Friday, October 12, 2007

Burn the Boats

As a venture capitalist, I am fortunate to meet with people brimming with ideas for new products and new companies. You can feel the excitement build as ideas percolate and mature from insights quickly scribbled down in the middle of the night, to application mock ups, late night Starbucks brainstorming sessions, and early team solicitation.

Often, however, the ideas never bear fruit and the excitement subsides and the spark of creativity dies. This week, I met with several good friends who suffer from both the blessing and the curse of a surfeit of choices and options. The blessing is that talented people are always in demand and there are many avenues of opportunity available to them. The curse is that they often sit stalled at the cross-roads of choice - start-up, large company, start my own gig....

Mark Gainey, the founder of Kana, once told me that the hardest step on the road to entrepreneurship is the first one. Once committed, the iterations come fast and furious and the pressure to make it work allows for moments of genius and insight simply not possible before diving in head first.

I continue to regret that so many brilliant people that I know, full of energy and ability, sacrifice their passions on the alter of safety or indecision.

The conquistador Cortes provided a model for all intrepid souls....that is to burn the boats on the shore and ensure no way back and the stark need to make the expedition succeed or go down trying.

In facing choice in a sea of opportunity, I think that Frost's road less taken is inherent in the spirit of the Valley. However, it often requires a moment a bit like sky-diving....i.e. to willingly jump out of a perfectly good plane and make the most of the free fall.

Like Cortes, it is often necessary to burn the safety boats in order to finally realize the promise of late night ideas and the passion that gets you jumping out of bed in the morning.


  1. I agree with your post 100 percent, but think that you should say the "illusion of security."

    People who have jobs think that they have security, and that was true for a long time, but it just isn't true right now. Even government jobs are not as secure as they once were.

    The only true security these days is being nimble, and having the confidence to go out and get things done.

    Your humble typist,

    -Scott Yates

  2. Anonymous1:32 PM

    As an entrepreneur, I wholeheartedly agree... Your first step is the hardest. Soon, you will find that even your worse days as an entrepreneur are better than your best days as a cog in the machine.

  3. Anonymous6:18 PM

    reminded me of a quote:

    Until one is committed there is the chance to draw back; always ineffectiveness.

    Concerning all acts of initiative (and creation) there is one elementary truth, the ignorance of which kills countless ideas and splendid plans:

    that the moment one definitely commits oneself,
    then providence moves too.

    All sorts of things occur to help one that would not otherwise have occured. A whole stream of events issues from the decision, raising in one's favour
    all manner of unforseen incidents and meetings and material assistance which no man would have dreamed would come his way.

    I have learned a deep respect for one of Goethe's couplets:

    "Whatever you can do, or dream you can, begin it! Boldness has genius, magic, and power in it."
    W.H. Murray
    from The Scottish Himalayan Expedition

    and Johann Wolfgang von Goethe

  4. Anonymous9:10 PM

    I love it, Will. I think I'm going to wrap this blog post up and send it to my "lukewarm" entrepreneur buddies for Christmas.

  5. will -- i couldn't agree more. the notion that there's no going back has a way of focusing the mind like nothing else. i'll leave it to sir sean connery to say it best:


  6. You're absolutely right about this Will. For that burning desire, that passion to truly manifest itself it needs committment. I recently went looking for some partners who both had day jobs while I did not. Each was happy to talk the talk over coffee but that drive and need to execute and make progress was not there. I eventually decided there was no partnership fit and have decided in hindsight it was the 100% right decision.

  7. I agree.

    It's not just when starting and it applies to recruiting co-founders and the initial founding team members also...

    From my own experience, it was hard to convince someone(however smart) to join an early stage startup, if he don't have a startup experience.