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

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.


Where to Startup: Seattle or San Francisco?

April 28, 2010

There is an ongoing debate about whether startups need to be based in the bay area.  Chris Dixon, who is a major leader in the movement to create a New York Startup Scene, wrote an entry titled It’s not East Coast vs West Coast, it’s about making more places like the valley.  But just this week, Michael Arrington made fun of Redfin, referring to Seattle as the minor leagues.

So, after my trip to San Francisco last week, do I feel the need to move my startup from Seattle?  Absolutely not.

Seattle is a fantastic city to launch a startup.  Here are some reasons:

  1. A supportive startup scene. There are successful startups in Seattle; many of their leaders go out of their way to be available to new founders.
  2. Many networking events. Weekly events include Open Coffee with Andy Sack and Hops & Chops with TeachStreet.  The Northwest Entrepreneur Network hosts classes, events, and even presentations to angel investors.
  3. Local Funding Options Abound. Microsoft made and still makes countless millionaires.  Seattle is also home to Amazon, Starbucks and Boeing.  There are plenty of venture capitalists and angel investment groups.
  4. Plenty of Talent: One of the biggest arguments for the Bay Area is the quality of engineers. But high-quality engineers and smart business managers are shipped to Seattle every day.  Seattle has a different type of entrepreneur; we are less likely to launch right into a startup after school.  Instead, we take a job at a large company like Microsoft or Amazon until inspiration strikes.  We learn until we have an idea we can’t let go and/or can’t take the corporate life any more, and then we are super motivated to build something for ourselves.  Believe me: we are motivated.
  5. Easy Travel to Bay Area: It’s a 1.5 hour, $180 flight to the bay area.  How often do you really need to be there, anyways?  Most of your time in the seed stage will be building your product.  Think about it this way: less distractions.
  6. Quality of Life & Cost of Living: Seattle is just a great place to live.  While I enjoyed my trip to San Francisco, I couldn’t stand how long it took to get around on public transportation.  In Seattle you can get a large apartment, cheaper office space, and even have a car.
  7. Productivity: It’s dark in the winter.  Personally, this makes me very creative.
  8. No shortage of really great coffee. I’m just contemplating my second cup of the day.

Seattle is a great option for startups.  I would not proactively pursue a move to the bay area unless it would have a huge business impact as we grow.  For now, I’m going to enjoy my 2-bedroom house that costs $1350/month, the views of water and mountains, my car, and the great outdoors.

Advice from StartupDay 2009

January 19, 2010

“Be careful whose advice you buy, but, be patient with those who supply it. Advice is a form of nostalgia, dispensing it is a way of fishing the past from the disposal, wiping it off, painting over the ugly parts and recycling it for more than it’s worth.” – Baz Luhrman

On September 26, 2009 I attended the StartupDay conference organized by Seattle 2.0.  The speakers were successful in the Seattle startup scene, and dispensed advice that was very valuable as I considered creating a startup of my own.  Now that I have a blog I can finally post the notes.

Key Takeaways

  • Don’t quit your day job.  (This was not what I wanted to hear)
  • Don’t just create a product, but a business (a revenue engine).
  • Need a way to generate income while working, or at least some revenue within the first ~6 months.  Some presenter did consulting on the side.
  • Don’t get venture capital or you’ll have new bosses to answer to.
  • Minimize regret.

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