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Blogging About Failure

Posted by Scott Kirsner  August 25, 2009 07:05 AM

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Waving the white flag after spending years trying to get a business of the ground is never pleasant.

But failures can often contribute more to the education of an entrepreneur than successes. And some entrepreneurs are willing to share those learnings with others via their blogs.

Here are four postmortem posts from Boston-area entrepreneurs, or companies with Boston connections:

1. Arlington entrepreneurs Abby and Ivan Kirigin (they're married) announced on their blog last week that they were shutting down their start-up, TipJoy. TipJoy had aimed to make it easy for you to leave a small tip -- say, 50 cents -- for a blogger whose site you read daily or as a thank-you for downloading some free music from a musician. But they said that a social network needs to integrate that kind of payment system and promote it to its members in order for it to take off:

    We have decided against continuing to pursue additional funding. After a long and hard look at the market and the situation, we didn't feel it made sense.

    ...We believe that a payments system directly and officially integrated into social networks such as Twitter and Facebook will be a huge success.

(Interestingly, Ivan promptly went off to work for Facebook.)

2. Also last week, Scott Rafer blogged that he was "commencing an 'orderly shutdown'" of Lookery, a start-up that built an online advertising network and also developed services intended to make online ads more effective. Rafer is a Silicon Valley entrepreneur who started the company with David Cancel, the company's Boston-based chief technology officer. Rafer wrote:

    The sins Lookery committed under my leadership were continuing our dependency on a large partner (March 2008), not knowing when to cut bait on a failing asset (September 2008), and building ahead of the market (December 2008). I and we made any number of other mistakes, but all the rest were correctable. Avoiding even one of the three big errors might have been enough to get us over the hump.

3. Chris Herot, co-founder and chief technology officer of Convoq, analyzed why the Lexington-based company's efforts to develop new software for online meetings didn't take off, in a December 2007 post:

    While the company was an innovator in on-line meetings, and had a core group of enthusiastic customers, it never achieved the traction that would have provided the necessary return on capital, and the investors, patient as they were, eventually called it quits.

    ...In hindsight, we spent far too much time iterating the [product's] features in the conference room before we tested them in the marketplace.

4. Gregg Favalora was the wunderkind founder of Actuality Systems, a Bedford company that first developed a really amazing 3-D display, and then decided to devote its resources to a specific medical application related to visualizing information: writing software to help doctors interpret ultrasound images they use in the treatment of prostate cancer. He wrote about the process of winding down the company earlier this year:

    ...I did the math, and absent any major commercial deals, our last paid day would be April 24 [2009]. That left us with savings to be a mensch about paying our vendors and maintaining our patent fortress.

I'd been talking with Gregg around the time of that post, and later included Actuality's story in this column about shut-downs.

Have you seen other blog posts that try to tease out some of the lessons of a failure -- whether one based in Boston or elsewhere? Do add 'em below...

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5 comments so far...
  1. Posted by Jason August 25, 09 08:49 AM
  1. I remember this one from Mike Troiano - when matchmine closed their doors last October:

    Keith Cline

    Posted by Keith Cline August 25, 09 10:28 AM
  1. Always enjoy your columns, thoughtful discussion of failures as well as successes is both rare and instructive.

    Interested readers might enjoy: (investments
    Bessemer passed on but wish they didn't)

    Two books:
    Burn Rate (
    What I learned losing $1M

    Posted by D August 26, 09 08:45 AM
  1. Mine from late last year, ending my first attempt at a startup:

    Posted by Jay Neely August 27, 09 12:51 PM
  1. "Failure is good" wisdom abounds, but it goes against our nature. I very much respect companies that build it in. One thing that's helped me a lot is treating new ventures as *experiments* - unknown activities (some large, as you list) that we pursue, but for which the outcome is uncertain. Crucial is how we define success. Naturally we want it to be big, such as a huge IPO. At the same time, there are other definitions, such as actually *creating* the company. Hats off to them. Finally, the one thing all experiments guarantee ... You. Will. Learn. Something. Probably a lot.

    Good article,


    Posted by Matthew Cornell September 2, 09 08:30 AM


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About Scott Kirsner

Scott Kirsner was part of the team that launched in 1995, and has been writing a column for the Globe since 2000. His work has also appeared in Wired, Fast Company, The New York Times, BusinessWeek, Newsweek, and Variety. Scott is also the author of the books "Fans, Friends & Followers" and "Inventing the Movies," was the editor of "The Convergence Guide: Life Sciences in New England," and was a contributor to "The Good City: Writers Explore 21st Century Boston." Scott also helps organize several local events on entrepreneurship, including the Nantucket Conference and Future Forward. Here's some background on how Scott decides what to cover, and how to pitch him a story idea.

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March 3: Web Innovators Group
Demos, drinks, and schmoozing at the Royal Sonesta in Cambridge.

March 7-8: MassDigi Game Challenge
Competition for aspiring game developers... plus panels and keynotes related to the business of play.

April 3-4: Mass Biotech Annual Meeting
Issues facing the region's life sciences community.