We had the good fortune of connecting with Jessica Caballero and we’ve shared our conversation below.
Hi Jessica, what role has risk played in your life or career?
Risk taking has always been my biggest teacher. I like to joke that my tenure at Home Depot gave me my MBA, but “daring greatly” as noted sociologist and lecturer Brene Brown calls it has taught me so many invaluable lessons in life and in my career. Fear used to be the reason why I tended to hold back, but I flipped a switch and realized that there are really only 2 outcomes when taking a risk: you either don’t succeed but you learn so many lessons along the way so that it’s never deemed a failure, or you make it. The human brain is really excellent at telling us what we may lose when taking a risk but it’s lousy at letting us understand what we may gain.
Getting comfortable with being uncomfortable is something that took me awhile to learn. So many people don’t want to alter their lifestyle when they take a career risk. But I was willing to live more meagerly for awhile. I had my Dave Ramsey courses and triathlon training that helped prepare me for the inevitable hardships that cutting the strings to regular paychecks every two weeks would bring.
I used a “burn the boats” mentality when I left corporate America by starting “Jess in the City” real estate. There was absolutely no going back even though it was extremely scary at first. If I had to distill it down, I’d say that it was my self-confidence that allowed me to succeed. At the end of the day, I knew that I wasn’t going to starve or be homeless. I knew that I’d figure out a way to survive initially and then that innate trust in my abilities allowed me to flourish by my second year.
But I wasn’t always that confident in my success. I had to escape that mentality. Evolutionary speaking, our brains were adapted to keep us safe in our caves which was equivalent to my 9-5 job in corporate America. By all measures, I was successful but wasn’t fulfilled. I knew there had to be more out there professionally and starting my own business where I could help people find their dream homes appealed to my empathetic nature. That allowed me to overcome that fear mentality that keeps so many of us stuck with our unsatisfying jobs.
I’m lucky to have found my passion where every day is different. There is no mundane, there is no routine so therefore, there can be no boring. I can be meeting new clients on Monday, working with lawyers on Tuesday during closings, mentoring new agents on Wednesday, arranging a house for showing on Thursday and touring luxury homes for clients on Friday and hosting open houses while meeting new people on the weekend.
The juice has been worth every squeeze along the way, and I’m just so happy that I conquered fear and took the risk.
Alright, so for those in our community who might not be familiar with your business, can you tell us more?
I sell the American Dream to people. I put them into houses where they raise their families and build their lives. It’s a personalized experience where I get to work with clients to provide them a curated and concierge level of service in their home buying/selling process. I know first-hand how important home ownership is and I see myself as an obstacle remover for my clients in all of this. Easing the stress of peoples’ dream home search is something I truly pride myself on. I tell my clients to let me worry about all of the details while they concentrate on imagining themselves and their décor in what may be their dream home. A stress-free experience is what Jess in the City strives for and I think my client testimonials attest to that.
It’s not been a straight line to success. Lots of trial and error. What I’ve settled on is a combination of things such as trying new ways of conducting business, seeking business coaching, and having a mentor early on in my career. But above all, being consistent with my marketing efforts has been instrumental. But I also don’t discount my diligent and punctual follow up to my clients and being there for them even after the transaction is complete. This is absolutely a relationship business.
It’s never been easy. You don’t get into the real estate business if you want an easy career. Every deal is different and while it thrills me, it does keep me on my toes, and it’s taught some tough lessons over the last 4 years.
I’ve learned that people work with people that they like. Timely follow up and connecting on a personal level really matter. I really believe strong connections are a huge key to my success. I know that people trust me and will call me when they have major life events. I’m part of the family. I want them to call when they’re contemplating doing home renovations, when they’re having a baby or considering buying a vacation home.
But on the other hand, I’ve also learned that not everyone is my client. I’m never going to connect with everyone and I’m okay with that. But it’s been one of hardest lessons to have learned.
I’d like the world to know Jess in the City is a lifestyle brand that will expand to other things related to the home in the future.
I continue to be a work in progress as it relates to the business and giving people exceptional service. I’m constantly learning and growing based upon all of the experiences and deals that I’ve been part of to become a better, more experienced realtor.
Let’s say your best friend was visiting the area and you wanted to show them the best time ever. Where would you take them? Give us a little itinerary – say it was a week long trip, where would you eat, drink, visit, hang out, etc.
Get ready for a week-long gastro-delight as Jess in the City has your entire week planned for you. We would start on early Thursday afternoon; Jess in the City would pick you up from Hartsfield-Jackson Airport and we’d immediately go to The Optimist to beat the crowds to enjoy the best oysters in Atlanta while sipping champagne. We’d then move to Westside Provisions for some shopping and Jeni’s Ice Cream, followed by a stop at my friend Jen Balcos Art Gallery to check out the latest works from Lynx Nguyen. We’d end the night at Marcel’s for their amazing fried bread starter, one of the best steaks you’ll experience and hands-down the most wonderfully sublime ambience in the city.
