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Quit Playing Small. What Would the Big Kids Do?


Quit Playing Small. What Would the Big Kids Do?

If ever you need to find me on a Sunday afternoon, I’m usually writing my weekly blog post. If I’m not, I’m out walking my dog, listening to a podcast, or an audiobook looking for inspiration on which to write my weekly blog post.

This chilly afternoon, I was listening to the Freedom Fast Lane podcast where one Jesse Itzler was interviewed by the guys at

Jesse Itzler is a wildly interesting individual.  He founded and sold multiple world-class companies, including Marquis Jets which he sold to Net jets (owned by Berkshire Hathaway), and Zico Coconut Water, which he sold to Coca-Cola. Obviously, the guy’s made it. He’s got a net worth of $100+million. Not only has he made it, he is married to none other than Sara Blakeley, founder of Spanx. And, guess what? Sara is no slouch herself. She just happens to be the world’s youngest female self-made billionaire – forget millionaire, because that’s so 2005… Billionaire.

Jesse’s latest thing is his new book “Living with a Seal. ” It’s about digging deep. When you think you’ve exhausted everything you have in you, there’s still a whole other level you didn’t know was there. In other words, Jesse’s got a few things from which we can learn.

Whenever I find myself in a predicament, making decisions based on scarcity, or being fearful (likely also due to scarcity), I tell myself, “Quit playing small. What would the big kids do?” Well, in the half hour ‘brain-picking’ with Jesse Itzler, I got a glimpse of what this crazy cat would do. And it’s awesome.

Lesson 1: There’s a First Time for Everything

That shouldn’t deter you.  You don’t have to know anything about the business in order to get into it. You only know until you try. Jesse reminds us that of all the notable successes for which he’s known, he’s had way more projects that didn’t work out. Who cares? Looking strictly at numbers, the more trials you do, the more failures you might have, but the more successes you have too. At the end of it all, people mostly only remember the successes. They only remember your failures when they need to incriminate you…or if you’re in politics. Since this blog has nothing to do with politics, that’s out of scope.

Starting Marquis Jets

Jesse Itzler and his partner started Marquis Jets despite knowing anything about the industry. They just knew that they wanted, and it wasn’t being met at the time. It was way too expensive to own a plane, or even own a fraction of one. They had experienced the magic of flying private and couldn’t go back to peasant class anymore.

Mind you, their peasant class was probably first class to the rest of us peasants. Even chartering a plane had a lot of work associated with ensuring safety and logistics. Their idea was then to sell 25 hr prepaid flight cards like a 10 class fitness pass: Marquis Jet Cards. It had all the magic of owning your own plane without zero hassles of trying to make it all happen. They pitched Net Jets to use their fleet of planes. This intrigued Net Jets because this presented an opportunity to expand their long time old-balls market to the next generation of wealthy young folk who wanted to fly private.

Jesse and his partner knew nothing of the aviation industry. Jesse was a rapper before! They just knew that they wanted. They researched. They figured it out.

There are so many of us who entertain the idea of starting a new business or pursuing a new passion, but never do anything to begin that journey because we’ve never done it before. There’s always a first time. All you have to do is be curious and resourceful enough to look into it.

Listening to the interview further, I drew a few other key things. We’ve gotten past the hurdle of getting started despite being a newbie to the industry. There was still the pitch to NetJets that Jesse and his partner had to sell. It’s not the powerpoint presentations or even the sales techniques that were key in their success. It’s these:

Key Success Factor 1: Failure is a facade, and is part of the journey. 

It’s there to nudge you in the right direction. When they pitched to Netjets the first time, they were kicked out of the meeting after only 12 minutes. The departing phrase from the Netjet Executives was “If you think I’m going to give two 29 yr olds access to my fleet of 800 planes, it’s not happening.

Luckily, they found out from the President of NetJets that they meeting actually went rather well. The CEO never gives anyone 12 minutes. They met again.

If Jesse had given up after the first meeting, thinking they had failed and weren’t meant to be in the aviation business, Marquis Jets wouldn’t ever have happened.

Everyone experiences failure some time or another. Sure it hurts when it happens… like doing a faceplant. But if you think of it as a facade… if you think of it as going through a maze and coming to a temporary dead end, you just need to change your course and find another way. Find that path that will get you out the maze. No one in their right mind would just sit in the maze, forlorn and cry about it. There’s always a path. You just have to find it.

Key Success Factor 2: It’s far more convincing to hear it from the Horse’s Mouth 

Instead of bringing in a PowerPoint presentation, Jesse and his partner brought in their own focus group. One by one these people stood up and gave a first-hand testimonial as to why they would buy that flight card.

Robert Cialdini wrote in his book “Influence: The Psychology of Persuasion” that there are six pillars of influence, as to why people make decisions. Social proof is Robert’s 2nd Principle of Influence. That is the winning secret of the focus group testimonials. It’s social proof. Numbers and stats only go so far. When we’re selling our idea, it’s far more convincing when you experience a testimonial.

Sure, Cat. I’m not selling anything, though. I don’t even have a business. What does this have to do with me?

What do you think you’re doing when you’re trying to land that next job? Think of the power of endorsements for your skills and expertise. How much more competitive would you be if you had a series of endorsements behind you? Perhaps this wouldn’t be included on your resume, but you can bet that recruiters are perusing your profile on Linkedin. In fact, there’s a dedicated section of your profile that is solely devoted to endorsements. If you’re not capitalizing on this, you’re wasting a huge part of Linkedin. It might have even cost you that previous job, and you’d have never been the wiser.

