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

Posted on Monday, Jul 27th 2020

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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