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Inspiring Conversations with Jessica Caballero

Today we’d like to introduce you to Jessica Caballero.

Hi Jessica, so excited to have you on the platform. So before we get into questions about your work-life, maybe you can bring our readers up to speed on your story and how you got to where you are today?
It sounds trite, but I got sick of the rat race of corporate America where I’d spent my entire career since moving to Atlanta after high school. It took me a long time to figure out that I’d be happier being my own boss. I got my first taste of it when I created a high-end fashion consignment concept called “Cycle of Style” which was a by-appointment-only styling and wardrobe reconstruction business. But trying to manage a full-time corporate gig with this initial dalliance in entrepreneurship proved too taxing at the time. I didn’t see it as a failure when I shut it down but just a series of lessons that served me well as I contemplated what was next.

In 2018 I made a giant decision–to close the book on a 9-5 job working for someone else and start the new venture of “Jess in the City” real estate. I used a “burn the boats” mentality. 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 be without. 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.

Can you talk to us a bit about the challenges and lessons you’ve learned along the way. Looking back would you say it’s been easy or smooth in retrospect?
I wasn’t always that confident in my success. I had to escape that fear-based mentality. That was the largest hurdle that I had to overcome. What I’ve come to learn is that 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 feeling truly fulfilled. I was no longer content to just feel safe and comfortable. 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. Sometimes the grass is not only greener but so much more rewarding when working by a different set of rules known as entrepreneurship.

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.

As you know, we’re big fans of Jess in the City Atlanta. For our readers who might not be as familiar what can you tell them about the brand?
Jess in the City Atlanta which was established in 2018 helps sell the American dream. Home ownership is near the top of adult accomplishments here in the US and I am honored to help my clients navigate that journey.

We attempt to provide a concierge experience for our clients beyond the standard real estate transaction. I bring a team of lenders, inspectors, contractors and designers to the table so that my clients can truly have it all in one single experience. Clients become friends and family. We live by referrals, so Jess in the City is never transactional. It’s all about the relationships. Not only do we want to help you with your current real estate needs but we want to be involved for the next two decades. The only way we can do that is by operating with integrity and honesty. You always get the direct truth from us, even if it’s sometimes hard to take especially in this wild Atlanta real estate market.

As a 24 year Atlanta resident, I’ve always been a city girl. I’ve seen Atlanta evolve and expand over the years. I pride myself on knowing the city very intimately. If you want mid-century modern at a particular price point for example, I can tell you exactly where to look. Jess in the City also is focused on helping folks get started in property investing and beginning the passive income building process which we hold near and dear to our hearts. Whether it be a long-term rental or a property that permits short-term Airbnb rentals, we can find the perfect place and bring the management company that will run it all in case you don’t want to be the day-to-day landlord. We do it all for our clients. We never leave our clients on an island when it comes to their real estate needs, whether it be arranging for custom closets, automated blinds, and audiovisual systems to working with some of the top interior designers in Atlanta that we can personally recommend.

Jess in the City strives to provide a bespoke experience for our clients and would be happy to help you in this shall we say interesting Atlanta real estate market.

What would you say have been one of the most important lessons you’ve learned?
Getting comfortable with being uncomfortable is something that took me a while 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 a while. 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. That mentality switch was difficult but it taught me so many things about myself. I’m much stronger and more resilient than I ever thought. That’s why I love talking to young people who are looking to get into the business. I tell them the truth that it will be really tough that first year. You gotta sacrifice, put in the work every day and create your own system and brand but to trust me that it will be worth it with hard work.

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