Writing

In 2022, I watched a client CEO distribute a comprehensive strategic analysis—a seven-figure project from a top consulting firm meant to guide a critical board decision at a Chevron-majority-owned joint venture I was advising.

The work looked flawless on paper: hundreds of stakeholder interviews, market intelligence, elegant recommendations, and near-exceptional board readouts. The CEO and I worked around the clock to support the implementation effort. I took the night shift, and he took the early mornings.

But in the following weeks, comments from those closest to the ground exposed a hard truth: The strategy hadn't accounted for storage constraints and logistical problems, conversion economics didn't match real market behavior, and ramp-up assumptions ignored fundamental customer realities. Each observation revealed the growing gap between strategic theory and operational truth.

I saw the same pattern again during expansion financing planning with a leading investment bank—another seven-figure engagement. The presentation was polished, but we struggled to execute it. Round-the-clock effort couldn't overcome board tension, capital overhang, go-to-market pain in the end markets, and internal alignment issues.

Over the last thirteen years, I've worked with many publicly traded and private companies at moments when strategy on paper connects with reality. Particularly on a smaller scale, mindset and human determination matter as much as great ideas. I've found that most companies fail at big inflection points because they don't connect the right conceptual frameworks with the human aspects that truly determine results. The academic literature supports that most major strategy and transformation initiatives fail to gain traction.

You see that in the acquisition that looked strategic in the boardroom but became a culture war in the hallways. In the succession plan that preserved the legacy so carefully, it strangled growth. In the pricing strategy that worked for fifteen years, until suddenly it didn't. By the time you recognize you're heading toward an inflection point, you're already deep in it, and the forces pulling at the business—and at you—have become very real.

I founded Ordiant in February 2017. I'm still here almost nine years later, and I've watched many companies navigate these moments. Some emerged stronger. Others didn't survive their choices. The difference rarely came down to intelligence or capital. It came down to quickly assessing the situation, engaging in honest dialogue that removed ego about how the business had gotten to that point, and maintaining rigorous focus that narrows management's efforts to the handful of significant drivers that will ultimately count.

Why I'm finally writing about this
I've always preferred client work to marketing. As the son of two journalists, perhaps I felt the "real" work happened behind closed doors—helping companies change strategy, navigate M&A, restructure capital structures, implement new management systems, and overcome complex situations. That work sits behind NDAs, and even if it didn't, it's so specific and technical that it wouldn't appeal to a broader audience. Plus, I needed more time and pattern recognition before I had anything worth saying.

Another explanation is more straightforward: Marketing intimidated me. Helping clients navigate fractured boards and hostile lenders seemed more straightforward than figuring out how to share what I'd learned. Broken covenants feel like a creative exercise, while “inbound marketing” has felt like attempting to master a difficult art.

Yet, driving through the ocher hills of California after getting married recently, my wife, Brooke, asked what I'd learned that might be useful to a broader audience. She wasn't asking about frameworks or theory, but about lived experience—what worked, what hadn't, the moments when smart people made decisions that looked obvious in hindsight but were anything but clear at the time.

That conversation led to this.

What this series covers
A qualifier: I recently formed an investment platform backed by a long-time client. While many concepts overlap, I'll focus on the advisory business and navigating "Big Tough Inflection Points."

Inflection used to sound like an investment banking term. Something you'd place next to a chart showing profits escalating up and to the right after sustained losses. Perhaps starting my career covering primarily small-cap public companies showed me the gap between marketing and reality. Despite all the AI hype, predicting business outcomes remains pretty tough.

But I've relaxed on the cliché. I now associate inflection with breaking down old heuristics that no longer serve a business well. That's the most challenging part—the starting moment—because concepts represent the beginning of momentum rather than facts and data. You have to suspend disbelief to expand your mind about possibilities. Entering the unknown brings out both good and challenging tension in teams. Then, you need to do that with a group of leaders who often have histories and very different views and experiences.

In other words, inflections begin with leadership accepting that starting with a blank canvas is crucial and that first principles thinking, where you must let go of past experience as your primary guide, becomes more critical. For most companies, that usually requires enough operational, organizational, or competitive positioning issues to blunt egos and open minds to fresh thinking. A small number of companies disrupt themselves, but that's rare. I've found that it usually involves founders with a high degree of control who truly act as owners, agitating for continual improvement, or activist shareholders doing the same.

Navigating inflection challenges the whole company. These exceptionally messy human affairs combine rigorous analysis with internal politics. Moreover, I don't believe the folks involved—particularly those orchestrating transformation—write openly about the stress and strain. The reality remains that humans run organizations while serving customers and stakeholders who are also human—complex creatures with mixed emotions that a financial model, banking process, slide deck, or AI prompt won't fully capture.

Inflections cover strategy (both organic and inorganic) and all the supporting levers: Organization, operations, finance, governance, and the human aspects of business. Companies usually perform them with a healthy degree of misalignment and internal factions holding different views of reality.

This series will not be academic or formulaic. It is my attempt to share what I've observed, imperfectly and incompletely.

What I may cover, but I tend to follow my interest, so I’m sure this will evolve a lot:

Foundation
The Gravity of Inflections – The unseen forces that decide outcomes.
The Soul of Strategy During Inflections – Finding a more profound sense of organizational purpose when it's all hands on deck.

M&A & Integration
M&A Illusions – Overcoming the overwhelming odds in M&A.
The Integration Window – Decisions that determine the outcome.
Cultural Breakpoints – The human part.
Year Two: When the Deal Underperforms – Repowering the strategy.

Leadership & Governance
Succession – The most emotionally complex inflection point I see.
When the Board Fractures – What happens when governance becomes the problem?
When the Owner Becomes the Constraint – When founder involvement shifts from asset to liability.

Financial & Capital
The Liquidity Trap – Remaining strategic under pressure.
Root Causes – Triaging root cause during pressure.
From Pressure to Distress – Recognizing a turnaround.
Pressure and Lenders – How lender relationships change under pressure.
When to Bring in Outside Capital – Timing matters more than structure.
When to Take Chips Off the Table – The exit decision.

Organization & Operations
When the Org Chart Is the Problem – Org development as the bridge from strategy to execution.
The Hidden Cost of Speed – Thinking fast and slow during inflections.
Customer Concentration Risk – Navigating asymmetric power.

Strategic Positioning
Moat Mechanics – Developing the moat.
Pricing Power as Strategy – How pricing creates both traction and control.
Triaging an Eroding Market Position – When it’s more than just better execution.

The Tension Points
Investor vs. Operator Mindset – The tension between building value and monetizing it.
What Advisors Get Wrong – What works and what makes things worse.

Synthesis
A Framework for Inflection Mastery – This is not a playbook but a way to think about these moments.
Postscript – Finding leverage and meaning beyond the inflection.

If you're in the middle of one of these inflections or three months into a whole company challenge that seemed straightforward but has gotten complicated in unexpected ways, this series is for you.

Many thanks to my wife, Brooke, who has been incredibly supportive and loving during the entrepreneurial journey; my parents, who always supported aspirational pursuits through persistence; and my clients, who have been an exceptional group of people to be affiliated with and who taught me everything that follows.