How Gene Learned the Importance of Health While Growing GreenPal to $30 Million in Revenue

How Gene Learned to Balance Life and Work While Growing GreenPal to $30 Million in Revenue

GreenPal assists homeowners in 48 states with lawn care while helping contractors and lawncare professionals find clients and make money. Gene Caballero and his co-founders implemented strategies similar to those of companies like Uber and Airbnb and applied them to lawn care.

Although the company is well established today, it took years of hard work to succeed. They grew the business slowly and organically, starting with their personal networks and door-to-door marketing.

The entrepreneurial grind and long hours impacted Gene deeply. For a while, he relied on medication to help with sleep and energy. Through the experience, Gene learned the importance of prioritizing both mental and physical health, even during the process of growing a business.

In this interview, Gene shares the details of GreenPal’s incredible growth, plus, he opens up about the mental and physical challenges he’s faced as an entrepreneur.

Key Takeaways

🌱 GreenPal grew steadily through networking, door-to-door prospecting, and the media
⏰ Like many entrepreneurs, Gene struggled with long hours and a full schedule
🗝️ Gene shares his advice for others and how he maintains a healthier balance today


Business Name: GreenPal
Website URL:
Founders: Gene Caballero, Bryan Clayton, and Zach Hendrix
Business Location: Online (US)
Year Started: 2012
Number of Employees/Contractors/Freelancers: 25

How much revenue and profit does the business generate?

In 2023, GreenPal generated over $30m in revenue–growing at 20% YoY.

Tell us about yourself and your business.

I am an entrepreneur with a robust background in business and technology. After completing my MBA from Middle Tennessee State University (MTSU), I honed my skills in the corporate world, working as a sales associate, sales coach, and then a sales manager at a Fortune 50 tech company. This experience provided me with invaluable insights into large-scale business operations and the technology sector, setting a solid foundation for my entrepreneurial journey.

Together with my co-founders, Bryan Clayton and Zach Hendrix, we started GreenPal, a venture revolutionizing the lawn care industry. Often described as the “Uber for lawn care,” GreenPal simplifies the way homeowners connect with local lawn care professionals.

Our platform makes it easy for users to find, schedule, and pay for lawn services. This innovative approach has transformed the traditional lawn care model, offering convenience and efficiency to homeowners, while providing lawn care professionals with a steady stream of business opportunities. Our journey with GreenPal reflects our commitment to leveraging technology to streamline everyday tasks for people.


What was your inspiration for starting the business?

My inspiration for starting GreenPal stemmed from a unique combination of my entrepreneurial spirit and exposure to cutting-edge technologies. From a young age, I always had a side business of cutting grass, which not only acquainted me with the lawn care industry but also instilled a deep understanding of the challenges and opportunities within this field. This early venture laid the groundwork for my entrepreneurial journey, fostering a keen sense of market needs and customer service.

Working in sales at a Fortune 50 tech company, I was privy to the latest technological advancements and business models reshaping various industries. Observing the meteoric rise of on-demand services like Uber, Lyft, and Airbnb, I realized the potential for a similar model in lawn care. This insight led to the birth of GreenPal.

I recognized that an on-demand lawn care service would fill a significant market gap, providing homeowners with convenience and reliability while offering lawn care professionals a platform to grow their customer base. This blend of personal experience and technological insight was the catalyst for creating GreenPal, a business model tailored for the modern consumer’s needs.

How and when did you launch the business?

The business launched in the summer of 2012 to only friends and family due to the fact that no one knew about the product.

What was your first year in business like?

The first year of GreenPal was a period of immense hard work and determination, truly being in the trenches. While I was still committed to my corporate job, my days often stretched to 15-hour marathons, balancing the demands of a full-time position with the rigorous efforts of getting a startup off the ground.

This phase was characterized by a hands-on, grassroots approach to building our customer base and vendor network. We went door-to-door, actively persuading homeowners to sign up for our service, and cold calling vendors to join the GreenPal platform. This direct interaction was crucial, not only for growing our user base but also for understanding the real-world needs and challenges of our customers and service providers.

Financially, the first year did not bring in any profit, and it wasn’t until 2016 that we started seeing monetary gains. Despite the lack of immediate financial success, this period was invaluable for product development and market understanding.

I invested a significant amount of time engaging with homeowners, gathering feedback, and using these insights to refine and improve our product. This continuous loop of feedback and improvement was instrumental in shaping GreenPal into a service that truly met the needs of its users. The challenges and learnings of this first year laid a solid foundation for GreenPal’s future growth and success.

Initially, how did you get users to try a new platform?

In the initial stages of GreenPal, our approach to attracting users to try the platform was hands-on and personal. We went door-to-door in neighborhoods, engaging directly with homeowners to introduce them to our new lawn care service. This approach allowed us to not only explain the benefits of GreenPal but also to establish a personal connection with potential users, which is often missing in digital marketing strategies.

Understanding that physical presence and visibility were key, we also rented a kiosk in a local mall. This strategic move provided us with a platform to interact with a larger audience, offering demonstrations and answering questions in real time, thereby enhancing trust and interest in our service.

