How Radical Honesty Landed Me My First Job on Wall Street

Editor's note: One skill can make the difference between being an ordinary investor and an extraordinary one. In this piece, recently published in the October 22 issue of the free Chaikin PowerFeed daily e-letter, our colleague Gabe Marshank explains how this one key skill helped launch a two-decade career managing hundreds of millions of dollars... and why it's so crucial in investing.

In 1997, I landed my first job on Wall Street.

I wasn't a finance major. I had never taken an accounting class. My Yale degree was in political science, and my career ambition was, in retrospect, almost comically modest – to make more than $25,000 a year and live in New York or San Francisco.

But I ended up working for Lee Cooperman – a Bronx-born Goldman Sachs legend who was, at the time, running one of the most successful hedge funds in the country. And I got the job, not because of a perfect resume or polish... I got it because I told the truth.

Let me explain...

My junior year at Yale, I interned at the Council on Foreign Relations. My mentor there, Jay, asked what I wanted to do after graduation. I had no idea – but I told him my goal was to make more than $25,000 a year. He laughed and said, "You should talk to my friend David. He works at a hedge fund."

"What's a hedge fund?" I asked.

"No idea," he replied. "But he makes a lot of money."

That was enough for me. I looked up "hedge fund" in the Sterling Library card catalog. The definition was vague. Something about private pools of capital. I still didn't really understand it. But I called David anyway.

He interviewed me over the phone and asked about my background. I mentioned I'd been on the Yale crew team.

"Why'd you quit?" he asked.

"Because I wasn't very fast and it stopped being fun."

"Not very fast?" he asked.

"I kind of stunk," I admitted.

There was a pause.

"That's the most honest answer I've ever heard in an interview," he said. "I think you might fit here."

He invited me down to New York. That's how I found myself in the offices of Omega Advisors – a hedge fund run by Lee Cooperman, who was already a Wall Street legend.

Lee wasn't a man of half measures. Big guy, bigger opinions. He had spent 25 years at Goldman, rising to become its chief equity strategist before launching Omega with his own capital. But despite his gold-plated career, he was at heart still a kid from the South Bronx.

When I got to his office, he barely looked up.

"Kid, I don't have time for this," he barked at David. "If you like him, I like him. See how cheap we can get him."

That was my job offer.

As I was leaving, I noticed a strange sculpture in his office – a box with dollar bills sticking out of it, covered in peanuts. I asked about it later.

"It's because I'm nuts about money," Lee said.

So I got the job. It was an environment without pretense – no one had time for anything but the truth. And I was about to learn that in several key ways...

Lessons Learned on Wall Street

I started at Omega with a $35,000 salary – a windfall compared with my expectations. My job? Do everything. Run down lunch orders. Make copies. Pass out end-of-day reports. It was the equivalent of starting in the mail room...

But I was curious, and I made myself useful. I listened. I asked questions. I sat in on company meetings and analyst calls.

And I learned. I had no finance background, so I got one – an Excel class, then one in accounting. Eventually, I took and passed all three levels of the Chartered Financial Analyst exam.

The hustle paid off...

One of the firm's top analysts, Larry Robbins, was alone in a two-man office. He invited me to take the other desk – installing himself as my mentor.

Larry would go on to found Glenview Capital and manage billions. But back then, he was just the smartest investor I had ever met.

He taught me how to tear apart a business model, from revenue to free cash flow. We built Excel waterfalls showing exactly how a dollar traveled through a company's financials. He emphasized understanding cash flow over reported earnings... substance over spin.

At Omega, I saw how even seemingly bulletproof businesses can implode. We invested in a funeral home company – stable, right? Steady demand, forever customers. But it collapsed under too much debt. That was my first lesson in the danger of leverage.

I also witnessed the Asian financial crisis up close. I had barely started when the Thai baht devalued and currencies across the region spiraled. It was called a "thousand-year flood."

It happened in my third month on the job.

What Omega gave me was more than just a job... It was an entire worldview. It taught me that numbers matter more than narratives... that leverage can kill even the most obvious investments... that honesty – with yourself and your partners – is a competitive advantage.

It also gave me access to people who thought differently.

Lee hired what he called "PhDs" – poor, hungry, and desperate. Not necessarily polished, and not always pedigreed... but always smart, curious, and ready to grind.

Wall Street has a reputation for being elitist, and in many ways, it is. But the best hedge funds know they're in the business of ideas, not appearances. They care about insight, not credentials. They'll take radical honesty over empty confidence any day.

That's why Lee didn't ask me what classes I had taken. He didn't grill me on valuation techniques. He trusted his guy to spot someone who had the raw tools and the right attitude. He saw that I put as much effort into delivering a trader's lunch as I did into building an Excel model... And then he tried to get me as cheaply as possible.

If my years on Wall Street have taught me anything, it's that you don't need to be the loudest person in the room. You need to be the one who asks the right questions. You need to know when you don't know. You need to see the thing everyone else missed – and be brave enough to say it out loud.

That started my two-decade career managing hundreds of millions of dollars in risk at firms like Steve Cohen's SAC Capital and David Einhorn's Greenlight Capital. But it all began with a brutally honest answer to a simple question:

"Why'd you quit the crew team?"

Because I wasn't very fast. And it wasn't fun. I kind of stunk... and I knew it.

Turns out, that was exactly the kind of thinking Lee Cooperman wanted to bet on.

So the next time you're trying to pitch an idea – or land a job – don't sell a story. Tell the truth. Investors can smell the difference. And sometimes, that's the edge that matters most.

Regards,

Gabe Marshank

Editor's note: In his 20-year career on Wall Street, Gabe generated multiple nine-figure wins for hedge-fund billionaires like Steve Cohen and David Einhorn. Today, he's stepping forward to share the keys to his success – and the hedge-fund-style approach he takes to navigating the markets... Plus, he'll reveal an idea from his new portfolio that he believes could turn every $1,000 into more than $25,000.