Tom Nassr – Checkmate Digital

2017 Entrepreneur of the Year

We recently had a chance to catch-up with Tom Nassr and ask him a few questions about his progress since being recognized as our first Entrepreneur of the Year. Here’s what he said.


How has your business progressed since you won the Entrepreneur of the Year award?

Overall, Checkmate is much more focused on what we do well. Our processes have been refined and most infrastructure has become automated. The business is making data-driven decisions as much as possible, and we’ve expanded into doing user-testing.


What was the impact to you and/or your business, if any, in being named Entrepreneur of the Year?

I’d say there was little external impact. But for me, it was an honor to be named, especially to be named first. I feel like the biggest ‘boost’ it gave me was a confidence boost that I’m doing the right things.


Knowing what you know now, what would you have done differently while you were developing your business?

I probably would have written a business plan. I think I took foolish pride in not having a defined and written plan, and now that I have the benefit of experience, I see the value in writing down and building a business model canvas or something like that, to understand the scope of the business.


Additionally, I’d focus much more on internal processes and on marketing/creating content. Those two, process and marketing tend to have compounding effects that would be super beneficial to have from the beginning.


What aspects or resources of the CT entrepreneurial ecosystem have helped your business the most?

The culture of the ecosystem is probably the biggest help. People in the CT startup community genuinely help each other, make introductions, and help each other succeed. Also, we have benefitted from the wonderful accelerator community that’s been established around here. from Techstars, Startup Bootcamp, The Refinery, among others, they have all been great to be a part of.


Looking ahead, what are the next major milestones for your business?

Our next major milestones are focused on a top secrets project we’ve been working on under the radar. We’re planning to come out with a product of our own over the 12-18 months.


Keep up the great work, Tom and team!


Learn more about Checkmate at

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