Talk: "Failed to Fail" at Drexel's Close School of Entrepreneurship
Rather than acknowledging reality, I made an attempt to fake it ‘til you make it. And the consequences were far worse than if I had just faced failure head-on.
I failed to fail.
But I didn’t come to this realization on my own.
I only understood it after hearing the weighty remarks of the judge in United States of America v. yours truly.
She took in everything in front of her, sighed, and said, “It looks like you just didn’t know how to fail.” That moment unlocked something for me—the unvarnished truth about the collapse of my adtech startup.
I never allowed myself to consider that the company wasn’t going to make it.
Instead, I doubled down, convinced that if I just pushed a little harder, we’d break through.
But there’s a fine line between resilience and delusion. I crossed it.
Rather than accepting reality, I made an (insane) attempt to fake it ‘til you make it, and the consequences were far worse than if I had just faced failure head-on.
That was the central thread of my talk at Drexel University’s Charles D. Close School of Entrepreneurship, where I had the opportunity to share the Benja story with students studying entrepreneurship, risk, and due diligence.
We dug into my mistakes, dangerous self-talk, gaps in due diligence, and how organizational governance failures played a role.
And then came the Q&A, which was terrific - thoughtful questions from the next generation of entrepreneurs at Drexel. We could have kept going for hours, expanding on founder psychology, systemic pressures, ethical fading, and the VC culture that prioritizes moonshots over sustainable businesses. Next time.
