He dropped out of Princeton and wrestles with imposter syndrome. Inside the unusual rise of a Wall Street tech banker. (2024)

As a kid, Rob Chisholm was not drawn to the fast-paced, jet-setting life of a Wall Street banker.

He and his two sisters were raised by a single mother in a tiny town on the coast of eastern Canada. There, he grew up playing lots of sports and working manual labor jobs like painting houses, cutting Christmas trees, and helping out on his uncle's farm. His skills on the ice helped earn him a hockey scholarship to Princeton, but filled with a deep sense that he didn't quite belong, he dropped out in favor of a small liberal arts school.

At the time, people warned that forfeiting the prestigious job offers and well-connected alumni that come with an Ivy League degree was a terrible mistake. Well, maybe if I wanted to be an investment banker or something, I would care about that, Chisholm remembers thinking.

Fast forward 25 years, and not only did he end up in the very job he once thought of as a cliché, but he has led deal teams at some of the largest banks in the world — including Citi and Goldman Sachs. Today he is at the center of transactions shaping the technology landscape at Qatalyst Partners, the investment bank cofounded by famed tech banker Frank Quattrone in 2008.

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Wall Street is generally known for its competitiveness and stoicism. Eager to always portray the persona of indomitable dealmakers, few industry insiders talk about experiences with self-doubt, let alone how to deal with such emotions. Chisholm, on the other hand, is very open about his unorthodox path to Wall Street and the resulting feelings of being an outsider.

"I think I must have the most persistent imposter syndrome of anyone in this industry," he told Business Insider in a recent interview.

Chisholm talked with BI about his unique journey from small town to top Wall Street tech banker and how he's turned his feelings of not belonging into a competitive advantage. He also gave advice to young go-getters on how to become a successful banker while staying true to themselves.

An unusual path

Breaking into the investment banking industry is extremely competitive and cutthroat — these days, it requires young people to start the recruitment process as early as freshman year of college. It takes intense networking, jockeying for coffee chats, and an impressive résumé.

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When Chisholm was in college, he rejected the "cliche" of going to an Ivy League and getting a job on Wall Street. He only ended up there by what he described as a combination of athletic skill and dumb luck.

"I didn't go into it thinking, 'This is my thing.' I went into it thinking it was a holding pattern to figure out what I wanted to do next," said Chisholm. "But when I got into it, it turned out I really liked it."

Chisholm grew up in Antigonish, a rural town in Nova Scotia, Canada, with a population of about 4,000. As a young teen, he was recruited to play hockey at Middlesex boarding school in Massachusetts by a coach his mother knew through her bookkeeping business.

"I bumped into him at a convenience store, and he said, 'What are your grades like, and how'd you like to go to prep school?' And I didn't know what prep school was. It was just so far away from my life in Nova Scotia." Chisholm said.

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At Middlesex, it was the first time he was surrounded by kids from extremely well-networked and wealthy families. But it wouldn't be the last.

His skills on the ice and in the classroom earned him a scholarship to play for Princeton's Division-1 hockey team. As he sat in the university's famous lecture halls, however, his mind continuously wandered back to a passion he had developed in high school and that was rooted in his childhood on the shores of the Atlantic — the environment and sustainability.

So, against the advice of most people in his life, he transferred to Middlebury College in Vermont after his sophom*ore year, which allowed him to major in environmental studies.

"Trying to stay true to that thing your gut is telling you to go do was something that continually guided me a lot in my career," Chisholm told BI.

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Immediately upon graduating, Chisholm won a one-year grant to travel around the world researching small fishing communities and fisheries. After that, his first job was at an environmental nonprofit — the kind of gig he had always dreamed of.

Once there, however, he found the pace slow and soon became restless. At the time, Chisholm admitted, Wall Street seemed like the "complete opposite in terms of the culture and the incentives" he thought he wanted. But at least it could help him pay his student loans.

He landed his first finance job at ACG Partners, a small investment bank in Boston. The intensity of banking culture was exciting, and in many ways, familiar to him.

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"What I liked about it then was that it was really challenging. I felt like I was an athlete again. It was like, where's the edge of what you can do? How little sleep can you get, and how many models can you crank out?" he said. "I like to be pushed and challenged and feel like I'm learning."

