Welcome to TEN, CORE Founder and CEO Shaun Osher’s rapid-fire interview series with prominent CORE figures. Read on to find out how this week’s subject deals with being on the hot seat.
Having taken the plunge into the sports arena, it wasn’t long before Jessica Chestler realized that she felt more at home in a career with real estate. Here’s a glimpse into Jessica’s life in TEN questions.
1. Tell me something about your home. 
I live in the Village. I love the feel of a “mood room” so I have lots of greys and pops of purple. I have large factory style windows from floor to ceiling so it brightens up the room. Art covers my wall space which always allows for inspiration.
2. What did you do before you found this career?
Prior to this career I wanted to work in Sports Marketing/Broadcasting. I tried a few different career paths and realized if I was going to have a successful career I needed to be passionate and feel rewarded. When working in sports, I worked with the Mets and although I am still a fan I realized my love of sports would be tarnished if I continued on that path. Real estate has been a long time passion and I definitely get out what I put into it.
3. What has been the highlight of your career?
It’s hard to pick one. I am lucky enough to work with someone who has allowed me to see things I did not anticipate having the chance to see within my first few years let alone the start of my career. Every experience has been rewarding and educational. I think the exposure I have gotten working with Emily Beare in and of itself has been the highlight thus far.
4. What is your greatest daily challenge?
I am quick to a fault. I am not someone who likes having 1293 unread messages so I am constantly immersed in making sure everything is taken care of. I think it is not necessarily a problem, but I think I would benefit from taking a few seconds to put everything in order before getting myself in too deep.
5. Where do you see yourself in 10 years?
I hope to be a well-respected broker with an investment portfolio of my own. I love watching the market and I think owning a few pieces of New York real estate is something that will never be a negative in the long run — no matter how the market shakes.
6. Where do you find inspiration?
I find inspiration everywhere. It depends on my moods. I like walking around the city and looking around. Some days looking at the megatowers gives the same inspiration as looking at the chess players in Washington Square Park. That’s the incredible thing about New York — everywhere you look there is something or someone to be inspired by.
7. What’s your favorite restaurant?
That’s a hard question. I grew up in a household filled with foodies so I have been exposed to amazing restaurants. That being said, my favorite restaurant is not eclectic, just a classic. Fred’s at Barneys has been a lifelong favorite. They are willing to make anything you want in any way. They also have the best aioli for French Fries in the history of condiments.
8. What’s your favorite movie or book?
I am a big bookworm. My favorite book of all time is “The Catcher in The Rye” by JD Salinger. I keep it on top of my nightstand and flip through it at least once a year. I love Holden Caulfield.
9. What do you do in your free time?
In addition to real estate my two biggest passions are art and sports. I have been collecting art for 8 years now. I frequently attend art shows or just pop into galleries to stay on top of the exhibitions. With regard to sports, I watch every sport from futbol to football. I previously worked in sports and am a major sports fan. I am known to be very spirited when cheering on my teams. Go Buckeyes!
10. Name one thing we might not know about you?
I was homecoming queen and I think in turn it probably means I am meant to marry Prince Harry. Perhaps royalty at Harrison High School is good practice for the throne? (Also, I am a very sarcastic person.)