My Business History: Reflections and Lessons Learned

I've been an entrepreneur since 1998, when I was 16 years old. Since then, my passion for entrepreneurship has been all consuming. This blog entry takes an candid look at my entrepreneurial experiences and shares my reflections on them.

Between our sophomore and junior year in high school, my business partner and close friend, Cal Newport, and I co-founded a web development company. We started off doing the work ourselves and then began outsourcing to India. We charged our clients $75/hour and the web development team in India charged us $25/hour. So, we made $50 for every hour the team in India worked. Things were going great until the bubble burst, our MBA CEO left the company to start a competing company, and my partner and I left to go to college. We tried to pick things up, but it never got off the ground again.

While I was disappointed, I realized how the experience had dramatically changed my life. At the same time, I realized that the entrepreneurial way of thinking was not talked about at all in school and if anything was discouraged. One night I wrote an manifesto called the "student entrepreneurship manifesto", which I sent out to many of my friends. I got great feedback and also started receiving emails from people in other countries who enjoyed it.

In my sophomore year (2002), I decided to take the spring semester off and write a book developing the ideas of the manifesto. I shared my ideas with Sheena who had similar ideas of her own. We had nightly discussions that lasted hours as we refined our ideas into what eventually became known as Extreme Entrepreneurship. The book eventually came out in August of 2003. Sheena and I officially co-founded Extreme Entrepreneurship Education, LLC in April 2003 and we've been working on it ever since part-time, until we took the full-time plunge a few months ago.

With that said, below is my financial history from these two businesses:

After looking at this chart and reflecting on my experiences, the following things come to mind for me:

1. A J-O-B would have made me more money. If I had spent the same amount of time on a paying job (even one paying minimum wage), I'd be doing very well financially right now.

2. A J-O-B almost definitely wouldn't have given close to the same... branding, networking, knowledge, and character-building.

3. I don't regret a thing. I made a huge amount of mistakes and have thus learned quite a bit. I think I've learned more from my entrepreneurial experiences than from my academic ones. In that regard, the entrepreneurial experience was much cheaper! At the same time, over the past few years, Sheena and I have built the foundation of Extreme Entrepreneurship to the point where it is poised to grow very quickly over the next few years.

4. I don't feel like a risk-taker in the least bit. For me (everybody is different), it would be much greater of a risk to do something that I wasn't passionate about. When I look back on my life, I want to see somebody who has lived their life to their fullest, someone who has unwaveringly followed their inner voice (the good one, of course). To me, doing anything else is a risk.

5. Markets can make dumb people look smart and smart people look dumb. Cal and I made more money off of web development working less time than Sheena and I have made off of Extreme Entrepreneurship even though we have more experience under our belt. At the same time, Sheena and I made the decision to go into an industry that was less profitable than other opportunities because it matched our values and interests in making a social impact.

6. My Interests in Entrepreneurship Have Changed. My initial goal with entrepreneurship was to make a lot of money. Over time this has been superseded by the lifestyle benefits it provides, the ability to control how I think and spend my time, and the ability to build the company around our values.

7. Entrepreneurship is more of a mindset than about starting and running a business. Ultimately, an entrepreneur is an employee of his/her company. As the company grows, the founder's position gets closer to that of a traditional employee at any company. At the same time, I think there are a lot of opportunities to join outside companies in very entrepreneurial roles.

8. Starting in School is the Way to Go. I think that starting in school is definitely the way to go if you're interested in entrepreneurship. You have the student, faculty, and alumni resources of the school at your disposal and many of your living expenses are taken care of. Upon graduating, you must deal with student loans, health insurance ($500/month), rent, and other living expenses. What this means is that if you want to start a business after graduating, you will either have to become profitable very quickly or take on a fair amount of debt so you can grow quickly to the point of supporting yourself. If you start in school, you have the leeway to grow slowly and organically and have a foundation by the time you graduate. Furthermore, you will have a great of practical knowledge on entrepreneurship, most of which a traditional job could never teach you. This will make future ventures less risky. I've met many people in their thirties making very basic entrepreneurial mistakes, but now they have much more to lose.