The Landscaping Rockstar: How Anthony Hilb Built Anthony’s Lawn Care Into An American Success Story

Anthony Hilb’s Interview with Will Troup

Anthony Hilb is the founder and owner of Anthony’s Lawn Care, a lawn care and landscaping business in Bloomington, Indiana.

He’s also the founder of Anthony’s Tree Removal, and Anthony’s Junk Hauling. He’s been in the business since 2011.

Anthony has an exciting story – from being a small-time musician to an entrepreneur who’s dominating the landscaping space.

Who is Anthony Hilb?

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Anthony Hilb with Dennis Yu at the Definitive AI Seminar

Anthony’s roots trace back to Hackensack, New Jersey, where he was born before moving to LaPorte, Indiana, at the age of five.

Raised by his third and fourth cousins who adopted him, Anthony’s early life was marked by a significant transition from a challenging beginning to a more stable and supportive family setting.

This foundational change instilled in him a deep sense of gratitude and resilience, qualities that would later define his professional and personal endeavors.

Anthony attended LaPorte High School, where he discovered his passion for music.

He played in various bands, navigating the local music scene and learning the ropes of managing and promoting music events. 

The intersection of Anthony’s musical and entrepreneurial ventures began in earnest during his college years.

While he considered a career in music, even contemplating attending the Berklee School of Music for percussion, his practical and business-oriented mindset gradually shifted his focus towards entrepreneurship.

Anthony recognized the precarious financial sustainability in music and opted instead to leverage his leadership and organizational skills into starting a business.

This decision marked the end of his active involvement in bands and set the stage for his transition into the business world, eventually leading to the founding of Anthony’s Lawn Care. 

Now he lives with a loving family in Bloomington, IN and manages these companies, all while finding time to coach other entrepreneurs who want to follow in his footsteps.

What are the lessons business owners can learn from playing in a band?

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Anthony Hilb with “Beauty School Dropout”, a music band

According to Anthony, playing in a band taught him many lessons that are directly applicable to running a business.

For example, stepping out of your comfort zone and making connections is like making cold calls or networking in business. Until you’ve actually put yourself out there, you’ll never know what you’re capable of getting.

Anthony recalled the nerve it took to approach club owners to let his band play.

“I was the guy in my band in high school that would have to muster the courage to go ask someone if we could play at their club.”

Dealing with public exposure and criticism was another hurdle to overcome, which is inevitable for bands and businesses.

Anthony learned how to handle visibility and feedback, both positive and negative, which prepared him for the public aspects of running a business.

Saying “And while I love marketing much more and people actually call us, in the early days of owning a business, when you don’t really have any marketing dollars, sometimes that’s just what you have to do.”

“You have to knock on doors, you have to pick up the phone, you have to send that awkward email.”

Out of all businesses, why choose landscaping?

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Tree Collapse From The Jobsite of Anthony’s Tree Removal

Anthony was drawn to the practical and in-demand nature of the landscaping business, recognizing early on that it offered consistent opportunities for growth and customer engagement. 

In short – people have lawns and these lawns need to be serviced.

Anthony’s approach to choosing landscaping was influenced by his understanding of the law of supply and demand, which he felt worked favorably in the landscaping sector. Saying, “I really like going into businesses that have a high demand with a low supply… I like being in an in-demand industry. This is basic economic 101, but it’s true.”

He noticed that many existing businesses in his area were failing their customers. This included not coming to jobs on the days they promised to, overcharging customers, and doing a poor job when they did arrive.

He explained, “If it is like a red sea type business where there are a lot of competitors, I like it to be where they’re not great at marketing or customer service.”

Anthony’s background in various hands-on roles during his early career, from moving services to junk hauling, provided him with a robust work ethic and a preference for physical, outdoor work.

This experience seamlessly translated into landscaping, where hands-on involvement and a direct relationship with the work’s physicality are daily realities.

In his own words, “It was, it’s actually a really great way to start with absolutely nothing because it really allows you to understand all aspects of the business rather than just jumping on, you know, a zero turn from day one.” 

