Gene Caballero

Talk to strangers, family, friends, co-workers and see if they would PAY for your product or service….not just if they like it or think its a good idea.


Gene Caballero grew up living in South America and Middle Tennessee. He has a MBA in Finance and worked as a corporate sales coach for a Fortune 50 company before co-founding GreenPal. He enjoys playing piano, is an avid marathoner, and enjoys anything food related.

Where did the idea for GreenPal come from?

My best friend had one of the largest landscaping companies in the middle Tennessee area and when he exited that company he approached me about some of the pain points that vendors and home owners had when trying to find each other. In 2012, that was about the same time that Uber, Lyft, and the whole share economy was gaining traction so we decided to launch GreenPal.

What does your typical day look like and how do you make it productive?

I don’t set an alarm so I just wake up. Sometimes that’s 530 or 730 but I immediately get my day started. I’ll eat a quick bite and head to the office. Once at the office, my daily initiatives are fairly the same but will vary in when they get done. I am either talking on the phone or behind my computer. I normally eat lunch at the office and then go to the gym around 3ish. I normally get back to the office from the gym around 5pm. Ill eat a quick dinner and then work until 8pm. I think staying on a schedule helps me stay productive and also doesn’t lend itself to distraction.

How do you bring ideas to life?

First, I think is that you need to vet the idea and make sure that its something that is needed or wanted. The idea has to bring true value to your processes–it can’t just be a “nice-to-have.” When an idea does pass that validation, you will to see how important that idea is and where does it stack in the rank of the other items that need to be done. When you finish ranking the severity or need of the idea, that is when you can actually assign the idea to your developers or creatives to make it happen.

What’s one trend that really excites you?

The automobile industry is something that really excites me. Things that are being done with vehicles and transportation are mind-blowing to me. Knowing that the battery technology is starting to give consumers unlimited travel opportunities is fascinating.

What is one habit of yours that makes you more productive as an entrepreneur?

When I am feeling unmotivated or lethargic, I will go play piano. We have a little music room in our office that my go-to when it comes to taking a mental break. Playing an instrument has been scientifically proven to engage practically every area of the brain at once especially the visual, auditory, and motor cortices so it gets my mental capacity going. Its like a mental full body workout.

What advice would you give your younger self?

I would have told myself to get into computers and programming at an earlier age. I was in my late 20’s before realizing that it was going to be the future.

Tell us something that’s true that almost nobody agrees with you on.

With so many advances in BioTech, I think there will be a cure for Cancer within the next 5 years. Hope I’m right.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Meditation. It truly relaxes the mind and body and its essential for the entrepreneur to stay sane.

What is one strategy that has helped you grow your business?

What we have done to grow our business is to create landing pages for smaller markets outside of our larger markets that we already operate in. For example, In addition to creating landing pages for large metros like Atlanta GA, we also create them for Marietta, Alpharetta, Decatur, etc. This will ensure that Google algorithm can detect the key words and our business in that specific location. This helps expand our business to a new city by ranking for search and has improved our business by 10% by launching this practice.

What is one failure you had as an entrepreneur, and how did you overcome it?

When we first started, We didn’t have a technical co-founder. With that being said, we had no choice other than to pay ($85k) a shop to build us a 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 video….$85k for a 1:30 sec video….and no it was not directed by James Cameron.

What is one business idea that you’re willing to give away to our readers?

On-Demand Tailgating….Customer goes onto a website and picks and chooses what they want at that tailgate. Company then outfits a small trailer with a grill, food and drinks that were chosen from the website, and then delivers that to the parking spot or area of the customer. Company then comes and picks the equipment up and uses it again next week.

What is the best $100 you recently spent? What and why?

I ran a half marathon a few weeks ago and bought myself a full body massage. It was the first one I have had in over a decade and it totally recharged my mind and body.

What is one piece of software or a web service that helps you be productive? How do you use it?

An innovative CRM app that I am thankful for is Intercom is a customer engagement tool that allows you to interact with your customers at any point in time while they are on your site. Along with being able to track customers purchasing habits with this tool and gathering useful data, We have inserted ourselves into our on-boarding funnel and can reach and talk to customers and get real time feedback during critical moments of the sign up process. With this data and real time feedback, we can make design or copy changes to improve our click through rate and overall customer experience. This tool also will easily allow us to create marketing campaigns and specific events when customers have not returned to our site or when the season for lawn care changes–saving us loads of time.

What is the one book that you recommend our community should read and why?

The book that changed my perspective on starting a business is “The Startup’s Owners Manual,” by Steve Blanks. For me, Steve laid out for me all of the pre-work that was needed to be done before any 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 your favorite quote?

My grandfather who barely spoke English told me this…”There are 3 8-hour workdays in 24 hours…pick which two you want to work and you will be successful.” He was not kidding.

Key Learnings:

  • Ideas are cheap. You will have to grind your idea out and you will hear no thousands of times. You have to be contrarain and right to build a great business.
  • Be like a cockroach because they never die. Defer taking money as soon as you can because it forces you to be metrics and ROI driven on every dollar you spend and it gives you the freedom to move at your pace and be stingy with your equity.
  • Make sure your product or service is solving a big enough problem. If your problem is not 10x better than the traditional product or service, it will be hard to have product market fit.
  • Talk to strangers, family, friends, co-workers and see if they would PAY for your product or service….not just if they like it or think its a good idea.