2008 was insane - moved from Seattle to Brooklyn (Amazon.com -> Etsy.com), started my Tumblr, broke up a 3 year relationship after she cheated on me the day Obama got elected, quit Etsy, parents going through marital trouble, and decided to do a startup. What happened in 2009?
January - As New Years resolutions usually go, I started a “food photo once a day” habit that lasted for about 4 months. Check ‘em out, there are some pretty decent photos in there. Also, the beginning of my relationship with Kara, who is wonderful in so many ways. She got me into hosting supper clubs through helping with her Ted & Amy Supper Club.
February - My friend / investor pulled out his support of waffl because for all the planning / designing / spec writing I was doing, I hadn’t actually done anything. This was a really valuable lesson for me and woke me up to the realization that results are what count, not effort.
March - Heroic push to launch waffl on March 31st, the first day of a big industry trade show. We succeeded and have the pictures to prove it. Not shown: $2900 in rent being due in 2 weeks and not having the money to pay it is a horrible experience many entrepreneurs will suffer through. Thankfully I was able to raise $15,000 in time. Sadly, things with Kara ended.
April - We got accepted into the DreamIt Ventures startup incubator program! Thank goodness, because we only had a few months of money left. My food photo taking died off around this time as waffl was nearing 100 registered inns.
May - The big move. My $2900/month apartment lease was finally over and I was moving to Philadelphia for 3 months (see: startup incubator program). Man, look at this gorgeous apartment! Even better, though, was meeting Jessica on May 4th and falling in love with her. We knew within 3 weeks that we were perfect for each other… I’ve never had that experience before, despite several multi-year relationships. Sometimes, you just know.
June - The beginning of my 3 months in Philadelphia. By June 15th, despite having over 130 innkeepers on the site, we had realized waffl’s business model had a fatal flaw (we couldn’t offer real-time online booking of rooms unless the innkeepers used our software to manage their room inventory, and that wasn’t realistically possible for us). But we remembered talking to innkeepers about how overwhelmed they were with managing multiple social media accounts and how they would pay for a tool that put it all in one place for them. And so, the idea for Postling was born.
July - Spent July 4th with my family, Will + Stacy, and Jessica. My parent’s house got a front row seat for the fireworks. Bonus: Postling got a logo, thanks to the fine work by Kien Tseng of Yippa, who also designed waffl’s logo, the waffl homepage, and the first version of Postling’s homepage.
August - Postling launched Aug. 1st, 6 weeks after we first got the idea. It’s amazing what experience can bring - it took me 4 months to get myself together and launch waffl but only 6 weeks with Postling now that we knew what to do. We were written up in ReadWriteWeb, Mashable, TechCrunch, PSFK, KillerStartups, and more. And you know what? I wish we hadn’t. The product wasn’t ready and the business model has changed since launch. But these things happen…
September - Now that my Philadelphia program was over, Jessie and I moved in with my best friend Will in Bayonne, NJ cutting my rent from $3000/month to $300/month. Yeah, how about that. I went on a camping trip with some friends (and forgot my sleeping bag at home. Idiot.) where we made the most delicious camping treat possible. Postling had several hundred users at this point, although we were disappointed by the conversion of trial users to $9/month paid users.
October - I spoke at the NY Tech Meetup to a crowd of about 650. That night, I met Kristin Maverick, who changed my life without realizing it, because she helped me understand that PR firms and digital agencies have a real need for Postling as a multi-user / multi-brand platform. So a couple weeks later, we launched a new version and new pricing, which is what we have today. Also spent a week in Seattle with my friends on the Pacific Ocean, which was awesome. Started the fundraising process.
November - The inaugural meeting of NYC Tumblr foodies, when we ate Korean BBQ. The beef tongue is delicious. Trust me. Over 500 Postling users, thanks to the new pricing and features. The Yankees win the World Series! Fundraising continues.
December - Close to 1000 Postling users now. 350 Tumblr followers, 4500 posts, 6000 likes, 730 reblogs. Sent out lots of holiday cards. Fundraising almost complete. Hot chocolate. Cupcakes.
Thanks to all of you, my life is a million times brighter and more interesting. Here’s to a fantastic 2010.
