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Bootstrapping with Paycheck to $15 Million from Tennessee: Gene Caballero, CEO of GreenPal (Part 2)

Posted on Tuesday, Oct 30th 2018

Sramana Mitra: Did you start this as a bootstrapped company?

Gene Caballero: Yes. We aggregated about $100,000 between the co-founders. We blew that by paying a custom shop to build us a website and a couple of apps. After about a year and a half of not getting what we want, they turned over a semi-usable product to us. They actually went out of business right after that. We knew that there was no way that we can move forward or get serious about starting a business without redoing the site.

We brought on one of our friends who was the engineering type. He went to software school to learn how to build websites. After about six months of him in school, he built the version that we’re using now. We scrapped everything that the custom shop had built. I wouldn’t say we wasted $100,000 but we certainly learned a lesson. After that, we launched the 2.0 version.

Sramana Mitra: When you managed to recover from this situation where you had a semi-competent team that put you in a bind, how much time had passed?

Gene Caballero: It was about two years. We launched in April. We had just a website. I would say about two years after that was when we had a product that we could actually use. We had the ball rolling on GreenPal in 2014 because of the setback that we had.

Sramana Mitra: Then you managed to launch in 2014. How did you bring the two sides together? You needed the landscapers and then you needed the homeowners. What was the process of bringing them onto your platform?

Gene Caballero: In the very beginning, it was all hand-to-hand combat. We went door-to-door. We knocked on a thousand doors every weekend until we had people using the site. We would go to their house and say, “I started a company. It is for lawn mowing and is purely online.” We explained to them the process. We didn’t go for the hard sale. We would just ask them if this is something that they would be interested in.

As we got deeper into the conversation, people were a little more interested in using the service. The same way for the vendor side. We got on Craigslist. There are probably 500 to 600 lawn care professionals that build their business that way, which is a tough way to build a business. It’s not very fast. We cold called those guys and explained to them what we were trying to do. We finally had enough supply that we could launch a couple of markets and get some users.

Sramana Mitra: You scraped Craigslist to get your suppliers and convince them to join you?

Gene Caballero: Yes. We spent a lot of nights and weekends texting and emailing vendors from Craigslist.

Sramana Mitra: You say nights and weekends, does that mean that you guys had to go back and get jobs in this timeframe?

Gene Caballero: I had my full-time job until about three years ago. I was basically heading the charge of aggregating vendors. During the day, the landscaping professionals are mowing and doing business. We knew that weekends and nights were the best time to reach these guys. We shifted our day to day operations around their availability.

Sramana Mitra: You’re basically bootstrapping with a paycheck.

Gene Caballero: It’s not the most fun way to do things but you don’t want to quit a job until you have some decent numbers.

Sramana Mitra: You have to pay the bills.

Gene Caballero: It’s worked out so far.

This segment is part 2 in the series : Bootstrapping with Paycheck to $15 Million from Tennessee: Gene Caballero, CEO of GreenPal
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