This Entrepreneur Learned About Business at the Blackjack Tables

blackjack business lessons

If you buy something through our links, we may earn money from our affiliate partners. Learn more.

Before launching a business, entrepreneurs often hone their skills and gather life experience that can help make their businesses successful. Those experiences can come from school, working for others, or some more unconventional sources. For Jeff Ma, many of the lessons he learned that helped him succeed in his many startup ventures came from his days playing blackjack.

It certainly seems like an unconventional source for business knowledge. But Ma wasn’t just a casual blackjack player either. As part of the MIT Blackjack Team from 1993 through 2001, Ma won about $2 million. The team used sophisticated card counting techniques that were perfectly legal, but still got them banned from casinos due to their constant winning. Their story was even adapted into Ben Mezrich’s book “Bringing Down the House” and the film “21.”

Since his days at the casino table, Ma has launched three startups that he eventually sold to the likes of Yahoo, Virgin and Twitter. The serial entrepreneur recently spoke with Inc about the links between his days counting cards and his career as a serial entrepreneur.

On the surface, it might not seem like the skills from one would transfer to the other. But Ma said that blackjack taught him a lot about teamwork, gathering data, and problem solving. Ma told Inc:

“When people ask me what I miss the most from those days, it’s not the rush or gambling, it’s really the camaraderie. I miss the feeling of when the team went into a casino and tried to beat the house. That is why I love working in startups. It’s the same feeling — you get a group of people together and try to tackle a big problem. You’re trying to work together to build something, make money, and win. That’s essentially what blackjack is.”

Experience and knowledge are key to running successful businesses. But that knowledge and experience can come from anywhere. There is no one correct path to success. So to be truly successful, you need to pay attention to the lessons you can gain from a variety of sources. You never know when you will learn something that might be invaluable to your future business journey.

Save money on shipping costs for your Amazon purchases. Plus, enjoy thousands of titles from Amazons video library with an Amazon Prime membership. Learn more and sign up for a free trial today.

Blackjack photo by Shutterstock


Annie Pilon Annie Pilon is a Senior Staff Writer for Small Business Trends, covering entrepreneur profiles, interviews, feature stories, community news and in-depth, expert-based guides. When she’s not writing she can be found exploring all that her home state of Michigan has to offer.

5 Reactions
  1. Interesting. You really get the best ideas in the most unlikely places. What amazes me is how he acted on the idea. People get ideas everywhere all the time but it is rare for them to act on the idea. I guess that’s the only way for you to see the idea bear some fruit.

    • You definitely have to act in order to get anywhere with your ideas. And it seemed like he had quite a few of them!

  2. If you look at the 150+ individuals who played for my MIT Blackjack Team, you’ll see that this business was a spawning ground for many successful entrepreneurs including:
    – Chuck Whitmer and David Weise, who sold their software company to Microsoft in the 80’s. David went on to be the lead person responsible for Windows 3.0, which put Microsoft on the map and helped launch the juggernaut it remains to this day. As Steve Ballmer told me “If it weren’t for David’s contribution of Windows, Microsoft might not even exist today.”
    – Jon Hirschtick, founder and CEO of SolidWorks, which sold to Dassault Systems for over $300MM in the late 90’s
    – Jeff Ma, whose entrepreneurial successes are described above
    – JP Massar, who coached two different players that went on to each win the World Series of Poker
    – Yuchun Lee, founder and CEO of Unica, which he sold to IBM for nearly $500 million
    – Bill Kaplan, the founder and leader of the MIT Blackjack Team, who built a $100MM+ real estate investment and development company as well as co-founded and leads, the industry’s leading email database services company. And demonstrating that the apple does not fall from the tree, Bill’s two children have founded and run two hot startups themselves:, run by Stephanie Kaplan Lewis, is the leading mouthpiece and community in the millennial space;, run by Jesse Kaplan, is a last mile delivery company out to disrupt the logistics and delivery industry.
    – and many, many others

    The entrepreneurial drive and management skills necessary to build a team of 80 blackjack players that consistently beat the casinos (at their own game) are transferable across all entrepreneurial pursuits and businesses. For entrepreneurs, “Everything in life, everything you pursue, it’s all about risk and reward.”

    Or as Jon Hirschtick will tell you: “The one teaching from my MIT Blackjack Team days that I will never forget is: When you’ve got the advantage, don’t be afraid to make your bet!”

    • Wow thanks for all of this great info! It’s awesome to see all of these entrepreneurs finding success. And clearly there are some links between those successes and their shared background.

    • wow really? that’s a great list of entrepreneurs you’ve got here. i enjoyed reading and very inspirational and informative. i love that he highlighted about camaraderie. something i expect he would mention the least.