ASA 9 | Famous Dropouts


There is no single path to becoming a success. Just like Sir Richard Branson, Barbara Corcoran, Mark Cuban, General Colin Powell, and Steve Jobs, success for them did not lie in formal education. They are dropouts, and they each have found a way to become good at what they do best and influence many people.

Get to know these five famous influencer dropouts and take comfort in knowing that we can still succeed without conforming to the usual way and that mistakes can make us great. Discover the definition of a dropout, why high intention and low attachment is the ideal business mantra, and why you should expand, not burst, your comfort zone.

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Five Famous Influencer Dropouts

I was once taught not to let my schooling interfere with my education, and so it is with some of the most famous dropouts in history.

In business, there are five dropouts I want to talk about. A special shout out and thanks goes to my good friend, Darren Hardy, who is the publisher of Success Magazine and he has written one of my favorite books on the topic of business called The Entrepreneur Rollercoaster.

From one of the pages, I’m borrowing many of the ideas and lessons he taught. You can go into Google or any search engine and check out other famous dropouts, but I’ve chosen five. Let’s discover what they had to do in order to be wildly successful.

Sir Richard Branson

The first dropout is Sir Richard Branson. You may know him for his Virgin companies. He started in the record business but Sir Richard is dyslexic. I’ve shared the stage with him and he won’t be noted as one of the great and dynamic speakers of all time, but he’s one of the greatest entrepreneurs of all time. In fact, when he was growing up, one of his teachers told him that he would end up in prison.

As a dropout, he did something that I do and is the same piece of advice I give to my students, my colleagues, even my family when they ask me, “What’s the secret of your success?” They’re looking for tactics. They’re looking for strategies. They’re looking for maybe a little inner game idea inside the mind and heart to make things better than they are, to get to the next level.

When people ask me, “Alex, why are you so successful?” I answer with, “How do you know I’m so successful? There are many more people more successful than I am. Many of my students have surpassed me,” which is one of my goals as a teacher and a trainer. The pat answer I give them is, “If I am more successful than you are, chances are I am more willing to look bad in public than you are.”

We’ve talked about A/B split testing in the past. With testing, not everything goes the way you want it to go. That’s why they call it testing. Whether it’s a dropout we’re talking about or someone who’s wildly successful who ended up getting a PhD in their area of expertise, chances are the reason why they’re successful is they have tried more things. As a result, they have become more successful.

Sir Richard Branson is definitely no exception. He’s had over 100 companies that he’s responsible for building. He has an island that has been in existence before it was wiped out by a hurricane. I think they’re rebuilding it. His early education and schooling, one of his teachers told him that he would end up in prison, but he didn’t buy into that. Instead he kept going and going aligned himself with other people smarter than him.

When he’s thinking about starting a new company, he’s not asking himself, “How am I going to do this?” He’s not asking himself, “What am I going to do?” He’s not asking himself, “Why am I doing it?” He asks himself, “Who am I going to find to run it?” which is a similar strategy of Warren Buffett. That question, “Who is creating a culture that’s made Virgin an epic brand?”

[bctt tweet=”Mistakes are great. The more we make, the smarter we get.” via=”no”]

In fact, he’s a brand builder. When you see Sir Richard Branson on stage or you see him on television, one thing that always strikes you is that white hair. You know it’s always him. He really is in the business of licensing. In fact, that’s his business model. I think at any given time, he has over 70 lawsuits happening because he has such a big empire. He is a billionaire but he doesn’t let those things that would make other people feel that they’re looking bad in public, get in the way.

Study Richard Branson and it’s a good idea to study his biography, along with these other dropouts because it will give you a sense of inspiration. It will influence you so that you can tell yourself, “I can do it too.”

Barbara Corcoran

Famous dropout number two is Barbara Corcoran. I’ve met Barbara when I lived in New York City. She was building her real estate company. In fact, my former wife worked for her real estate company.

What a lot of people don’t know about Barbara Corcoran, other than being on Shark Tank, is that she is one of eleven children. She indicates that she’s been fired from many jobs and yet, she became the queen of New York City real estate.

I don’t think she is focused on looking bad. I don’t think she’s judging herself, there’s any guilt or shame with bad decisions she’s made because as the great Buckminster Fuller said, “Mistakes are great. The more we make, the smarter we get.” I think Barbara is the epitome of that.

She has landed on Shark tank. She is known throughout the world. Imagine, here was a woman starting out as a girl, one of eleven children, and she’s gone from being fired from as many jobs as possible where she was working at and she became her own entrepreneur, the queen of New York City real estate.

Mark Cuban

ASA 9 | Famous Dropouts

The Entrepreneur Roller Coaster: Why Now Is The Time To #Jointheride

Our third famous dropout is Mark Cuban. His father was an auto upholsterer and Mark was a bartender at one time and he got fired. That’s a good thing he got fired as a bartender because if he hadn’t, he probably would be tending bar as I speak. Instead, he got into the software business.

This is a man who is fearless of taking calculated risks.

