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His Side Hustle Solved a Common Problem for Homeowners. Now the Business Brings in $3 Million a Month During Peak Season. GreenPal co-founder Gene Caballero had always been drawn to the "allure of entrepreneurship."

By Amanda Breen

Key Takeaways

  • Gene Caballero saw an opportunity to innovate in the landscaping industry.
  • GreenPal connects landscapers to clients across the U.S., like an "Uber for lawncare."
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This Side Hustle Spotlight Q&A features GreenPal co-founder Gene Caballero. Founded in 2012, GreenPal is a Nashville-based online freelancing platform that connects landscapers to clients across the U.S., much like an "Uber for lawn care."

What were you doing before you started your side hustle, and why were you interested in entrepreneurship?

Before diving into the world of entrepreneurship with GreenPal, I was a sales manager at a Fortune 50 tech company. However, the allure of entrepreneurship was always there. Growing up in a family where everyone ran their own business, the desire to be my own boss was a natural inclination. This deep-rooted ambition, combined with my corporate experience, became the foundation upon which I built my side hustle, eventually transforming it into the successful platform it is today.

When did you start your side hustle, and where did you find the inspiration for it?

GreenPal started in 2012, sparked by the entrepreneurial spirit of my childhood friend, who had the largest landscaping business in our hometown. Witnessing his success and the potential for technological innovation in the landscaping industry inspired us to create a platform that would redefine how homeowners connect with lawn care professionals.

Related: 44 Side Hustle Ideas to Make Extra Money in 2023 | Entrepreneur

What were some of the first steps you took to get your side hustle off the ground?

To launch GreenPal, we hit the ground running — literally. We went door-to-door, signing up homeowners for our service, and devoted countless hours to cold-calling vendors to join our platform. We even set up a kiosk in the mall, engaging directly with the community to spread awareness about our service. Each step was a lesson in persistence and grassroots marketing.

What were some of the biggest challenges you faced while building your side hustle, and how did you navigate them?

The biggest hurdle we faced while building GreenPal was getting our website developed. We contracted a local firm, and after a lengthy process, they delivered a product that was nearly unusable. To make matters worse, they suddenly went out of business. This left us with a stark choice: give up or adapt. We chose to adapt. One of our co-founders took the initiative to attend software school, learning the ins and outs of web development. With determination and new-found expertise, he rebuilt our website from scratch, overcoming nearly two years of setbacks. This challenge taught us resilience and the critical importance of having in-house technical skills.

How long did it take you to see consistent monthly revenue, and at what point did the side hustle's income surpass your full-time job?

It was 2017 before we saw consistent monthly revenue. 2021 was when my GreenPal income surpassed that of my full-time job.

Related: I Built My Multimillion-Dollar Side-Hustle While Working a Full-Time

You've turned your side hustle into a full-time business. How much average monthly or annual revenue does it bring in now?

Since GreenPal is very cyclical, our highest growing months are in the summer, and our revenues surpass $3 million per month.

What's your advice for other side hustlers who hope to turn their ventures into successful full-time businesses?

My advice to those who want to go "all-in" on their side hustle is to know this: It's going to be tougher and more time-consuming than your day job. Be ready to invest countless hours, often more than your regular employment. My full-time job was a breeze compared to starting something from scratch. Also, passion is key; it'll fuel those long nights and early mornings. Hold onto your primary job as long as possible; it's the financial backbone for your side hustle during those early, uncertain days. Use every bit of your vacation and paid time off to focus on your side business. Those hours are yours, earned for your dreams. This strategy gives you a safety net while building the foundation of your future business. Your passion, coupled with strategic use of time and resources, will be the engine driving your side hustle forward.

Amanda Breen

Entrepreneur Staff

Senior Features Writer

Amanda Breen is a senior features writer at She is a graduate of Barnard College and received an MFA in writing at Columbia University, where she was a news fellow for the School of the Arts.

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