Lessons From the Other Side: What Three Years of Building Taught Me That Twenty Years in Corporate America Couldn't
- May 18
- 8 min read
Updated: May 20
I spent more than two decades at one of the largest and most influential consulting firms in the world, working with some of the leading global organizations on their most complex company lifecycle events — IPO readiness, multi-billion dollar transactions, cross-border transformations, system implementations. I understood how markets work, how deals get done, and how organizations make decisions under pressure.
Or so I thought.
A few years ago I stepped outside that world and built something from scratch. Three years, multiple business model iterations, sustained effort across every channel available to me — and an education in what simply cannot be learned from inside an institution, no matter how good that institution is or how senior you become within it.
What follows is a set of observations grounded in that experience. Not a playbook. Not a framework. Just some perspective on things that surprised me — and that may be relevant to how many of you are leading, investing, and building teams right now.
1.- Product-Market Fit Is Not a Slide Deck Moment
In boardrooms and investment committees, product-market fit gets discussed as though it is a destination you reach — a box you check, a milestone you hit, a slide that says "validated." Having now lived the actual process of finding it, testing it, losing it, and finding it again across multiple iterations, I can tell you: that framing doesn't do it justice. It is one of the hardest things to do in practice, and one of the most consistently underestimated by people who haven't done it themselves.
Product-market fit is not a moment. It is a continuous, iterative process of hypothesis, test, honest interpretation, and adjustment — uncomfortable by design, because every iteration requires admitting that something you believed was wrong, or incomplete, or right for the wrong reasons. And that admission has to happen in real time, under financial pressure, without the luxury of a planning cycle.
What my experience specifically taught me is that timing is often the dominant variable, not positioning. In the market I was operating in, you can have the right offering, the right team, the right credibility, and the right relationships, and still not convert — because your market buys at the moment of acute need, not because the offering is compelling in the abstract. The infrastructure that large, established firms have — embedded client relationships, ongoing work that keeps them in the room, brand pull that generates inbound demand — solves the timing problem in ways that maybe invisible from the inside. You only fully appreciate what that infrastructure does when you're operating without any of it.
That dynamic plays out differently in every market. But the underlying question is the same regardless of context: are you measuring urgency, or are you measuring interest? A strong pipeline of engaged conversations, warm introductions, and positive feedback is not product-market fit. It is evidence that people find the offering relevant. Conversion under real conditions — with real urgency, real budget, and real decision-making authority — is fit. The gap between those two things is where most assumptions break and most capital gets misallocated. The iteration required to close that gap is harder, slower, and more humbling than almost any slide deck ever captures.
2.- Building Outside Institutions Develops Capabilities That Safety Nets Cannot
This section is not about failure. It is about what gets built in you when you operate without a safety net — and what doesn't get built when one is always there.
Traditional corporate careers are structured, by design, to minimize exposure to uncontrolled consequence. You operate within institutional frameworks, with established processes, brand support, and risk management systems built up over decades. There are operating plans to achieve, performance reviews to navigate, and structures that catch most mistakes before they become crises. That is genuinely valuable — and it also means that certain capabilities never get tested, because the conditions that develop them never fully arrive.
Building something from scratch removes all of that. Every decision is yours. Every miscalculation costs real time and real capital. The market gives you feedback that is direct in a way that internal processes rarely are. And the emotional experience of continuing to move forward when outcomes are uncertain, when efforts don't convert, and when there is no institution absorbing the downside — that experience builds something that I am not sure can be fully developed any other way.
Resilience is the obvious word, but it understates what actually happens. It is more specific than that. You develop the ability to separate your identity from your results — to process a setback as information rather than verdict. You develop genuine comfort with ambiguity, not as a personality trait but as an operational capability. You develop self-knowledge about how you actually make decisions under pressure, which turns out to be quite different from how you make them when the stakes are managed. And you develop the habit of honest self-assessment, because in the absence of institutional feedback structures, self-deception becomes immediately expensive.
The organizational implication is worth sitting with: institutions, by design, insulate their people from the conditions that build these capabilities. Performance management systems, approval processes, risk frameworks — all necessary, and all quietly preventing certain kinds of development. The leaders who have genuinely built resilience and adaptability as operational skills, rather than just as talking points, are increasingly distinguishable from the ones who haven't. And as environments become less predictable, that distinction matters more.
3.- The Skills That Actually Matter Now Are Not the Ones You've Been Hiring For
The professional profile that succeeds in a stable, institutional environment is different from the profile that succeeds in a rapidly changing one. And the environment has changed — faster, and more fundamentally, than most hiring practices have caught up with.
