Lessons Learned: Fail and Fail Again (Until You Succeed!)

Michael is an NYU student and serial entrepreneur. He recently founded Skylight, an app that's transforming how you find your new home.  Michael is a graduate of Draper University and the Founder Institute.

Life takes us onto very interesting paths. An advertisement came up in my Facebook Newsfeed, and suddenly, a stroke of serendipity followed. I was presented with the opportunity to attend Draper University for the summer, a school for entrepreneurs founded by the famous Silicon Valley venture capitalist, Tim Draper. Attending DU has proven to be one of the best decisions of my life, but that's a story for another time. (Can you spot me in the picture above? That's Tim is on the right.)

While Draper U had a lot of interesting traditions, one of the keystone habits of my mornings there began with an oath. Our entrepreneur oath contains the key tenets of an entrepreneurial mindset, but one line in particular helps me relate to a very important lesson I learned this year.

"I will fail and fail again until I succeed." Draper U cemented the idea in my mind that every failure you experience is a stepping stone on the path to your success.

For if you don't risk enough for the possibility of failure, how will you have the opportunity for success?

So are you saying I should aim to fail? This certainly isn't a piece that celebrates failure, nor does it encourage it for failure's sake. My goal for this post is to help you see failure from another perspective, and to do that, there is a very useful thought process you can use. In order to determine whether or not a "failure" would actually be detrimental to your life, challenge yourself for a moment. Imagine what would happen if you fail. Imagine the crowds of people booing you, or the disappointment of looking your parents in the eyes. Except it doesn't happen that way - ever. No one becomes disappointed with you, and you never get a crowd that boo's you. What really happens is something magical...


After your first failure, your knowledge and experience begin to compound. Instead of learning in a linear fashion - from one step to the next - you begin learning exponentially. Your failure serves a base for your future success -- a virtuous cycle that builds you into an entrepreneurial machine.

Who am I to preach about failure? I've had two startups "fail" in less than one year, and here I am on my third company. What you should really be focusing on is succeeding, because I can assure you that once things go right, it makes up for all of the despair that came before. The first company I worked on did not have a product after 9 months. The second launched within four months, and had no paying customers. My latest company has launched cross-platform in about a month, and while I can't disclose our metrics, I can assure you that I'm very pleased with our results so far.

People see my current company and they see an overnight success. People see the "event." People ignore the process.

People ignore the hundreds of hours of hard work that poured into developing the apps, customer development, marketing development, and building relationships. People ignore the companies in my past that have failed. People assume it's luck.

The media tends to sensationalize entrepreneurship and skew entrepreneurs with a success bias. Within its sensationalism, its begun celebrating failure. While I'm not celebrating my failures, they are the only reason that my company is where it is today. They are the only reason that I'm able to know as much as I do, in the short amount of time that I've learned it. My learning curve has been quite steep, and I've never been happier or more fulfilled in my life.

I entered Draper University with an idea that I worked on throughout the program. I pitched the idea to Tim Draper and his friends in the audience. The day after we had follow up meetings, and the same day, my company failed. My co-founder and I spent 4 months building a product around customer feedback, but we had absolutely no traction.  I used my follow up meeting with Tim to pitch a brand new idea, and two months later well known VC's have committed funding to our seed round.

Now it's your turn. Go out there. Take a chance. Life is short, and you only have one life to live. You're either going to build your dreams, or help someone else build theirs.  Accept that it's possible. Your wildest dreams can succeed. Accept that those that you admire are just regular folks, with extraordinary persistence and work ethic. Become the guy or gal that the next generation will admire. The only person stopping you is you.