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Bootstrapping with Paycheck to $15 Million from Tennessee: Gene Caballero, CEO of GreenPal (Part 1)

Posted on Monday, Oct 29th 2018

This is a fantastic story of a founder duo bootstrapping with a paycheck, now growing from $5M to $15M in one year, with a virtual team of freelancers. Your classic 21st century internet business. No outside financing whatsoever!

Sramana Mitra: Let’s start at the very beginning of your journey. Where are you from? Where were you born, raised, and in what kind of background?

Gene Caballero: I was born in Lima, Peru. My dad’s side of the family are all entrepreneurs. My grandfather had his own propeller business. We made propellers for boats. My dad actually has that business now. I’m the black sheep. I’ve gone into the technology side as opposed to the manufacturing of propellers.

I was raised in Nashville, Tennessee and went to college in Middle Tennessee State University. I also got my Master’s at MTSU. I started in the corporate world. I was in technology sales for 10 years until the opportunity for GreenPal came. Up until then, I was looking for a way to do my own thing. Some friends were chatting about different ways to make money and the pain points.

There’re a lot of young entrepreneurial kids who mowed lawns for a living at some point in their life. We knew that there was a possible business in that industry. It’s been pen and paper. It has been a cash business. When we first started in 2012, that was the time when Lyft and Airbnb were gaining traction on the West Coast. If people were going to summon a stranger to come and pick them up and drop them off, at some point they would sign on lawn care. That’s the reason we started GreenPal.

Sramana Mitra: When did you start GreenPal?

Gene Caballero: We officially launched it in April of 2012.

Sramana Mitra: What was going on around you at that time?

Gene Caballero: I was just immersed in my day-to-day corporate life. One of my childhood friends who had started a landscaping company grew that to be one of the largest in the area. He was talking about pain points that he had with his business. He wanted to grow faster but couldn’t. It was all word of mouth or traditional advertising. He explained the pain points of all that to me.

I had heard of Airbnb and Uber just because I was in the tech side of things. I was privy to new startups that are hot because my territory was on the West Coast. We put our heads together and knew that there had to be a better way for a homeowner to find a landscaping professional and also for a better platform to ensure that landscaping professionals can run their business more efficiently. After a few weeks of conversation, that’s when we decided to go for it and put it all in.

This segment is part 1 in the series : Bootstrapping with Paycheck to $15 Million from Tennessee: Gene Caballero, CEO of GreenPal
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