Last week, I elevated a partner of 20 years, Derek, someone who joined us as an intern before WatchMojo had even published its first video – to the role of COO. Another co-founder, Kevin, was promoted to SVP, having been with us since day one, alongside my spouse and co-founder Christine. Earlier this year, another foundational teammate, Raphael, stepped away after two decades, and to the team’s credit, we had the depth, trust, and continuity to step up and deliver one of our strongest years yet. How does an organization pull that in the face of all of the risks, uncertainties & threats? Culture. Which boils down to communications, relationships, feedback loops…

In 2012, when I was $1M in the hole and buried in personal debt to keep WatchMojo afloat, I wrote a TechCrunch piece on the Top 10 Greatest U.S. Digital Media M&A Deals of All Time. At the time, my advisor and first investment banker, Jim Conley, told me that Peter Horan, former CEO of About.com and Ask.com and a participant in two of those transactions, had shared it. Given where we were then, that alone felt like a win (I was running out of ways to “fail”).

I met Peter later that year in Manhattan. We stayed in touch, and over time he became an informal advisor. A recurring motif in our conversations was something investors and corporate development executives would often ask him: “Is Ash coachable?”

To me, an eternal student who built WatchMojo on feedback from all, it was a silly question, but understandable given the “myth of the entrepreneur.” A decade later, Peter introduced me to our current private equity partner and now serves as the independent director on our board – having seen me under-promise and over-deliver throughout the 2010s.

Coachability, in its simplest form, means that when someone wants to give you feedback, it isn’t a painful process. I’ve always considered myself a sponge, a perennial student. I built WatchMojo initially on instinct, but scaled it through feedback, data, and systems: viewer comments (I moonlit as Mr X in the comments section for years), analytics, our suggestion tools, and constant iteration.

I try to distill the signal from the noise, and then, much like WatchMojo’s curated lists, share what matters most to help the team execute. Not all feedback is correct, but even glib or poorly framed comments often contain a nugget of truth if you’re willing to listen.

The same applies internally. Feedback is essential, but how and when it’s delivered often matters more than what is said. After more than 20 years in business, I’ve gone from writing about the future to being measured against past performance. Yet despite being generally right about where the puck was heading, my nature hasn’t changed. If anything, one reason I write publicly is to invite scrutiny, challenge, and dissection of my hypotheses.

With experience and success comes a new dynamic: more established individuals begin seeking your advice. My framework there is constructive. It’s about helping people understand the motivations behind their impulses, emotions, and decisions, so they can better achieve what they want, regardless of how accomplished they already are.

Recently, while seeking perspective, I encountered a response that went something like this: we did everything right, we went deep, the process was sound, the outcome was final, and there is nothing we would change.

That position is not unreasonable. In many institutional or multi-generational contexts, it is entirely rational. When your role is preservation of capital, relationships, and legacy, knowing when to stop can be a form of discipline. Closure is often framed as wisdom.

But it is also, by definition, not coachable.

When outcomes fall short, the risk is viewing failure as the result of others not bending to your wishes. The real world, of course, doesn’t work that way. If I’ve been effective as a founder, leader, or teacher, it’s largely because empathy requires genuinely seeing problems from other people’s perspectives.

Coachability doesn’t mean assuming others were wrong or that you were right. It means leaving open the possibility that even a sound process might be revisited under different conditions, with new tools, new structures, or a longer time horizon. It means being willing to operate in the space between improbable and impossible, not because success is guaranteed, but because exploration itself has value.

There’s a meaningful difference between saying “we did everything right” and saying “given what we knew then, this was the best path, but the environment may one day change.” One closes the loop. The other keeps it open.

This isn’t a critique of experience or success. It’s an observation about orientation. Second- and third-generation stewards are often optimized for preservation and continuity. They’re acutely aware of the old adage about going from shirtsleeves to shirtsleeves in three generations.

First-generation entrepreneurs are wired differently. We’re shaped by operating without a safety net, iterating in public, being wrong repeatedly, and being fueled, not discouraged, by doubt.

In my own work, I’ve learned that the most dangerous sentence isn’t “this is hard,” but “there is nothing I would change.” The moment you stop inviting feedback, you stop learning. And when learning stops, the outcome may be settled, but the opportunity hasn’t been fully explored.

Praise is pleasant, but improvement comes through critique. Ideally that critique is constructive, diplomatic, and clear. But even when it isn’t, there’s still something to learn.

Context matters. Timing matters. And above all, mindset matters.

Coachability isn’t about disrespecting the past. It’s about refusing to let past conclusions become permanent ceilings.

When I reflect on what I’m most proud of at WatchMojo, it’s not just watch time or financial performance. It’s retention, trust, and job satisfaction (2021, 2023, 2025 employee surveys). Herb Kelleher famously put employees first. Peter Drucker observed that culture eats strategy for breakfast.

When listening to coaches, or when you become one yourself, the goal isn’t to be right. It’s to build the systems and surround yourself with the people who ensure the organization continues to progress and grow.