How do you eat an elephant? Notes on doing the impossible

Peter speaking to a large crowd at the International Startup Festival in Montreal

Peter speaking to a large crowd at the International Startup Festival in Montreal

How do you create a plan to change the world? Entrepreneurs (and the VCs who back them) like big audacious dreams that are the equivalent of building the proverbial rocket while on the way to the moon. But even audacious dreams need to be broken down into actionable steps that can be planned, assigned and measured.

I have spent many years trying to find the balance between audacity and actionability. This came home to me again yesterday as I was thinking about my keynote address for the International Startup Festival in Montreal. It was a fabulous event with a great line up of speakers and an engaged and energetic crowd of about 750 people.

Although I was supposed to broadly talk about role of startup culture in the evolution of Silicon Valley, I decided to take a slight conversational detour. As I thought about the transformation of the Santa Clara Valley from its fame as the “Prune Capital of America” to its present status as financial powerhouse and center of transformative technology, I was drawn back to how different the world looked forty years ago.

Now, it’s clear that there is a big market for technology and a path to liquidity for successful technology companies. Then, there was a whole lot of open space in the market. And yet, we believed that we could change the world and set about to do it.

At times like this, it’s surprising how often I draw lessons from old, bad jokes–often to the frustration of friends and embarrassment of my children. Just yesterday, I broke out one of my favorites, which starts “How do you eat an elephant?” The answer of course is “One bite at a time.” Dumb?? Yeah, probably. OK, almost certainly. But it reinforces the notion that every big, scary audacious goal needs to be broken down into bite-sized chunks.

More than 20 years ago, I ran the Microsoft ad account for Ogilvy & Mather. Now Microsoft is a behemoth known for everything from games to enterprise software. At that time, Microsoft was best known as on operating system company for DOS. Their top selling application was flight simulator. No one in the IS department of a big company would consider welcoming their software inside the corporate doors.

Yet, the mantra was “a computer on every desk and in every home running Microsoft software.” There were times when it was tough to say that without laughing nervously. But even then, the conversation was about how to take that seemingly crazy goal and break it into doable pieces. Get Windows actually installed. Get people to boot their computers into it. Get people to buy and use Windows apps. Then put hooks for enterprise apps into the desktop versions to seed demand. It was tough but it worked because Microsoft executed at every stage. They cut the elephant into bite-sized chunks.

There are three ways that this experience is relevant to the entrepreneurs that I spoke to yesterday. First, it’s important to dream big dreams. Second, it’s okay if those dreams are scary. In fact, if they don’t cause you to occasionally break out into cold sweats in the middle of the night, they probably aren’t big enough. Finally, they need to break those big goals into steps that are actionable, assignable, and measurable.

And now, we can ponder the existential question of how to fit five elephants into a Volkswagen bug…