Justice Notes: Over-Confidence
A White-Collar Journal forum for criminal justice, lived experience, and the personal search for redemption
Editor’s Note:
This week in Justice Notes, I’m featuring an essay by my colleague and fellow member of the White Collar Support Group, Drew Chapin. Drew writes with striking clarity about the slippery slope of overconfidence—how entrepreneurial ambition can drift into hubris, and how that distortion of judgment can lead to serious ethical lapses.
An enterpreneur who served time for his mistakes, Drew now speaks and writes about his experience to help others recognize the warning signs before crossing that invisible line. His message is not only about business but about human nature—the ways we rationalize, justify, and deceive ourselves when confidence turns into conviction.
The Dangers of Over-Confidence
by Drew Chapin
My biggest mistake wasn’t failing. It was thinking I couldn’t.
Founder confidence is incredibly powerful.
It’s what powers irrational ideas, napkin-stage concepts, and “this shouldn’t work” bets that sometimes do. That confidence—and our romanticized vision of entrepreneurship—is what gets investor checks written and teams assembled.
But left unchecked? Confidence can calcify and harden into hubris.
That’s when founders stop listening, stop testing assumptions, start believing their own mythos—and that’s when things become seriously dangerous.
I would know. I crossed that line in the operation of my adtech startup.
The Rise
In 2014, I launched an adtech startup that I believed would reinvent e-commerce. Despite having little experience in either adtech or e-commerce, I believed our fresh eyes would sweep aside multi-billion-dollar incumbents and rewrite the rules.
I received validation in the form of winning pitch competitions, nodding journalists, and investor interest. I’d attend networking events, show people our app, and believe them when they told me it was “cool.”
(Spoiler alert: it wasn’t that cool.)
But I was hearing what I wanted to hear. I quickly decoupled from the anchors of honest reflection and probabilistic thinking.
I stopped asking the pesky questions that would kill my buzz, like:
Are people actually using the app?
Are they finding value in it?
Are those KPIs really the key performance indicators—or just the ones that look best?
I saw red flags and explained them away as “early-stage volatility.”
I treated legitimate doubts from teammates as a lack of vision.
I dismissed uncomfortable data.
With the benefit of hindsight, it was delusion, hubris, and textbook overconfidence.
The Return
That’s why returning to the Bay Area to give my talk at the Haas School of Business felt entirely natural.
Being back where startup culture runs hottest—where the future leaders of Silicon Valley are being schooled in the art of “believe big”—placed me squarely inside the same ecosystem where I once wandered unanchored.
I had the privilege of spending time in a class led by Don A. Moore, a leading researcher on overconfidence, forecasting, and decision-making, and the author of two terrific books: Perfectly Confident and Decision Leadership.
What I Shared with Students at Berkeley’s Haas School of Business
After sharing the story of my failed startup, I highlighted a few key lessons:
1. “Everybody does this” obliterated my objectivity.
The most dangerous belief I held was that my behavior was normal.
I never asked, What’s right? Instead, I asked, What’s acceptable?
That mindset moved me away from objective truth and led to an outcome that was plainly incorrect. I didn’t see where I crossed the line—because I convinced myself there wasn’t one.
2. The myth is useful, but the myth must be tested.
Every startup story requires a little boldness. But you also need people in your corner who will challenge that boldness. You want—need—mentors who aren’t afraid to “spoil the vibe” and are willing to ask hard questions.
3. Complete a premortem, and keep it nearby.
One of Dr. Moore’s most useful insights is to imagine why your venture might fail, and work backward. It’s a tool that protects you from your future self.
If I’d taken that step early on—and revisited it regularly—I believe I would have maintained greater objectivity about how the company was truly performing.
For more about this subject from Drew “The Patterns of Startup Failure” click here: https://chapin.io/patterns-of-startup-failure/
Drew Chapin is a writer, speaker, and advocate for ethical leadership. After serving time for a white-collar offense, he now works to help founders, executives, and investors recognize the warning signs of overconfidence before they cross the line.
If you’re drawn to the idea of storytelling as self-reckoning, I’d love to hear your thoughts in the comments.
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