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John Kealey

John Kealey


The beautiful Black Cat Island in Moultonborough, NH on wonderful Lake Winnipesaukee 

How would you describe your role? 

As Chairman, I advise Ryan and the leadership team on strategy, leadership, and other macro issues impacting Mainstay. I serve on the Board of Advisors for a number of companies and I see my role as challenging the CEO and leadership team to think broadly, and creatively about their business’ opportunity.  

What are your professional specialties and accomplishments? 

With decades of experience running and advising companies, my specialties are business strategy, business model, and leadership. In addition to Mainstay, I am currently on the Board of Advisors of: RF Smart, Evident Systems, Threat Tec, Second Mountain, Tailwinds Talent, and a Board Observer at Canvs.

I am the former CEO of a number of companies. The company I am most proud of leading was iDirect Technologies. While at iDirect, I was named Satellite Executive of the Year and Ernst &Young Entrepreneur of the Year in the Washington, D.C. area in 2005. We were also named to the Inc. 500 List of fastest-growing private U.S. companies 3 years in a row (2003-2005), and we were named #19 in the Deloitte Technology Fast 500 in 2005. 

As a result of what we accomplished at iDirect, I had the opportunity to speak on my experience with Stanford University’s executive education program for 6 years.  My message to each class was, if you focus on building a great culture and making the employees, not the shareholders, the center of your attention you can build something truly great. 

Locally, I volunteer with the University of New Hampshire in the Entrepreneur program and am on the Investment Committee for the Rines Fund at UNH, a student-led start-up investment fund.  

What was your first memory of using computers? 

My first memory of using a computer was in 1984 while working at Coopers & Lybrand in St Louis. The firm bought a few computers and put them in an unused office and let us use them to begin to see what was possible. Unimaginable today, it really wasn’t clear then how computers would help us. 

When you’re not found in front of a computer you are…? 

When I am not working, I am hanging out with my family, spending time out on the lake, playing golf, or walking our dog. 

What was the last great book you read? 

The last great book I read was the Life and Times of Frederick Douglas. It is his autobiography, and what an amazing story it is. He was such an exceptional person and accomplished so much while the world tried to hold him back.  

What is an experience you’ll never forget and what did you take away from it? 

One of my greatest memories is the legal adoption of my great-niece by my niece and her husband. It was just before the pandemic and we went to a courthouse in Southern Illinois, where they live, and witnessed the formal process of an adoption. When the formal proceedings were complete the judge came out from behind the bench and took pictures with the family. It struck me that this must be the happiest thing that happens in a courtroom. It was magical.  

What would you do if you had an extra 5 hours every week? 

If I had an extra five hours each week, I would spend more time helping my son with his start-up business. I spend a lot of time on it already, but if I had 5 more hours, I would gladly give the time to him.  

If you could go anywhere for an entire month, where would it be? 

If I went anywhere for a month it would be Italy and I would just visit as much of the country as possible.  

Favorite sports teams? 

My favorite Sports team is The St. Louis Cardinals! I grew up just outside St Louis and have been a lifelong Cardinals Fan!