Gene Caballero: Co-Founder of GreenPal, Inc

Gene Caballero

Gene Caballero is a co-founder of GreenPal. Having come from an entrepreneurial family, Gene is helping revolutionize the landscaping industry by creating the nation’s largest on-demand lawn mowing platform.

GreenPal has helped thousands of lawn care professionals grow their businesses and make their lives easier. In his spare time, Gene loves to play piano and train in Mixed Martial Arts.

What is GreenPal all about? 

GreenPal has been described as Uber for lawn care and is the world’s first operating system for landscaping professionals. Not only does GreenPal handle landscaping pro’s demand creation, we also handle their scheduling, route optimization, asset management, and payment processing. 

Tell us a little bit about your background and how you started your company? 

I have been in the landscaping industry since I was sixteen years and mowed lawns part-time–through college–until the concept for GreenPal came about. I was mowing yards to make extra money and found that it was very flexible and lucrative for a young entrepreneur. My first job after receiving my MBA was a sales job. My territory was the west coast so I was privy to newer technologies such as Uber, Lyft, and Airbnb. I knew that if a stranger was going to summon another stranger to take them places, then consumers would do the same with home services–and that is how the idea for GreenPal came to fruition.  

What was the biggest problem you encountered with your business and how did you overcome it?  

The biggest problem we encountered was building the website. We didn’t have a technical co-founder so we paid ($125k) for a local company to build our website. They had a good reputation, but they built, what they thought our future customers wanted. 

It took them almost a year to build our site and was barely usable. It has since been rebuilt by a co-founder (after he went to software school), and the only thing that was kept was the video–$125k for a 1:30-sec video–and no it was not directed by James Cameron. What did we learn? It’s almost impossible to not have a technical co-founder on the team. If this shop would have delivered a perfect site, they would have bankrupted us for any updates and bugs along the way.  

What were the top mistakes you made starting your business, and what did you learn from it?  

One of the biggest mistakes we made was allowing homeowners to book appointments only when they needed a lawn mowing. This did two things:  

It didn’t allow for vendors to efficiently plan out their routes and gave the homeowners a bad experience if that vendor couldn’t make it when they added a last-minute appointment. So, we eliminated that option and now only allow homeowners to book either weekly or biweekly services on our platform.  

Sometimes it’s not about getting the most customers, it’s about getting the right customers.  

What is one thing that you do daily to grow as an entrepreneur?  

Meditate every morning. This clears my head and allows me to focus on the most important details of my day.

What are three books or courses you recommend for new entrepreneurs? 

One book that every entrepreneur should read is “The Startup Owner’s Manual,” by Steve Blank. For me, Steve laid out all of the pre-work that was needed to be done before a company should even be started. From “getting out of the building” and getting feedback from random strangers to being on top of your company and not in it, Steve takes real-world examples and explains everything in detail. 

He gave me the confidence and the reasoning to get the ball rolling on becoming an entrepreneur.  

What is the one thing you wish you knew before starting your business? 

I wish I knew how lonely the journey was going to be. Immediate family and a few friends will always be supportive–sharing on social media, writing reviews, actually using your product, bringing food to the office at midnight, etc.  

Second-tier friends, like your bar buddies and old co-workers, just don’t understand the work it takes to build something from scratch. They can’t fathom why you are not able to grab a happy hour or grab dinner on a Tuesday because you have to work. Slowly but surely, these friends will eventually quit asking and become mere acquaintances.

What has been your most effective marketing strategy to grow your business?  

Public relations has been the most effective strategy to get our name out there and grow our business in new markets. Get with PR professionals and pay them to teach you how to get the PR windfall going. PR hits also have a direct connection with search engine optimization. 

If you only had 1000 dollars to start a new startup, knowing everything you know now, how would you spend it?  

I would register on Upwork and consult with whatever my strengths were. Then take that feedback on those companies that I consulted with and start my own.  

What’s your best piece of advice for aspiring and new entrepreneurs? 

One piece of advice I would give to any potential entrepreneur is to make sure your company or service is solving a big enough problem. If your company’s problem is not 10x better than the traditional product or service, it will be difficult to have a product-market fit. Talk to strangers, family, friends, co-workers and see if they would PAY for your product or service–not just see if they like it.  

What is your favorite quote?  

There are 3 8-hour workdays in 24 hours…pick which two you want to work and you will be successful.

How can readers get in touch with you?  

The reader can get in touch with me via my email, gene@yourgreenpal.com, or follow me on IG @gene_caballero

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Opinions expressed by interviewee participants are their own. 


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