The Power of Entrepreneurs

We need to reinvent America because our system is broken. Technology is making us radically more empowered as individuals and our culture is rapidly changing. But the institutions that define our country haven't changed with them.

The question isn't whether we have to change. It's how.

The answer is simple: we need to unleash the American people and our entrepreneurs. The frustration that we all feel when we look at our country today represents a massive market opportunity. I'm hell-bent on convincing the entrepreneurial talent in America that our crisis of confidence in the way our country works is actually the greatest opportunity for launching new ventures that we'll see in our lifetimes. And even more importantly, tackling these really big problems is the single most patriotic thing you can do.

It will be our entrepreneurs who reinvent this country -- not our corporations, or philanthropists, or dysfunctional political system -- for three powerful reasons.

First, our entrepreneurs are the ones who get it. They're the ones most naturally attuned to the way in which our world is changing. They understand how technology and new ways of doing things are opening up incredible new frontiers of possibility. They understand that it's not about replacing one set of monolithic institutions with another, but rather reinventing an America in which the individual and community matters far more than any institution.

Second, our entrepreneurs have a vested interest in change. We cannot expect entrenched institutions to reinvent themselves, any more than we would have expected Sony to welcome the iPod. They're the insiders who benefit from the status quo, while our entrepreneurs are the ones chasing the wealth and glory that comes from creating a world that unlocks our full potential as individuals.

Third, entrepreneurs are in the business of reinvention, of change, of disruptive innovation, of making everything all over again in a better way. We desperately need creative destruction in the way our corporations provide us with goods and services, the way that we educate our children, the way that we manage our health, where our food, energy, and information comes from, the way we manage our resources, the way we elect our representatives, and the way our government works. Bluntly, our entrepreneurs are the only ones crazy enough to spit in the eye of the status quo and with the fortitude, creativity, and passion to make their dent in the universe that's necessary to succeed.

Startups are hard. We all celebrate the success stories, but the journey along the way is scary and lonely with the reality of probable failure always staring you in the face. It's why we have to celebrate failure with at least as much gusto as we laud the self-made billionaires. It's the least we can do if we're going to ask these people to fix our country.

I learned about how scary, lonely, but ultimately enriching a startup can be at a young age. I've never looked back since. A month before the end of my senior year at the Thomas Jefferson High School for Science and Technology, I decided not to go to college.

My parents were surprisingly supportive. Perhaps it was their own status as grown-up hippies with anti-authoritarian streaks, but they responded with a shrug and asked how I was planning to support myself. I continued living with my mother while Eric, my high-school rowing coach, and I come up with an idea for a business, Semper Liberi. We decided to hire Jefferson students to tutor other students. We paid the kids $12 per hour and charged the parents $24 per hour -- in return we handled all the marketing and payment processing. I convinced my sisters and their friends to put fliers on all the cars at back to school nights across the region, which was all the marketing we needed. As it was 1995, we didn't even have a website!

While the tutoring company and some odd jobs were supporting me, I became interested in another idea. My girlfriend at the time was a year behind me in school, so I'd hang out at her house and eat dinner with her family. Her father was always talking about his frustrations with financial planning, as he didn't trust stockbrokers, and personal financial software at the time was limited. Over a series of family dinners we came up with an idea for a better way to model your personal financial life. He asked me if I could write a prototype. I had taken two years of computer science at Jefferson, but nothing relevant to writing this kind of application, so I wandered into a CompUSA and bought a book on Microsoft Visual Basic. I then took a month to drive to Vail and live as a ski bum, working and skiing all day, while learning to code at night. When I got home, I started on the prototype and by the spring we had something cool to show. He knew someone who owned a government contractor and might like to invest. In August of 1996, we pitched the idea and walked out with $1 million in angel investment. At 19, I was the co-founder of a software company, netDecide.

Unfortunately, we quickly realized that none of us knew anything about building a company. And I mean nothing. The technology team was stellar, but my partner was a big believer in focus, so preferred not to waste time by going to business events. After a while, I started to panic as I watched our investment capital dwindle away. I found two business school professors at the University of Virginia who were willing to mentor me and slowly started to figure out how to build a company -- one painful mistake at a time.

It took us two years before we figured out that our market wasn't consumer software but actually enterprise software for big financial services firms. At 23, I walked into a board room at Bank of America, put a marker to a whiteboard and explained to room full of executives that their brokerage business was dying and they needed to make a radical shift to financial advisory services, which our software could support. For some baffling reason, they believed me and we signed a $3 million annual license within a few months. From there we raised $7 million in venture capital and signed a string of top-tier clients -- Legg Mason, Ernst & Young, Mutual of New York, State Farm, and so forth. We grew from 20 people in a townhouse to 120 people in a sexy office in Tysons Corner. I found myself winning awards and appearing on magazine covers. More importantly, our vision was actually happening, as stock brokerages across the country transformed into asset management and wealth advisory firms. 2000 was an exhausting but wildly exhilarating year.

Then everything crashed in early 2001, and I found out what it was really like to be an entrepreneur. I remember sitting in a room telling good people with families that we had to let them go. I wanted to hug them and tell them it was my fault, but our HR consultants had given strict instructions that we could only tell them the basic facts. We had horrible board fights and political backbiting among the management team. I learned that the only thing more powerful than greed is fear and how valuable it is to be able to maintain trust and calm in the face of crisis. Eventually we stabilized the company at breakeven cash flow with 65 employees. Then in August 2001 my board fired the CEO that I had hired and asked me to resign as a member of the management team and transition to being a consultant. I went home, slept for a week, signed up for a triathlon, and felt the oddest sense of freedom. Unfortunately, when life decides to test you, it usually does it in bunches.

Two weeks after I was removed at netDecide, I was on a train from Boston to New York. Without any explanation, the train went into reverse and returned to Boston. When I walked off the train at Boston South Station, there was complete chaos. The first person I found told me that "they" had flown "hundreds" of airplanes into New York and Washington and that both cities were rubble. We were locked in the station, nobody could get cellular reception, and the rumors of nuclear Armageddon quickly replaced the airplanes. Given that my family lived in Washington, it felt like hours until someone managed to turn on a television in a bar and we watched the towers fall. It was several more hours before I could reach my family to make sure they were all safe.

While the country was coming to terms with that blow, I had another more personal one. We had hired my mentor and old rowing coach, Eric, as our director of training at netDecide. When the board removed me, they also fired him, about a week after he and his wife had their first child and while she was suffering from postpartum depression. Over Thanksgiving weekend, he came downstairs and found her stabbing herself with a kitchen knife. He tried to stop her and in the process she stabbed him once with a glancing blow. He managed to crawl to the phone to call 911 and tell them his wife was in critical condition. The paramedics arrived in time to save her. Eric didn't make it.

Getting pushed out of the company I founded, the attacks on September 11, and losing a mentor in horrific fashion, all within a few months, was obviously shattering. Luckily netDecide had given me the financial flexibility to really think about what I wanted to do next in life. Like America after September 11, I responded to that adversity by picking up the pieces and moving forward, onto even greater adventures.