From MIT Blackjack to E-Mail Databases: We Catch Up with the Other Micky Rosa

Lots of folks are excited about the movie 21, a semi-fictionalized account of the exploits of the MIT blackjack team in the 1990s. That’s clear not just from the film’s box-office-leading performance last weekend, but from the fact that so many people are coming out of the woodwork and identifying themselves as members of the team.

In fact, there’s a bit of a controversy brewing in the comments section of Bob’s piece last week about team member John Chang, one of the models for the Micky Rosa character in Ben Mezrich’s 2002 book Bringing Down the House, upon which the movie is based. Bill Kaplan, who co-founded, trained, and financed the blackjack team, commented that, “While I know John likes to say he’s Mickey Rosa…the fact is he’s a dead ringer for the character Choi.” (Note: the book spelled Rosa’s first name “Micky” but everyone routinely adds an “e.”) And later Kaplan e-mailed Bob the following note:

“The Mickey Rosa character as developed in the book and the movie is fictitious. But as he represents the founder and leader of the team who made everything happen (e.g. supplied/raised the capital; determined the original playing strategy; structured the compensation terms and incentives for investors, players, and management; put the business processes, training rules, checkout procedures, player tracking and supervision, etc. in place; gone out as a player on top), that would be me.”

We aren’t about to take sides on this one. But it’s obvious that the Rosa character (played by Kevin Spacey in the movie) is likely even more of a fictionalized amalgam than has previously been reported. And what’s also becoming clear is just how many of the people who did time on the blackjack team have gone on to become prominent members of the Boston technology and innovation scene. Kaplan is a prime example of that, as I learned in an interview with him this week.

Bill Kaplan, CEO of FreshAdressKaplan is a 1977 economics graduate of Harvard College (the same class that included Steve Ballmer, and that would have included Bill Gates, had he not dropped out). Among the many feathers in his cap are a former world ranking in professional squash and a 1980 MBA from Harvard Business School—he had to fight to get his initial admission to HBS reinstated after the school found out about his history as a card counter.

Kaplan says he co-founded the blackjack team in 1980 with MIT student J.P. Massar (who went on to be a well-known LISP programmer, an employee at Danny Hillis’s pioneering computer company Thinking Machines, and a professional-level poker player). Kaplan ran the club as a limited partnership bankrolled by outside investors; at its peak in the early 1990s, it “employed” as many 80 players, Kaplan says. He departed around 1993—before most of the events depicted in Bringing Down the House—to focus on his Boston-based real estate investment company, Linden Properties, which he had started in 1980 and which has acquired and developed over $100 million in commercial real estate, most of it within a two-hour drive of the city.

And for his latest act, Kaplan has remade himself again, this time as an Internet entrepreneur. The problem Kaplan and his Newton, MA-based company, FreshAddress, are trying to solve is one endemic to the net, where people are even more transient than in the physical world. It’s the fact that people switch e-mail addresses every three years or so, on average. While that may not seem like such a big deal from a consumer’s point of view, it causes fits for any organization that depends on e-mail to communicate with its customers, donors, or alumni. It means that if a company assembles a database of 3 million e-mail addresses, after a year only 2 million of them will be usable. And that’s something companies are willing to pay to prevent.

When Kaplan and business partner Austin Bliss started FreshAddress in 1999, however, they were thinking of it as … Next Page »

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Wade Roush is a freelance science and technology journalist and the producer and host of the podcast Soonish. Follow @soonishpodcast

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5 responses to “From MIT Blackjack to E-Mail Databases: We Catch Up with the Other Micky Rosa”

  1. Steve says:

    FreshAddress is a terrible idea. There are reasons people have multiple addresses and only give out certain ones to certain people. Companies will just use this service to send people crap they don’t want. If I need something from a company I will e-mail them.

  2. Lanny says:

    There is a patent on a database of (old address, new adderess)? How is that not obvious?

  3. Yawn says:

    Yet another “we’ll help you spam” business. They should be illegal..

  4. VJ Agrawal says:

    Short and sweet, why bothering using all these complicated software claiming being the “silver bullet” to verify emails or online solutions that are not more than simple automated scripts, while there are real companies out there actually performing the verification of email lists/databases? I have tested most of them; some are good and others not so good. A while ago, I found and it was the final solution for me. Their business model is simple yet strong; I just have to upload my email list and they take care of the entire validation process. They keep me posted and when the “green light” is given I download the file back. What a concept! Hope this helps