When Robert (Rob) DelMastro ’86 entered Clark, he had no idea what career he wanted to pursue. He first planned to declare a biology major, then switched to geography, psychology, and again to computer science before graduating with a degree in mathematics. Though he did not know it at the time, his combined academic, social, and cultural Clark experience set Rob on a path toward lifelong entrepreneurship.

Today, Rob is the owner and CEO of Clearly Coworking, a business center and coworking facility in Worcester, and has hired several Clarkies over the years. More than 30 years since his own graduation, Rob has continued to stay connected to the Clark community. He has been invited to speak to numerous classes about entrepreneurship, and he recently presented to the Clark Entrepreneurship Club about his experience launching, growing, and eventually selling businesses. Clark made a lasting impression on Rob in the 1980s; he continues to come back to campus to meet and mentor students and hire Clarkies at his own organization, and is an active alumni user on the ClarkCONNECT platform.

Below, Rob talks about how the Clark community has contributed to his professional journey — and offers some advice for students!

What did your career path look like after graduating from Clark?

I applied to jobs at 40 different companies after graduation. I got one interview and one job offer, at Hanover Insurance Group. As a math major, I was hired as an actuary; I spent two years in the actuarial field at Hanover and realized I didn’t really like that career. That’s when the personal computer started making its way into the business world, and I enjoyed working with them, so I went into IT and taught myself how to be a software developer and network engineer. I stayed at Hanover for 10 years — eight of those years were in the IT world. From there, I left to start two insurance companies (with a group of about 20 people), one in Massachusetts and one in Connecticut. My role was to build the entire system’s infrastructure for the Massachusetts organization and write a lot of the software. I did that for five years, then decided to start my own technology company, Blue Cod Technologies, with two other people. We ran that for 12 years out of Marlborough, Massachusetts, until I left and started my current company, Clearly Coworking.

How did your time at Clark prepare you for entrepreneurship?

Clark just changed me. It made me realize who I was. I was a pretty shy, quiet kid and I grew up in a vanilla town, so coming to Clark and being exposed to more diversity was such a great experience. The Clark experience is what changed me, not necessarily the classes I took or what I learned academically. That’s why I think Clark is so special: a lot of learning happens outside of the classrooms. That helped me figure out who I was and what I was going to do.

How have you tapped into the Clark community to build your team at Clearly Coworking? 

One of my two current employees is a Clark grad, and I found her through posting a job through ClarkCONNECT. What’s interesting is that way back in 2014, before ClarkCONNECT existed, I hired an employee who was graduating from Clark. She spent the summer with me as I was starting the business and she helped develop my entire social media presence. I’m actually in the process of hiring my third Clarkie right now, my college roommate’s daughter, who is now in Worcester. I’ve met a lot of Clarkies on this journey who have helped me with this business.

What do you like most about working with Clarkies?

Clarkies are unique people, and they’re always a pleasure to work with. I know it’s a great pool of talent to pull from, and I’ve had very good luck with my Clark employees. I think the attitude of most Clarkies is something that just works for me.

What career advice do you have for current students?

I know they teach this at Clark, but pursue your dream. I can’t tell you how many people told me that every idea I had was stupid and would never work. If I had listened to them, I wouldn’t have started the three companies that I have started. If you believe in yourself and feel as though you have a good idea — you obviously have to do your homework and make sure there’s a market out there, but pursue it. And when you get out of Clark is the time to do it. Once you have a family, it becomes a lot more difficult to take the risks you can when you’re 20 years old. So do it soon, that makes a big difference.

Why should alumni stay engaged with Clark after graduation?

When you get into life after Clark, you start to realize the importance of networking and having connections with people. I think that having that Clark commonality is a great starting point from which to build that network — and there are a lot of successful Clark people!