Gene Caballero | Crain's Orlando

In this ongoing series, we ask executives, entrepreneurs and business leaders about mistakes that have shaped their business philosophy.

Gene Caballero


Nashville-based GreenPal is a mobile app that connects homeowners with lawn care professionals with a business platform that provides bids, invoicing, marketing and follow-up. Founded in 2013, the service now serves the Nashville, Atlanta, Houston, Tampa, Orlando, St. Petersburg, Charlotte, and St. Louis markets.

The Mistake:

We spent a small fortune on a website that was unusable.

When we first started we were like, we’re three guys who are hungry. We know what we want. We know how we’re going to do it. But none of us knew how to write a line of code. None of us.

So what do you do? You pay someone to build a website for you. And we paid $85,000 for somebody to build our website and it was horrible. It was hard to use. It was confusing. It was basically the opposite of what you needed to hatch a successful business. The only thing that we kept from the shop that built the site is a video they did that was 32 seconds. And that video was not directed by James Cameron.

After a year of it, we knew it was unusable.

There are three of us co-founders. One of our co-founders actually went to software school here in Nashville then learned how to build [a website], and then built what we currently have now, which works really, really well.

Don’t put the fate of your business in the hands of someone who’s not invested in your company.

The Lesson:

What I learned is, don’t put the fate of your business in the hands of someone who’s not invested in your company. Investing [instead] in ourselves has definitely paid off.

A demographic that’s really grown exponentially for us is multiple properties. We had a bunch of real estate agents who were like, “Hey, I’ve got three properties. How do I add a property?” We were like, “Well, do you have another email address? Because you have to create another account.” 

We saw this pattern, so we took three months and built a new multiple-property feature for these property managers and real estate agents. And that’s a demographic that’s really taken hold of our product and uses it well. We’ve got hundreds of vendors that have four or five properties on our system and they’re able to manage it with one account [using] multiple vendors.

[The web company] would have nickeled and dimed us to bankruptcy with every little change. There are certain things that need to happen at one o’clock in the morning, you know? I don’t know how you could do it any other way, honestly.

Follow GreenPal on Twitter at @YourGreenPal.

Photo courtesy of Gene Caballero

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