Category Archives: VI. Startup

Startups and slowdowns

The startup has officially been put on the back burner. The last several weeks have been spent intensely exploring the concept and its potential, involving myself with MassChallenge, networking, and to a large extent tearing my hair out during the many learning processes – about startups, about entrepreneurship, about running solo, about working from home. is not dead, but it’s not doing jumping jacks.

Working off of the MassChallenge timeline, the first round of judging will come to a close this Monday so I have a few more days to collect votes and endorsements, which have been every bit of tangentially beneficial as MassChallenge touted them to be; you go in asking for approval of your concept, but the real value is in the discussions, insights, and connections. I’m not hopeful. I’m realistic about my chances. I believe there are over 700 applicants, and 300 will be selected to move on to Round 2. When I applied back in March, the concept was so small and unformed, I can’t imagine that version resembles anything close to what I’m staring at now – which isn’t a bad thing. I just think, looking back, the March version is probably too weak to handle much scrutiny. Basically, I’m using this as an opportunity to scale back the entire operation.

If MassChallenge was a catalyst to get me to spend the time and energy – and a few dollars – on really focusing this idea into a potential business, mission accomplished. I have my criticisms of their processes, but they’re definitely overshadowed by my positive experiences. Ultimately, you get out what you put in, and admittedly I didn’t put enough into the challenge itself. The startup scene is interesting to say the least, but ultimately is a part-time project. You haven’t heard the last of it, but you won’t be hearing much about it again for a while.

Lastly, every person in my life – my family, friends, internet buddies, people I met during the challenge, and especially AwesomeWife™ – have been nothing but supportive. Even through a lot of vagary and probably some (much?) doubt, it’s just been enthusiasm and well wishes. It goes without saying but it still needs to be said: thank you everyone, for every little bit. I truly could not have done any of it without you. Much, much love.

I & need your help

Friends, I’ll keep it brief:

It’ll cost you 60 seconds & an email address. I recognize that I’m asking you to give them up without giving you much back, least of which being the actual startup idea. But think of it this way: it’s definitely a 5-star idea, so if you trust in me at all, you’ll be doing the right thing!

So call it a favor, call it blind faith, call it obnoxious – but if you could do it anyway, it would be much appreciated. (And apologies in advance for the next couple of weeks, when I bug about it repeatedly.)

Also, I’ve set up a temporary blog on the site, including a form to sign-up for launch updates.

Startup changelog v0.2


  • Outline is at 90-95% status
    • Originally intended as a pitch deck outline, quickly realized this is an outline of practically the entire startup
    • Pitch deck will be derived from this
    • Feeling good about how the major questions being answered
      • Still got the nagging “is this really possible” thought (may drink more)
  • Attended Venture Café for the first time
    • MassChallenge had a networking event at Venture Café, in Cambridge at MIT
    • Met some very smart, very interesting folks looking to participate in the challenge
    • Lots of biotech representation in the competition; feel sort of goofy in comparison (note: when billionaire, fund them all for the greater good)
  • I has lawyers!
    • I had an immediate legal question and found a good consulting add-on with legalzoom
      • The idea that I “have lawyers” is endlessly amusing to me; phrase being abused at home hourly
    • I now have a valid and binding NDA that uses me personally as the party in question, until the IP transfers to the startup
    • NDA already in use
      • Also hilarious: NDA’ing my parents
  • Growing concern about a bubble
    • This week alone there’s been a lot of startup news that’s got me (somewhat) reeling
    • On the one hand, you have Foursquare going for some well-deserved funding
      • Keeping in mind Foursquare has real revenue
    • On the other hand, free app Flipboard gets a $200 million valuation
      • As far as I can estimate, acquisition to a sucker whale (new term) is their only exit strategy (if they even have one)
      • I do wish them the best, it’s a great app
    • Most concerning: Color receives $41 million investment (read: real money)
      • I’m holding judgment on this but only for a week; my trustworthy gut is ready to call bullshit
  • AwesomeWife™ sent me this interesting Mashable post about Groupon’s development choices in cloud computing
    • Now I’m looking at, Amazon services, etc.
    • Might need less from-scratch development than originally thought
  • Next steps:
    • When outline breaks 95%, create entire roadmap
    • Order business cards
      • But before that, creating logo
        • But before that, create branding
          • But before that, solidify look and feel
            • Consider announcing the name next week for gathering thoughts, opinions, and insights from networks
    • Grow beard back

Startup changelog v0.1

I think I’m going to post updates on the startup in the form of a bulleted changelog. It seems only appropriate. I want to be able to update quickly, skipping any real organization of thought, but post all of the disparate threads, thoughts, and learnings that I’m running through rapidly.

Here’s where things are as of today:


  • (Initial idea came in 2003. I can’t divulge any details about it just yet, but for the purposes of this changelog, this is when it all started.)
  • First notes and thoughts written down and organized.
    • I’m using Google Docs to store all notes, links, and thoughts.
    • Everything is a mess right now but with the April 11 deadline for MassChallenge, it’s quickly becoming time to make some decisions, organize, and create both an early pitch deck and the main MassChallenge application.
  • Last Friday, a name was picked.
    • Most companies and services online get named by whatever domains are available, which is exactly what happened to me.
    • I went back and forth on a few names and variations, emailed a few domain squatters and offered deals, but was ultimately struck with a new idea that was available and – I believe – will work swimmingly.
    • The domain was purchased last Friday night, 3/18/11 and the name of the company was born.
  • After much research, yesterday I filed the startup for incorporation.
    • For what I’m setting out to do – organize a company, seek funding, etc. – a C Corporation is the best route.
    • I incorporated in Delaware instead of Massachusetts. I may need to pay a little extra later on for operating out of state, but from what I gathered, it will be worth it.
    • I used to file, which I learned isn’t necessarily the most rigorous for document creation, but it was cheap and it’s all I need for right now; my future high-priced lawyers can tighten it up later if needed.
      • (Proposed name has been preliminarily approved; papers now with Delaware’s Secretary of State.)
  • Next steps:
    • Pull together notes and create pitch deck outline.
    • Begin networking with Boston-based entrepreneurs (aka “players”).
    • Begin looking into seed companies (aka “small fish”).
    • Shave beard and get blazer dry cleaned.