about us
Life, business,  every decision you make – it’s all about risk and reward!
Bill Kaplan

Bill Kaplan

CEO & Co-Founder

Responsible for the strategic development and growth of FreshAddress, an expert on analyzing the risk/reward equation as it relates to growing successful companies. Bill was the founder and leader of the MIT Blackjack Team, featured in bestseller, “Bringing Down the House,” and the blockbuster movie, “21.”


  • Magna Cum Laude in Economics from Harvard College where he received the “outstanding scholar-athlete” award upon graduation
  • MBA from Harvard Business School

Joined FreshAddress in


Interviewed By

  • Bloomberg Radio
  • Inc. Magazine
  • New England Cable News
  • NewsCenter 5
  • USA Today


Co-founder and President of Linden Properties, which developed and owned approximately $100 million of retail and office space for tenants including Bank of America, CVS, Stop & Shop, and Walgreens. Former World Professional Squash player.

I might be a geek because I…

wrote my college thesis on calculating the costs of aircraft noise using hedonic regression analyses of housing prices and air traffic patterns surrounding Logan Airport.

I’m not like everyone else because I…

am a former world professional squash player who has captained the U.S. Squash Team multiple times in the World Maccabiah Games.

Favorite TV Show

“24” – Jack Bauer could certainly get a lot accomplished in 24 hours!

Whether you think you can, or you think you can’t–you’re right.

― Henry Ford