This Is New York: Robert ‘Toshi’ Chan, From the Trading Floor to the Party Floor

NEW YORK—Imagine only having to work four months out of the year by throwing wild parties for thousands, and spending the rest of your time traveling the world.

The party thrower and now novice hotel owner, Robert Chan—also known as Toshi—was not always so popular.

Chan is an only child; he grew up as a first generation Chinese-American in San Francisco. His father owned a grocery store in Chinatown. “My childhood was hard, but I don’t think it was different from any other immigrant family that came with not a lot of money,” he said.

Chan went to a Catholic high school, where most of the student population was Italian. “No one called me by my first name. All the other kids had real names, but I was only Chan,” he said.

Chan was good with numbers, good with words, but bad with people. He went to Columbia University to study mathematics; he was unrecognized at his high school reunion.

So why did he begin throwing parties?

Chan left for New York, unhappily and quietly, at age 17. He wanted to change himself, start over in a new city. Upon arrival, he started going by the nickname “Toshi,” the name of the most popular guy at his high school.

He didn’t adopt Toshi’s personality, but began throwing parties at Columbia with the new vibe that came with the name.

At first, all went well. Chan made friends, girls talked to him, he wasn’t alone anymore. His parties were the events to go to on campus. As time went by, however, the parties became larger, wilder, and more rampant.

They started raising safety concerns, and Chan was expelled in his senior year.

Luckily for Chan, his freshman year internship at Wall Street led to a job training offer.

Without finishing school, he was offered a part-time job at Citibank. Chan went directly to the bank’s training program and became a trader.

As a twenty-something, he suddenly controlled billions of dollars every day and received a promotion within five years.

“Trading is not so much [based] on raw intelligence, it’s about how quickly you make decisions that will limit your losses,” Chan said. “I was good at video games; it’s not so different from that.”

But Chan’s communication skills were still not ripe. “I used to think if you made money you’re the most important person in the world,” he said. He often disrespected his co-workers and seniors on Wall Street, considering his ideas more efficient than others’.

“I couldn’t see myself moving up because I didn’t have the people skills,” he said. “I didn’t have the maturity to be a team player.” Chan felt that he was still young and wanted to explore his interests. And just like that, he decided to pursue an acting career.

“Everyone thought I was crazy to leave Wall Street to become an actor,” he joked. “And they were right.”

Chan had never acted before, but for the ensuing years he put his heart on the line for just about every audition he could find, receiving little in return.

It was 10 years before he booked his first significant role in a short ABC series.

When he found out he got the part, Chan told every soul that he knew, from close friends and acquaintances to people he saw on the street.

The debut was going to open doors for him—it was set to air on national television. However, the night it was supposed to air, President Bush declared war on Iraq. The show was rescheduled and eventually canceled.

“It was my first major heartbreak,” Chan said.

A few years later, he landed a role in Martin Scorsese’s The Departed. His character was only in one scene. He didn’t tell anyone about the role until the movie came out and he was sure the scene was still there.

In the meantime, Chan had continued to throw parties as a side job and was making hefty profits. Although the parties had expanded to 4,000 people, Chan said he tried his best to preserve the “same kind of ‘come into my home’ feeling.”

Chan said his starting point was to break down people’s social barriers.

“When you go to a club, they can show you a good time. But you never feel like you’re going to someone’s home,” he said. “People want to be cool, they don’t mingle so much.”

Taking Chances

For most people, having a reliable source of income from a job that does not require much effort is more than enough. Not so for Chan. He decided to dabble in the hospitality industry and now runs the Flatiron Hotel. It’s his first hotel, first restaurant and bar, and first penthouse.

“It was something I never thought I’d do. It’s just part of the fluidity and being open to opportunities,” he said.

People come through word of mouth. “We have 500–600 people come through every night, even Mondays,” he said. His Broadway friends he met through the actors union have Monday nights off and often stop by to sing a tune.

According to Chan, his restaurant has become a springboard for novice performers.

His bar books 18 lesser-known bands and amateur singers a week. One of their regulars, “City of Six,” recently signed a contract. “And we discovered them here,” he said. “My joy comes from their success. I’m older now, and I realize that it doesn’t have to be just about me.”

“It’s hard to find a place in New York City for musicians and artists where the owner cares for them. We pay them, we feed them. We give them a lot of love here,” he said. “When the performers feel love and happiness, the performance is so much better. My job is [for them] to use this as a launching pad to go on and be too big for us. That’s my purpose in life,” he said.

He works hard to ensure the noise coming from the hotel doesn’t upset his Flatiron neighbors.

“These are skills I didn’t have in my early 20s,” Chan said. “After experiencing a life of adversity, I realize you need to be a consensus builder. That change happened in growing up, meeting more people. You realize it’s not just your way.”

Now, at 38, he has enough money to retire, but chooses not to. “Having a comfortable life, to me, is no life.”

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