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It Pays to Be Curious
Toshi Chan with dog Ponzu

Robert “Toshi” Chan: From Trader to Actor to Hotelier

The seasoned entrepreneur offers advice on how to make seamless career transitions, even when the jumps are big ones

For Robert “Toshi” Chan, 39, making a career change isn’t just the norm, it’s a way of life. Twenty years ago, the artistic director and founder of the Flatiron Hotel made a name for himself by throwing parties by night while trading on Wall Street by day. The soirees began as intimate gatherings at his house and quickly morphed into grand affairs at spaces like the Puck Building with sell-out crowds in the thousands. Along the way, the ambitious entrepreneur, who currently lives in Williamsburg, ditched his Wall Street day job to pursue acting. Recently, he’s come full circle and is back to holding more intimate soirees, albeit now at Toshi’s Living Room and Penthouse, a bar, restaurant and event space at the hotel he founded. In our interview, Chan recounts his own career journey, one that’s tied to his insatiable curiosity for life.

COOL JOB Q&A

NY: What originally brought you to New York?

RTC: I left San Francisco to attend Columbia University, and I never left. I came here when I was 18, and I’ve been here ever since. New York has been my permanent residence. I completely changed myself. I didn’t know anyone; I made up this name “Toshi,” and I said, “This is a fresh slate for me.” And you throw away with abandon all of your fears, all of your limitations, all of the things you think you couldn’t do, you just change. New York is a city of millions and millions of people. You can completely reinvent yourself. It’s very common for people who come here to reinvent themselves.

NY: What do you look for when hiring an employee to work at The Flatiron Hotel?

RTC: The most important things I look for are cheerfulness and friendliness. You can teach skills, but you can’t teach people to be naturally cheerful and friendly. You get that feeling right away; it’s not really scientific. It’s just a feeling that you get and hopefully for everyone we hire we can say, “This person made me feel happy for no apparent reason.” It’s important for me in life. I’m not so corporate. I have a completely different set of criteria than what’s standard.

Toshi Chan

Toshi’s at the Flatiron Hotel

NY: We heard you book 18 bands and amateur singers each week for Toshi’s Living Room at the Flatiron Hotel. What do you look for when booking them?

RTC: Yeah, that number’s going to increase because I was only booking for Toshi’s Living Room downstairs, and now we’re opening Toshi’s Penthouse upstairs as well for private events. Right now it’s anywhere from 12 to 18 every week. Here’s where the friendliness and warmth come in again, and after that, you look at talent. First it’s charisma. Does this person make me feel happy? Then with talent, how do they move on stage? How is their tempo? Are they on key? Those are things I know people will be looking for when I audition. I’m an actor, but some of the philosophies and principles are the same. You want to be able to effect positive change in the audience.

NY: What’s the biggest lesson you learned in resiliency from your acting auditions?

RTC: Don’t get too high when you’re up and don’t get too low when you’re down. Try as [much as] humanly possible to remove yourself from the need to separate your feelings and your self-worth with what’s going on in acting. Always when things go really well for me, I’m never super excited — I made that mistake when I was young. And when things don’t go well, I do my best to not get discouraged. That way you won’t get too satisfied when you do something well because you can always do something better, and it doesn’t last forever.

NY: Considering you morphed from Wall Street trader to actor to party promoter and now hotelier, what advice do you have for people looking to change careers and start all over from scratch?

RTC: Frugality’s the most important thing. When I made the change, it was about being able to live simply and live within my means and give up what I thought I needed. I live very simply even now. In order to have that freedom to take that risk, you have to reduce your living to what really makes you happy. You don’t have to go to a huge, expensive restaurant. Find a big bag of pasta and cook it; it’s cheap. The heavier you are — not physically but the more weighed down you are with expenses — you’re never going to be able to take a chance. But if you’re light, you’re frugal, yeah, you can take a chance!

NY: How is it making a career change? What makes it easy? What makes it difficult?

