Gene Caballero has always been an entrepreneur. From his early days, he has always been interested in business and tech. Co-founder of GreenPal, which has been described as Uber for lawn care, Gene has made ordering lawn care from your smartphone as easy as ordering a ride. Gene and his cofounders started GreenPal in Nashville, Tn, and now are the nation’s largest on-demand platform for finding, scheduling, and paying your lawn guy operating in over 48 states and 250 major cities.
What were the top 3 mistakes you made as an entrepreneur, and if you could start over what would you do differently?
Hiring a firm to build our first website
We didn’t have a technical co-founder so we paid ($85k) for a local firm to build our website that was based on what they thought our customers wanted. It has since been rebuilt by a co-founder (after he went to software school) and the only thing that was kept was the “How It Works” video–$85k for a 1:30-sec video and no it was not directed by James Cameron. We could have certainly used that $85k to pay for usability tests or to test some advertising methods in the early stages of our growth. Mistakes like this one can sink a business before a revenue dollar is generated.
Trusting your own knowledge
Being from the landscaping industry, I second guessed how landscaping professions would react and use our app based on digital behavior. Going into a digital world, I had reservations if the user behavior would differ from the analog world. This cost us precious time in design and development. Trust your gut and let your users prove years of your own expertise wrong. When your gut talks, you listen to it. If your gut or instinct is wrong, let the hundreds decide what the thousands will do on your site.
Make sure all of the cofounders are on the same page about company vision, duties, time commitments, expectations, and what happens if those are not met.
Have that conversation early with everyone. Make sure all legal documents are bulletproof just in case someone wants to leave the company or has to leave for personal reasons. We had a situation in which a fourth co-founder had to make a personal decision to leave. Amongst his departure, his wife was entitled to half of his shares if a divorce was finalized and therefore she would have been a shareholder to a company that she wasn’t even involved in. Ensure that you are all on the same page and make those sentiments into a legal binding document.
If I could start over and do it all over again, I would have outsourced tasks much faster. When you are first starting out, you want to learn how to do as much as possible. Learning the concept of something you are trying to outsource and then outsourcing that is far much more efficient than trying to gain the knowledge to do something yourself. Learn to let go and hire someone in the areas that you are weak. Some of the minuscule tasks that are handled by a co-founder are not as important as you think and are truly hindering your growth. Fire fast and fire faster. Be on your company, not in it.
Gene Caballero Cofounder of Greenpal
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