Navigating the Heights: The Arduous Journey of Achieving and Maintaining Success

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I was talking about sports with an entrepreneur the other day regarding whether it is harder to get to the top or stay on top. We debated the differences between dominant team runs vs. single season great teams that come out of nowhere but can’t stay up competing for championships year after year. We then transitioned that same discussion to startups.

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Getting to the top

This is the equivalent of coming up with an idea, proving authentic demand, getting product-market fit, building a team and culture, and ultimately solving a big must-have problem with exponential growth. It involves visionary skills to find a problem, recruit a team, and sell on that vision before it fully exists. You can sometimes fly under the radar until the big players notice (and by then it can be too late for them). In this early stage, you can often get fortuitous (lucky) breaks from the market that can propel you forward. Creating the belief in the team that this can be done is critical.

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Staying on top

This is the equivalent of achieving industry leading status in your space while continuing to meaningfully grow year over year and fight off market challengers. At this stage you rely a lot on the culture and team you have built to keep things moving; as the CEO you no longer can have your hands in every area. Process and repeatability become much more important to creating the consistency to stay on top. You rely on exceptional talent to make the key decisions and execute the playbook. You also must keep evolving with the market to stay on top, otherwise what worked in the past might not work in the future. Competitors are giving you their best shot.

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Both are difficult, but ultimately each requires different skill sets. Depending on your traits as a leader, you may be better suited to get to the top or stay on top. This is why you often see a founding CEO get the company going, and at a certain point a new CEO is brought in to keep scaling and growing. But to answer the question, I do think staying on top is more difficult. The “chip on your shoulder” that motivated you to get to the top becomes harder to keep once you get there; complacency is a real thing.