Learning to let go: care vs. laissez-faire
Gil Dibner

At the beginning of a recent pitch meeting, a founder asked me if I was a "hands-on" investor. I responded, quite honestly, that I didn’t know or, in other words, that it depends. The best answer I could give was that it’s a continuous balancing act. On the one hand, I pride myself on caring deeply about the companies I work with. In a concentrated early-stage portfolio, there is no other way. Every investment matters - and every partnership with a founder becomes a meaningful relationship. But on the other hand, I am not here to run companies or tell CEOs how to run their businesses. That would be a recipe for disaster.

At the end of the day, I choose to back founders that I believe in. I back founders that I trust. I back founders that have a wealth of experience and knowledge in their domain. Even the youngest and least experienced first-time founders I back know infinitely more about their markets, competitors, technologies, and opportunities than I could ever hope to learn. The best I can do—and the highest value role to which I can aspire—is to be a trusted thought partner in enough cases to matter.

As years pass and the consequences of past strategic decisions unfold, I have been gradually forced to acknowledge just how little I know and just how little is knowable by anyone. Those who know me know I am opinionated. It is a personality type. But it is also—in many cases—a personality flaw and a limiting behavior. I am learning (too slowly) to focus my efforts to affect outcomes only on cases where two conditions are met: First, I must have high confidence in my strategic or tactical judgment. Second, I must have high confidence in my ability to influence decision-making. In the majority of cases, one or both of these conditions is not met, and the company would be better off without any attempt by me to set the course. In most cases, asking the right question is far more impactful than making the wrong statement.

One of the primary responsibilities of an early-stage VC board member is to raise a yellow or red flag when a founder appears to be headed down a dangerous path. That is a core tenet of responsible governance and, I believe, an act of trust and love. But honest feedback is one thing, and prescriptive interference is another. Many of my least effective interactions with founders have been driven by attempts to be prescriptive. Many of my most effective interactions have been associated with a far more relaxed approach. Sometimes it’s as simple as raising a flag, putting an issue or two on the table, making sure some alternative perspectives are introduced into the discussion, and then simply letting the founders go and figure it out.

I am learning—slowly—that a laissez-faire approach to the VC-founder relationship can go hand-in-hand with a deeply caring approach. I'm learning that one often enables the other. My self-image as caring and passionate often leads me to a thought pattern of “I care about the outcome, so I will attempt to drive the situation towards a better outcome.” But the reality is that a different thought pattern is often (usually, in fact) more effective: “I care, so I am always available to you as a thought partner. But I trust you and will give you space to think creatively about a solution and give full expression to your unique genius. If you feel you need me, I am here.”

Taking this fully on board has not always been easy or natural. I am opinionated and vocal, and I am conditioned to associate caring with solution-oriented intervention. But I’d like to believe I'm improving on this dimension and learning to approach partnership with founders in an even more constructive way. Finding the right balance between being constructively hands-on when it is actually likely to improve outcomes and caringly laissez-faire in most other cases is perhaps one of the most powerful leverage points in venture capital. I’m still working on it—and I hope I’ll get there one day.

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