On Friday morning, we’d start at Buttermilk Kitchen for an amazing breakfast before heading to Bloomingdales to see stylist Derek Reid for the latest fashions. We’d then head to a not-to-be missed lunchtime event at Kura conveyor belt sushi, followed by getting manicures and pedicures (don’t miss the honey and lemon experience) at Jade Nail Salon and massages at Iyashi (tell Aaliyah hello from Jess). We’d try to catch some jazz at The High Museum before enjoying dinner at Secreto in Brookhaven and feasting on the city’s best boneless fried chicken and corn muffins. Say hello to Rodney tending bar and you’ll be lucky to have Sebastian as your server. We’d stop at nearby Southern Custard for their seriously delicious chocolate custard with sprinkles for dessert. We’d end the evening at Eleanor’s, our favorite speakeasy in the city.
On Saturday, we’d start at the St. Phillip’s Cathedral farmers market in Buckhead before enjoying brunch at Canoe. We’d then try out the Porsche Experience and put a 911 through its paces. We’d grab a late lunch at the Grana rooftop and enjoy one of the city’s best wood-fired pizzas near its second-story fire pit area. We’d then head on over to Midtown Beach Club for some fun in the sun at its rooftop pool. Jess in the City would then sojourn for a quick 9 holes at Putt Shack (think Top Golf but for putt putt) while enjoying one of the best espresso martinis the city has to offer. We’d then head on over to Eclipse de Luna for some small plates and salsa dancing until the wee hours of the morning.
On Sunday, we’d start with a tour of Atlanta homes with our Xander lattes in hand, showcasing my top 10 must-see Atlanta homes and then drive down for a quick brunch at Blue Eyed Daisy at the elegant Serenbe community south of the city to do some zip lining, marvel at the unique architecture of its homes, and finish up with some goat yoga and drinks at The Hill. We’d then rush back to the city for a quick style by Jessica GoldStein at J Gold Salon before heading to enjoy amazing craft cocktails and chicken barb at Rumi’s Kitchen—a true gastro delight in Atlanta.
To work off that extravagant weekend, we’d start Monday morning with some walking or cycling at East Palisades Trail in the Smyrna area before heading up to the mountains and some pontoon boating at Big Canoe for the afternoon. We’d get back just in time to do yoga at Battery Park and then grab some pizza (yes, Jess in the City is a huge pizza fan) at Crispina (hi Chef Rafael). We’d freshen up before finishing the night at Yebo Beach House for its Rosemary Vesper Martinis.
We’d start out Tuesday properly at the Silver Skillet for a true Southern style breakfast. Jess in the City would then shoot over with you to Cos at The Shops of Buckhead to be styled by my bestie Faye. We’d then find our way to Swoox for luxury furniture and decor along with our designer friend Pam Sessions for the latest in-home stylings (Jess in the City has to keep up on the latest trends in design for her clients after all). We’d then grab some tacos at Taqueria del Sol before trying out the new Float Atlanta for some serious float therapy and relaxation before heading to the Atlanta United soccer game at Mercedes-Benz stadium.
We’d finish out the week properly by starting out Wednesday at Woodhouse Day Spa for its signature four-handed massage before heading over to OVME for a laser facial. Then we’d head over to The Atlanta History Center to learn more about the city’s history and grab lunch to go from the onsite Souper Jenny (and hope they are serving their to-die-for cream of mushroom soup). A can’t miss site would be next at the Atlanta Botanical Gardens to see the SUPERnatural Aerial Art and Alice in Wonderland exhibits. We’d then have to jaunt over to The Garden Room at the St. Regis hotel for their signature Bend and Snap cocktail and finally finish up a lovely week at one of Jess in the City’s favorite restaurants Lyla Lila (hello chef Craig Richards) for their squid ink spaghetti and olive oil cake.
After a full week of exploring the city, we’d have to go check out some homes because you’d sure want to movie to Atlanta after all of that wonderfulness.
Who else deserves some credit and recognition?
I’d like to thank my significant other for his undying support and faith in my business, especially during those times when I don’t have faith in my success. Without him, well, I don’t even want to think about where I would be without his vocal enthusiasm and time devoted to making sure that I’m safe when showing houses. He’s my true co-conspirator in Jess in the City.
I’d also like to thank a feisty realtor named Karen who was an acquaintance (now friend) at the time who told me that if I wasn’t spending 8-10 hours a day on real estate, then I should be doing something else. That was a harsh lesson to hear but it molded me to become the successful agent that I am today. Had she not called me out of the blue with that advice, I’d not be here today as a realtor. I’m so appreciative of that type of tough love.