As we talked about, he thinks big and acts small. He has massive and wild success, but it’s not by acting small and betting the ranch on a hunch. If he has something that he knows in his gut, he’s thinking big and he’s maintaining that vision. Like Branson and Corcoran, he acts small and make sure that he has the right people around him in order to get the job done and experience wild success.

General Colin Powell

Our fourth dropout is General Colin Powell. He was born in Harlem and his parents were Jamaican immigrants. Right there, he could have taken on the victim mindset and not take that any further. Did he do that? Did he care about what other people thought about him? I don’t think so because he didn’t just burst through his comfort zone. He expanded it.

When you burst through your comfort zone, you’re in no person’s land because you are in a place that is uncomfortable, and the tendency is to come back into a comfort zone that hasn’t expanded.

What I want to invite you to do is expand your comfort zone. I can’t say with absolute certainty that Branson, Corcoran, Cuban or even Colin Powell thought this way, but this is what I’ve observed because this is what I do. When you expand your comfort zone, then your entire comfort zone expands, and what was at one time uncomfortable becomes something that’s comfortable that you’re willing to do day after day.

Think about comfort zone expansion versus breaking through the comfort zone, which is usually the philosophy that many teachers teach their students. It’s way too scary because if you go beyond the comfort zone and come back in, it’s a metaphor. If you go beyond the comfort zone and then you decided to come back, you’re still worrying about what other people think.

Don’t let schooling, don’t let any formal education interfere with your life’s education. These are dropouts. They dropped out and they became thinkers that changed not only their industries but had many people and still have people following their examples.

Check out Colin Powell’s biography. Go online, you can find it like Cuban, Corcoran and Branson. Checkout his biography and it will give you influence and inspiration to expand a comfort zone just like you would blow up a balloon.

When you blow up a balloon, the balloon never comes back to the same size it normally was. In fact, it’s a lot easier to blow up a balloon. When is the toughest time to blow a balloon up? If you’ve ever done it at a party or at a birthday gathering, the toughest and the time that it takes the most amount of force is when you’re first blowing it up. After you’ve blown it up, it doesn’t come back to the same shape. I know you know this, but your comfort zone is exactly the same way.

We’ve talked about four influencers who are dropouts and one thing they all have in common in my view is they have high intention, they have a vision, but they have low attachment to what happens along the way, so that they give themselves permission to make mistakes.

Mistakes are great. The more you make, the smarter you’ll get. My root guru, my root mentor, the Tibetans call it Lama, Buckminster Fuller said that and I believe it’s true. The definition of dropping out is not about dropping out from life. It’s just from formal education. That should never interfere with your schooling. If you’re going to school, my recommendation is not to drop out because of the stories I’m sharing with you.

[bctt tweet=”Don’t let any formal education interfere with your life’s education.” via=”no”]

My recommendation is not to take formal education too seriously because the person who’s training you and teaching you, if they have the results you’re looking for, then keep going. If they have results that are irrelevant to what your goals are, such as becoming a PhD in an area of expertise, maybe you don’t want that.

Maybe you want to be a coach or a consultant or a service professional that enrolls new clients, new patients, new members, new students, new customers, whatever you choose to call them. I call them students. They do that by beating to their own drum. It’s not someone else’s.

We’re not talking about mentorship. I have three mentors currently and that’s not about formal education to me. I model what they’ve done and half the time they’re sharing stories with me that give me courage so that I can do the things that scare me.

I have a little exercise that will change your life if you do it one day at a time. It’s very simple and you can feel free to teach your clients, your students, members and you don’t even have to give me credit for it.

Steve Jobs

Our fifth famous dropout is Steve Jobs. I have to talk about Steve Jobs when we talk about dropouts because he was given up for adoption and he was fired from the company he started with his then partner, Steve Wozniak, yet he comes back and he turns this company into the most valuable company on Earth, in my opinion.

It’s either Google or Apple. I believe Apple is the most valuable company on Earth. This is the second act in business that he took. I think it’s the best second act in business history because not worrying about what other people thought, not worrying about what people were thinking of his ideas.

In fact, from what I understand, and I got to meet and speak to him once, he wasn’t very nice to people but he drove people to get the right team so that they fell in love with Apple. That was one of his criteria.

If they fall in love with Apple, then that’s the first criteria to the next step in vetting them and that’s how they work. Long hours for him. That’s how he helped develop the iPod, which was not a success in 2001, was not as success in 2002 or 2003. It was within three and a half and four years where it became wildly successful and it changed the way we listen to audio. It changed the way we listen to music and buy music.

Instead of buying the whole CD or album, if you’re old enough to remember a long-playing vinyl album, chances are you never have played a vinyl record if you’re a Millennial. You can buy any song you want. That started at $0.99 and he democratized the music business. He did shake things up, but he didn’t care because ultimately it was for the final user. Jobs did not let his schooling interfere with his education.

ASA 9 | Famous Dropouts

Famous Dropouts: The secret to wildly successful entrepreneurship is the blind willingness to look bad in public more often.


The Alexism that I want to share with you for this is that the secret to wildly successful entrepreneurship is the blind willingness to look bad in public more often. Richard Branson has done that. Barbara Corcoran has done that. Mark Cuban has done that. General Colin Powell has done that. Steve Jobs did that. I hope you’re willing to do it as well.

