A A notorious Mexican drug baron’s audacious escape from prison in July doesn’t, at first, appear to have much to teach corporate boards. But some in the business world suggest otherwise. Beyond the morally reprehensible side of criminals’ work, some business gurus say organised crime syndicates, computer hackers, pirates and others operating outside the law could teach legitimate corporations a thing or two about how to hustle and respond to rapid change.

B Far from encouraging illegality, these gurus argue that – in the same way, big corporations sometimes emulate start-ups – business leaders could learn from the underworld about flexibility, innovation and the ability to pivot quickly. “There is a nimbleness to criminal organisations that legacy corporations don’t have,” said Marc Goodman, head of the Future Crimes Institute and global cyber-crime advisor. While traditional businesses focus on rules they have to follow, criminals look to circumvent them. “For criminals, the sky is the limit and that creates the opportunity to think much, much bigger.”

C Joaquin Guzman, the head of the Mexican Sinaloa drug cartel, for instance, slipped out of his prison cell through a tiny hole in his shower that led to a mile-long tunnel fitted with lights and ventilation. Making a break for it required creative thinking, long-term planning and perseverance – essential skills similar to those needed to achieve success in big business.

D While Devin Liddell, who heads brand strategy for Seattle-based design consultancy Teague, condemns the violence and other illegal activities, he became curious as to how criminal groups endure. Some cartels stay in business despite multiple efforts by law enforcement. Liddell genuinely believes there’s a lesson in longevity here. One strategy he underlined was how the bad guys respond to change. In order to bypass the border between Mexico and the US, for example, the Sinaloa cartel went to great lengths. It built a vast underground tunnel, hired family members as border agents and even used a catapult to circumvent a high-tech fence.

E By contrast, many legitimate businesses fail because they hesitate to adapt quickly to changing market winds. One high-profile example is movie and game rental company Blockbuster, which didn’t keep up with the market and lost business to mail order video rentals and streaming technologies. Liddell argues the difference between the two groups is that criminal organisations often have improvisation encoded into their daily behaviour, while larger companies think of innovation as a set process. “This is a leadership challenge. How well companies innovate and organise is a reflection of leadership.”

F Cash-strapped start-ups also use unorthodox strategies to problem solve and build their businesses up from scratch. Both criminals and start-up founders “question authority, act outside the system and see new and clever ways of doing things,” said Goodman. “Either they become Elon Musk or El Chapo.” The co-founders of music streaming service Napster, for example, knowingly broke music copyright rules with their first online file sharing service, but their technology paved the way for legal innovation as regulators caught up.

G Goodman and others believe thinking hard about problem-solving before worrying about restrictions could prevent established companies from falling victim to rivals less constrained by tradition. In their book The Misfit Economy, Alexa Clay and Kyra Maya Phillips examine how individuals can apply that mindset to become more innovative and entrepreneurial within corporate structures. They picked out five common traits among this group: the ability to hustle, pivot, provoke, hack and copycat.

H Clay gives a Saudi entrepreneur named Walid Abdul-Wahab as a prime example. Abdul-Wahab worked with Amish farmers to bring camel milk to American consumers even before US regulators approved it. Through perseverance, he eventually found a network of Amish camel milk farmers and started selling the product via social media. Now his company, Desert Farms, sells to giant mainstream retailers like Whole Foods Market. “In many cases, scarcity is the mother of invention,” Clay said.