Why I stopped writing, and how I found my voice again

By Cack Wilhelm

Writing my way made me a better investor and partner to founders

Writing, like running, is often used as an example of operating in a flow state, in which one is deeply focused and performing optimally. Last fall, while in just such a flow state, I wrote a series of short essays about time constraints, venture capital as a team sport, and the lessons I’ve taken with me from jobs in sales.

But then I stopped writing and haven’t written since. I stopped because I had told myself my next piece would conform to a different style. But because that style was so unnatural to me, I never wrote the piece. The difference was that instead of writing about a ‘soft’ topic, like my previous pieces, I would focus on something ‘hard’ — tech valuations, metrics, evaluating companies, or industry trends.

It would be more like the material my peers at other venture firms were writing. If that’s what they were doing, I figured I should do the same.

So, head down — a few ideas emerged, but nothing clicked. When speaking or writing for a particular audience, I have an obligation to provide value and insight. But the topics and points of view I was trying to explore all seemed stale or unoriginal.

I realized I was in an anti-flow state.

Only later did I come to understand that trying to write something completely inauthentic meant I wouldn’t write at all. In the words of Thomas Merton, “It is therefore, a great thing to be little, which is to say: to be ourselves. And when we are truly ourselves we lose most of the futile self-consciousness that keeps us constantly comparing ourselves with others in order to see how big we are.”

I also realized that no longer writing would come at a personal and professional cost. For that epiphany I credit another first-rate thinker: Charlie Munger.

Among the few materials I saved from business school is a printout of the May 5, 1995, edition of Outstanding Investor Digest, which includes a transcript of Munger’s lesson to a USC class in 1994. He has this concept he calls “elementary, worldly wisdom,” in which he says, “you’ve got to have models in your head. And you’ve got to array your experience — both vicarious and direct — on this latticework of models…”

Writing, I came to see, helps me organize my experiences on that growing latticework of models. Even more than reading, writing helps me map the world, reconcile disparate pieces of information, and integrate them into my evolving understanding. I am simply more tuned in when I am writing; I prefer that to letting the world slide by.

This lesson also informs my work as an investor. What I have from working across companies, throughout board rooms, with myriad CEOs, is the greater picture, whereas a single, highly talented CEO may just have his or her company as context. Very many of these mental models are venture-specific, developed from seeing variations on a given theme across companies and experiences.

So now I’m writing again, and while I will pen a few “hard” venture capital treatises, I will gravitate toward the lived experience, which is to be myself.

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