Focus on your vision and that’s never about what other people think about you. Think big, but act small so you’re testing, tracking and you don’t lose a lot of money along the way.

The shortest distance between two points is not a straight line. It is always the path of least resistance until you find your flow.

Here’s a little trick that I play on my mind and my heart every night and I’ve been doing it for years. Every night, I write on an index card one thing that scares me. Scary work pays well, which is something else I learned from Darren Hardy, from his Darren Daily morning show, morning podcast, five days a week. I recommend that you go get it at He heard it from somebody else, but scary work pays well.

The way to do scary work is put it up front and center. Let your mind marinate and percolate on what you believe is scary. It could be a task or it could be a person. No matter what it is, chances are that it’s scary because you have the fear of looking bad.

I’m not trying to mind read, but I’m guessing. At least I’m speaking from my point of view, so these are my projections. If they are resonating with you, then keep reading.

On this index card, I write down one thing that scares me that I want to do the next day. That one thing could be a task or that one thing could be calling up a person. It could be calling a person to support me with this, give me a rating and review, which I hope you’ll do. It could be calling up a person and inviting myself or at least offering to speak at one of their events. It could be tackling a task that I’ve been afraid to try because I thought it was beyond my ability or skillset.

I write that on the front of the index card. On the back of the index card, I write down why it scares me. I use that word, scary, because scary is in my face. Frightens me is not as strong. Scary is strong for me. He said those are the words that work for me.

On the front, what scares me, on the back of the index card, I write down why it scares me.

[bctt tweet=”Your vision is never about what other people think of you.” via=”no”]

Usually that “why” is an unsupported belief. It’s something I’ve made up. It’s a story. We have stories that persuade and influence, and we have stories that prevent us from doing the things we need to do, which also is influencing us only not living into the life we want to live into.

What I do is I write what scares me on the front, why it scares me on the back, which is typically an unsupported belief. If I do it the next day, which I do, sometimes I take two or three days to do it because it scares me that much.

I’m making a confession because I’m sure there’s something that you know you ought to do, but it scares you. Not that you should do, you get to do, I don’t want you to should all over yourself, as they say.

After I’ve done that thing, rather than throwing that card away, and here’s the key, I save it. I save it because after three months, after a year, after several years, I have a stack of things that have scared me and I have overcome.

On the back, I’ve written down why they scared me. It’s almost comical when I’m looking at them and I’m saying to myself, “This scared me? I can’t believe this scared me.”

It’s something that I’d like to hand to my kids if they ever fall victim or volunteer into the range of not being able to expand their comfort zone. That’s my wish for my kids, both Gabriel and Brianna. I want them to expand their comfort zones.

That little trick where I do it at night, my mind will sometimes have it marinate and percolate in my dreams, then I do it the next day. I cannot tell you how it can change your life faster, better and easier to the point where you actually look forward to doing things that scare you because your comfort zone has expanded.

Here’s our quick review about the specific insights you and I discovered.

Number one, study the biographies and stories of wildly successful influencers, especially high school and college dropouts such as Sir Richard Branson, Barbara Corcoran, Mark Cuban, General Colin Powell, Steve Jobs and many others.

Number two, focus on having a high intention but low attachment, which means you correct and continue. High intention, low attachment means your vision is high, you’re maintaining it but you’re not attached to the result.

Many times, the result is none of your business because you can only take the next action and you keep taking new actions until you get the result you want. Number three, master the ability to expand your comfort zone, not just burst through it and don’t worry about other people’s judgments.

They will prevent you from living into the life and growing the business you know you’ve always deserved. Remember, these insights can only work for you if you work them.

Speaking of reviews, I want you to go to and type in your biggest takeaway or a-ha moment you experienced. You can do this in the review section.

When you do it, iTunes will ask you to rate. Go ahead, declare your one big takeaway in iTunes review section. If you’ve already done it, then it won’t allow you to do it again. You can write it down on an index card. That’ll take three minutes out of your day, but what you declare to the rest of the world could provide you a lifetime of learning.

I have one final gift to give you an honor of this and that is a complimentary copy of my eBook that’s titled, Alexisms: Useful Lessons from a Recovering Serial Entrepreneur. That’s me. You can instantly download it at It’s available on Amazon for $20, but why pay $20 when you can get it for free as an eBook? That does it.

I hope our paths cross again next time at All Selling Aside.

This is dedicated to making ethical influence within your reach so that you can achieve and even exceed your sales potential and your comfort zone. Do whatever it takes to join me next time because our topic will be the power of ruthless compassion.

I encourage you to invite a friend or bring a study buddy because it’s so much easier to do this with others than to do it by yourself. There’s no such thing as a self-made success. None of the people I mentioned were self-made, not Richard Branson, not Barbara Corcoran, not Mark Cuban, not General Colin Powell or Steve Jobs. Don’t buy into the myth that self-made success is the way to go.

Have a community that helps you get to where you want to go. I can’t wait to connect with you.

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