A Serial Entrepreneur’s Journey in Real Estate Tech: Cloud CMA CEO Greg Robertson (Part 1)

Greg has done multiple ventures in Real Estate Technology and discusses his long career as an entrepreneur in the field.

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born and raised? What kind of background?

Greg Robertson: I was actually born in the Seattle area way back in 1967. My parents split up when I was about five years old. One thing that is unique about me is that they had a unique custody arrangement. I would, for a time, spend a year with my father and then a full year with my mom.

In the meantime, my father, being a special agent for the government, would get transferred a lot and my mom would move a lot. During the course at high school, I think I moved thirteen or fourteen different schools – up in the Seattle area, down in the Bay area, in San Francisco, San Jose, Texas, San Antonio, Honolulu, Oahu, and then down here in Southern California as well. 

Sramana Mitra: What about school? Where did you do college? 

Greg Robertson: I ended up back here in Southern California for 11th grade. I was supposed to go back to my mom in Texas, where she was living but I had decided at that point that I wanted to graduate with people I knew from high school in my 12th grade because going back to another school in Texas, I wouldn’t know anybody for my senior year.

I stayed here where my father was and concluded high school here and one of my friends ended going to DeVry institute of technology that had a Bachelor of Science program in Electronic Engineering Technology. I didn’t know what I was going to do. He was my best friend and my father heard that he was going there and we all went to that campus and checked it out and I enrolled half there.

This was pre-internet, they did trimesters so you would go to school all year round. I basically got a four-year degree in about three and a half years. I have a Bachelor’s in Science in Electronic Engineering Technology. 

Sramana Mitra: What did you do? Was it programming concentration?

Greg Robertson: Electronic engineering technology. 

Sramana Mitra: What year did you come out of college?

Greg Robertson: I graduated in 1989.

Sramana Mitra: In 1989 the internet was not yet in play.

Greg Robertson: In the last couple years of high shool, I was really into computers. I had bought a radio shack. I saved a bunch of gift certificates from Radio Shack and bought a TRS-80 color computer and I did some programming on that with my friends. It was really early.

I think my senior in high school actually started to have a computer program and I think I knew more than the instructor in that program. I went to get an electronic engineering degree that was in my interest. Going to that type of school was good for me after high school. 

Sramana Mitra: What happens next?

Greg Robertson: One of the nice things about DeVry was they’re very helpful in helping you find a job. As soon as I graduated, they hooked me up with a lot of interviews and I found a job right after college.

I was going to work for a sound and lighting company. They did a lot of special events work and corporate gigs like IBM’s general annual sales meeting. That would be mixed in with music festivals. It was still the same thing – lighting, PA, and back then they had slide projectors and multiple panels with the speakers where they had multiple microphones and mixers.

This segment is part 1 in the series : A Serial Entrepreneur’s Journey in Real Estate Tech: Cloud CMA CEO Greg Robertson
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