What was starting the business like?

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Anthony’s Tree Removal Postcard

Anthony’s Lawn Care began with the most modest of setups—a single minivan, which served multiple purposes from hauling to moving services.

This van was the beginning of everything. Anthony recalls, “So I started, believe it or not, it was actually, with that same minivan, I would help students that lived in dorms move.” 

Anthony didn’t have the money at the time to buy expensive equipment, let alone hire workers and automated a sales process.

With just a push mower and essential tools like garden shears and a push broom instead of more advanced equipment, Anthony painstakingly built his business from the ground up.

The lack of resources such as a handheld leaf blower or a weed eater didn’t deter him; instead, it forced him to innovate and find manual solutions to the tasks at hand.

He described his early days, saying, “I would literally take those garden shears and I would use those to trim around mailboxes and garden beds where the grass gets a little bit longer because I didn’t have the weed eater.”

This period of his business life was not just about physical labor but also about learning every aspect of the trade, which later enabled him to appreciate and empathize with the challenges his employees would face as the business grew.

What’s been the hardest part about running these businesses?

The answer, like many business owners face, was cash flow.

One of the most challenging periods was when despite long hours and hard work, the financial returns simply weren’t meeting expectations.

“No matter how many hours I put in, no matter how hard I work, no matter how intelligently I worked, there is still no money at the end. Actually, it was in the negative.” 

This reflection underscores the brutal reality many entrepreneurs face—working tirelessly with little or no immediate financial reward.

As a solopreneur this might be fine – but Anthony had employees on payroll and business expenses to manage, eating into his bottom line.

The struggle extended to making sure his employees were taken care of, often at his own expense. The stress of managing payroll and ensuring the business could continue operations was immense.

Anthony recounts the sacrifices required to keep the business afloat, “I didn’t know it was sweat equity at the time, but I put in a lot of sweat equity… I had to work 14 hour days on Saturday and Sunday. That way I could take that money that I made and it would allow me to make payroll next Friday.” 

This phase of his business life highlighted not only the financial hurdles but also the emotional toll of entrepreneurship, where the responsibility for others weighs heavily.

Despite these hardships, Anthony’s story is also one of perseverance and eventual triumph.

Where do you see your business going in the next 10 years?

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Anthony Hilb Standing Besides His Company’s Logo

Over the next decade, Anthony has ambitious plans for the expansion and evolution of his businesses.

He envisions a significant scaling of operations, aiming to establish a presence in multiple new cities beyond his current base.

Anthony’s strategic vision includes franchising or licensing his business model, which would allow for a broader geographic spread and operational scalability.

He mentions, “I would like to either make this a franchise or be able to keep growing in a way where we pay people as if they’re owners in other cities and states.” 

This approach reflects his desire not just to expand territorially but to replicate his business’s success and culture in diverse locations, thereby amplifying his impact.

Anthony is deeply committed to maintaining the core values and culture that have been the bedrock of his business, well beyond his business for tree removal.

As he plans for growth, he is equally focused on ensuring that the company culture of respect, quality service, and community integration is preserved and strengthened. 

“Patience will definitely be at play,” he notes, indicating his awareness of the challenges that come with maintaining quality and culture during rapid expansion

 Anthony is looking to build a sustainable expansion model that fosters a positive work environment and strong customer relationships, even as the business scales.

Anthony sees his companies playing a larger role in community and charitable efforts. 

Inspired by successful entrepreneurs like Perry Marshall, Anthony hopes to leverage his business’s success to contribute significantly to societal causes, particularly those aimed at improving health and the environment.

He wants his philanthropy to be linked to business growth.

“I would like to be able to donate the majority of the money a guy like him would need because a guy like him is going to change the world,” he said.

Through these efforts, Anthony aims to create a legacy that transcends the typical boundaries of business, making a meaningful impact on both local communities and broader societal issues.

Parker Nathans
Parker Nathans
Parker Nathans is an entrepreneur and founder of Analytic Aim, a digital marketing agency specializing in getting more calls booked for local service businesses.