The Owners Mindset Series with Shawn Shepheard featuring Kevin Cassidy

Welcome to the first edition of ‘The Owner’s Mindset.’

In this new series, you’ll be introduced to some of my all-star clients, as they share their story on the journey as a business owner.

First up is Kevin Cassidy, President and Founder of Cassidy Corp., a leading commercial asphalt paving company in Haverhill, Massachusetts.

Kevin is an entrepreneur at heart, having started his first company when he was just a teenager. Today, he oversees one of the largest driveway and parking lot paving companies in New England, all while maintaining his reputation as an amazing employer who truly cares about his employees.

Shawn: Kevin, we first met at Strategic Coach a few years ago. As I seem to recall, we bonded over a love of beer, the Bruins, and entrepreneurship. I want to start off our conversation today by going back to one of the questions we tackled that night – one of my favourite questions, really. Where did you get the entrepreneurial bug?

Kevin: You know, I imagine it probably came from growing up with not many means or material things, and just wanting more. I was raised by a single mom, and I had two younger brothers. It was wild. We had a lot of love, but not a lot of money.

Shawn: Fast forward to high school, when you started your first business. What was that about?

Kevin: The want for money! I had a job at a local hardware store, and I noticed that people were always looking to get landscaping work done – picking up weeds, cleaning up yards, that kind of thing. The typical stuff people do in high school for extra pocket money. From there, it just got bigger and bigger, to the point where I had eight employees by the time I graduated.

Shawn: Help me fill in some blanks here. How did you go from working in a hardware store to being self-employed?

Kevin: I bought a truck – before I had a license – and I paid somebody who had a license to drive me around. We would go around and mow lawns, and I made some okay money – a lot better than what I was making at my minimum wage job, anyway.

Shawn: And then what happened, in terms of your decision to bring on more people? Did you get to a point where you had too much work that you couldn’t do it on your own?

Kevin: Yeah, it was pretty much just a necessity thing. I reached out to one of my classmates in high school and asked if he wanted to work a couple days a week mowing lawns with me. Then I asked a second classmate, and a third, and a fourth, and so on. Just grabbing bodies. Pretty soon we even had a name – ‘Groundmasters Lawn Maintenance.’ 

Shawn: I didn’t know that, amazing. I imagine it didn’t take long before you went from cutting the grass yourself to managing the team. Tell me about that.

Kevin: The Company just kept growing. It got to the point where it became a fulltime job just to go out and look at the work and bid the work, and so that’s what I started to focus on. It forced me to change my mindset in terms of the role I had to play in the company.

Shawn: Looking back to when you started out, just cutting grass on your own, did you imagine the company growing as much as it did?

Kevin: No. I just thought it was a good way to get paid.

Shawn: And then you sold the company, is that right?

Kevin: That’s right. It was 2007. By then, the company had 15-20 employees, and honestly, I was starting to get a little bored. I’d been doing it for five or six years out of high school. It was around then that I heard about this guy in my neighbourhood who paved driveways – including my mother’s. I found out he paved four driveways on my street in one day, at four grand a piece. That’s 16k in one day!

Shawn: You were inspired.

Kevin: Oh yeah. I couldn’t stop thinking about it. Then, that spring, I couldn’t find anyone to fix my curb, which had been broken by the snowplough in the winter. So, I bought a machine to fix it myself. It wasn’t long after that I started working with asphalt. I thought, there might be a real business here. So, I sold my landscaping company. 

Shawn: And that was the birth of Cassidy Corp?

Kevin: Yes it was.

Shawn: Did you know a lot about the paving business back then?

Kevin: Not a thing.

Shawn: So, how did you get there?

Kevin: Sheer stupidity.

Shawn: Well, in that case, I wish I was as stupid as you, my friend.

Kevin: Honestly, I was young and dumb. When you’re young, you don’t even think twice. You’re just like, ‘screw it; I’ll give it a try.’

Shawn: Tell me about your first year in business. What was that like?

Kevin: Oh, I got a hardcore education the first few years. Really got my ass handed to me. I quickly learned how much of a capital intensive process it all was. There’s a lot of equipment involved. To make matters even more challenging, it was the start of the 2008 recession. It was a few years of losing money before we were able to turn the tide. Definitely a painful time. Looking back, though, I’m lucky I kept my head down. Too stupid to do anything other than just keep plowing through.

Shawn: Were there days when you didn’t want to do it anymore?

Kevin: Oh yeah. The struggle was real, no doubt about it. You’re barely making money, it’s not easy work, and it’s tough to see the light at the end of the tunnel.

Shawn: Did your friends and family think you were crazy?

Kevin: Definitely, whether or not they admitted it. I remember one of my best friend’s dads, a guy who was very successful in real estate, asking me if I had rocks in my head.

Shawn: I don’t think we talk enough about the real struggles of those early days; the losing money and the doubtful voices of those around you. But that’s where the lessons are. It takes courage to keep going through all that. So, what was the turning point?

Kevin: It was slow. I can’t put my finger on the exact year that things started to turn around, but it would have happened around the time that I learned about the importance of human capital. I started to get talented people, and that’s when things started to fall into place. Looking back, I can think of a couple key hires that made a huge difference.

Shawn: It seems you’ve always placed a lot of importance on finding good people – would you say that’s true?

