What do you do when they cancel your flight?

In the late 70s, a man and his fiancée were visiting the Caribbean. They found themselves stranded in an airport when their airline canceled their flight to Puerto Rico. The man was disappointed, but based on his experience running a record business that he had founded, he took initiative to solve the problem.

Noticing other people from the same flight were also stranded, he called a chartering company to find the cost to charter a plane. $2,000. He agreed to charter it.

He divided that cost by two less than the number of seats in the plane, wrote a sign to show that price for a seat on a chartered plane to Puerto Rico, walked around the airport terminal, and sold those seats to the other people from his flight. The full plane flew to Puerto Rico.

As best I can tell, everyone benefited:

  • The man and his fiancée got a free flight
  • The chartering airline sold a flight
  • The airline that canceled his flight avoided angry customers
  • The stranded passengers got to Puerto Rico instead of being stuck

How do you describe what he did?

It was more than sales and different. He didn’t just sell the seats. He found and chartered the flight. He found the opportunity. He figured out the financing.

It was more than entrepreneurship and different. He made no business plan. He didn’t plan anything. He didn’t (yet) create a sustainable business out of it, or even try to.

It was more than leadership. He sold the tickets. He found the opportunity.

I call what he did hustling–a mix of leading, selling, entrepreneuring, empathy, and experience leading to act to everyone’s benefit.

By the way, if you didn’t know the story, the flight took off from the Virgin Islands, his name was Richard Branson, and the story was his start with Virgin Airlines. Or Virgin Galactic, if you prefer. In his words:

In ’79, when Joan, my fiancée, and I were on a holiday in the British Virgin Islands, we were trying to catch a flight to Puerto Rico; but the local Puerto Rican scheduled flight was canceled.


I walked around the airport terminal and soon filled every seat on the charter plane. As we landed at Puerto Rico, a passenger turned to me and said: “Virgin Airways isn’t too bad—smarten up the services a little and you could be in business.”

Did your business role models hustle?

Richard Branson’s story is unique, but hustling isn’t. Think of your role models in business.

Were they handed their success? Did they inherit it from their parents? Were they born with connections and resources most people never have access to?

Or did they create their success?

Did they create their own luck?

Did they create their own resources?

In short, did they make things happen in ways conventional business doesn’t explain? Did they do things nobody explains how to do?

My role models did. Most people look at self-made successes as lucky or having some magical trait that if only they did too they could achieve something big too. The magical trait could be to have a great idea, to be in the right place at the right time, to have been born with more discipline, focus, or something similar.

The more I learn about how successful people became successful, the less I find evidence of successful people having superhuman abilities. The more I see patterns of some people appearing consistently lucky, the more I conclude what looks like luck results from skills.

And the more I teach leadership, entrepreneurship, sales, and related so-called soft skills, the more I see that you can learn the skills that lead to success like my role models’ and have comparable results.

Sadly, the more books, videos, and courses I see the more I see nothing to teach hustling, despite its value in business and prominence in the origins of so many successful people in business. Well, except my own courses, which is why I offer them.

What is hustling, what are The Fundamentals of Hustling, and why should I care?

Hustling in everyday speech can mean physically moving quickly, a dance, or con artistry, but everyone I talk to in business uses the word to mean none of those things, with no fear of confusion.

In business, to hustle means a mix of leading, selling, entrepreneuring, empathy, and experience leading to act in a way to benefit everyone. A hustler makes up for lack of resources (money, connections, time, etc) with insight, skill, initiative, action, gumption, empathy, and calculated risk taking beyond the bounds of its subfields of leadership, sales, and entrepreneurship.

hustling venn diagram

I call the opposite of a hustler a clown—someone who talks big game without delivering, often leaving someone else with their mess.

For years, I’ve said that calling someone a hustler in business is one of the highest praises you can give them.  Here’s a video of me interviewing a guy I know who sold an apple to someone for five dollars, with a satisfied, knowledgeable customer, who would have paid $7. It’s unedited and long but anyone can learn from him.

Leadership literature and courses overwhelmingly focus on leading teams in large organizations seeking stability, or personal leadership—rarely dynamic change and creating teams and opportunities from scratch. Leadership coaches overwhelmingly dream of clients paying $1,000 per hour as CEOs of Fortune 100 companies. Few leadership teachers in business schools, if any, hustled like Branson did, studied such behavior, know how to teach it, or imagine anyone could.

Entrepreneurship literature and courses overwhelmingly focus on processes to plan and create businesses systematically, teaching about what they consider the standard parts of entrepreneurship—venture capitalists, angels, minimum viable products, and so on. Lean methodologies, for example, teach a scientific approach nothing like Branson’s success.

Sales literature and courses overwhelmingly focus on influencing and persuading people and closing deals, rarely about creating larger opportunities from scratch.

The result of all these myopic focuses is that few people learn all the skills, those who do rarely integrate them, few of them practice what they’ve integrated, and everyone sees successful hustlers as outliers instead of people they could emulate if they learned how. Instead, people learn to create with processes and structures that are constantly stable and predictable. Nothing wrong with them, but they become blind to alternatives, such as hustling.

It’s like everyone wants to drive three- or four-wheeled vehicles because they’re stable, even when they stop. Two-wheeled vehicles aren’t stable when they stop, but if you know how to ride them, you can do things with them more stable vehicles can’t.

Many people want success like their role models. As I often say:

They want to be like Richard Branson, we teach them to be like Albert Einstein, and they end up creating the DMV.

My niche

My courses teach the comprehensive, integrated mix of skills that enable hustling. So far I’ve posted the online versions of leadership and entrepreneurship. The online sales class is coming soon. Not that this post was to sell my material, but if your role models include hustlers and you want to emulate them, I recommend my courses. Besides leadership, leadership, entrepreneurship, and sales, they teach empathy, initiative, compassion, self-awareness, and related skills while giving experience in everything they teach. If you want forever to work for someone else, or don’t like taking initiative or responsibility, or prefer not to overcome your anxieties and fears, you won’t value my courses.

In any case, I recommend at least knowing the practice of hustling as distinct from the mainstream resources that vaguely resemble it and don’t help you develop it.

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1 response to “Hustling

  1. Pingback: A Leadership Lesson From Nelson Mandela (Happy Birthday) | Joshua Spodek

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