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Imposter syndrome as an advantage

For the past 25 years, Chisholm has focused on covering various aspects of the technology sector, from hardware and semiconductors to cleantech. Now he covers software and AI. He has had stints at some of the most prestigious banks out there, including several years as a director at Deutsche Bank and as a managing director at Citi.

Most recently, Chisholm led Goldman Sachs' TMT team in San Francisco. In June 2023, just six months after landing the prestigious partner title, he departed the firm.

Chisholm said Goldman "wasn't an easy place to leave," but that Qatalyst's culture drew him in.

"Of all the things that investment bankers do, M&A is by far the most interesting to me, and unlike traditional bulge bracket banking, that is everything we do at Qatalyst," he said. "You can wake up on a Monday morning and the world will be different than it was Sunday night when that deal you were working on for six months or a year gets announced."

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Throughout his career, Chisholm has been part of transformational tech deals from Salesforce's $15.7 billion acquisition of Tableau, to Figure's $675 million Series B capital raise, which included a strategic partnership between the AI robotics startup and OpenAI.

But through it all, he still thinks of himself as the small-town hockey kid from Antigonish. In fact, he was reluctant to be interviewed for this story for fear of tooting his own horn too loudly. When he did agree, Chisholm was adamant that the piece not be so much a profile as a service story to help young professionals. (We landed on a mix of both.)

Investment banking at the highest level is a relationship business — so it's not unusual that top banks are filled with charming personalities. What seems to set Chisholm apart is that he isn't afraid to be open and vulnerable (his candidness about having imposter syndrome caught BI's attention when we interviewed him for our AI Banker List in 2023).

Chisholm says he is just trying to build real, personal connections and that these qualities are what help make him successful. Investment bankers work on high-stakes transactions that can create a lot of stress for clients, said Chisholm. So if you don't have a trusting foundation, it's harder to give clients advice they might not want to hear.

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"The first thing people think about when they think 'investment banker' is not necessarily someone with a really high degree of empathy who understands people at an emotional level and can help them make hard decisions in a moment of high stress," Chisholm said.

"It's a trust relationship, and that's the best part of this job. That's when I feel like I'm doing something important in the world in the same way as when I went into the environmental nonprofit world."

Covering a high-profile industry like software technology can be particularly intimidating, he said, because he's advising huge companies with whip-smart leaders. But something he has learned over his career is that clients are people first.

"Yes, the reason you're sitting in the room is because you do a certain job that is presumably helpful to them in some manner, but the only reason they're going to work with you and not the other guy who just walked in here saying the same thing about software multiples is because they have some kind of human connection with you."

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If you walk into a room thinking you know everything, you might set yourself up to fail. That's why Chisholm views his imposter syndrome as a "strategic advantage" in his career — it makes him work harder.

"I try to use it as a motivating factor, and it's probably pretty consistent with a healthy fear of failure I've had my entire life."

Advice to up-and-comers

To be successful bankers, young people should focus first and foremost on their relationships, Chisholm said. This may seem contrary in a business where juniors spend most of their first years building financial models in Excel or putting together slide decks, but the people at your own level are going to be key to your long-term success.

"They will be shocked when they turn 40 that people that they were hanging out with when they were 25 are now starting to run hedge funds and become leaders at private equity firms, and they're CEOs of companies," he said. "The passive act of going out and being an interesting human being in the world has longer-term benefits."

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Chisholm also believes young people need to accept and normalize making mistakes. He grew accustomed to being critiqued in hockey, which has taught him to welcome feedback rather than dread it.

"Feedback isn't negative. It's a way to learn and grow. When you're an athlete, your coach is always telling you what you're doing wrong and correcting it," Chisholm said. "So take feedback as something you're really grateful for."

Chisholm says he sees many young people wanting to know how they can get to the top as fast as possible. But a career in banking is a marathon, not a sprint to the top.

Have patience, he says, because there are no shortcuts, and experience is the only way to build real confidence and skill.

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"If you're someone who wants to be at the highest level of your industry by the time you're 30, don't do this. You're not going to be there," he said of being a banker. "Recognize that this is a long road, and enjoy the ride."

He dropped out of Princeton and wrestles with imposter syndrome. Inside the unusual rise of a Wall Street tech banker. (2024)
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