AI is not coming for your organization. It is already inside it — and the leaders who treat it as a peripheral tool rather than a core capability are making a mistake that compounds quietly until it becomes visible all at once. But here is where the risk for senior leaders is specific and underappreciated: the leaders who get the most from AI are not the ones who delegate it downward and wait for output. They are the ones who get into the weeds themselves — who experiment, who understand how the tools actually work, who can tell the difference between genuinely useful output and plausible-sounding nonsense.
I built Kebla largely alone. What would have required a team of ten to fifteen junior professionals a few years ago, I was able to build and operate solo — because I was willing to go deep with AI, integrate it into every workflow, and leverage it thoroughly — while verifying carefully — with real work rather than using it only for surface-level tasks. That experience permanently changed how I think about leverage, efficiency, and what a lean capable team actually looks like.
Leaders who haven't touched the actual work in years are operating on a mental model of how things get done that may no longer match reality. AI is accelerating that divergence. The tools are changing what is possible, what takes how long, what requires human judgment and what doesn't — and if you're not periodically going deep enough to see that firsthand, your strategic assumptions are drifting away from ground truth faster than you realize.
This is where seniority and domain experience become an advantage rather than an obstacle — but only if they're combined with genuine engagement at the operational level. A junior person experimenting with AI sees what works within their narrow lane. A senior executive who gets into the weeds brings something entirely different — the ability to see across the whole system, to identify where a 10% efficiency gain in one area creates a 40% gain somewhere else because of how everything connects. That pattern recognition, combined with ground-level experimentation, produces insights that neither a purely strategic executive nor a less experienced operator can generate alone.
The talent implication follows naturally: curiosity over credentials, people who have built things and figured things out without a manual, people genuinely comfortable saying "I don't know yet, but I'll find out." In a rapidly changing environment, the ability to iterate fast and learn honestly is worth more than deep expertise in a world that no longer exists.
4.- Getting Comfortable With What You Cannot Control
The hardest professional adjustment I made over three years of building was accepting that some of the most important variables were entirely outside my control. Market timing. Deal flow. Whether a potential client had an active need at the exact moment I reached them. Whether the broader environment was creating conditions for urgency or suppressing them.
Corporate careers train us — implicitly, constantly — to believe that outcomes are a function of effort and quality. There is an enormous emphasis on planning and achieving the plan. Work hard enough, do good enough work, execute the strategy well enough, and results will follow. That belief is functional inside institutions where most variables are managed and most risks are bounded. Outside them, when the environment itself is the variable, it needs real recalibration.
The trap — and it is a specific, recognizable trap — is responding to uncontrollable variables by doing more of the same thing harder. More outreach. More calls. More iterations of the same approach. Corporate training produces exactly this response, because inside institutions, sustained effort usually does eventually move outcomes. Outside them, in markets driven by timing and urgency, it can produce a lot of activity that looks like momentum but isn't. Recognizing that distinction in real time, under pressure, when stopping feels like giving up, is genuinely difficult.
What this has required is developing a clear internal framework for separating what I can influence from what I have to wait for. Not as passive acceptance of circumstances, but as an active discipline. Keep doing the things that build positioning and relationships. Stop doing the things that create activity without real progress. Stay anchored to a clear north star. And build the patience to act decisively on what you can influence without losing momentum or conviction on what you cannot.
The variables that cannot be controlled are multiplying for everyone in this room. Geopolitical disruption. AI-driven market shifts. Interest rate environments that move independently of strategy. Regulatory changes that outpace planning cycles. The leaders who navigate this period most effectively are probably not the ones who try hardest to predict and control — they are the ones who have built the internal discipline to move decisively on what they can influence, and stay disciplined about what they cannot. Knowing the difference, in real time, under pressure, is the work.
A Final Thought
Twenty years in corporate America gave me deep technical expertise, relationships built over decades, and genuine impact on organizations navigating their most critical moments — a front-row seat to how large, complex operations actually work, and pattern recognition I draw on every day. The business models, the cultures, the decision-making dynamics, the moments where strategy meets reality. That is a wealth of experience that cannot be replicated quickly, and I do not take any of it for granted.
But three years of building from scratch taught me things that two more decades inside an institution never would have. What product-market fit actually costs. What gets built in you — and what doesn't — when there is no safety net. What it means to operate when the mental model you've been using no longer matches reality. And what genuine accountability feels like when there is no organization absorbing the downside.
The world may not be going back to the environment that made conventional wisdom conventional. The leaders who thrive in what comes next are likely the ones who stay curious, keep iterating, get comfortable with uncertainty, and build teams wired for a world that doesn't stand still.
That is the work. And it is more interesting than it has ever been.
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The information provided on this blog is for general informational purposes only and should not be construed as professional advice. Please consult a qualified professional before making any decisions based on this information.