“Before success comes in any person's life, he is sure to meet with much temporary defeat, and, perhaps, some failure. When defeat overtakes a person, the easiest and most logical thing to do is to quit. That is exactly what the majority of people do.”
Oliver Napoleon Hill
Harvard Business School invited me to speak in their Why Start-ups Fail course.
The subject of this class was a once high-flying ice cream company where I had been part of the executive team. The spectacular failure of the business meant the company—and all our mistakes—had become the subject of an HBS case study.
This was the first time I was speaking publicly about my experience with the company, having been connected with the professor who teaches the course (and wrote the case study) a number of months earlier.
For so long, I carried a significant amount of guilt and shame about the outcome. I had believed that I was to blame—that all the investors I had represented, introduced to the company, and who had invested alongside me, blamed me for what happened.
Over time, through reflection and dark moments, I realized this: the fears we amplify in our minds are rarely the reality
That’s not to say people weren’t annoyed, angry, or disappointed—they definitely were. I was too.
People lost money. A lot of money.
But the perceptions of who, why, what, and how things went wrong varied greatly.
Most importantly, I discovered something unexpected: The majority of people were realistic about how hard it is to build a company, to succeed. They understood the risks. They knew what they were getting into when they invested.
Ironically, I had accounted for the financial risks when I invested my own money.
What I hadn’t accounted for was the personal cost of failure—the toll it would take on me emotionally, professionally, and psychologically. That ‘loss’ came out of a blind spot.
Sitting down to reflect on my time with the company was long overdue. Yet, in true student fashion, despite having four months to prepare, I left everything to the last minute.
The professor explained that after analyzing the case, I’d have time to share my deeper takeaways.
I hadn’t planned to create a formal presentation—just a few notes to guide me.
But my wife insisted otherwise, pushing me to make slides and images to bring it to life. It forced me to confront my limited presentation skills—and in doing so, sharpened my focus on the lessons I had learned.
If there’s one lesson this experience hammered home for me, it’s that business—and life—are never really about the product; they’re about the people.
Who you choose as co-founders, early hires, or partners in any venture will determine your success or failure.
It’s the people who bring your vision to life, execute your strategies, and engage with every aspect of your business. Without the right people in the right roles, even the best ideas can falter.
Ironically, during my very first week at the company, an investor—who had founded and still ran a multi-billion-dollar salad bar chain—offered this advice:
“No matter what business you think you are in - be it fancy salads, accessible eye-glasses, sustainable sneakers, or gourmet ice cream - you are actually in the people business.”
That insight felt profound, though I only truly appreciated its weight after everything had gone wrong.
As an investor and a coach, I've seen organizations with mediocre strategies but exceptional people succeed, while brilliant strategies executed by misaligned teams inevitably falter.
No matter the industry, success is about people. Helping leaders realize this has become central to my coaching.
So I told the class: “MAKE SURE YOU HIRE THE RIGHT PEOPLE!”
I wasn’t the right person for the job. So why was I in it?
I had been an angel investor in the company for two years when they began raising their Series A.
While helping the founders in this effort, I realized I knew one of the groups they were negotiating with and offered to assist. Ultimately, I advised them to walk away—I felt the terms were too onerous, and we could do better.
Unintentionally, that moment built trust. I had advised them to reject people I knew personally, reinforcing their confidence in me.
When we successfully raised the round elsewhere, that trust only deepened.
Then, after six fruitless months of searching for a COO—and with pressure mounting—they turned to me:
“Why don’t you be our ‘Chief of Getting Shit Done’?”
Why did I say yes?
I wasn’t looking for a job. But I was wrapping up my Executive MBA, grappling with doubts about whether my four-year stint as an angel investor had been a mistake. My first investment had been a rocket ship; everything since had felt slower, murkier.
This role fit neatly into the story I wanted to tell myself:
And let’s be honest—this was a high-profile consumer brand in a hot market, backed by marquee NYC VCs.
My ego said YES. My fear agreed.
With our third child on the way, I felt the weight of needing something ‘more stable.’
So I took the role.
Looking back, I can see the red flags I chose to ignore:
A six-month COO search yielding nothing—why were candidates walking away?
Founders desperate to ‘just get moving’—what were they trying to bypass?
Operational issues that experienced executives likely spotted—and I missed.
I also failed to question why the role felt so compelling to me at that moment.
When we construct a perfect narrative that justifies what we already want to do, it’s worth pausing.
My eagerness to validate my MBA, my fear of financial uncertainty, my craving for external success—these clouded my judgment. I saw only the reasons to say yes, ignoring the ones that screamed no.
Today, when coaching executives, I ask:
“Why are you so drawn to this opportunity right now? What might you be missing because of that attraction?”
Sometimes, the real question isn’t “Is this a good opportunity?”
It’s “What does this opportunity reveal about me?”
At first, I didn’t realize how out of my depth I was. Then, all at once, it became impossible to ignore.
The factory, set to open weeks into my tenure, launched nearly a year late.
The CFO resigned—at the end of my first week.
New packaging, meant to streamline production, caused delays instead.
Key employees resisted the aggressive expansion, unwilling—or unable—to adapt.
Throughout two funding rounds, investors repeatedly challenged the company’s operations and strategy. Each time, we found ways to reassure them.
But the truth? None of us had done the deep diligence required to fully grasp where the company was—or where it was really headed.
Despite bad leases signed long before I joined and the many mistakes I undoubtedly made, in hindsight, none of it truly mattered.
The fatal decision was made long before I arrived:
Jumping from a 1,000-square-foot commissary kitchen to a 15,000-square-foot, state-of-the-art continuous production facility—in one leap.
Blinded by Hollywood supporters, high-profile brand collaborations, and advice from industry icons, we charged ahead, fueled by the expectations of hyper-growth from an ill-suited group of investors. And there I was, in the cockpit.
A talented retail executive we hired in my second year put it best:
“It’s like trying to fix a race car that’s moving at 100 mph.”
The crash was inevitable. We just didn’t see it yet.
It sounds obvious. Because it is.
But for a room full of Harvard MBAs—many of whom had likely known nothing but success—it felt like an important lesson to share.
My biggest mistake? Taking too long to get back in the game.
I see that now. But at the time, I couldn’t.
So how do you avoid delaying your return? Or, better yet, how do you avoid taking the wrong job for the wrong reasons in the first place?
After failure, what you need most isn’t time alone to ‘figure it out’—it's an honest perspective from people who know you well but won’t just tell you what you want to hear.
I told them: Build a Personal Board of Directors.
“A curated group of trusted individuals who provide guidance, challenge your thinking, and help you navigate key decisions.”
Their immediate question? How do you build one?
The answer? With difficulty. But that’s a lesson for another post.
At the end of the class, I could see in the faces of some of the students, the rawness of what I had shared and the vulnerability I had been willing to expose to them had landed.
A number of students stayed back to ask questions, with one saying how rare it was to see such humility and vulnerability - that it felt refreshing and very real.
The most powerful lesson emerged not from what I shared about failure, but from the simple act of sharing it at all.
By going to Harvard as the subject of a case study on failure, I had inadvertently demonstrated its most important lesson: failure is not final unless you make it so.
The ice cream venture melted away, but the insights it yielded have become the foundation of how I now coach, how I parent and how I try to live my life.
So I’ll leave you with the same challenge I left the students with:
Take a hard look at your next big decision.
Where might your biases be blinding you?
Who will challenge your blind spots?
And most importantly, are you willing to admit—before it’s too late—when you’ve already hit the iceberg?
