Checkers (Execution) and Chess (Strategy)

I’ve been thinking a lot about strategy vs. execution lately – how it maps to founders’ strengths and experiences, how it changes by stage, and how to play each well at the right moment.

As a generalist investor, I don’t have deep operating experience in every vertical we back. This is where my MBA and prior work experience help, but also where they fall short. As a board member, I’m mostly pattern-matching and offering strategic suggestions. Much of what actually matters lives in the nuance of a specific industry.

And yet, it’s often the checkers – the day-to-day execution that builds a good company, while the chess – the strategic choices – is what makes it exceptional.

When Eric Paley and I were building Brontes, most days were consumed by engineering, manufacturing, product and sales challenges and improvements. There was never enough time, and the to-do list was always a mile long. But some of the most interesting and impactful conversations were the bigger ones:

• Should we be an open platform or a closed ecosystem?
• Should we sell direct or partner?
• Should we go deeper in one market or expand?
• Should we sell the company or raise more capital?

These are the chess moves. They shape the 10-year outcome. Some of our portfolio companies have added service businesses to accelerate growth, some have taken them away to improve margins. Some have gone all in on AI and others have acquired small firms to grow market share. There are a lot of moves to be made, and you can’t simply make them for the sake of it, but can be formative.

At the same time, the day-to-day mattered enormously in the short run: closing the quarter, fixing a critical bug, hiring a head of sales.

Over time, though, as I’ve now been sitting on boards for close to a decade, the strategic questions do start to matter more. My role isn’t to have the industry-specific answer, but to help frame the decision while respecting that the founder knows the terrain better than I ever will.

This is where a good board really helps: industry experts alongside thoughtful VCs, together helping founders navigate when to focus on execution and when to lift their heads and think long-term.

You have to be a tactical animal to survive, so that you can become a strategic leader to win.

I’m still learning how to recognize the right moves at the right time and how best to guide founders through that transition. Curious how others think about this, or what experiences you’ve had navigating the same tension.