Happy Retirement: Barry Simon’s Datamax Career Built on Relationships

Barry Simon is well known for his signature phrase “The best is yet to be.” The president of Datamax, who recently announced his retirement, can take heart in knowing that his 45-year career was pretty special in its own right.

The slew of testimonials on his LinkedIn post announcing the news is proof that he influenced a great deal of dealer principals and other industry notables. Truly one of the industry’s good guys who made it his quest to “Create Raving Fans,” Simon is set to appear at next week’s Executive Connection Summit (ECS) in Scottsdale, Arizona. Expect a line of people bidding him well wishes if you’re hoping to shake his hand. For those who won’t be attending, we offer you this Two-Minute Drill, where Simon provided insights into his successful career.

Simon’s long embraced the servant mindset and is extremely grateful to those who helped shape his industry experience. And while he won’t be tending to the day-to-day activities for Datamax, you can rest assured that he remains just a phone call or an email away.

45 years is a long time. What stands out to you the most about your career?

Simon: Our industry has certainly changed a lot in the last 45 years.

As I reflect on my career, it’s always great to see employees come to Datamax early in their professional journey; they stay with us and build a successful career, and watching them expand and grow and their families grow has been very rewarding for me personally.

Another item would be the relationships that I’ve had with our manufacturers. I consider some vendors but I have always considered the people we deal with as partners. They always listened to what we had to say, and we always talked through things. That came through especially throughout the pandemic.

Lastly, another thing that stands out to me is all the organizations that we’ve been involved in that have helped me grow professionally, along with the people who have mentored me throughout the years. The Copier Dealers Association, which I joined in 1985, has been a guiding force for decades. In all these years, I’ve missed only one meeting. The relationship with Mike Riordan, which began with a handshake in 1995, shaped so much of who we became at Datamax. The relationships we’ve built with Andy Slawetsky at Industry Analysts, with Susan Neimes at ENX Magazine and Frank Cannata at The Cannata Report have been extremely beneficial for me.

With that, I’m also very proud that we’ve earned “Best Places to Work in Arkansas” for eight years, and been named an Elite Dealer by ENX Magazine for nine consecutive years. 

Datamax is your professional legacy. What are your hopes for its future?

Simon: I want to see the company never get away from our culture. Culture to me still trumps everything. All we’ve done at Datamax has been rooted in that understanding. I want to see our people grow; I want to see the company grow even bigger and better than it was with my leadership. I have all the highest faith in the executive team to take it to that next level.

How would you like to be remembered in the industry?

Simon: I’ve always worked to guide employees and help them reach their full potential through positive reinforcement and an openness to their needs.

I’d like to think I made the industry a better place, and that I left my mark in it. In all the areas I’ve dealt with over the years, I’ve always tried to position myself with honesty, trust and value. I’d like to be looked at as a person who didn’t put myself first but was looking after what was best for both our company and our industry.

If you could start over again today, would you do anything differently?

Simon: I really don’t think so. I always felt that if I needed to make a change I did it, whether it was through acquisition, recruiting or how we go to market.

What are the plans for your second act?

Simon: One, I’ve got to stay out of wife Patti’s way! There will still be things I’ll be involved in throughout 2026 that I’ve committed to do, including the Executive Connection Summit in Scottsdale Feb. 8-11. I’ll just have to see what this next chapter brings me. Right now, I’m enjoying the grandkids, and being any help to anyone that I can be. If anyone has questions, I’m available. 

Erik Cagle
About the Author
Erik Cagle is the editorial director of ENX Magazine. He is an author, writer and editor who spent 18 years covering the commercial printing industry.