I was never prepared for 80% of the opportunities I have been presented.

Success is when preparation meets opportunity

Success is when a great opportunity meets a talented driven person.

“I am always growing and improving myself in core success skills but the opportunities are unknown.”


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I was never prepared. Pre-35, I was never prepared for anything that was extraordinarily great that happened to me other than sports. In sports, you can prepare. You have a season ahead of you and then you have different goals. So in sports, I agree, preparation is critical to success. 

Outside of sports, I believe success is when a great opportunity meets a talented, driven person.

If they’re talented, they can figure out how to take advantage of the opportunity. If they’re driven, they will do what it takes to make the opportunity work. They’ll put the time and the energy into it.

Recently, I was interviewing Jesse Itzler. He’s one of the co-owners of the Atlanta Hawks. He was saying this to me…”I was never prepared… I wasn’t prepared when we started a publishing company. I wasn’t prepared when we started marketing jets”. He had no background in it at all.

Personally, I am always growing and improving myself in core success skills, but the opportunities always come when you’re not expecting them to. Again, personally, I’m always growing and improving myself in core success skills such as time management, communication, team building, leadership, sales, strategic planning, but I never know when opportunities are going to present themselves

I’m working on one right now that came via an email that I never saw coming. It’s in something a little different than what I’m comfortable with, but I’m ready to jump on it. I know I have the personal skills to make it work. I understand business well enough.

I have seven opportunities that I had, none of which I was prepared for.

1. First job out of college was Director of Development. They kind of offered it to me like seven or eight months in with a non-profit. I never saw it coming. They offered to me because I had high energy and I had shown over that previous year, the ability to get things done, get things off the ground from scratch, and then they offered me the opportunity to be a Director of Development.

2. That Director of Development turned into an opportunity with an insurance company that I never saw coming. One of my roommates from college reached out to me and know I was doing fairly well pre-25, and that led to doing really well in insurance. I had no preparation for it and knew nothing about it.

3. Then I had an opportunity to start investing in realestate I knew nothing about. My first real estate deal was I was at lunch and they were buying a strip of townhouses, and somebody fell through on one of them. I had 10 minutes to make a decision to put up $10k. So I bought my first piece of investment real estate at 23 years old. Was I ready for it? No, I couldn’t even barely spell realestate. I still own that house to this day, so it worked out okay, but I wasn’t prepared for it.

4. Then I had another opportunity to own a business. I wasn’t prepared for that. I use a direct mail magazine and where I live to promote this business it did really well. Money Magazine had come up with locations in America to live, and one of them was in Charlottesville, Virginia. So I moved to Charlottesville and started this magazine. I was absolutely ill-prepared, I had never done advertising. Didn’t understand it. I had no experience in publishing, had no experience with graphic design. I had no experience with anything other than I was driven. I wanted to succeed and I could sell, which I learned how to do through insurance, so I was grabbing pieces of core skills that would allow me to succeed in all these, but I had no background in all the key areas of those businesses. 

5. I started a home improvement company, specifically a handy-man company, because I couldn’t get anybody to do any repairs at my home and had a few bad home improvement experiences. So I started a handyman company. I don’t know the difference between three different tools. I have a toy plastic tool set hung in my office because it’s so comical. I knew there was a tremendous market demand, because when I try to hire handy man, nobody could refer anybody. I started a handyman company hoping it would pay for golf, knowing nothing. I literally learned it along the way. That company now is an eight-figure company.

It’s expanded Wasn’t ready for it, wasn’t prepared for it, haven’t been prepared for the eight different divisions that have evolved over the years, but it’s one of my core values is to grow, to take advantage of opportunities, to give generously to give gender, so you gotta make some money.

6. One afternoon I sawthey tore down a farm in our area. There were five lots, and I bought a lot that day on a Sunday, I’ll never forget it. And you had to build a house. There were no developers there, so I built a 9000 square-foot house. I had no idea what I was doing. Was I prepared for it? Absolutely not.

But what I had learned, just like I learned in the home improvement where I partnered with someone, is I realized I could buy knowledge. I hired a consultant, paid them $10k to work with me step-by-step on that house. After we built it, it got appraised. It was worth $960k more than I paid to build it. 

7. I wanted to write a book. Have I ever authored a book before? Absolutely not. I take a Brian Tracy class for $500 on how to write a book and kind of put it together. Was I building my core success skills? I was disciplined, so I knew that to succeed at something, you need to have a good daily habits. I started getting up earlier and I’d write for 15 to 20 minutes every single morning. A year later, I had a book.

8. I started a digital marketing company three years ago. That’s unbelievable. It very well could match one of my current holdings pretty quickly. I wasn’t prepared for it. I did not know anything about online marketing. The whole reason why I got involved in it is as I need to understand it from the companies that I own, so I hired a firm to do my digital marketing, and the one person who led my campaign, I specifically made sure that he worked with my company and I knew he was smart and could do it.

Now we have an unbelievable digital marketing company. I kind of pitched him on the idea of us starting a company. Now we own one. We’re up 48% this year. But again, was I prepared for the opportunity? No. Did I see it coming? No.


The title of this lesson is Preparation is Overrated. If you’re waiting to be prepared for every opportunity that presents itself, you’re going to be late, and you’re never going to feel completely prepared. You can’t do it in business like you can in sports.


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