06/15/2012 03:52 pm ET Updated Aug 15, 2012

The Serial Entrepreneur

I'm a serial entrepreneur and I want to convince you to change the world. I'm currently chairman of Startup DC, chairman and founder of Synteractive, a mentor and limited partner with The Fort, a mentor to a venture accelerator program at the Thomas Jefferson High School for Science and Technology, a husband, an uncle, a son, a brother, and a provider to my wife's five cats.

While those are my qualifications at this point in time, my journey has done much more to shape my thinking than any particular destination. I've been kicked out of school. I've been told that I was destined to be a failure. I've been told that I was not very smart. I raised $1 million before I turned 20. I've won the Webb Medley award at Oxford University. I have failed, I have succeeded, I have lost mentors and family members, and I have created jobs, disrupted industries, and hopefully changed lives. All the while, I have been constantly questioning the institutions that attempt to pigeonhole us and make us conform.

My experiences as a citizen and entrepreneur led me to a simple but powerful conclusion: The time is now to reinvent America.

We have to reinvent America because our system isn't working anymore. The world has changed radically in a short period of time but the institutions that define American life have not. As a result, we've lost faith in almost all these institutions and with good reason: some have become expensively irrelevant while others are causing active damage to our freedom, prosperity, and security. We have to rethink, reinvent, and rebuild the way our country works from the ground up and we have to do it now.

When I say reinvent the way our country works, I mean every aspect of the way our country works: the way our corporations provide us with goods and services, the way we educate our children, the way we manage our health, where our food, energy, and information comes from, the way we manage our resources, and the way our elections and government work. Basically: everything.

Let me be clear, I do not believe any one politician or party can lead us out of this mess. I'm not here to promote or defend one particular political ideology or another. Our political institutions are a key part of the problem. How are bold new solutions going to come from tired ideologies, increasingly irrelevant political parties, a broken system of elections, and a Congress that has completely lost the confidence of the American people? The only ideology that I'm espousing is American pragmatism coupled with our capacity to innovate.

We have lost faith in our institutions but I don't believe we've lost faith in each other. Rather than making a political argument, I'm issuing an urgent challenge to the crazies, the rule breakers, the delusional optimists, the masochists, the women and men with the ego and pride to persist until they make their dent in the universe. In short, I'm calling on our entrepreneurs to reinvent this country. And I'm asking each and every one of you reading this to do whatever you can to celebrate and support them.

Before we go further on our journey together though, I'd like to take this time to tell you about the formative experiences that led me to become an entrepreneur. My career as an entrepreneur and institutional troublemaker started at an early age. I grew up utterly loathing the public schools. The progression (or lack there of) went something like this:

In kindergarten, my teacher decided that bribery would remedy bad behavior, which worked for ten weeks or ownership of the complete collection of He-Man action figures.

In first grade, spilling my milk every day in the lunch room earned me a seat on stage with the teachers overlooking the other kids. My parents were told that I had severe behavioral problems and I was referred to a psychiatrist who prescribed valium for a 7-year-old. My parents "politely" refused.

Second grade led to a series of tests for learning disabilities and IQ to determine whether I would go into the gifted and talented program. It came back saying that I had below average intelligence as well as complete disregard for adult disapproval.

After a huge fight, my parents succeeded in getting me into the gifted and talented program for third grade, but I lasted less than half the year before I was kicked out of the public schools for the first time.

My parents pulled together all their savings to enroll me into an alternative private school, where we learned French, read the Canterbury Tales, made electric motors from magnets and wires, and studied the nature of infinity. Oddly enough, I didn't have any behavioral issues.

The money for gifted schools ran out after half a year and my parents moved to a new home so my mother could take the Metro downtown to law school. I remember being crushed when they told me I was going back into a mainstream school.

Back in the public school system, I managed to survive fourth and fifth grade despite being constantly teased by the other kids and told that I was a screw up by the adults.

In sixth grade, I entered middle school. I managed to get suspended for various reasons for a total of 29 days over a six month period of time. Some suspensions were for getting into fights with kids that were teasing me, but most were essentially for challenging authority. I was suspended for loudly announcing in family life class that it seemed idiotic to spend a semester studying why it was important to feel good about ourselves rather than actually teaching us things that would give us reason to have self-esteem. I was suspended for writing a report for the D.A.R.E. program arguing that the real drug epidemic in Falls Church was the abuse of prescription mood management drugs and painkillers by adults. And I was suspended for arguing loudly with the principal that her constant suspensions were really about me questioning received opinion and was at a minimum a gross violation of due process and really another form of institutional hazing. In front of my parents and teachers, she informed me that I had no rights and was destined to be a failure. She then kicked me out of the public schools, for the second time in four years.

Throughout that exceptionally painful period in fifth and sixth grade, my mother would tell me almost daily that if I could just survive until I turned 18 with my spirit intact then I would be stunned by what the world could offer me. My respite from school was to read voraciously about everything and anything and whenever they would suspend me she would take me to law school with her so I could sit through her classes and read along in her law books. By sixth grade, I wasn't too great on my state capitals but was a whiz at the philosophical underpinnings of habeas corpus. Whenever she would drop me at school, she'd give me a conspiratorial smile and tell me to make sure to learn something that day despite being in school.

When I was 13 and everyone in a position of authority was telling me and my parents that there was something wrong with me because I couldn't conform to their system, I felt indescribably alone. As I grew up and joined communities of other innovators and disruptors, it was a revelation to find out that many of us have had similar experiences and felt the same way. Kids can be cruel and hazing sucks. When I think back on my formative experiences, however, I don't really remember the teasing by other kids. What I remember was the overwhelming and consistent message from those in authority that I was wrong for constantly questioning and getting bored with what they wanted me to do.

You may notice a persistent skepticism that our traditional institutions are particularly good for us as we become increasingly empowered as individuals. If you feel that I'm quick to give up on institutions, it's because they were always quick to give up on me.

It's important to dig into data to justify this argument that we've lost faith in our institutions and to share how finding the right cultures will enable us to start to get stuff done. Let's do so together.