Today we’d like to introduce you to Jon D’Allessandro.
So, before we jump into specific questions about the business, why don’t you give us some details about you and your story.
It all started in the spring of 1986 when my drive to “do more” really kicked in. It was always a dream of mine to own my own business. I wanted to help people, provide exceptional service and build a company where I could do small projects build them to perfection, and, at the same time, provide a great environment for the people who worked with me.
At the time, money was scarce and like most people, I lived paycheck to paycheck with little or no extra money. I was told that I could never start a business like D’Allessandro and be successful and that I should just go home, relax and have a beer. I was told to keep working for someone else, make good money and enjoy my life. Despite friends’ and family’s best intentions, that advice didn’t sit well with me. I wanted to do more, learn, get out there in the business world and create a successful company that was known for quality work.
The prior year,1985, I spent doing odd jobs on the side with my old pickup, and finding a helper when I needed one for the bigger jobs. There was so much construction work around that by 1986 it was easy to grab a job. I took all that I could handle and soon I needed more help to get all the work done. I found the perfect partner and we worked together for a year building small roads, working in new home subdivisions, installing sewer lines and learning a lot about business and people in the process.
I also wanted to learn all that I could about the construction business and wasn’t shy about asking for advice or finding out what I could do better. A former co-worker took the time to teach me how to properly estimate the work that I was bidding every Sunday at his home. He was excellent at his trade and provided me with a wealth of knowledge. In April 1987, I launched D’Allessandro Corp with one full-time employee who still works with me today. We continued working as I had in the past, but now I was able to take on larger projects, add more help, and eventually buy new equipment to get the jobs done well and on schedule for our growing list of clients.
We worked diligently to get into the public market and worked for both municipalities and educational institutions. I enjoyed working in and around the cities of Boston and Cambridge. The challenges and the work continually kept me engaged and I always strived to learn more.
Through hard work and determination, we grew the company to eight employees in the first year and then 12 by our second. We had three crews working efficiently and making an impression on our clients who often commented on our professionalism, the quality of our work and our dedication to getting the job done right the first time. We treated everyone with respect and clients kept calling us back to do more work.
The recession that lasted from 1989-1991 was rough – we took it on the chin – but it offered lots of teachable moments that helped me prepare for future recessions. As I looked out my office window at the machines I owned that I had to pay for every month just sitting there with little or no work, I quickly learned how to navigate through financially lean times. Competition for work was stiff and I learned that public work was the way to go. It was our future – we needed to work for customers who paid well and on time – and where the money was almost guaranteed.
By the time 2008 rolled around, D’Allessandro Corporation had a hundred employees and lots of bills. We worked as a team to make it through that tough time.
I learned that I had to take care of the people who worked with me and ultimately, we would take care of each other. We helped business owners that worked with us as suppliers and subcontractors, stay solvent during those difficult times so we could all make a difference in what we did and how we did it.
The health and safety of our employees and subcontractors is my first concern every day and second is treating people well – that comes back to us tenfold. The good fortune I have enjoyed comes from treating people the way I would want to be treated and helping others along the way whenever I am able.
My unwavering drive has gifted me with the success that I currently enjoy…success that has even exceeded my own expectations! I currently own or co-own eight businesses (D’Allessandro Corp being the largest) including an equipment rental company, a fence company, a landscaping company, three restaurants and a small bar. All of this came from the relationships I have built, the people I have helped and the respect and friendship I have earned from them in return.
Great, so let’s dig a little deeper into the story – has it been an easy path overall and if not, what were the challenges you’ve had to overcome?
Two of the biggest issues I’ve faced over the past 30 years, have been navigating through the recessions and learning to deal with the scarcity of work while making difficult budget decisions. The second challenging area, one all contractors face, has been the government’s shifting regulations and compliance requirements and the sanctions contractors face if not in compliance, even though the regulations are a work in progress.
It is particularly frustrating that there is no real communication between government officials and contractors to make the process easier or less problematic. I’ve volunteered to help sit on or start a committee to bring contractors and officials together to begin a dialogue that leads to positive change that would ultimately help the taxpayer too. Alas, that offer fell on deaf ears as no one ever took me up on it.
Alright – so let’s talk business. Tell us about D’Allessandro Corp – what should we know?
D’Allessandro CORP focuses on civil, heavy highway and utility work in the private and public sector. We specialize in building complex water, sewer and road projects in Eastern Massachusetts and build beautiful parks, roads and manage site work for new buildings and residential developments.
Our dedicated team of experienced construction professionals work together to help solve clients’ problems, spot unforeseen issues and resolve them with the owners and get their projects done safely while adding value and quality.
We pride ourselves on helping everyone involved the project including the residents of the neighborhoods we work in by showing up with the attitude that we are here to make a difference and help improve the quality of their environment. Whether it’s helping with trash collections or shoveling snow from someone’s walkway, we are working collaboratively to get our work done in a safe, efficient and friendly manner before we move onto the next project.
Is there a characteristic or quality that you feel is essential to success?
Our team shares a set of core values that make it easy to be safe and productive at the same time while caring for each other and the people around us. Those are:
- Working to the highest standard
- Loving what you do
- Maintaining integrity
- Acting professional
- Possessing job competence/knowledge
- Being accountable
- Demonstrating leadership
Contact Info:
- Website: www.dallessandro.com
- Phone: 508.559.6400
- Email: info@dallessndro.com
- Instagram: @dallessandrocorp
- Facebook: @d’allessandrocorp
- Yelp: D’Allessandro Corp.
- Other: D’Allessandro Corporation


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