About Jim

Hello there. My name is Jim Flynn. I live in Northampton, Massachusetts with my beautiful and smart wife, four awesome kids and a hamster named Polkadot.

Way back in the early days of the Internet (circa 1996), I launched a software company in New York City. At the same time, I did some moonlighting as a journalist. One of my first assignments involved attending back-to-back developer conferences in San Francisco. Upon returning, I proceeded to disappoint everyone (including myself) by predicting there would be no “Internet war” between Microsoft and Netscape. I said that Microsoft was going to crush them. I’m only bringing that up because: (1)  I was right; and (2) I want you to think that I’m really smart. Well, the truth is that I don’t get everything right, but I try. I like to think that I often have useful insights and that I’ll adjust when the evidence says that I’m wrong.

I started, built and sold a few technology businesses. I made a decent amount of money for other people and sometimes a little for myself, too. Once when I was nearly broke,  I almost closed a deal that would have made me filthy rich, only to see it go “poof” at the last minute. I also had the soul-crushing task of winding down a business that didn’t work out, cost me a lot of money, and took away years of my life. Sometimes you can learn more valuable things from debacles than you can from successes. I’ve dealt with venture capitalists and angel investors involving multi-million dollar deals. I can tell you true stories that you wouldn’t believe a word of.

I’ve worked (roughly in chronological order) as a software developer, computer hardware engineer, salesperson, bizdev guy, CEO, COO (of a public company), CEO, CTO, and as a software developer/president. I also co-authored a 666-page book on the Java programming language. Writing a book was actually an incredibly stupid thing to do while struggling to build a start-up with no funding. But the book looks great on my coffee table now, or at least when I can find the darn thing. I suspect the book is under the couch at the moment, probably covered in dust bunnies. I can do a broad range of things. Not many people can both write software and sell it. Sometimes I even sold companies. That involved doing a lot of negotiating, contractual, audit and due diligence thingies for which I’ve always risen to the challenge.

This blog is my attempt to get back into what used to be my hobby and has always been my passion: Looking at technology and trying to figure out how it might impact people’s lives.

If you’re still reading at this point, then there’s something wrong with you. Gosh. I guess I shouldn’t insult people who take the time to pay any attention to me (Sorry, Mom!). So I’ll wrap up the personal-touchy-feely part of my “About Jim” page here. If you’re interested in reading the corporate-speak version of my bio, you can see it below. For a real snoozer, you can also check out my LinkedIn page. You can also follow me on Twitter.

Bio in Corporate-Speak

Jim is currently the President of Overlook, LLC, a leading provider of Over-the-top (OTT) video streaming solutions. Before Overlook, Jim co-founded and lead EZTakes, one of the first movie download companies. Under Jim’s leadership, EZTakes achieved profitability, recruited over 100 film distribution companies as content partners, licensed over 8,000 feature films and TV shows, and closed a multi-million dollar round of outside funding. Prior to EZTakes, Jim was the Chief Operating Officer of a Pitney Bowes (NYSE: PBI) subsidiary that provides software and services for business-to-consumer electronic communications and Internet commerce. Jim came to Pitney when it acquired Alysis Technologies (NASDAQ: ALYS), where Jim also served as COO. In 1996 Jim co-founded @Work Technologies, a leading global provider of Internet billing and payment software used by numerous billion-dollar organizations, including several national postal services in Europe and Asia, to deliver electronic bills and receive payments over the Internet. Jim served as @Work’s CEO until Alysis acquired the company in 1999. During his career, Jim started and built several other highly successful technology companies in industries as diverse as document management and international banking. Jim began his career at AT&T where he held positions in sales, computer hardware engineering and software development.

Jim Flynn was the principal author of one of the first books on the Java programming language, “Visual J++ Java Programming.” He earned an MBA from New York University with dual concentrations in Finance and International Business, as well as a Bachelor of Science with magna cum laude honors from Manhattan College. In 2017, Jim earned a Certificate in Fintech from the Massachusetts Institute of Technology. He has authored a number of patents, of which one has been issued so far.

Jim lives in Northampton, MA.

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