do the same work five times faster on three hours of sleep. One of them could underwrite a billion-dollar deal over a weekend.

I'd been a sales manager with eight people under me. On Wall Street I was the oldest analyst on the bottom rung, making $80,000 in New York City. My ego took a beating.

But I was in the room. I watched people negotiate $50 million price swings the way I'd negotiate $50 with a friend. Effort got me through the door. What I actually learned came from being surrounded by people who were better than me.

It's the same reason I want to join a great sales team now, even if it means starting near the bottom again.

A question for you

Have you ever taken a step down to be in a better room? Email me and tell me how it went. I read every one.

One thing worth your time

Think and Grow Rich by Napoleon Hill. Building that cash flow model in a hotel room off YouTube videos, it felt like I was summoning the "infinite intelligence" he writes about.