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I don’t know why, but two unrelated ideas/themes have been on my mind…no title to this post, because I can’t think of a good one…

The first is about “entrepreneurial journeys.” I know, that is a cheesy term. Believe me, I cringe writing it. Anyway, semantics aside, this term came up in an interesting conversation I had with a close friend. We were discussing how we both haven’t seen a close mutual friend recently. This friend is building his own company, his first time in a founding/CEO role. The conversation ended with something like this: “Well, Semil, I guess he’s on an entrepreneurial journey.” I don’t know why, but that phrase has stuck in my head. It’s slightly different than saying “he’s building a company,” or “he’s really busy,” or “entrepreneurship is all-consuming.” As I’ve been thinking on this, it struck me that everyone in and around technology startups are on journeys of different speeds, directions, and arcs. Even though so many of the people we know best who are all crammed living in proximity to each other can actually drift apart because the trajectory of the journeys each person can be very different. It’s like a diaspora, of sorts, excepts the physical distances traveled aren’t great — but in the mind, those distances can feel vast.

Now, next, unrelated…

The second thing that’s been on my mind is about the word “empathy,” particularly in the context of what I hear (and read)  founders discuss they want in their investors. Disclaimer, I’m no expert here and have limited experience. Caveat out of the way, it seems most people equate empathy with having been a founder/CEO of a startup before. Unfortunately, I’m not sure that’s true in practice. In the dictionary (Merriam-Webster), “empathy” is defined as the feeling that one can “understand and share another person’s experiences and emotions.” The ability to share understanding is important, but longer-term investments seem more like business partnership, and the good ones seem to be more driven by an honest alignment of interests among both parties versus whether one side is empathetic or not. Empathy may help in the sales process of investing, when an investor courts a founder. And if empathy is important (to a point, right?), it can be gained in different ways in and around startups. Some investors with deep operating experience (but no founding experience) can breed their own style of empathy; some investors without any real experience whatsoever can build empathy as they continue to invest; some people pick up empathy by doing something hard and getting their butts kicked, repeatedly, and surviving; and some investors who have been founders even more than once may not be empathetic as investors. On a different plane, empathy can also be gleaned from trying, difficult experiences.

And while empathy may work up to a certain stage or maturation of a company, after a while it may diminish in utility — think, for instance, of entrepreneurs who have shepherded their company through a Series A round only to be stuck without Series B offers — at that point, “empathy” doesn’t really creep into those conversations. Of course, people are human about those discussions, and some of those discussions can be hard, but empathy only goes so far. Empathy is something folks to should ideally show to everyone — not just investors in a sales process with founders, or founders managing their key employees. Empathy is cheap to deploy. It’s quite cost-effective. What isn’t cheap is a partnership where parties’ interests are aligned. Sometimes that means difficult conversations. Sometimes empathy may take a back seat to the truth — even a harsher truth the investor may need to hear from a founder. Anyway, I know everyone talks about “empathy” and I know it’s generally important on an interpersonal level (way beyond startups), but it has lately struck me as an abstract word people think they want or need, perhaps distorting reality — a reality we all need — as a cost.