This story is part of a series called The Climb that highlights entrepreneurs and the challenges they face as they launch, grow, and scale their ideas. Each story explores the inspiration, the struggle, and the obstacles they face on the journey upward.

It all began with the grocery store

Chris Penny’s lawn care business began with his job at the local grocery store. He was in high school and working at the store to make some extra cash. The store was poorly managed and as a result, the people who worked there weren’t very nice.

“The meat guys would play these games where somebody would call to ask the price of something, and they would put the phone down and have a 10 minute conversation just to make the person wait. They thought it was funny, but it was just nasty.”

Chris was appalled at what was happening around him on a daily basis. This was his first job and he didn’t have any other idea of what a job looked like. His boss despised her job and was very unpleasant to work with.

“I’m kind of grateful for the horrible boss I had at the grocery store. That’s what motivated me to mow lawns in the first place, to get away from this boss.”

He saw his lawn care business as a way to remove his dependence on his grocery store job—and the first step to that freedom was finding more lawns to mow. But where would he find the lawns? This was a time when most lawn care companies were advertising with fliers in the mail, and customers weren’t yet comfortable giving out their email address.

In the early 2000s, people were increasingly searching for what they needed on the internet. Chris discovered a burgeoning online advertising platform called Google AdWords, and started to experiment with online advertising. He created ads that targeted his ideal clients and tested which ads got the best results.

Before long, this new acquisition channel began to send new clients his way. With more lawns to mow, Chris needed to hire more people before he could serve more clients.

As he hired, Chris heard horror stories of working in the lawn care industry. He heard about workers not being paid on time, getting money taken out of their checks, and not being cared for. And because of his time at the grocery store, he knew how it felt to work at a job where nobody cared about their work or the people they worked with.

Chris made a promise to himself. He would care about his workers as people, pay them above average wages, and pay them on time every week.

“I felt like I treated them pretty well. But they thought that I treated them really well. I think that was because of how badly they had been treated before. And that really kind of opened my eyes to how some companies treat people in the industry.”

His workers were cared for and well paid, but things weren’t all sunshine and roses with Chris’s business. The growth of the business was now causing operational problems. Lawns weren’t getting cut, phone calls and emails weren’t being answered, and his team was behind schedule.

Everything Chris had built was on the verge of falling apart.

“It was a chain of events that led to us not being able to provide the services that we had promised. And the company was falling apart around us. There were lawsuits involved. It was a mess.”

“We’re all still people here.”

The chain of events began with a loyal customer being upset. He had unanswered questions about the service he was getting and when he couldn’t get ahold of Chris, he started commenting on the company’s Facebook page.

After long days of cutting lawns and running the business, Chris had no energy left to deal with this customer’s problems. So he deleted the customer’s messages.

But the Facebook comments kept coming.

When Chris arrived at the customer’s house late to mow his lawn, he slowly walked up the path to the front door and knocked. The customer opened the door, surprised to see Chris.

Chris immediately apologized and took full responsibility for the customer’s lawn not being mowed. He explained how he was the owner of the business, how the business was experiencing some growing pains, and how much he truly cared for his customers.

“It was the human side of the failure. I wanted to show him that, even though he’s not being treated fairly, we’re all still people behind the scenes here. This is really not what we’re trying to do as a business. I wanted him to know that we’re gonna try and that we cared about him.”

The customer was blown away by Chris’s honesty and transparency. The customer apologized for the comments he made on social media and revised many of the negative comments he made on the company’s Facebook page. The care and personal touch Chris showed the customer moved him so much that the customer increased the services he received from Chris’s company.

Growth and success bring problems

After the business had grown a bit, Chris decided to start franchising to college students. The students could make some extra money while in school and Chris’s company could expand its customer base. At least, that was the idea in theory.

The problems began when a few graduating students tried to keep their franchise after graduation, which went against the franchise agreement. The students began notifying customers that Chris’s company had gone out of business and that their franchise was taking over.

“They did it in spring, which is a really critical time for us to get clients committing for the summer. A majority of our customers were like ‘you guys are a mess. Forget both of you.’”

Lawsuits were filed to straighten out the confusion, and restore the reputation and customer list that Chris had built. The legal process was a long and difficult one. The entire debacle showed Chris that franchising wasn’t a good fit for his business. 

He also realized that no matter how bad things had gotten, he knew he loved building his company.

“Even though it was all falling apart, there was nothing else I’d rather be doing.”

Chris realized he really enjoyed the marketing side of the business. He had a lot of knowledge of what worked and what didn’t work, gathered from his years of experimentation building his company.

What if he could take the knowledge he’s learned over 10 years and help other businesses learn it in a fraction of the time?

Transitioning to consulting, and beyond

Eventually Chris decided to sell his company and found a buyer who wanted to give work to people in his local community. With more time on his hands, Chris wanted to learn more about how he might be able to offer his marketing services to lawn care companies. He took a job in sales for a local marketing agency and was quickly disappointed in what he saw.

“They had no idea what they were doing. They were just lying to everybody. And I was thinking, wait a moment. What I figured out by myself to make my company grow is way better than what these guys are selling.”

That settled it for Chris. He was ready to break out on his own and help grow lawn care companies like his, using his knowledge of marketing and his experience treating people right.

Lawn Authorities was born. Their mission is to eradicate the poor treatment of staff and clients in the lawn care industry by leveraging technology. 

When he reflects upon what he’s learned on his journey so far, Chris keeps coming back to the idea of always learning and not giving up.

“Enjoy the process and just keep growing and learning. There are going to be times where you think that maybe it was all for nothing. But it almost never is, as you’re always going to be finding new ways to apply what you’ve learned as you go.”

“As long as you don’t stop, as long as you don’t give up, it doesn’t matter how big or small of a step you take every day. But you have to take some sort of a step.”

This story is part of a series called The Climb that explores the challenges entrepreneurs face as they grow and scale their businesses.