BEHIND THE BUSINESS

Each week, we’ll introduce you to one of our Point Loma Association Business Members who is helping our community thrive. Get to know your neighbors, hear their stories, and discover the local talent behind the work.


Name: Robert Tripp Jackson
Business:
Catalina Realty and Property Management

How long have you been in business?
September of 1995

What do you love most about what you do?
I really enjoy accomplishing the task of putting people and a deal together. I also enjoy coordinating property improvements and seeing a positive final result.

What’s your favorite local spot for a client lunch?
The Bali Hai or the San Diego Yacht Club

What’s your favorite object or item in your workspace — and what’s the story behind it?
The picture of SDYC, the Bay, and Downtown San Diego from 1970; my grandfather’s enormous rosewood desk from Teledyne Ryan, which I rarely use; and the proclamations and service awards I’ve received from my community service over the years.

Tell us about a moment when you knew you chose the right career.
I started in this business when the real estate market was flat. The training provided at the time focused more on sales tactics than on learning the practical aspects of the business. When I joined Mark Winkler’s office, things finally started to click, and I began receiving business.

What’s a lesson you’ve learned the hard way in business?
Being an independent contractor has its privileges, but you have to work at it every day. When you’ve just closed a successful transaction, don’t become complacent and take that trip. As one of my former managers, Dianne Reichardt, said, it’s like a clown juggling balls — some will drop, but you have to keep juggling.

What’s a piece of advice you give your clients or customers that will save them time, money, or both?
Let me do my job and find a solution before a conflict arises.

Which part of your job will AI never be able to do?
It’s an interesting time with AI, and learning about it is exciting and challenging. But I don’t think it will ever replace the human touch when showing property or performing certain tasks.

What makes your work environment somewhere you enjoy being?
It’s in the center of Point Loma at the Jensen’s shopping center. I’m just a couple of minutes away from OB and PL, and I can always grab a sandwich next door.

What’s your go-to music while you work?
I attempted some upbeat and relaxing music years back, but my neighbors next door found it disruptive. My taste ranges from Enya to Johnny Cash.

What other local clubs or associations do you belong to besides the PLA?
Former member of Point Loma Rotary and the Planning Board; current Trustee of the Cabrillo National Monument Foundation; YMCA Board member; SDPD Advisory Board; and a member of the San Diego Yacht Club. Also a member of the RNA and The Friendly Sons

Where’s your go-to spot in Point Loma when you need to think, recharge, or celebrate?
Cabrillo National Monument, the tide pools, or Sunset Cliffs.

What’s a local business that’s gone away that you’d love to bring back?
The Chart House, Casa de Loma, and many of the small businesses that used to be in the Village.

What’s something interesting, fun, or unique about you or your business that might surprise us?
Some of the things I run into are hard to believe — recently, getting a listing where the owner had passed away and wasn’t found in a timely manner, or the tenant who blew his lid during Covid and started a fight with nine other tenants while SDPD was nowhere to be found.

What did you want to be when you grew up — and if it’s not what you do now, why did you give up on that?
Like many kids in the 1970s watching Emergency, I wanted to be a firefighter — maybe a lawyer or a CEO. But I grew up around the real estate business with my mother being a local Realtor and community leader. So at 25, I decided to do what I do now and subconsciously followed in her footsteps.

What’s a TV show or movie that accurately or inaccurately portrays your profession — and why?
If it’s Modern Family or any movie involving a real estate agent, they usually portray the profession as corny.