Take the money, keep the plan

In 2020 we were raising a seed round for Rosalyn and one of the VCs introduced us to Coursera. Their CEO called. They wanted to invest, and they had a thesis: Coursera for Campus needed proctoring, ours fit, and they'd bring us go-to-market through their platform. They put in about a million dollars.

Along with the check came a request. We had spent two years learning that certification buyers couldn't move proctoring alone, because three or four incumbents controlled the whole chain from exam authoring to delivery, and those systems were old and bad. So we had decided to build the modern end-to-end platform, anchored on proctoring, and replace them. Coursera asked us to drop that and focus on cheap, scalable proctoring for their roadmap.

It was a great proposition. Hundreds of thousands of exams, a big partner, a name investor. We took it. We abandoned our thesis and built to theirs.

Two pilots, both successful. Then an acquisition conversation, where I named a number without a banker and scared them off. Then their stock fell, their strategy changed, and Coursera for Campus was gone. We were a year behind, with a low-stakes, cost-optimized product, and no plan of our own to fall back on. The enterprise customers who showed up next wanted high-stakes. We had built the opposite.

The plan we abandoned was sound. I knew it was sound. I let a strategic investor's roadmap replace it because the money and the promise were attached to each other, and I didn't separate them.

The rule I took away is short. Take the money. Keep the plan. If an investor's thesis and yours differ, that's information about the investor, not a reason to change the plan. If you do decide to change it, do it because the customers told you to, and write down what would make you change it back.