One Life

May 3, 2011


On Saturday, I proposed on a sailboat on Bainbridge Island. When I started searching for a boat, the task seemed daunting, but a quick search on airbnb didn’t just locate a boat – it yielded a sailboat bed & breakfast. How romantic is that? I found the perfect restaurant for the night using yelp, and emailed with the chef to arrange a special desert. A simple update to my Facebook relationship status saved me hours of phone calls, allowing me to turn off my phone and enjoy quality time with my new fiancé. The internet didn’t just help me with my proposal: I met my fiancé on match.com.

The experience made me think about who I’d be without the internet. In college, almost all of my plans were made by instant message – I’ve never liked using the phone, and I was lucky enough to live in the first generation that could get away without it. I found my first job out of college, at a startup in New York City, through craigslist (along with a sublet, an apartment, furniture and a mover).   I even found my job at Microsoft through craigslist. The job was in internet advertising.

The internet has shaped my life as far back as I remember. As a shy teenager trying to figure out life, I realized I probably wasn’t the only one, so I started a website called Teen World where I gave others advice. Over time, it grew into an interactive community for young adults called CheekFreak. Around 1,000 users visited each week to escape the real world and be themselves, and it was a huge part of my identity. I only made a few hundred dollars before I went to college and shut it down, but I don’t regret all the work. I still smile when I read emails from visitors, including several who said they were considering suicide before visiting.

When you get knee deep in your startup, you get lost in topics like fundraising, usability and dashboards. But let’s not forget why we’re really here: to shape lives. While many think task management is a boring subject, I’m excited by how it directly ties to people’s quality of life. What if I can increase your free time? What if I can help you feel better at the end of the day? The spark that gives birth to most startups is a selfless realization that you can help others. Making it sustainable is secondary, and it’s only here that most fail.

When you read that 90% of startups fail, remember that the definition is strictly financial. Don’t forget that you originally set out to help people. You’re only a true failure if you don’t improve 1 user’s life. Of the 90% of “failed” startups, I wonder how many founders consider themselves failures. I wonder how many have a letter from a user that still makes them smile. I wonder how many are proud of the lives they shaped. And I wonder how many wouldn’t say their startup shaped them.