Reflections on a bad deal

I wrote the following as a part of my process dealing with the recent loss of our business. Thought it might be helpful for others. Enjoy… :/
Lately, I’ve been introspective, grappling with what happens when a plan 4 years in the making simply doesn’t deliver. The eventual collapse of the venture was a stark lesson in this reality. The Company that seemed like a sure bet was on life support starting about 2 years ago, and unrelenting headwinds forced me into a cycle of constant recalibration—moving from Plan A to Plan A.1, A.2, and so on until we flat out ran out of options. It was a stark reminder of my time as a Coastie, where a routine rescue mission could swiftly devolve into a scramble to maintain control. I repeatedly had to shift gears, scrambling to keep the mission on track even when everything seemed to be spiraling.
Many rare and terrible things happened during our time in the seat, some of our own making and several that weren't. Ultimately, the things that killed us were headwinds and being over-leveraged. As costs rose and gross revenues disappeared overnight, the debt's weight became overwhelming. We fought for almost two years after our apocalyptic moment, running on cash fumes until shutting down the business became the only viable option. It was a tough decision, marked by the stark realization that sometimes, no amount of pivoting can compensate for being financially stretched too thin. This experience taught me the brutal reality of over-leverage: it can fuel returns but also be the anchor that pulls you under when market conditions turn against you.
These last few weeks have been more than just a tactical review; they have been about coming to terms with the emotional repercussions of failure. Watching the fund falter wasn’t just a professional setback—it felt deeply personal. The employee layoffs, the impact on my investors, and the weight of my own unmet expectations are heavy. It’s a painfully humbling experience that shakes your confidence and makes you confront the uncomfortable reality of utter failure.
Despite the sting of failure, I’m learning (or attempting to learn) that this is an opportunity to pivot, rethink, and return with a sharper, more resilient approach. I've enjoyed re-reading Teddy Roosevelt's speech, "The Man in the Arena" lately, and put it up in my home office. It’s a powerful reminder that no matter how much work/time/effort you put into Plan A, it's what you do after it crumbles that defines you. I’m still navigating through my new Plan A for this next season (it will probably take a while), but I’m finding my way with a clearer sense of purpose and a deeper appreciation for the hard-won lessons that come when things like these last 4 years don’t go as planned.

I want to thank this community and my investors, it's been a wild road; writing this truly sucks, but at least others can hopefully learn from it.