An Investment Banker Who Just Won Olympic Gold Shares His Secrets

Between photo ops, celebrations, and press gatherings, Best, 26, sat down with Business Insider to talk about how he juggled his job as a banker and his intense training schedule. Speaking via Zoom (on the side of a Parisian street while waiting for a car to take him to his next event), he said part of his strategy has been overcommunication with his bosses and finding ways to work smarter instead of harder.

Rower and Analyst

Best won gold in the coxless men’s four event, which is a 2,000-kilometer race between boats with four rowers and no steering captain. It’s his first-ever Olympic medal, but Best also competed in the 2020 Olympics in Tokyo in an eight-person boat event, where he and his team came in fourth place.

He studied business, engineering, and finance at Drexel University in Philadelphia, and after a couple of other analyst roles, landed at Union Square in November 2021. The technology-focused bank has represented companies like private-equity firm Carlyle and startup Blue Apron, according to its website.

“I’ve loved the sectors that we cover. Hearing what the big companies are looking for in acquisitions or investments, seeing the metrics within the company and the technology, it’s exciting to me,” Best told BI.

Best started at Union Square Advisors a few months after he competed in Tokyo in 2021. Until about March of this year, he followed an intense daily schedule that split his time between training and in-person work.

His schedule went as follows: Wake at 5:30 a.m. for training in the East Bay area. Finish around 8:30 a.m. and take the BART train (Bay Area Rapid Transit) to the office in San Francisco. Arrive at work by 9:30 a.m., work until about 5:30 p.m. Take the BART back into the East Bay for a second round of training until about 8:30 p.m. Go home and finish any other work. Go to bed by about 11 p.m.

Getting it all done

Best said the keys to maintaining that lifestyle were communication with his bosses, organization of his work and self, and practicing efficiency skills.

“For me, that meant keeping a daily to-do list and a detailed, structured way of looking at it,” Best said. He categorized the items in that task list into three categories: “I have emergent tasks, I have medium tasks, and then long-term tasks. And the key is just keeping on top of those items as they move around so that nothing gets dropped.”

When he first started, he said he studied YouTube videos on Excel shortcuts so he could move through tasks more quickly and be more efficient.

“Tasks that you would take a first-year analyst 45 minutes, you can kind of buckle down to 15 or 18 minutes. You start finishing those projects a little quicker, and all of a sudden you have 45 minutes at the end of the day that you can be more efficient with,” he said.

As he got closer to the Olympics, his routine had to become more focused on training and less on work.

“It was hinged on over-communication and being like, ‘Hey guys, this is kind of my capacity.’ Towards the really heavy ramp-up, I moved into a more back-office support role, off of more active deal teams.”

That also meant moving to a fully remote schedule as he traveled across the country to compete in races.

“COVID was kind of a blessing in disguise in that it enabled remote work, and we saw one of our most successful years fully remote,” he said “It was kind of a proof point that it was possible.”

Union Square’s rowing tradition

Best credits the flexibility of his bosses with helping him achieve his Olympic dream. It wouldn’t have been possible, he said, if he worked at a large investment bank.

“The boutique investment bank model, it’s kind of like that lean deal team structure. So the circumstance that I found myself in, I don’t think necessarily would work in a bulge bracket where you have your rigid analyst class, you have your associates, you have to do this X, Y, and Z.”

It doesn’t hurt that Union Square has a rowing tradition. Devon Ritch, one of the bank’s partners, was a rower at the University of California Berkeley in the mid-90s and had connections to the USA national team program for rowers interested in careers in finance. Jordan Vanderstoep, a rower a few years older than Best who previously worked at Union Square, also helped Best get the job.

Best said of Vanderstoep: “He blazed the trail and showed there was a value-add in the position in addition to supporting the rowing, so long as you can make sure that your deliverables were communicated appropriately.”

Indeed, Best believes that there are a lot of similarities between being a great rower and working as an investment banker.

“At the end of the day, you need to get the boat across the line as fast as possible, and there are a lot of things that go into it — dialing in your nutrition, dialing in your sleep, making sure you’re training in the smartest way,” he said.

“It’s the same thing with the deal process,” he said, adding, “You’re baking off against some of the best people in the world, and knowing what your client is looking for and how you can best position yourself to deliver exactly what they’re looking for is part of the competition.”

Creating a roadmap

Best wants to see more companies support Olympic dreams.

“Not everyone is Simone Biles, who has the athletic contract to look forward to — $3.2 million a year and on the face of every Got Milk? ad and whatnot. In rowing, there’s not that much outside of the Olympics in terms of financial income,” he said. “So having places that support Olympic dreams truly makes it possible, and I’m happy to say Union Square is one of those.”

When Best and his three teammates won gold on Thursday, it was about 3 a.m. in San Francisco.

“The race was very early in the US, so we were all asleep — but we all watched the replay immediately, saw them win, and then saw the medal ceremony, and we all started crying,” Mike Meyer, the CEO of Union Square, wrote in an email statement to BI. “I sent the video of the race and the medal ceremony to 50 people on Wall Street and everyone was amazed that someone could be an Olympian and a Wall Street analyst — and were further amazed that he and his team won the gold.”

Best will stay in Paris for the rest of the Games to walk in the closing ceremonies and then stay in Europe for another week to celebrate. After that, then he plans to fly home to the Bay area and spend the next year fully focused on work before he decides whether to pursue the 2028 Games in Los Angeles.

“I’m looking forward to getting into the full-time gig — working with the analyst class we have, a great group of people, and kind of being more of a senior analyst. I actually still have to take my Series-7,” he laughed.