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A Serial Entrepreneur’s Journey in Real Estate Tech: Cloud CMA CEO Greg Robertson (Part 5)

Posted on Friday, Jul 31st 2020

Greg Robertson: Dan and I stayed there for a couple years, but it was brutal. We then got a call from a friend of ours who was restarting a company that he had sold again to another company. They had given it back because they got caught up in shenanigans. He was restarting that company. It was called E-neighborhoods. He wanted to approach Dan and me about joining him in restarting it. He was going to give us a piece of the equity back. The only problem was it was in Florida. It was in Boca Raton, Florida and we’re here in Southern California. We like it here and our families are here.

Because we respected him a lot, we said we’ll come. Dan and I flew down to Florida, and we liked what we saw. He had a pretty good team. He had a great idea. It was right in our wheelhouse.

He was making reporting software for neighborhoods. You would type a zip code, then you would see a 60-page report of demographics and recent home sale. It was pretty slick.

I remember driving back from the Miami airport when I was with Dan in the rental car. Neither of us wanted to speak, because I was thinking that if Dan wants to come, then I’m coming. If he’s not, then I’m not coming down here alone. I think Dan was thinking the same thing. We had this awkward silence. I finally broke the silence and said “What do you think?” He goes “ I don’t know. I think it’s actually pretty cool though.”

A few months later, we found ourselves moving. I wasn’t married at the time. He was already married with one kid and another kid on the way. I was moving with my girlfriend. In a few months, I proposed to my girlfriend, and then we were heading to Boca Raton, Florida.

The premise there was that he had this great reporting software but it wasn’t hooked up to any MOS system. He thought we would be coming there and bringing the relationships of the MOS organization, add MOS data to his reports, and blend that data and come up with these innovative reporting software for real estate agents.

We thought that it sounded cool and that we would grow that and sell that. We moved down. The way the owner operated was that he sold the software, but he sold it on CDs and he would send agents a monthly CD with the most recent data on it. He was basically selling subscription-based software before the internet and before anyone caught on to this.

We were charging monthly fees to realtors for the software, and he’d been doing that for a while. I was fascinated by their model. When we upgraded to the Lightning 97 edition, we’d try to sell the upgrades.

His subscription thing was really odd at the time but the model intrigued me a lot. What we didn’t realize at the time was we’re getting a master’s course in subscription-based software before it even took hold. At that point, we were making $40,000 a month in shipping and handling charges.

One of our partners was like “We’re losing all that money.” That was the mentality. When we switched to the internet, we had this zero cost. We already knew the lesson of onboarding of free trials to conversion of email marketing. All the stuff that basically became fast. We learned all that. We did exactly what we wanted to do.

We grew that company. We got some big accounts.We acquired a couple of companies. We had some great growth. I don’t remember the exact figures. I want to say it was in 2007 or 2006 that we began to explore selling the company. We went on a road show. We talked to a bunch of companies.

There was a company called the Dominion Enterprises that had previously bought another real estate portal called They were the company that owned all those farm and home magazines. At one point, they also owned Auto Trader and Boat Trader.

They realized that the print business is going out soon, so they started a strategy to acquire online subscription-based companies and we were right in that sweet spot. We sold E-neighborhoods to them in 2007. It was perfect timing because the market collapsed right after.

We sold and got a little bit ahead. That whole year up to the crash, it was just off a cliff. In the end, Dan and I worked there for a year. We had always talked about starting a company together. It was never really a good time for it. We were getting tired of these guys. We weren’t particularly fond of the leadership. I was the  General Manager of the company. I was running the company. Dan was the CTO. We decided to leave in February of 2008.

This segment is part 5 in the series : A Serial Entrepreneur’s Journey in Real Estate Tech: Cloud CMA CEO Greg Robertson
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