Business Lessons from a Serial Entrepreneur and Blackjack Star

To most people, blackjack is nothing more than a part of the entertainment space; it’s a game to be played for fun at casinos and online. As a form of gambling, this has to be how people look at the classic game of “21,” as the house edge always has the casino winning overall in the long run. Still, this hasn’t stopped the public’s fascination with the game, which has been especially fuelled by other realms of entertainment. At the movies, the awards-sweeping Rain Man put blackjack on the map, so much so that the iconic film was parodied decades later in The Hangover.

Blackjack has a special appeal among its table game peers as it gives the feeling of taking on the house head-on. Unlike in the likes of roulette and baccarat, player decisions play a part in the outcome of a round in blackjack. It’s this shrewd decision-making and ability to analyze each situation that forms an initial pillar of why this form of entertainment can be interesting for the business-savvy mind. A prime example of this comes in the form of a serial entrepreneur and one of the most famous blackjack players in the world: Jeff Ma.

Jeff Ma is the leading example

In the business world, you need to be dedicated, quick on your feet, and have an iron-clad strategy to find success in most areas. It’s a tough world to navigate, and there’s a lot to learn, but sticking to the tenants of optimum blackjack play can help a great deal. Jeff Ma didn’t make his way as a blackjack star initially; he was an entrepreneur first and then built his skill through the card game. The 1994 MIT graduate had already co-founded ProTrade – which evolved into Citizen Sports and was then sold to Yahoo – by the time he was finding a tremendous amount of success at the blackjack tables in Las Vegas.

Since then, he has founded and sold more startups and was then brought onto the books of Microsoft. Now a veteran entrepreneur, Ma is the vice president of Microsoft for Startups, using his expertise to identify and empower new businesses in Silicon Valley. Even though he’s now at the pinnacle of the startup ecosystem within the tech industry, Ma continues to make it very clear that it’s his time at the blackjack tables that have helped him to become a stud in the business world.

This is the recurring theme throughout his book, The House Advantage: Playing the Odds to Win Big in Business, which was originally published in July 2010. It’s made clear that, regardless of if applied to a game of blackjack or business, the focus has to be on data: trusting the data, analyzing every scrap of it, and then making informed decisions. It’s all about keeping focussed and trusting what is real, not unlike the so-called “Moneyball” approach from baseball mastermind Billy Beane, who changed the MLB forever with his application of data analytics.

Trusting the data and in-the-moment probability in business

Blackjack remains popular with players because it’s a casino game of perceived skill. As you can influence the outcome after the initial bet, there is some truth to this as you can apply rules of mathematics and probability to determine the optimum move in any situation. In business and blackjack, this all comes down to collecting and analyzing as much data as possible, as Ma details in this interview. He says that “you need to look at situations and understand what you need to be remembering.” With a startup, you need to collect, analyze, and track as much data as possible.

Taking variables and the given environment into account is a cornerstone of both blackjack and business data analysis. In blackjack, the analysis begins with the table or type of blackjack selected. Between Vegas Single Deck Blackjack, Classic Blackjack Multi-Hand, and Premier Blackjack with Buster Blackjack, the rules and payouts differ, creating different environments of play. These differences need to be factored into the analysis enacted with each hand as the probabilities will swing slightly as a result. The same can be said of creating a business plan, as it needs to analyze the current environment and adjust the approach accordingly. It may also need tweaking down the line if the situation in the industry changes or presents an unexpected opportunity.

By preparing through data analysis and establishing the probability for success in each situation or facet of business or blackjack, you can effectively create a model to follow. It’s integral that you stick to this model and avoid making risky plays or taking a chance on a whim when those actions are counter to what the data shows. Just as you would never hit on a hard hand of 17 or more, you wouldn’t try to pivot your startup from its core product into a new area because you have a gut feeling about an opportunity in this other market.

Blackjack is all about using the data available and making cold decisions to enable optimal plays on each hand. Business should be treated the same way, driven by data and analysis to make the right moves each time.