This month I attended my first Creative Destruction Lab (CDL) session in eight months. I realized I had learned a few things. Because, in that time, I’ve had dozens, maybe hundreds—of one-on-one meetings with founders.
Some I’ve been working with for years; others closer to the start of their founder’s journey, but all of whom have survived the very first throws of starting a company in the harsh reality of the space business.
Coming back into the CDL room after that gap, I was struck by how different those two groups felt.
By and large the CDL founders are on the starting line. They’re excited, full of momentum, convinced that their idea is the one that will break through. They’ve read the stories, built the decks, and believe it is now just a matter of finding someone with capital that believes in them and in their idea.
The founders I work with week to week on the other hand, carry themselves a bit differently. It’s hard to put my finger on, but there’s less flash, more focus. They still believe deeply in what they’re doing, but the energy is steadier, quieter.
Let me put it this way: the difference really has nothing to do with intelligence or talent. Instead, it’s all about where they sit on the curve between the Dunning–Kruger effect and the resolution of the Stockdale Paradox.
Maybe that requires some explanation.
For the benefit of those who do not followed this column. Most of us have met the Dunning–Kruger effect in passing when someone knows just enough to think they understand everything. But instead, they are not really competent to judge their own competence. It’s not arrogance so much as lack of reference points. When you are just starting a business, you may be very familiar with your technology, but you don’t yet know how many ways things can go sideways when you try to make the innovation into a business. So, you kind of assume that the hard part is over.
Early-stage founders often live in that space. Their confidence is contagious—and useful. It’s what allows them to face an impossible problem without blinking. You need that sort of optimism to get something started.
But it also comes with blind spots. They underestimate timelines, overestimate investor readiness, and mistake encouragement for commitment. When things don’t move as quickly as they expect, they assume that something is wrong. The market is slow, investors are fickle, partners are distracted. The fact, this is how it always feels—slow, uncertain, messy—hasn’t settled in yet. They seem to feel that their problem is that they just haven’t found the right person to pitch yet.
I don’t mean that as criticism. Naïve confidence is almost a developmental stage. Every founder passes through it. The trick is not to stay there too long.
But the smart founders are the ones who can survive being humbled a few times. They’ve watched their best ideas unravel under customer feedback and come to understand that while their technology is impressive, it does not actually solve the problem that customers want to solve.
They’ve waited on the edge of their seats for that phone call from investors – but when the phone rings they get the message that the investor feels “It’s not the right time” to invest in them.
But still, they get up the next day and go back into the arena – ready and willing to find another way to get where they know they can go. They are the people who embody author Jim Collins called the Stockdale Paradox: the ability to confront brutal facts while maintaining absolute faith in the outcome.
When I talk to founders at this stage, those with a few hard-earned battle scars, the conversation is… different. There’s less talk of what they are sure will happen and more investigation of what might happen – and how to react when it does.
These founders no longer need to convince themselves that the journey will be easy. What matters is that they are convinced that it’s still worth doing.
They don’t get thrown by slow progress or mixed signals. They’ve stopped treating bad news as proof of failure. It’s just information, sometimes painful, always useful.
That’s not cynicism. It’s maturity.
From naïve confidence to grounded optimism
The shift between those two mindsets – from “Dunning-Kruger” to “Stockdale” is one of the most important transitions a founder makes. It’s not about losing confidence in your vision; it’s about replacing illusion with resilience.
The new founders believe things will go well because they haven’t yet experienced why they might not. The seasoned ones believe they’ll prevail despite knowing that it won’t go the way they expect it to.
That’s a very different kind of faith. I see it every week when I work with these founders.
I see it in how they listen. Early founders either nod enthusiastically at every suggestion, or they reject them out of hand without considering them because they don’t match their expectations of reality. The experienced ones listen carefully, then sort ideas into piles: “helpful”, “maybe later,” and “not our problem right now.” They have learned that the most important skill they have is how to set priorities to learn.
I also see it in how they react to feedback. The new ones defend. The mature ones ask follow-up questions. They don’t need to be right in every moment; they just need to keep getting better.
And I see it in how they plan. The new founders set linear “success-oriented” goals: “We’ll raise this much, hire that person, launch by this date.” When reality starts to depart from their plan they spend their time trying to recover that original plan. Or they convince themselves that where they have ended up is where they really wanted to be all along.
Experienced founders, on the other hand, have become comfortable with contingency. They know that they need a plan, but they also know that the plan will almost certainly not work as expected and that their success will come from their ability to adapt and keep moving towards their objective and not in trying to rescue a plan that has ceased to be relevant.
Living the paradox
It’s easy to misread the Stockdale Paradox as stoicism or pessimism. It’s neither. It’s resilience and emotional realism. It’s the ability to accept that the world won’t bend just because your idea is good—and to keep showing up anyway and learning what does work.
Stockdale survived years of captivity in Vietnam by holding two truths simultaneously: he never doubted he’d get home, and he never pretended it would be soon.
Founders who internalize that same mindset stop wasting energy on outrage or disappointment. They expect things to be hard. But they also expect that even hard lessons will advance them toward their ultimate goal.
Very few founders start out with this mindset, but the good ones get there – usually fairly quickly. This is, in some ways, the necessary first step in any founder’s maturation from innovator to business executive.
Because maturity in a founder doesn’t announce itself. It shows up in small behaviours that add up to credibility. But the first step is almost always to accept that their job comes down to knowing where they want to go and finding a way to get there. The outcome is what matters and getting there requires patience and resilience combined with curiosity and insight.
How can I tell a mature founder from one that is still in startup mode? Well, for one thing, they don’t oversell. They make sure that the story they tell is credible and resonates with their audience. They don’t seek to be impressive, they seek to be effective. They also give credit easily and take responsibility quickly.
And perhaps most tellingly, they’re not disappointed when things are harder than they thought. They treat such times as opportunities to learn. They get curious about why things played out the way they did. They look for patterns, so they can apply the lessons next time.
That’s what struck me most after eight months away: how the founders I know best have come to expect difficulty without resenting it. They’ve stopped being surprised that everything takes longer and costs more. Instead of frustration, I hear curiosity— “why is it slower this time?”—and then a plan.
The vision and passion are still there. They’re just better informed.
If there’s a lesson in this, it’s not that early optimism is wrong, it’s that it needs to evolve. Confidence gets you started but it’s perspective that keeps you going. You can’t build a durable company on faith that things will be easy. You build it on faith that you’ll keep finding a way forward when they’re not.
That’s what makes a successful founder. I know because I see it every day. More than ever I am grateful to the founders I work with for showing me what success looks like – and I hope I can share those lessons with more founders who want to learn.