Setting and Hitting Early Milestones

To read the Green Pants Chronicles from the beginning, click here.

Act 2: Launch

If you remember back a few posts, I’d rationalized in my mind that I wasn’t going to die, destitute and alone, if the Windsor Circle thing didn’t work out, and that the worst that could happen was that I’d go back and get another job. Part of that calculus was naming incremental steps that would prove that we were on the right track, and to provide opportunities along the way to stop the process if we didn’t have the basics down.

Egregiously Comparing Ourselves to Astronauts

Think of it like the Gemini and Apollo missions to get into space and land a man on the moon. First we had to get a rocket to fly into space and come back. Then we needed to stick some living thing in the rocket, and hope that we could get poor Miss Baker back alive. Then we needed to put a human in the rocket and hope to get him home alive, and then get to the moon, and then land on the moon, etc, etc. Each successive step reduces risk and frames the knowledge required to get to the next step.

Windsor Circle’s First Milestones

For Windsor Circle, I remember our risk milestones in those early days as being something akin to:

1. Get a Team to Commit by February 28
2. Build a Working Prototype by April 30
3. Sell it to Someone by June 30
4. Sell it to 50 Someones by Decemeber 31
5. Raise venture capital by December 31

If we didn’t make it anywhere along the way, we would stop and recalibrate or exit.

The Bruce Boehm Rule

This is chronologically out of order, but one of the most important lessons of the journey was something that local angel investor Bruce Boehm taught us (paraphrased):

At any given moment, ask yourself what the biggest risk to creating enterprise value is, and what the least resource intensive way is to prove that you can solve for that risk.

This doesn’t mean not to invest resources heavily when needed. It just means that for each given risk, fire a few bullets to see if you’re on target before firing the cannon. This came up over and over again in our journey, and not just at the beginning stages.

Generally, I think we did this well. We had a corporate value of taking calculated risks and learning from failures, so when we failed this maxim, it was either because of a lack of creativity or energy.

A Caveat: It’s Your Job to Take Calculated Risks.

One caveat, however. An entrepreneur’s job has a lot to do with taking calculated risks and being decisive. We had moments as a team where we were too diligent. Clearly, your risk increases when you move too quickly, but I think at times we found ourselves seeking too much data. For example, we could have made the market segmentation decision faster and moved more quickly to our pivot based on early observations, but we were digging too deeply for data to justify the moves. So, be careful about wrapping yourself up in “testing” and “gathering data.” If you know, you know, and it’s your job to be decisive and take calculated risks.