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I quit a comfortable tech job to launch a startup. Moving back in with my mom was humbling, but now I make $400,000 and travel all the time.

Perri Ormont Blumberg   

I quit a comfortable tech job to launch a startup. Moving back in with my mom was humbling, but now I make $400,000 and travel all the time.
  • Gene Caballero left his stable job at Dell to cofound GreenPal, an on-demand lawn care service.
  • He had to make financial sacrifices in the beginning, but now he earns more and travels often.

This as-told-to essay is based on a conversation with Gene Caballero, a 44-year-old cofounder of GreenPal, based in Nashville. It's been edited for length and clarity.

I'm a cofounder of GreenPal, a platform that connects homeowners with lawn care professionals.

After purchasing my first home, finding reliable lawn care for myself and my mom was a daunting task. Working in tech on the West Coast and watching companies like Uber, Lyft, and Airbnb get started opened my eyes to one of my cofounders Bryan Clayton's initial idea of on-demand lawn care.

Before working full-time at GreenPal, I spent nine years at Dell, where I first held a sales role. Five years in, I transitioned into a management role, where I stayed until 2017. I learned invaluable lessons in leadership, strategic planning, and team management, all of which have been crucial in steering GreenPal toward success.

I left my stable job at Dell to find a more meaningful career

I had a six-figure salary and was comfortable at Dell, but launching GreenPal was fueled by a quest for greater purpose. I was driven by the urge to solve a common problem. This venture into entrepreneurship was not just a career change but a commitment to innovating how lawn care services are accessed.

Financing GreenPal's inception demanded significant personal sacrifices. Because of my belief in GreenPal, I sold my house and cashed out my 401(k). To make this work, I moved home with my mom for a year, which was humbling, but I knew it was the right choice. I then got a small apartment with Bryan.

A key part of our early strategy was going door-to-door to gather feedback from homeowners. This direct engagement was crucial in validating the demand for a service like GreenPal and refining our concept based on real user insights. It gave me the confidence to go all in.

We're now making over $40 million in revenue

Since our founding, we've hired 20 employees. The financial health of the company affords me personal freedoms that were once unimaginable — especially in the corporate world.

My compensation of $400,000 annually supports my lifestyle of travel and exploration. In 2023, I visited 15 countries, and I've already planned five international trips, including summiting Kilimanjaro in September, for this year.

I work every day, but I've streamlined my responsibilities so I never exceed 20 hours a week. Every morning, I look at the number of transactions and revenue we booked the previous day. I then tackle emails, prioritizing our customer care app to promptly address all inquiries and issues. I'm usually done working by noon, if not earlier.

My entrepreneurial journey was both exhilarating and challenging

One of our most impactful mistakes was hiring an external firm to develop our website and apps. Entrusting this critical component to an outside company for a six-figure fee, we expected a seamless launch and a robust platform. The firm failed to deliver a product that met our specifications and went out of business shortly after. This left us without a functional website and with no recourse to recover our investment.

The setback delayed our market entry and forced us to reconsider our strategy. This experience taught us a crucial lesson about the importance of having technical expertise within our founding team. My other cofounder, Zach Hendrix, went to Nashville Software School and learned how to build the current website and apps we use today.

I absolutely do not miss my 9-5 at all

One piece of advice I'd share with other entrepreneurs is to brace yourself for a ride that can be lonely and seemingly without reward for a long stretch. Success in entrepreneurship often comes after enduring periods of uncertainty and solitude. Stay resilient and keep pushing forward, even when the immediate outcomes aren't visible.

I consider myself an entrepreneur, but I will never start another company. If you do it right once, you don't need to do it again.

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