Every investment requires a leap of faith, an emotional act that’s not pure reason, and that’s got to carry you through in the inevitable many months, sometimes years, of horrific bad stuff that comes with the company. And you’ve got to have that energy, that sustaining belief to carry you through, because if you don’t, then you regret having done it. So when I have regret, it’s when I didn’t have that, and I’d logically talked myself into [the investment] and checked the boxes. So it was really helpful [to have a failed investment] that taught me, ‘don’t invest like that.’ You have to have the love affair, and if you don’t, then you shouldn’t do it.

Peter Fenton said this in a Stanford Business School case I happened to read over the weekend. The sentiment resonates deeply with me. Every investment is an emotional commitment to support and grow the business and to build long-lasting relationships with the founders.

More important, though, is the founder’s love affair. The investor’s commitment is after all a tiny simulacrum of the founders'.

In the quote above, swapping the word investor for entrepreneur and what results is profound and true.

Every startup requires a leap of faith, an emotional act that’s not pure reason, and that’s got to carry you through in the inevitable many months, sometimes years, of horrific bad stuff that comes with the company. And you’ve got to have that energy, that sustaining belief to carry you through, because if you don’t, then you regret having done it. So when I have regret, it’s when I didn’t have that, and I’d logically talked myself into [the startup] and checked the boxes. So it was really helpful [to have a failed startup] that taught me, ‘don’t found a company like that.’ You have to have the love affair, and if you don’t, then you shouldn’t do it.

Find your love affair.