RTC: It’s hard for most people to quit a job because they have a family, and everyone has to decide for themselves what the trade-off is. How much risk are you willing to take versus the reward? Those people who take the risk sometimes succeed.

I think failure is an exceptional fertilizer for success. I’m not saying I’m successful at all; I’ve gotten an inordinate amount of failure in my life, and I never ever forget it. For example, a complete failure was being popular with the opposite sex. I thought, I’m throwing a party and things changed and all of the sudden girls will talk to me! And by throwing the party, I try to be fluid and see what works and doesn’t work, so a lot of trial and error. The more something goes well for me, I remember that always, and it centers me, and it keeps me hungry, too. It’s psychotic! [laughs]

Taking a risk is difficult for most people. I have a huge appetite for risk. I’m very comfortable with uncertainty. It’s just the way I am. What I cannot control is what I find interesting. If I find something interesting, I have to do it! — like acting — I had to be an actor even though it’s so hard to sustain a living or when I went to parties or the hotel. My fear of taking too much risk is overridden by my insatiable curiosity.

Toshi Chan

Ground floor of Toshi’s at the Flatiron Hotel

NY: What advice would you give someone who was looking to follow in your footsteps in terms of starting a nightclub/lounge?

RTC: You have to truly enjoy it. I learned by necessity because I could not get any girls to go out with me and I stumbled upon the idea [that] if I threw a party, girls would talk to me. It sounds so stupid and simple, and when I came to New York and I was no longer in San Francisco, I changed myself. And even now, I learn by doing.

NY: Looking back at your many transitions, what would you do differently?

RTC: When I worked in Wall Street, I could have shared more of my journey with people that I worked with, rather than cut off all my ties. I wanted to focus so strongly to work on my acting ability at all costs – [it was] at the cost of all my personal relationships that I did not continue them. If I could have made more people happy in situations [where] there were confrontations [and] where I could have resolved it with the other person, that’s one thing I would correct. I don’t think I’d want to change any mistakes — of course, you don’t want to change the things that you did well — but if I changed the things I didn’t do well, then I wouldn’t be able to learn. It’s a tough one.

NY: What advice would you give to people juggling multiple gigs?

RTC: I think there’s only one thing that’s important — you have to love it! If you love it, you’ll find the time, you’ll find the energy, you’ll find the concentration. Any other thing will not work — if you do it because you want the money or something else. If you want to be an actress because you want to be famous, it’s not going to work.

I think diversity is really important. To multi-task is important for everyone. If you’re not multi-tasking, you might be too bored doing just one thing. It could be a job and a hobby or a family. I don’t have a family so I’m able to do all of this.

NY: Your transition to acting is unusual: How did you get the guts to leave your day job on Wall Street to pursue acting?

RTC: I was working on Wall Street, and I had been there for a long time. I started when I was 19; by the time I was 25, I had gotten my second bonus. I said okay, “I have a good down payment for my house,” and I got it in my mind that I wanted to be an actor, and I couldn’t stop thinking about it. I made that crazy leap! It’s one of those things you can’t help but make.

NY: Where are the best places for entrepreneurs to network in New York?

RTC: I’m not a very good networker; I’m a bit shy. I don’t think I’ve ever really networked. I prefer to let your work speak for yourself. If you really do good work, you’re going to be excited by it, and work is going to work for you. Word of mouth is going to spread about your work, and when you do meet people, you’re not so much networking, you’re talking candidly about your work. You’re being honest in the message you send and about your work — that’s the kind of networking you do. In the traditional sense, I’m not sure I’m the best person to tell how to network, but that’s how I do it.

NY: What does an average day look like to you?

RTC: When I wake up, I work in my home office and do my e-mails and phone calls and do my corporate work during the day, reports for the hotel, come to the hotel early afternoon to check rounds, and then I run the food and beverage operations and entertainment until closing — so it’s usually until two in the morning.

Find out more about how New Yorkers are making it in the big city with our Cool Job Q&As.

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