Being Right
Success and the Price of Accuracy
This story is based on real events from my life. I have changed the names and titles of the individuals involved to protect their privacy. I spent a large portion of my career believing that the ultimate currency of leadership was certainty. I thought my value was measured by the precision of my logic – the “rightness” of my conclusions. I had to learn, through realizations in my own home and the near-collapse of a multi-million dollar company, that you can win every argument and still lose the war. Success isn’t a trophy for the most accurate person; it is a byproduct of being the most adaptable one. And now the story…
There is a specific kind of silence that falls over an investor’s boardroom in Greenwich, Connecticut, when a “perfect” plan meets a quarterly business review.
It isn’t the high-voltage silence of Sand Hill Road where everyone is performing for their next round. In Connecticut, the silence is muted, filtered through the grey, flat light of a late winter afternoon. The air in the room felt thin, as if the oxygen was being slowly consumed by the tension between the four people sitting around a glass table.
I was there as a contract “truth-teller.” A small, high-conviction VC firm used to keep me on speed dial for when their normal investment SOPs weren’t working. When the status decks looked perfect, but the cash kept disappearing, they’d call me. I was the guy hired to uncover in four hours what a standard due diligence team would take four weeks to miss. I didn’t look at the features; I looked for where egos and hubris had replaced reality.
Sitting across from me was Mark. Mark was the archetype of the “accurate” founder. He was a former quantitative researcher with a physics degree from MIT, and he had built a risk analytics platform that promised to predict portfolio and market volatility with mathematical certainty. He was the kind of person who spoke in three-decimal-place precision, even when talking about the weather.
On paper, his models were beautiful. In the real world, the company was bleeding out.
“The predictive integrity is holding at 98.4%,” Mark said. He didn’t look at me; he looked at his laptop screen. He was pointing at a heat map that showed a massive cluster of red in his user engagement data. His voice was clipped, a flat staccato that left no room for interpretation. “The churn we are seeing is a data-collection error on the client side. They aren’t tagging the risk events correctly. If they followed the protocol I designed, the efficiency gains would be undeniable.”
I looked at the churn report. It was 40%.
In the real world, a 40% churn isn’t a “tagging error.” It’s a riot. It’s the sound of customers walking away from a tool they find useless or impossible to use.
The market was screaming at Mark, but he couldn’t hear it because he was too busy being right. He was obsessed with the “correctness” of his protocol. It appeared that he would rather the company die in accordance with his math than survive by admitting his math was not reality.
The Managing Partner of the VC firm looked at me. He had spent six months trying to be the “supportive investor,” and he was exhausted. He needed someone to break this down for Mark.
I felt a familiar, prickly heat at the back of my neck. It’s the physiological signal I get when I’m about to stop being a “visitor” and start getting into “uniform”. It is a reflex I carried over from the Naval Academy. You get into role, check-in and you own the next watch.
“Mark, the protocol doesn’t matter if the customer hates using it,” I said. My voice sounded rough in the quiet room. “You’ve built a perfect system for a world that doesn’t exist. You’re arguing for your own brilliance while your customers are walking away to a competitor because that competitor actually solves their problem.”
Mark’s jaw tightened. I could see the pulse hammering in his throat. “The competitor is guessing, Meer. They are lucky. My system is accurate.”
“Your system is accurate, and your company is failing,” I replied. “Success isn’t about the precision of the model. It’s about the result. Right now, your result is zero.”
The silence that followed was heavy. Mark’s eyes went cold. He wasn’t looking at a partner; he was looking at an intruder who was insulting his intellect. I could see the rebuttal forming in his mind – a list of three reasons why my assessment lacked statistical significance. He was preparing to win the argument.
But as I watched him prepare to fight, a memory from two weeks prior hit me. It wasn’t a boardroom memory. It was a late evening conversation with my daughter.
I was sitting in my car with my sixteen-year-old daughter, Sam. We had been arguing about her SAT prep. I had designed what I considered to be a “perfect” study schedule for her – a system based on spaced repetition and optimized time-blocks. I had proven, through three different articles and a spreadsheet I’d built, why this was the only “correct” way to study.
Sam was crying. Not the loud, dramatic crying of a child, but the quiet, exhausted sobbing of a teenager who felt like a project instead of a person.
“You’re right about the system, Dad,” she had whispered. “But I’m so burnt out that I can’t even open the book. You’re right. I don’t know what to say or do anymore.”
I had stood at her door, stunned. My “perfect” spreadsheet was glowing on my phone like a taunt. I had won the debate. I was “right.” And I was currently watching the relationship with my daughter erode in real-time because I couldn’t let go of the need to be the smartest person.
Standing in that Greenwich boardroom, looking at Mark’s defiant face, the two moments snapped together.
I saw in Mark the same pathology I had shown Sam. The need to be “right” is a defense mechanism. We use logic as armor to protect us from the messy, uncertain work of actually being successful. We’d rather hold onto our pride than admit that the world doesn’t care about our spreadsheets.
Success requires the courage to be wrong. It requires the strength to say, “The math failed, let’s find a better way.”
I looked at Mark. I forced myself to take a breath. Tongue to the roof of the mouth. Uncurl the fists. Let the “fixer” adrenaline settle.
I didn’t offer a strategy. I offered a mirror.
“Mark,” I said. “I did this two weeks ago with my daughter. I proved I was right, and I broke her trust. I won the logic, and I lost my girl when she needed me. You are doing the same thing here. You are winning the argument with the market, and you are going to lose your company. Would you rather be the smartest person in the bankruptcy court? Or would you rather be successful?”
The room went completely still. This wasn’t “due diligence.” This was a strike to the hubris that had been masquerading as “data-driven, logical leadership.”
Mark started to offer a rebuttal – something about the volatility index. Then he stopped. He looked at the Managing Partner. He looked at the report of his financial projections. He looked at the heatmap of customers who were leaving him.
The armor didn’t crack – it dissolved. For the first time in four hours, Mark wasn’t looking at a spreadsheet. He was looking at the truth.
“I don’t want to be right anymore,” he said, his voice sounding thin. “I just want this to work.”
He picked up a whiteboard marker. He didn’t draw a new architecture diagram. He didn’t talk about “predictive layers.” He just asked: “If the experience is the problem... what is it they actually need to see to trust us again?”
Later that night, I got home late after several delays at White Plains airport. The house was quiet. I found Rani in the kitchen, finishing a glass of water. She looked at me, saw the weight I was carrying, and didn’t ask about the deal.
“You’re still in ‘Truth-Teller’ mode,” she said, her voice gentle. “I can see the gears turning. You’re trying to optimize the rest of the night before it even happens.”
I put my keys on the counter. I put my phone face down.
“I’m done optimizing,” I said. “I spent the day telling a founder that his pride was the only thing standing between him and success. I think I need to take my own advice.”
I walked over and just sat down at the table. No checklist. No strategy for a “productive evening.” Just being there.
Rani sat across from me. The tension in her shoulders dropped. “How was Greenwich?”
“It was expensive,” I said. “But I think we extracted the value. Mark finally stopped arguing with the market. He’s going to pivot the platform. He realized that being right was just a hiding spot.”
Growth, I have learned, is the process of shedding your defenses. It is the realization that the armor you built to survive the climb – the certainty, the logic, the need to have the last word – is the very thing that prevents you from enjoying the view at the top.
You can be right about systems and be completely wrong about humans - your family, your customers. And in the end, the humans are the ones who will affirm and scale your value and impact.
I hope you enjoyed the story.
Enjoy your loved ones and the rest of your day!
And thank you for spending some of it with me.
Warm regards,
Adi