Bill Kaplan

Bill Kaplan Profile Summary

Bill Kaplan’s Net Worth in 2024: $100 million

If you love the thrill of blackjack and professional gambling in general, you’ve probably watched the movie 21 about Bill Kaplan and his MIT team. He was known for leading a group of brilliant minds to win big at blackjack tables in casinos around the world. As a Harvard student, he took a hiatus, went to Vegas, and used his intelligence to count cards, winning millions with his team. His current net worth is $100 million. 

Everyone is constantly watching everything and catching errors or finding ways to maximize revenue or minimize costs. Knowledge is power. The more people on the team that have the knowledge, the more powerful the team.

What Does Bill Kaplan Do?

Bill Kaplan is best known for his blackjack strategies that consistently beat the house with his scientifically proven system. His company, Strategic Investments, trained bright students to card count and gamble with great success. 

Later, he co-founded and was CEO of FreshAddress, a Massachusetts tech company specializing in email verification. Kaplan scaled the company and later sold it to a private equity firm in 2018. He orchestrated the 9-figure merger and continued as CEO before stepping back to become one of the company’s strategic advisors.

Kaplan is also the Co-founder and President of Linden Properties, a real estate investment and development company. Linden Properties owns and rents over $100 million of retail and office space to major companies, including Bank of America, CVS, Massachusetts Institute of Technology (M.I.T.), Spotify, Subway, and Walgreens - to name a few.

How Did Bill Kaplan Make His Money?

Bill Kaplan took $1,000 and turned it into $35,000 in nine months using his strategy to count cards. He graduated from Harvard and continued playing blackjack. In the 90’s, he was overheard by a group of MIT students talking about his success with the game. He then started a blackjack team with this group of students, creating strategies that allowed him and his team to win big at the game in many casinos. 

Kaplan’s background was in statistics, so he was able to apply mathematics and computer science to create a winning card-counting strategy. Using this betting strategy, he could play each hand to its full potential, based on which cards were in the shoe and the expected advantage.

Bill Kaplan and his team won millions of dollars before he eventually walked away, leveraging the money he’d made to create his real estate and development dynasty.

What’s Bill Kaplan’s Game of Choice? 

Blackjack, also known as 21.

What is the Most He Ever Won?

Kaplan once left a table with 10 million dollars in winnings.

How Does Bill Kaplan Like to Spend His Money?

There’s not much known about his spending habits though he would have invested in his real estate and development business after retiring from playing Blackjack at the casinos. His older son went to Harvard so we know he spent some serious coin for his kids’ education.

Key Gambling Stats 

• Highest win – Approximately $1 million
• Highest loss – Not publicized but someone on his team lost $10,000 in Atlantic City.
• Used his winning strategies from the late 1970’s to the 1990’s

Gambling Lessons From Bill Kaplan

“Winning at blackjack requires time and strategy. Sitting down at a table for a few hours is gambling”, he said, not the analytical activity he pursued before.

Before you even hit the table, invest in how to use the best strategies available. This will increase your chances of winning. There are books out there that teach you strategies of Blackjack and make sure to practice on low stakes. To be successful, you want to practice discipline and maintain patience. The strategy is the most important part of playing.

Stick with the Formula

Kaplan was something of a genius and never considered himself a gambler. He kept to his winning formula and, with the help of his team, found great success. He focused on blackjack because it was a game he knew how to win. His trick was sticking to the rules of mathematics; he maintained a certain structure, which significantly improved his chances of winning. 

When it comes to gambling, it’s believed that the house always wins, but Bill Kaplan and his team proved that this doesn’t always have to be the case. Since Kaplan’s heyday, casinos have implemented technology to adapt to their now widely-known vulnerabilities around things like card counting, demonstrating the impact he and his peers had on the industry.

For two decades, Bill Kaplan consistently beat the house. For that, he should be an inspiration to other aspiring gamblers out there.