Here’s another. Think of when you need to pitch your idea to a group of stakeholders. Imagine how much more effective it would be to bring in a few testimonials as to how your idea would impact them, and how necessary your idea is. It’s like watching reality TV v. looking at a graph. No one cares about the graph (even though they might pretend to). Everyone cares what happens on reality TV (even though they pretend not to!)

It’s not all about numbers. Sure they probably had ample numbers to support what they were pitching… to prove that the demand was out there. But the fact that they brought in their own social proof skyrocketed their persuasive power.

Key Success Factor 3: Emotional Connections 

People want to know that you’re committed to the project. They want to know that you’re dependable before they invest their time and money in your baby.


Jesse and his partner had a strong emotional connection in two dimensions. The first was the CEO of NetJets: The boss was perhaps willing to give them a chance because maybe he saw them as a younger version of himself. The second was that despite not being really anything special, they did truly believe in their idea. They knew with certainty that they could sell a ton of these cards to a younger crowd. They knew they could do it quickly. They had the key to the younger money, the relationships to folks like the New York Nicks that Netjets couldn’t even come close with their old-balls marketing. None of this would have happened if the relationships weren’t there.

Applying this to an individual level, I wrote in my post How to Super-Charge Your Power of Persuasion, people buy from you when they like and trust you. If you don’t first establish the relationship, though, you won’t get anywhere. Even if you have the best skillset in the world… even if you have a proven track record in projects coming under budget and over delivered, your longevity with a client is limited if all they do is want to punch you in the face when they see you.

In a world where everyone is superman, the only way to get to the top is to build the winning relationship.

Living with Navy Seal

In a race that he ran, he met a crazy Navy Seal, who inspired Jesse so much that he invited the guy to live with him and his family for a month. After his transformational 31 days that sometimes involved oxygen deprivation and denying the opportunity to pee, Jesse recorded all the lessons that he learned from this incredible individual in a book “Living with a Navy Seal.”

Limitations are Self-Imposed

Be it physical, or mental he learnt that whatever limitation you think you have is created in your own mind. Limitations are self-imposed. The reality is that you actually have a lot more from which you can draw. The key is having the resolve to dig deep enough to extract it like oil from the ground. Jesse, despite having accomplished all these crazy things in business, he still had so much more that he could do. Living with the Navy Seal, he learned how to reach down and extract that hidden energy when it was required. He threw himself out of his comfort zone.

Whatever we haven’t done in our lives is likely from a self-imposed limitation.

“Oh, I wouldn’t qualify for that job.”

“I can’t be my own boss.”

“The market is terrible to leave my company now.”

“Why break something that isn’t broken”

This is the very mentality that creates frustration and keeps us down. It’s not a boss, or the company, or the market. It’s us. It’s how we think. If all of those statements were true, there wouldn’t be any entrepreneurs who build successful companies. There wouldn’t be any self-employed contractors. We would still be doing things the way they have always been done. But that’s far from reality.

The reality is that people try for jobs they without past experience or credentials every day! The new US president hasn’t ever been president. Yet he’s the one in office. People start new and successful start-ups every day! The market will never be optimal for you to leave your job. And without challenging whatever works, we cannot…simply cannot have improvement.

Routines Can Turn into Ruts

Jesse was living a great life thus far. He’s the leader of world class organization. He’s married to a billionaire. He’s a billionaire himself. Like everyone, he gets up, goes to work. He works the work. He comes home. He spends time with his family. He sleeps. Then the next day he does it all over again. His life is great. Here’s the thing, though. Even the most fabulous routine, when repeated over and over again on autopilot will turn into a rut. In Jesse’s case, he found that he stopped taking chances. He stopped dreaming big. He started procrastinating.

Sometimes the training was pretty unorthodox. There were instances where he was told to jump into a hole in a frozen lake. The underlying lesson was that this: When you’re in a difficult circumstance. I mean a really difficult circumstance. You’re going to go into offense mode, and attack instead of defense.

This not only applies to unconventional billionaires. It could apply to anyone, anywhere in life, and especially us:

  • You get rejected for that dream gig you’ve been banking on
  • An unforeseen circumstance happens in your family, your health, your marriage, your kids
  • You run out of money
  • Your house collapses

As long as you’re in control of your own destiny, your own path, that offense play is super critical to getting you back on the path that you designed for yourself. Obviously, it doesn’t require 30 days with a Navy Seal yelling in your ear, telling you to jump in a lake. Attack instead of hiding from it.

The Price of Success

Building a brand takes time. We live in a world of instant gratification. It’s ok to go slowly, as we progress. But the overnight successes on averages take 8 years. It’s a journey of mistakes, trusting that gut. It’s a process, which you can’t circumvent. You can’t cheat the system.

The time needs to be invested. The great Brian Tracy once said, “The price of success needs to be paid in full and in advance.”

If ever there were two virtues that will help guide your ship to success, it’s patience and presence. You need both to journey your ship. Patience without being present is like working out while watching TV. Your body is on auto-pilot. Sure, if you show up and put in the work long enough, you’ll still see results. But if you’re looking to optimize that workout, and optimize the journey, there is no substitute for being mentally present to what you’re doing.

Whether or not you’re on the path to becoming a billionaire, these lessons are truly universal truths. The fact of the matter is that each of us has a set of gifts that is unique. Each of us has a reason we were put on this earth. In trying to do the very best with the gifts that we have, sometimes we need to dig deep. Often we are impressed with what we can achieve.

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