Debrief Through the Curve.

Timing is the lesson I have mastered least. I have debriefed everything since my days in the Navy. Every flight ended in a debrief. So when Internet Venture Works failed, I ran it through the same four questions. What did we intend? What actually happened? Why was there a gap? What will we do differently? The answers were true. The vision was right, and the timing was wrong. Years later I ran the debrief again and found the question the four had missed.

In 1999 we built the dot-com version of businesses owned by large buyout firms. Projects like farmandcountry.com and basspro.com. Our customers were the private equity firms, and they were visionaries. They could see the future and wanted to get there first. But the people who had to use those businesses were ordinary shoppers. Most of them were not ready to buy a heavy bag of dog food from a website. They were pragmatists, still on the far side of the chasm. We had sold to the left side of the curve and were waiting for the right side to arrive. It did not arrive in time.

Here is where I got it wrong. I already had the tool. Three years earlier, at WiseWire, our investors brought Geoffrey Moore in to teach their companies. He drew the adoption curve and asked us where we stood, and why. He did not accept the first answer. We found our beachhead, and it was Lycos. At Internet Venture Works, I never asked that question of myself. I should have.

Lycos Clubs failed from the other direction. We had the audience. We built for innovators, with every option a power user could want. Yahoo Clubs came six months later and did less. A pragmatist could understand it in one look. Moore called that the whole product. The audience was there. The product was built for the wrong side of the curve.

COSIMO is the case still open. We went into tokenization very early. In Moore’s terms, we sold to innovators and a few visionaries for years, waiting for pragmatists who were not ready. Was I too early? Probably. The difference this time was staying power. The second time I was early, I made sure we could stay in the game.

Amy Edmondson of Harvard Business School calls this kind of loss an intelligent failure. It happens in new territory, chases a credible opportunity toward a goal, is informed by what is already known and is kept as small as it can be. Being early is new territory by definition. The fifth question turns a vague “the market was not ready” into a finding you can use: who was ready, who was not, and how far apart they stood.