My Story: From A Dot-Com Bust To Harvard

Why did our business fail? Part of it was it was a tough fundraising environment. We were trying to raise money in August of 2008. We didn’t have the right set of investors whose goals were aligned with the goals of the co-founder and I and that is something that can be a make-or-break issue. Ultimately, my co-founder and I hoped to work with a set of investors and a board of directors who would be able to support us in scaling up and running after the success we were seeing with We didn’t find that. I wish I could be more direct but I can’t.

From that failure, there were some valuable lessons. One thing I learned is that you always need to be very careful about the people you work with—in terms of who you take money from and who is on your board. You need to make sure everyone’s interests are aligned. I got that advice time and time again, but it’s hard to listen to it when you’re head is down working on a very cool project—and your investors are writing you checks every month.

The other thing I learned is that you need to fail quickly. When something is not working, that’s a learning point and you do something with it. If you make the same mistake the second and third time, you’ve wasted resources and energy. Probably the number one lesson was learning when to say no. Saying no helps you prioritize, save resources and meet expectations. About 99 percent of the business development and strategic partnerships that came up we should have said no to. We spent a lot of time and resources chasing a lot of things.

Being inside a failing company was a life changing event for me. Over the course of three years, I worked alongside my team, night and day, on a project about which we were passionate. And our users and the media shared in our vision: we grew quickly, and had our story told on CNN, in the new York times, and by bloggers and reporters nationwide. Everything must have looked great externally. But as our company fell apart, we had to tell vendors to stop working, go through the lay-off process, and ultimately, admit failure. This of course caused me to question my own self-worth, and wonder what I, and my team, could have done differently.  For so long, my personal identity was tied up with the company: it’s what I worked on feverishly, and I was always talking about it with the media, our partners, and our customers.  Almost over night, I had to re-establish my identity, both for myself, and others. The experience was life changing, and I’ll carry with me forever those lessons and emotions.

Other “My Story” features:

From a Hollywood Talent Agency to Chicago’s Booth School of Business

From an Army Ranger in Iraq to the Harvard Business School

From Deloitte Consulting to Harvard Business School

From West Point to Berkeley’s Haas School of Business

From Communist Romania to London Business School