The Founder's Edge: Why Being Wrong Is How You Win

Every founder starts with a spark — an idea too compelling to ignore. We step into the unknown, fueled by vision but shadowed by uncertainty. Early wins build momentum, but soon, the path becomes rugged. Challenges rise, decisions become clouded, and cracks form in once-confident strategies. Moments like these separate dreamers from builders. It’s here we face the quiet question every founder must answer: Can I keep going if I’m wrong?

The truth? We have to. Because being wrong isn’t failure — it’s feedback. And for any founder anchored in purpose, it’s the very fuel that sharpens our vision and fortifies resilience and antifragility.

The most successful founders aren’t the ones who avoid mistakes; we’re the ones who get stronger because of them. This is antifragility: learning, adapting, and becoming more effective under stress, like a muscle tearing after a workout and building itself back through continued resistance. But antifragility doesn’t happen by accident. It demands more than just grit or openness to feedback. It requires an anchor: purpose.

Why Purpose Builds Great Companies

Without purpose, every misstep feels like erosion. But when your company is guided by purpose, mistakes transform into markers of progress. Purpose clarifies why our Work matters, giving us the courage to lean into failure, iterate boldly, and adapt without losing direction. It’s not visionless conviction. It’s clarity — knowing the destination even when the visibility changes.

Every great company needs a Compelling Why — a reason for existing beyond simply making money, one that aligns with our values. (As I always say, we don’t make money because we want to make money; we make money because people value what we do.) A Compelling Why informs both the day-to-day work and the visionary execution that helps companies achieve sustained growth as they climb the Stages of Development. By building with purpose from day one, we reap the benefits:

1. Vision contextualizes failure: When we’re clear on the world we’re building, setbacks become feedback, not threats.
2. Purpose shields against self-doubt: In moments of uncertainty, purpose reminds us why the journey matters, keeping us calm and stable even when the world around us shifts.
3. Confidence unlocks action: The antidote to paralysis isn’t simply certainty — it’s trust in our direction. Confidence empowers us to make bold moves, pivot fast, and keep momentum alive.

Embracing a Learning Mindset

Founders who embrace being wrong and learn from those failures can weather and harness storms that often devour other leaders. We build cultures where learning beats perfectionism, where feedback loops fuel innovation, and where “wrong” isn’t shameful but expected.

Truly great founders consistently model the learning mindset we want to nurture in all our Ideal Stakeholders, which allows us to embed purpose in every action our companies take. Regardless of what stage your company is in, these steps will help you reach the next level:

1. Define your Forever Agreements: They're your Northern Constellation, and they're more than a mission statement. This is your guiding system. What are you building? Why does it matter? Who does it serve? What are you selling? Clarity here turns adversity into plot points, not dead ends.
2. Reframe mistakes as data: When you know your "why," missteps don’t attack your worth. Instead, they reveal gaps in your thinking. They become the next best step, clearly marked.
3. Move between modes: Great founders shift between different modes, including Visionary Mode, Coach Mode, Leader Mode, and more. But in moments of challenge, Warrior Mode is king. This is where antifragile founders thrive, asking hard questions, testing assumptions, and adapting in real time.
4. Build strong feedback loops: We should surround ourselves with systems and people who align with our vision even as they challenge us to be better and better versions of the best version of ourselves. At Ninety, we’re developing Maz, an AI companion, to help leaders surface weak spots and spark reflection — because growth requires mirrors.
5. Play asymmetrically: When we know our purpose, we spot small risks with outsized rewards. We take calculated bets, fail fast, and win big — not despite setbacks but because of them.

Antifragility as Culture

The mindset of antifragility doesn’t stop with us. When we lead this way, our companies follow. Teams take smart risks. They speak objectively, fail forward, and stay aligned — not just with tasks but with purpose.

At Ninety, we see it every day in the founders and companies we serve: Those who treat stress as a learning opportunity are more likely to drive change when it matters most. They turn uncertainty into advantages. They build enduring legacies.

So, the next time you’re wrong (and you will be), don’t shrink from it. Lean in. Ask what it’s teaching you. Let it sharpen your leadership, strengthen your company, and fuel the extraordinary work you’re here to do.

Even good founders make mistakes. But truly great founders are committed to using that negative feedback to build something enduring that matters.

And that? That’s the founder’s edge.