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Best of Bootstrapping: Bootstrapped with a Paycheck to $15M

If you haven't already, please study our free Bootstrapping Course and Investor Introductions page. In 2018, GreenPal Co-founder Gene Caballero shared a fantastic story of a founder duo bootstrapping with a paycheck, 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.

GreenPal mowing service calls itself the Uber of lawn care

GreenPal, based in Nashville, self-described “Uber of lawn care” owned by three Middle Tennessee State graduates, has expanded to yards across the U.S. border while navigating a pandemic. The company is now a national (soon-to-be international) operation, but it planted its seeds with door-to-door beginnings in Rutherford County. “It all started in Murfreesboro,” said GreenPal co-founder Gene Caballero. The company’s three co-founders — Caballero, Bryan Clayton and Zach Hendrix — are all Rutherford County natives who went from playing soccer together at Oakland High School to operating a digital service connecting homeowners with a one-stop option for local lawn maintenance providers.

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