Startup Lessons: Be the pirate and the navy

Lesson #2 from the untold stories of Appirio

This post is the third part in a series. The original post sets the context, provides the disclaimers, and gives a preview of all of the lessons.

Who would believe epic nights emerge from strong discipline?

I always loved the Steve Jobs quote “Why join the navy if you can be a pirate ?” So when we started Appirio with two naval co-founders, at first I worried if their discipline would impair our ability to be disruptive.

Yet in time it became clear the structure their “naval” perspectives brought shaped the company as much as our desire to be disruptive. This discipline allowed the organization to understand where it could improvise. Often when we appeared reckless, angry or spontaneous, it was done by design. When we first raised seed money from salesforce.com they loved our bravado. But when we received our first venture round from Sequoia they were attracted by the balance Mike and Glenn (our naval academy co-founders) brought with it.

Glenn and Mike , Class of 1990 Naval Academy Graduates served our country proudly and used what they learned to shape our company. Their performance in our founder football games, however, did not live up to Naval Academy standards.

The balance of our approaches paid dividends well beyond our funding. One summer I sat with a few salesforce executives after a major New York event. As was our custom, we began talking trash about each other. I taunted one executive that they would announce anything for attention and their one-time concern about compelling customer examples had been replaced by worship of Global Systems Integrator (GSI) sponsorship dollars. Another salesforce executive offered to barter a deal between us to remedy our division. He suggested that increasing support for the development of salesforce employee culture through better through social bonding was they key. Ultimately, this escalated and the ridiculous became a reality.

I offered to pay for the entire night out for the group (up to $5,000) if they would make their best effort to get myself or my co-founder (CEO Chris Barbin) into any executive event outside of Dreamforce for the next two years. The deal was made, we shook hands, and had an epic night out in Manhattan.

Admittedly, our CFO was a bit perplexed when I logged the expense. Yet it was quickly settled as I walked through the scenarios and how even if we only got into 1–2 incremental events it would be a net benefit. Because we were careful planners and understood our strategy for engaging prospects, we got to be pirates for the night and while generating a clear cut ROI. On this night, and many days and nights to follow, the discipline of our naval roots helped us to fully understand how and where we could get wild.