The last B2B I did we built a product for a couple of “whales” and then struggled making money off of the long tail. They had such peculiar business rules we had to thread a needle to get our top three working. We had one team pull a RedHat on us, essentially forking the code to make big changes for other customers, and didn’t tell us about it. When we started refactoring and rearchitecting to fix some of our biggest problems, we broke all of their stuff. Way to communicate guys.

In the end it turned out the goal of the company was to sell it to deep pockets. Having prestigious customers is how you do that. But the employees including some of the salespeople thought we were trying to serve an entire global industry. If that had been the case we should have started with customers about 1 std below median size, and built momentum toward landing large customers.

Because what happened is that we had contracts with the big companies we couldn’t net a profit off of, and they liked to keep paying what they were already paying. If we were solid with mid sized customers first, we could have asked for more from the biggest ones because we were selling a mature product. Instead they bought a fixer upper and wanted to pay the same as we fixed issue and added tons of functionality.