I've Taken 7 Startups to Exit: Pivoting is a Feature, Not a Bug

But most organizations aren’t ready to pivot when given the chance

In every startup I’ve been a part of, there's a moment where it hits you: the original plan wasn’t enough. Not wrong. Not broken. Just... not enough.

It was time to “pivot,” which is a terrible name for what actually happens: You start to see the real shape of the opportunity and you go after it.

I’ve lived through this moment seven times, each on the path to an exit. And let me tell you: “pivot” is a terrible word for it.

It sounds like you made a mistake and you need to course correct. It sounds like you followed the wrong road when the correct road was there the whole time. But, in reality, that’s not what happens. What’s actually happening is integral to the process of building, not a deviation from it. It is learning and adapting.

The problem is that many organizations arrive at this inflection point and they aren’t organized enough to take advantage of it. Chaos kills pivots. And that’s a shame, because the ability to pivot well is often the difference between becoming a footnote and becoming a category leader.

The Idea and The Team are Only Part of the Equation

Everyone loves to talk about big ideas. But in startups, the real key is execution and that means putting the right team together. The best idea in the world won’t survive without a team that can adapt under pressure, move fast, and stay focused on solving the real customer problem as it evolves. Defining what to work on is hard — so it’s the execution that turns that “what” into reality. Both are equally important and must be coupled.

A good idea and a strong, talented team? That’s table stakes.

The reason I do repeat it, though, is to point out that this is also where many promising startups get into trouble. They have a good idea and a capable team, and they make the mistake of thinking that this is all they need to be successful. It goes like this.

Early on, every startup starts with a hypothesis. This is the thing you think the customer needs. Usually, you’re partially right. The idea addresses part of a customer's pain point.

So, you hire a team and you build something. The customer likes it, but as you get more users you start to see more pain points that the product needs to solve. Your initial idea wasn’t wrong, but it only covered a small percentage of the solution that customers really desire.

If you don’t start to address a larger chunk of their problem, they will search for other solutions.

What if the best opportunity isn’t the one you set out to build at all? That’s the real question.

This is the moment where the real challenge and opportunity are revealed, and it’s the moment you need to be ready for. If you can’t adapt, you’ll miss it, and your customers will be gone as quickly as they came.

And this isn’t the only moment that tests you. Another one comes when a startup reaches an inflection point on its S-curve shifting from innovation to growth, or from growth to maturity. The best teams don’t wait for that shift to surprise them. They stay one step ahead, anticipating what’s needed next to stay relevant and keep climbing.

How to Be Ready

Years ago, I joined a startup that had already gone to market. Customers liked the product, the sales team was closing deals, everything looked great. On the surface, at least.

On the inside, the engineering team was stuck. They couldn’t deliver what the sales team was promising, their tech stack was outdated, and the team was demoralized. On top of that, they were split between San Mateo and Bangalore, which led to very little trust, an “us vs. them” mentality, and a whole lot of finger-pointing.

When I joined, I found a culture problem disguised as a tech problem. Everyone hated engineering and engineering felt like they were being unfairly sold out. Every team had their own ax to grind and their own view of what mattered.

We weren’t one company, we were four.

We started slowly rebuilding the architecture, modernizing what was outdated and, more importantly, rebuilding the relationships between teams. We finally got to a place where teams could work together effectively, respond with agility, and get new features out the door fast.

Just in time.

Because seemingly a day later, the market crashed.

Right On Time

This was 2008. The financial crisis hit hard, budgets froze, and nobody wanted to spend on software. But in our sales meetings, new faces started to show up.

Data center and infrastructure teams started to attend, and when we asked why they were there. The answer was simple: internal cloud. They were witnessing a new phenomenon in their engineering teams: developers were bypassing IT and spinning up servers on Amazon with a credit card. The CFOs were fine with it because it was saving money during the recession, but compliance was not ok with it.

So, these teams wanted to know if our software could manage their internal cloud like Amazon did while keeping everything in-house for compliance purposes. They wanted to use our catalog model to turn their data centers into private clouds.

This was a massive opportunity for us, and had it come a few months earlier, our internal chaos never would have allowed us to seize it. But, because we had done so much cleanup, we could handle it.

We were able to adapt quickly to the demand, and within a few months, we had transformed into a trusted partner to global enterprises wrestling with the shift to cloud and that positioned us perfectly for acquisition by Cisco. We didn’t exit based on our original idea, we exited because of what it became.

Clean the House, You Never Know When Guests Are Coming

We have all scrambled to clean the house when we knew guests were coming over, and we have all likely felt the shame of having someone drop by to find our place a mess. When that happens, it is only natural to think “I’ve got to keep the house clean! You never know when someone will drop by!”

In startups, cleaning up the chaos is the high-stakes version of this same concept. You never know who will come knocking and show you an opportunity that could lead to amazing things, so you need to be ready at all times.

In the case of my example, if we hadn’t done the work and had still been arguing about architecture or who was screwing who over, we never would have been ready to pivot into internal cloud architecture. We wouldn’t have been acquired by Cisco. We would have bled money through the recession, and who knows what would have happened.

Our organizational chaos wasn’t just a pain in the moment, it was a liability for everything we were working toward.

The best companies I’ve worked with “pivot” to success because they see an opportunity that is bigger than their initial idea, and they are well prepared to act on it. They have everything in order so that when the time comes, they can pounce.

These companies are not precious about ideas. They’re ruthless about execution. They stay close to the customer, chase solutions, and build fast. They see their company as something that can evolve, not something that stays fixed from birth.

Pivoting is not a weakness; it's a sign of life — and the ultimate test of your ability to execute. It shows that you are following the path of innovation and building the muscle to see opportunities and respond to change. That’s what makes a company durable through tough times and ultimately what lets them land on something that gets them to exit.

The exit rarely comes from your first idea; it comes from your ability to evolve and execute, so be ready to change.

When the unexpected door opens, will you be ready, or still cleaning up?