Simon is the principal owner of Command Entertainment Group, a company that connects brands to celebrities and influencers. He started as an intern, moved up the ranks to partner, and now runs the full-fledged entertainment agency day-to-day.

SO, HOW'D YOU GET STARTED?

I moved to New York in 2005 to start my career in public relations. I was working for a woman named Lizzie Grubman and I knew absolutely nothing about the PR industry. Within four to five years, I became partners with an offshoot company called Command PR with my soon to be business partner, Jonathan Cheban. In 2011, I acquired Command PR. At that point, it was a full-service lifestyle PR agency and we transitioned it into a talent procurement agency. We help brands connect with celebrities. We don’t represent talent, we represent brands. So that’s been my trajectory over the past 14 years.

"One of the things I had to learn really early on — and this is a struggle for me — is learning to cope with the unknown."

LESSONS LEARNED ALONG THE WAY?

One of the things I had to learn really early on — and this is a struggle for me — is learning to cope with the unknown. Running a business forces you to deal with uncertainty in so many different situations, whether it’s with clients or potential new hires. You also have to learn to be a ruthless prioritizer because it’s just not possible to do everything.

ACCOMPLISHMENT YOU'RE MOST PROUD OF?

Last year, I decided to embark on something that I knew nothing about. It was a passion project called A. Human and it was this experiential art installation. I was so intimidated by doing anything in the creative field. It's not something that I've ever felt well versed in, but I was really interested in learning more. Entertainment marketing has always been like second nature to me. It's something I feel very comfortable in. I can talk about it for hours. It doesn't feel like a job, it feels like an extension of my personality. While the creative field and building this art installation was very much unknown to me and very much intimidating. So building it, I was immensely proud of what we had created together.

HOW DO YOU DEFINE SUCCESS?

Success for me has always been about progress. There's that famous quote, “Happiness is progress.” As long as I’m growing and learning and challenging myself, I consider that to be success. Even in situations where there is failure, there is still elements of success because you took that risk.

WHAT ROLE DOES FAILURE PLAY IN BEING SUCCESSFUL?

All the cliches around failure ring so true to me. You learn more from failure than success. That’s something, had you told me at 21, I’d be like, Okay, that’s too new-agey and cliche for me. But over the years, some of the biggest failures in my career have led me to opportunities that I would have never in a million years had contact with.

WHAT INSPIRES YOU?

My friends and my colleagues inspire me. I'm so proud of the things they've accomplished and it inspires me to take the same risks that they take. When someone has the gusto to start something, it's such an inspiration. I like to surround myself with those people because it motivates me to do and try new things.

"Get rid of all those toxic naysayers because they will crush your dreams."

GO-TO PRODUCTIVITY HACK?

Consuming ungodly amounts of coffee.

PIECE OF ADVICE?

Surround yourself with people who are your number one supporters and believe in you. Get rid of all those toxic naysayers because they will crush your dreams.

HOW DO YOU ACHIEVE WORK-LIFE BALANCE?

Work-life balance is critically important to myself and the folks that work for me at Command Entertainment Group. We have a rule that there is no emailing, unless it's critically important to a deal, after 7:00 p.m. We're in this culture now where you are constantly on call. If you're constantly on your phone responding to messages, it doesn't allow you to enjoy an evening out with your friends or destress after a crazy day. So we try not to respond to emails past seven. Clients will email us, but there will be no interoffice chatter throughout the weekend.

MOST UNUSUAL ITEM IN YOUR HOUSE?

I am Marie Kondo before Marie Kondo. I am not a thing collector. I live a clean life inside my office and apartment. The one thing I think that is potentially a little strange is the motorized standing desk in my guest room.

FAVORITE SELF-CARE PRACTICE?

Journal writing. Our mind works in mysterious ways. You only remember the bad. You forget the accomplishments and the progress you’ve made unless you document it. What I like to do is go back and look at all the progress I’ve made. So journal writing has been a really therapeutic way to just increase my mental clarity.

"As long as I’m growing and learning and challenging myself, I consider that to be success."

FAVORITE WAY TO LET LOOSE?

I have a beach house in Montauk and I go out there with friends and we have the best time. We do absolutely nothing. There tends to be a lot of margaritas and we just unwind and destress from the week.

WHAT'S NEXT FOR YOU?

I am working on several projects, none of which I'm ready to share. I am constantly looking for ways to evolve and find new things that inspire me. I’m excited for what the future holds!