From the moment you were born, you were told who you had to be. You were told what to eat, what to wear, and what school to go to. You were told what job you should take, by what age you should be married, how many kids you should have, and what someone like you is "supposed" to do. Nobody thought to ask what you actually wanted for your life.

So you tried a few things to break free from the box you were put in but they didn't work. You had a money dream, a health target, a relationship goal, and you didn't reach them... so you had to get more practical, more "realistic" and fall back into the plan that they created for you. It's ok. It's not your fault. 

You didn't learn how to do this in school. The people around you couldn't teach you either because they're barely hanging on themselves. You didn't have the money, resources, equipment, time, connections, background, or education to make it work. You did the best you could with what you had. It's ok, it's not your fault. But where you are right now does not have to be where you end up.

I always seemed to be a slow learner. It took me 19 months to learn to walk and people kept asking my parents what was wrong with me. When I went to school at 3, I spent a lot of time sitting under my desk instead of participating in class. I was sick all the time, constantly on antibiotics for terrible ear infections, and in and out of surgeries to try to fix my hearing problem. I jumped between three different schools and my parents were worried that I wasn't getting the extra attention I needed, and that I also wasn't making any friends.

My mom said she began to notice some serious changes in me as I went from being a happy child, adventurous and curious, to becoming more withdrawn and developing nervous ticks. So they took me to a child psychologist who suggested that I change schools and go to an all-boys one until I finished high school. I never did well in school, never really had many friends, and my teachers always accused me of just doing the bare minimum and not trying.

But my parents always told me, "You are Evan Castrilli Carmichael and you can do anything you believe you can." And in my final year I was assigned Mrs. Farr as my teacher-mentor. Most kids rarely met with their teacher-mentors but I met Mrs. Farr every week and she helped me believe in myself too. In that last year of high school I went from getting B's and C's to getting an A+ in every class and landed a full scholarship to the university of my choice. I wasn't stupid! I just needed a little extra help.

When I graduated high school I thought I had it all figured out. Go to university, study economics, and become an investment banker. But when I got to university, I got the opportunity to join two entrepreneurs who had started a software company and they offered me a 30% stake in the business to join them. The more I worked on my new business, the more I realized that nothing I was learning in my university economics classes was helping me. I thought university was going to be the answer to everything but quickly saw that, unless I wanted to become an economist, everything I was learning for four years was pretty much useless to me in practical real life.

So at 19 I had to make the hardest decision of my life: Stay with the company I owned where I was only making $300 per month or take the six-figure investment banking job I dreamed of. I struggled a lot with the decision. What if I'm not good enough to be an entrepreneur? What if I don't make it? What if I can never support myself? What if I blow my one chance to make it as an investment banker? Can I really turn down six figures when I'm only making $300 per month? What will people say if I turn this job of a lifetime down?

In university, some of my friends were taking a year off to travel and explore before getting a job, so I decided that I'd take a year off and invest in myself instead by trying to make my business work. I was inspired by Amazon founder Jeff Bezos, who left his high-paying investment banking job to become an entrepreneur because he didn't want to live with the regret of not knowing. So I decided that I didn't want to have regrets when I was older and that I would rather know and fail than not know. I turned down the job and went to work full time on my business. You don't know until you actually try, so I went for it, and then almost instantly regretted it.

I was working all day, every day on my business, but nothing seemed to be working. No matter how much I tried, how long I worked, how many ideas I came up with, none of them had an impact. I couldn't believe it and went back to feeling like the dummy I was for most of my school life. I also wasn't making any money—$300 a month only goes so far. I stayed at home, living with my parents. I took the same bean salad to my business partner's apartment because it was cheap and would fill me up. I only said yes to one social event per month with my friends because $25 for pizza and beer was usually too much for me to afford.

I made it harder on myself because I didn't tell anyone I was struggling. I was embarrassed and ashamed that I wasn't having success. I told my friends that I couldn't go out with them because I was "hustling" and "living the entrepreneur life," but really I was just broke and felt like a loser. I went to the bank to ask for help but they turned me down because my business was a startup and I had no assets that were worth anything. So one day, after having this feeling of being a worthless failure building and building inside me, I called my business partner and said, "I quit. I need to feel like I have some kind of value as a human and this business of ours is not working."