Additionally, we tapped into our personal networks, politely asking friends and family to use the product. This strategy was crucial in building an initial user base for the platform. Leveraging these personal connections not only helped in gaining early users but also in receiving honest feedback, which was vital for improving the service.

Our friends and family became advocates for GreenPal, helping to spread the word through their networks. This grassroots approach to user acquisition, combined with our commitment to continuous improvement based on user feedback, laid the groundwork for the growth and success of GreenPal in its early days.

What strategies did you use to grow the business?

To expand GreenPal’s reach and solidify our market position, we employed a blend of innovative and traditional growth strategies. A pivotal move was enabling our homeowners to share their GreenPal experiences on social media. This integration allowed for easy broadcasting of positive feedback, harnessing the power of digital word-of-mouth. Such personal endorsements on social platforms were invaluable, creating a ripple effect of organic promotion and increasing our visibility in a more authentic and relatable way.

Alongside digital strategies, we leveraged local news media to gain traction in new markets. By engaging with local media and sharing our story, we gained credibility and widespread awareness, essential for breaking into new areas. This coverage not only introduced GreenPal to a broader audience but also instilled trust in our brand, particularly important when launching in regions unfamiliar with on-demand lawn care services.

Crucially, we also focused on optimizing our website for search engines (SEO), ensuring top rankings in searches related to lawn care. This approach significantly increased our online visibility, drawing more users to our platform.

Furthermore, we introduced a feature allowing vendors to upsell additional services to their existing GreenPal customers. This not only increased revenues for our vendors but also enhanced the overall user experience by providing more value and convenience, ultimately contributing to GreenPal’s sustained growth and success.

How have the pressures of entrepreneurship impacted you?

The journey of entrepreneurship, particularly in the early stages of GreenPal, significantly impacted my personal well-being, especially in terms of sleep and focus. With my mind constantly racing with ideas, strategies, and concerns, I found it increasingly difficult to switch off and get the rest I needed. This led me to seek medical advice, and my healthcare professional prescribed Ambien to help manage my sleep issues.

While Ambien was effective in helping me fall asleep, it was a solution that addressed the symptom rather than the underlying cause – the relentless pace and pressure of managing a startup while holding down a demanding corporate job.

To cope with the long hours and the need for sustained concentration, I also started taking Adderall as prescribed by my doctor. This was to help me stay sharp and focused during the late hours when I dedicated time to GreenPal. While Adderall provided the necessary alertness and focus, it was a delicate balance to maintain.

Relying on medication to modulate wakefulness and sleep highlighted the intense demands of entrepreneurship. These pharmaceutical aids helped me manage the immediate challenges but also underscored the importance of seeking sustainable ways to handle stress and workload in the long term. This experience was a poignant reminder of the physical and mental toll that starting and growing a business can take, and the necessity of finding healthier, holistic strategies to maintain personal well-being amidst the rigors of entrepreneurial life.

Did you feel like you were able to be open with others about these struggles, and did you feel like you had support?

During this period, I adopted a mindset of just doing what needed to be done without perceiving my situation as a problem that required sharing with others. As the prescriptions for Ambien and Adderall were provided by my medical provider, I felt that I was managing within the bounds of professional advice. This approach led me to internalize my struggles rather than seeking external support or discussing them openly.

I focused on the immediate task of growing GreenPal and maintaining my corporate responsibilities, prioritizing these over the potential need to address the underlying stress and health implications. This perspective, while helping me push through the immediate challenges, also meant that I largely navigated this phase without leaning on a broader support network, whether professional or personal.

What did you learn through the situation, and how does it impact you today?

The experience taught me a vital lesson: irrespective of whether your company soars to great heights or faces setbacks, prioritizing your health is non-negotiable. This realization came sharply into focus as I navigated the demanding early years of GreenPal.

Today, I stand as the healthiest I have ever been, both mentally and physically. This transformation is a direct result of acknowledging the importance of well-being in the entrepreneurial journey. I’ve learned to balance the rigors of business with personal health, understanding that success is not just measured in business achievements, but also in maintaining a sustainable and healthy lifestyle. This holistic view now shapes my approach to work and life, underscoring the value of health as a foundational aspect of true success and fulfillment.

How do you manage the balance between running a successful business and taking care of your mental health?

Managing the balance between running a successful business and maintaining my mental health has become a crucial aspect of my daily routine. To achieve this perfect balance, I have incorporated several practices into my life.

Meditation has become a cornerstone of my mental wellness strategy, helping me to center my thoughts and alleviate stress.

Playing the piano offers a creative and therapeutic outlet, allowing me to disconnect and rejuvenate. Additionally, I’m mindful of my screen time, ensuring I don’t overindulge in digital consumption, which can be mentally draining.

Importantly, I’ve learned the value of delegation; outsourcing tasks that no longer require my direct involvement frees up time and mental space, allowing me to focus on high-priority aspects of the business and personal well-being. These practices collectively contribute to a healthier work-life balance, supporting both my business success and mental health.

What advice do you have for others who may be going through something similar?

For those facing similar challenges, my advice is to recognize that your body and brain are as crucial as any milestone your company aims to achieve. It’s essential to give equal attention to your physical and mental well-being as you do to your business goals. Balancing these aspects is key to not only sustaining your health but also ensuring the longevity and success of your entrepreneurial journey.

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