Chapter 5: Building a Plane on the Way Down

In Chapter 4, I blogged about how team rapport and camaraderie is a common theme that’s emerged in many of our lectures and readings.  Another common theme is the usefulness of iterative design.

Iterative design is the ongoing cycle of releasing a product, letting users play with it, gathering feedback, and improving it based on what you learn.  This is especially important in the tech space, where rapid innovation means that your cool new idea can quickly become outdated — or that someone else can release it first.

In a sense, it means that you have to be okay with releasing an imperfect  or limited product.  This is a very scary thought, but the perfectionist in me was able to relax somewhat after Jeff Veen of Typekit shared one of his favorite quotes:

“If you’re not embarrassed when you ship your product, you waited too long.”

– Reid Hoffman, LinkedIn, on iterative design

Jeff emphasized that for a tech startup trying to gain a foothold, the speed of iteration beats the quality of iteration in necessity.  He explained how Typekit is constantly evaluating the list of features they’d like to add and “punting” the less crucial features to tackle later.

Jeff had me pretty convinced, but I asked him whether he sees any danger in releasing an early version of the product — only to have users walk away disappointed with its lackluster features, never to return.  He agreed that this is a potential hazard, but argued that users would return if the idea was a good one, and gave the example of his own readoption of Twitter after the site gained a critical mass of users.

I’m experiencing iterative design firsthand in my job at Assistly as their beta customer service platform nears release.  Assistly iterates the product literally every week based on user feedback.  In the handful of weeks I’ve been working there this summer, the product has seen the addition of chat, back-end optimization, and a redesign of the UI from this early iteration:

to this more user-friendly version, which features more screen space, easier navigation, and a cleaner list view option:

Another enormously useful aspect of the iterative design process is that it emphasizes collecting user feedback throughout the creation process.  Chris Golda from BackType shared his take on one of his favorite Reid Hoffman quotes, as applied to iterative design and the previous startup that he and cofounder Michael pursued:

“Entrepreneurship is throwing yourself off a cliff and building a plane on the way down.”

– Reid Hoffman, LinkedIn, on uncertainty

“In our case, we spent half the time on the way down building a bicycle.”

– Chris Golda, BackType

Thus, it seems that a founder must not only build better and better iterations, but also keep an eye on the big picture to chart where these iterations are going.  In fact, the crucial “pivots” in strategy that I’ve discussed in earlier weeks have, in essence, been nothing more than large-scale iterations on the startup’s business model — or, in Chris and Michael’s case, on their career goals of being entrepreneurs who successfully “built the plane” on their descent from the “cliff” of the unknown.

Entrepreneurship is throwing yourself off a cliff, and building a plane on the way down.

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