I barely slept that night and the next morning I sat in my room and realized that I couldn’t quit just yet. I hadn't given it everything I had. I felt like I would regret quitting now and that it was still too soon. But I couldn’t keep going like this. I had to find another way to win. Something. Anything! So I asked myself a simple question, "Who has built a successful software company before?" The first person I thought of was Bill Gates from Microsoft. I studied how he built Microsoft from zero and applied that to my business. Shortly after, I got my first deal for $13,500. I couldn't believe it! That may not sound like a lot of money to you, but it was more money than I had ever seen in my life and, more importantly, I had a system I could follow to get more deals. I wasn't worthless! I just needed the right model to follow.

I've always been a perfectionist. I'm afraid of making a mistake, getting it wrong, and embarrassing myself. Once my company started to do well, I worked on a new plan that would blow up our business, make us millionaires, and give us financial freedom forever! I worked, and I worked, and I worked on this business plan. And when I was almost done, I second-guessed yet another thing I had in it so I worked on it some more. But finally, FINALLY, I decided that it was perfect. It was done. It was exactly what I wanted and so we took it to market. Our bold new plan to get our business acquired and make us rich was ready! The big idea was to have a giant company in a competing industry buy us. So we went to the #1 player in the industry, the big multi-billion dollar kahuna . . . And they said, "No."

No? Wait, what? The plan was perfect. How could it be a no? Can you read it again? "Sorry, no." I was shocked. All that time invested for nothing. But then we thought, "Hey, the #1 company won't buy us but maybe one of their smaller competitors will?" So we started reaching out, eventually getting a meeting with the #4 biggest company. They were super interested, had just raised a bunch of money to buy companies like ours and we got in for a meeting with them. They told us that they were indeed looking to buy a software company like ours and had already been talking to our biggest rival for the past three months. They really liked us, our plan, our software, and us as people . . . but they were going to buy our rival because they had already spent so much time talking to them and they wanted to move quickly. They bought our rival for $40 million.

Immediately I thought, "Why did I have to be such a perfectionist? What if I had the plan ready sooner and we were here talking with them three months ago?" I didn't know if it would have made a difference but even if we had a 50% chance at $40 million, I'd sign up for that! Now, we eventually did get acquired by another business, and I got paid pretty well for a 22-year-old, but it wasn't $40 million. And ever since then I've tried to value progress over perfection, and I’ve realized that the single thing that I was missing is just momentum. I didn't have a mentor this time. I didn't model someone to learn from their success this time. And I paid the price for it.

(The picture is of me above is when I was 25 and thought the only way to be taken seriously was to wear a suit. LOL)

After I sold my business I did a bunch of speaking gigs around the world, started another software company that did not succeed, became a venture capitalist raising $500,000 to $15 million for businesses, started a popular website off of my name with over 100,000 pages of content . . . and then eventually started a YouTube channel in April of 2009. I'm a visual learner so I would much rather see something than read it or hear it. Looking back on my early struggles in school, that's probably at least partly why I didn't do well. So when I heard about YouTube, I decided this would be a cool place for me to share some visual content to help other entrepreneurs! But I was shy, nervous, afraid, and felt like an introvert couldn't win on YouTube. I was scared that I would let people down.

In one full year of my first video being up, only three people left a comment: my mom, my older sister, and some random guy who found my video. Three comments in one year. See, I'm an introvert. I didn't go on YouTube to be famous. I did it to try to help. But it took me a long time to get comfortable in front of the camera. I never felt like my story was good enough or that people wanted to hear from me. I couldn't film with anyone else in the room, even if it was my sister. I was nervous, shy, and disappointed with everything I made. But I still created because I had learned my $40 million dollar lesson of being a perfectionist. I created, but I was still scared of letting myself and my small audience down.

And then I met my now-business manager, Steve. He's a hardcore New York guy who helped build people like Mel Robbins and Grant Cardone into brands. He told me my problem was that I didn't want to get famous, and he hadn't met anyone as nice as me, so he'd take a chance on me. It wasn't easy but Steve punched, kicked, and hugged me through the now 10,000+ videos that I've now made and he helped me get better. In the first 6 years without him I went from 0 to 9,000 subscribers. Over the next 6 years with him I went from 9,000 to over 2 million subscribers. Again, without the mentor or model, I failed. With them, I succeeded.