Kevin: Most of my success in my 15 years in business has happened in the last three or four years, and it’s all thanks to my team. There’s some stuff that goes on day-to-day that I don’t even know about, and honestly, I think that’s the real turning point.When you can let go of things and admit there are people on your team who are more talented at doing certain things than you are, that’s when real growth happens, because that’s when you can focus on what you need to do: growing the company.

Shawn: What is the key to hiring a great employee?

Kevin: To me, it’s all about how you show up. I’d much rather have someone on my team with a great attitude but less in the way of skills; everything else, we can work out. That’s why, when I see talent, I grab it. It’s also important to remember that it’s not the end of the world if it doesn’t work out. If it works out 8 out of 10 times, you’re doing awesome.

Shawn: So, what’s the world look like right now for Cassidy Corp? In 2021, what kind of shape are you in?

Kevin: We’ve got about 40 employees, and we do about 10 million a year on municipal work, state/federal government work, commercial work, and residential work. I’d say most of our work is at the municipal level, currently.

Shawn: And talk to me about your company culture. I know that’s really important to you. What kinds of opportunities do you strive to create for your employees?

Kevin: The bottom line is that we’re people helping people. That goes for me, my employees, and our customers. At the end of the day, I’d rather lose money on a job and have our people be successful than anything else. It’s people over profit, all the way. Too many times, that’s a tagline for companies and they’re full of shit. But we try to live and breathe that.

Shawn: You care about people. You know their families. You provide a really good wage and benefits. There are a lot of things you do that other companies don’t.

Kevin: There are a lot of guys in this business who are really greedy. My thinking is: at the end of the day, if there’s a million or two lessin the bank, does that really matter? No. Did we take care of our people? Did we treat them the way we want to be treated? That’s what it comes down to.

Shawn: I’d love to hear a little more about some of the challenges you may have faced around growing the business over the years. We’ve all heard the saying, ‘what got you here won’t get you there.’ It’s a cliché, but it’s a cliché for a reason. So, tell me, what have been some of the biggest challenges for you in terms of getting to the next level?

Kevin: In the first five or six years of Cassidy Corp, we were making between 500,000 and 1.3 million. It really felt like we were stuck in that million dollar run. At that point, I started investing more in people, and more in myself. I joined some entrepreneurship organizations in Boston, I joined the Strategic Coach program, and I started doing more professional development overall. From that point on, we grew to 2.3 million, to 2.6 million, to 4 million, and it just kept going up year after year. 

Shawn: And you attribute that to your own commitment to self growth, and the growth of your employees?

Kevin: It was strictly because we developed people. I also developed myself, and came to understand what my blind spots were. I realized where I needed to be focusing my attention to help the company grow. As much as I love to be in a Caterpillar – digging in the dirt is every big kid’s dream, right? – my energies are best put toward developing scalable business ideas. Opening my eyes to that – and actually following through with it – was huge. I used to be convinced I was the best person in the world at grading parking lots and driveways. Now we’ve got four guys who do it better than me.

Shawn: I want to rewind to about a year ago, when you reached out to me and said, ‘Hey, I might need some help here.’ What was going through your mind at that point, and what’s changed since then?

Kevin: Well, it was the start of the pandemic, and I felt like I had climbed into my procrastination bed and pulled the sheets over my head. I wasn’t pushing myself enough out of my comfort zone. I knew you from Strategic Coach, and so I reached out to see if we might be able to work together. You proceeded to beat me over the head with all that ‘focus time’ stuff – which turned out to be the very thing I needed to do in order to move the needle.  

Shawn: As you know well by now, investing in ‘focus time’ is all about committing to  an hour a day, 4-5 days a week, reflecting on the big things that will help grow your company. When we first started working together, did you find it difficult to invest in that time? Even just to turn your phone off for an hour?

Kevin: Oh, it was extremely painful. My phone vibrates 60 or 70 times a day, and it’s really hard to just turn it off. But once you’re there, it’s a good spot to be. Everybody wants to have the 1-year plan, the 3-year plan, all of those plans for their business put in place. But in order to do that, you need to be willing to go through some of that pain, and for me, that meant turning off my phone. It really helped me get into the zone.

Shawn: Tell me, what would you say to new entrepreneurs or business owners? Now that you’ve gone through the battleground, you’ve had struggles and successes, what are two or three tips you might share with the owner of a company who wants to grow?

Kevin: First things first, the struggle is real. Success doesn’t happen overnight. It’s a long, long process, and even when you think you’re at the top, you’re not. Secondly, don’t judge yourself against anyone else. There’s always going to be somebody with more, somebody who got there faster. But at the end of the day, it’s irrelevant. The race is only with yourself. Lastly, as cliché as it sounds, I’d say it’s not how many times you fail, but how many times you get back up. It’s easy to throw in the towel. There are times I wish I still just had the one crew, and we were just doing driveways. Those were simple times, without real problems. But with those perceived “problems” has come a lot more profit.

Shawn: Last question. I want to know you’re deeper “why” for the work you do. I know your family means a lot to you, and you love getting to spend more time with them. So, how do your goals and your love of your family fit into all this?

Kevin: Being an entrepreneur, you get that freedom to do what you want when you want. Even if that isn’t the case 100 percent of the time, 60 percent of the time is still a really good place to be. Having the freedom to come and go, and to spend more time with my family, that’sone of my biggest driving factors.