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Updated Oct 23, 2023

Business Advice from Uncle Al … (Capone, That Is)

Al Capone may have been a gangster, but his illicit business success still offers some insight for legal business owners.

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Jeanette Mulvey, Business Ownership Insider and Senior Writer
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Al Capone might not have been your typical entrepreneur. After all, he was convicted of tax evasion and was actively involved in prostitution, bribery, smuggling and selling illegal booze. But just because his business wasn’t legal doesn’t mean Capone didn’t know a thing or two about running a successful operation. In fact, Capone owned more than 300 businesses, and he knew how to get things done and command respect and loyalty from his employees

In fact, Capone’s business acumen may well have been one of his greatest assets, according to Deirdre Marie Capone, Al Capone’s grandniece, who lived in the house of her famous (and favorite) uncle. Capone, the last member of the family born with the Capone name, authored an explicit memoir that details her efforts to hide the fact that she was related to Capone and recounts her decision to eventually embrace her name and family history.

The book, “Uncle Al Capone: The Untold Story From Inside His Family” (Recap Publishing, 2011), tells many revealing facts about this iconic figure’s life, death and business dealings.

Who was Al Capone?

Sometimes known by the nickname “Scarface,” Al Capone worked his way up to running a criminal empire in Chicago during the Roaring Twenties. While the core of Capone’s business was illicit bootlegging during Prohibition, Capone’s overall business acumen allowed him to expand his influence throughout Chicago as a whole. During this time, Capone cultivated business interests in a range of fields, including cleaning and dyeing, while garnering the support of public officials, unions and employees’ associations. 

[Read next: 10 Tips for Managing Small Business Finances]

Capone was arrested at the age of 33 by the FBI following a seven-year run as the boss of the Chicago Outfit. While Capone was implicated in bootlegging, prostitution and murder, he was eventually charged with 22 counts of tax evasion. He was found guilty on five counts and sentenced to 11 years in federal prison. 

Did You Know?Did you know
The FBI's investigation into Capone arose following his reluctance to appear before a federal grand jury following a subpoena in March 1929.

Capone’s business acumen

Capone recalls in her book what life was like as a child growing up in the Capone household and shares fond memories of the man who taught her to ride a bike, swim and play the mandolin. 

Capone said she knows what the “family” was really like and what the “outfit” was all about. In her tell-all book, she shares untold details, including her claims that Ralph (Al’s older brother) and Al Capone lobbied the Nevada legislature to legalize gambling, alcohol and prostitution in that state; that they were the owners of the first upscale casino in Las Vegas way before Bugsy Siegel came to Vegas; and what really happened in the St. Valentine’s Day Massacre.

In an exclusive interview with Business News Daily, Capone offered some business tips that could have come directly from her notorious uncle:

    • You’re only as good as your word. Al Capone ran a very efficient business, she said. He taught every person who worked for him that “your word should be your bond.”
    • Remember where you came from. When Al Capone saw one of his employees strut around acting like a big shot, he would tell him, “Don’t let your head get too big for your hat.”
    • Be honest with your business partners. Ralph and Al Capone needed to give orders just once to employees, and they were expected to do their jobs correctly. Al Capone would instruct them, “Don’t lie to the people you work for.”
    • Remember, it’s never easy. Al Capone at one time ran more than 300 establishments. When a reporter wrote about how easy it was for him to make money, he was quoted as saying, “Find out what it’s like to run a business and meet a payroll.”
    • Earn your customers’ loyalty. Al Capone supplied good-quality alcohol to the citizens in Chicago from 1920 to 1931 during Prohibition. He was quoted by a reporter as saying, “Be loyal to friends and invincible to enemies.” [Read related article: Customer Loyalty Programs: A Must-Have Retention Strategy]
Key TakeawayKey takeaway
Despite his larger-than-life impact, Capone believed employees and businesses should be humble. Businesses should keep their word, be honest with partners, and never expect a customer's loyalty, but work hard to earn it.

Other business lessons to learn from Al Capone

In addition to the lessons Deirdre Marie Capone shares from her uncle, there are other business lessons to be learned from the notorious entrepreneur. Businesses would do well to keep the following lessons from Al Capone’s successes and failures in mind:

  • Make sure you’re legally compliant. The last thing a business wants is for the authorities to come along and find you’re not in compliance. In the best-case scenario, the business may be facing a hefty fine. In the worst case, the owners and operators could be seeing some serious jail time.
  • Pay your taxes and keep documentation. Remember, taxes are what brought down Al Capone. Always pay taxes on time. And, for business expenses and tax write-offs, keep thorough documentation and accounting on hand if worse comes to worst in the form of a tax audit.
  • Don’t be a wise guy. It’s perfectly normal to not know everything as a business owner. Accept that fact and, when necessary, look to hire outside experts who can help keep the business operating. Common potential stumbling blocks businesses may face are in navigating small business taxes and handling cybersecurity measures
  • Grease the wheels. Employees expect businesses today to offer a range of additional benefits and employee incentives beyond a simple base salary. Every business should learn what similar companies are offering employees in terms of salaries and benefits. Don’t be afraid to shower some job perks on employees to keep them happy, as well as to attract new talent.
  • Don’t be afraid to “know a guy.” A successful competitive analysis doesn’t just help with employee retention. Performing regular competitive analyses can help a business discover where it’s doing well, where it may need to improve and what emerging trends it may need to get ahead of. 

Entrepreneurs learn from everything

The best entrepreneurs draw inspiration and lessons from everything, including historical figures like Al Capone. Thanks to Capone’s niece, we have some insight into how the man viewed life and business. And even though he may be notorious for his illicit activities, some of those business lessons he left behind may be valuable to legal small business owners as they grow their companies and aim for success.

author image
Jeanette Mulvey, Business Ownership Insider and Senior Writer
Jeanette has been writing about business for more than 20 years. She has written about every kind of entrepreneur from hardware store owners to fashion designers. Previously she was a manager of internal communications for Home Depot. Her journalism career began in local newspapers. She has a degree in American Studies from Rutgers University.
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