Talk: "Failed to Fail" at Drexel's Close School of Entrepreneurship

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 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 attempt to literally 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.

Key Takeaways

• There's a fine line between optimism and dangerous self-talk. Startup culture celebrates and honors relentless optimism - but that becomes dangerous when it blinds you to reality. I believed I was demonstrating perseverance but reality is I was ignoring the market and had crossed the line into delusion.
• It's easy to justify cutting corners as "just this once," or "everyone is doing this." My rationalizations, compounded by stress and tunnel vision, led me to cross ethical lines I never thought I would. Ethical fading doesn't happen overnight: it's a gradual process that can have devastating consequences.
• Startups move fast and break things - that should not include basic governance and due diligence. The failure of Benja is a cautionary tale about what happens when founders sidestep accountability structures and ignore red flags. Clear and strong governance is not just for big companies - it's essential at every stage to protect both the business and its people.

I greatly appreciated the opportunity to share with the next generation of entrepreneurs at Drexel, and know the Q&A could have continued all day - much to unpack on founder psychology, systemic pressures, ethical fading, and the VC culture that prioritizes moonshots over real business.

Next time.