Why Great CEOs Live in the Future

Finding product–market fit is usually a process of iteration. Build, measure, learn, repeat.

And it’s so powerful that, when it works, it creates a false sense of security.

Some founders extend the logic and think: “If I just keep iterating the product, I can build a billion-dollar business.”

However, truly at-scale businesses rarely get there through iteration… if at all.

If you want to scale by orders of magnitude, you eventually need to transform the entire company.

Iteration vs. Transformation

I was working with a CEO whose company was doing really well. They were at $20m in revenue, growing, with a strong team.

However, the CEO was maxed out and losing motivation.

I asked him: “Where are you spending your time?”

“My Chief of Staff takes care of all the admin, so I spend all my time on the strategic bets we’ve made to get us to $30m ARR.”

“How much time do you spend on your future goal of $100m?”

He paused and thought about it. Then said: “If I'm honest, I haven’t thought that far ahead.”

“Will doing the stuff you’re doing to get to $30m get you to $100m?”

He paused again.

“Probably not.”

In that moment, three things became obvious to him:

1. Getting to $100m required a different kind of thinking than getting to $30m.

2. No one in the company was focusing on figuring out how to get to $100m.

3. The strategic bets suddenly seemed short-term, not long-term.

If you look at any big tech company that scaled, it wasn’t just through linear growth.

That’s why iteration eventually fails.

Iteration is based on a course correction to the same destination. Transformation is about charting a new course to a different destination. 

The 10X Bets Only The CEO Can Take

Here are just a few of the classic big bets that helped companies jump from one path onto a much bigger one:

• Mark Zuckerberg betting on mobile i.e. the big blue app and Instagram
• Uber going from black cars to ride-sharing
• Netflix going from DVDs to streaming
• Amazon going from selling books to selling cloud computing
• Tesla going from cars to humanoid robots

And there are as many examples of failures too (the Facebook Phone, Google Glass, and Apple Intelligence, to name a few).

When these bets work out, they can literally add zeros to revenue and enterprise value.

And this is the key point: if the bet doesn’t have the potential to add a zero, it’s probably not the right bet. 

Instead, it’s an iteration… something that improves the past, but doesn’t transform the future.

These aren’t minor tweaks. They are 10X decisions that were not obvious or popular at the time. And the founder-CEO was the one thinking them through.

This is the model:

• The CEO builds a team that lives in the present. They focus on short-term goals and make things real.
• The CEO lives in the future, wrestling with much bigger goals on a different time horizon, then travels back to the present to share what they’ve figured out.

The 25% Rule

I have a simple rule for scale-up CEOs: you need to spend 25% of your time on long-term strategy.

The essence of this is working out how your company can become a massive company in less time.

In practice, this is often unscheduled time where the CEO can think. They research trends, speak with investors and CEOs further ahead than them, read, write, and process.

Many CEOs don’t do this because they worry people will think they aren’t working hard. But this is the work.

So if you’re scaling up and find yourself only working on today’s problems, be careful.

You might win the battle and hit your short-term goals—but realise your long-term goals keep moving further into the distance.

Related reading:

• Are you building a company you’ll eventually want to escape? Learn how to design real freedom into your future as a founder.
• Do you feel misaligned with the CEO your company now needs? Explore how founders evolve their strengths without losing themselves.
• Are today’s decisions quietly narrowing your options? Learn how to avoid complexity that locks in an unwanted future.

Originally published on January 18, 2026.