Exit conversations with founding CEOs

Over the past few months, I’ve had the privilege of interviewing some incredible founding CEOs who’ve transitioned out of their roles and moved on to new opportunities. These conversations have been both eye-opening and deeply reflective, helping me uncover key themes and lessons about what I call “CEO end-states.”

I recently spoke with the new Techstars Boston class, focusing on an essential but often overlooked aspect of building a company—starting with the end in mind. As early-stage founders, we can become too focused on immediate milestones, but it’s equally essential to envision your end state and build optionality into every decision.

One of the most common questions I get is: When does it make sense for a CEO to start thinking about their end state? The truth is, there’s no definitive answer, but I believe the right time to start is when your departure would truly impact the company—when you’ve built enough value that your absence would matter.

When discussing the journey of a founding CEO, navigating the end state of a business is often complex and varied. While each founder’s experience is unique, there are a few common paths that many follow when reaching this stage.

Are you a founding CEO considering shutting down your startup? First, remember that no matter where you are with your business, you’ve gained valuable experience. If you do decide to shut down, know that great opportunities will follow. Your value is clear, and others will see it too.Here are some common traps to avoid:

When a CEO departs before a major milestone like an exit, acquisition, or IPO, we often hear euphemisms like “stepping aside,” “finding a growth partner,” or “bringing on adult supervision.” While these soften the reality, the truth is that the board is effectively firing the CEO. This may sound harsh, but recognizing this potential is crucial.

As a founding CEO who has transitioned out of a company multiple times, whether by shutting down a startup or stepping aside as the CEO of a growing business, I often felt there were no resources to help navigate this process.

When founders start their companies, they’re usually not thinking about how the journey will end. In the military, generals always talk about the “end-state” of a mission, but as founding CEOs, that’s not really on our radar in the early days.

I’m excited to announce an open call to all founding CEOs to join CEO End State. As founding CEOs, we often receive more credit than we deserve, but we also carry the heaviest burdens and face the largest challenges in building our businesses.