October 24, 2025
Story [#66]

The lessons you’ll never hear from winners

Or minute of silence for the stories that never returned home

We are wired to celebrate those who “made it.”

The founders who scaled. The companies that sold. The people who survived the storms.

We study their stories, copy their tactics, and try to reverse-engineer their luck.

But here’s the brutal truth: most of the knowledge you need isn’t in their stories at all.

It’s hidden in the wreckage of those who didn’t make it back.

That’s what the statistician Abraham Wald realized during World War II.

The military studied planes that returned from missions, analyzing bullet holes to see where armor was needed.

The plan was simple: reinforce the areas with the most damage.

But Wald saw the mistake.

“These are the planes that survived,” he said. “The real weakness is where you see no holes at all. Because that’s where the planes got hit and never came back.”

That insight changed military strategy.

And it should change how you think about business.

My Own Blind Spots

When I look back, the biggest risks weren’t where I thought they were.

I worried about competitors.

About losing clients to cheaper offers.

About missing the latest marketing trend.

But the things that almost killed my business were quieter.

  • One client making up 30% of revenue.
  • A single bank account that froze overnight.
  • A key employee walking away with critical knowledge.

None of those show up in the shiny case studies.

You don’t read about them in Forbes.

Because those who didn’t survive aren’t there to tell their story.

I learned it the hard way. Through fear, panic, and a pile of sleeping pills.

And every time I came out alive, I realized I had been looking at the bullet holes on the wrong side of the plane.

Survivorship Bias in Business

Founders fall for this every day.

We copy what’s visible: the success stories, the growth hacks, the big “wins.”

We armor the wrong parts of the plane:

  • More headcount instead of process.
  • More hustle instead of clarity.
  • More “visibility” instead of resilience.

And then one quiet crisis—one client walking, one account frozen, one illness that takes you out for a month—shows where you were truly exposed.

If you only study those who “made it,” you’ll miss the reasons so many others didn’t.

The Founder I Needed

If I could go back, I’d tell my younger self:

Don’t just chase what others show you. Look for the blind spots.

Study the silence, the missing data, the founders who burned out and never posted their victory threads.

Because that’s where the real lessons are.

Practical Section:

Founder’s Risk Management Framework

Survivorship bias blinds you to the real dangers. Risk management makes them visible and survivable.

Here’s a structured way to approach it:

1. Identify the categories of risk

Most founders only think of “money” or “clients.” But risk hides in multiple layers. Map them clearly:

  • Financial risks: cashflow gaps, frozen accounts, client concentration.
  • Operational risks: single points of failure, undocumented processes, tool dependencies.
  • People risks: key-person dependency, unaligned culture, poor succession planning.
  • Market risks: new competitors, regulation, demand shifts.
  • Founder risks: burnout, illness, decision fatigue, personal crises.

2. Assess likelihood & impact (The Risk Matrix)

Draw a simple 2×2 grid:

  • Likelihood: Low vs. High
  • Impact: Low vs. High

Focus 80% of your energy on High Impact + High Likelihood.

For example:

  • Losing your biggest client (high/high).
  • An intern quitting (low impact).

3. Build mitigation strategies

For each “critical” risk, design a preventive buffer and a reactive backup:

  • Diversification: no single client >15% revenue; at least two banking partners.
  • Redundancy: cross-train staff; have a backup payroll system; shadow key processes.
  • Documentation: SOPs, knowledge base, contracts — reduce dependency on memory.
  • Insurance & legal: liability coverage, IP protection, solid contracts.
  • Founder protocols: health, calendar architecture, decision ladders.

4. Escalation ladder

Every crisis needs a clear chain of response. Define:

  • Who acts first (by role, not name).
  • What’s their scope (budget authority, timeframes).
  • When to escalate (trigger thresholds).
  • Who to escalate to (next level, response SLA).

This prevents paralysis when things go wrong.

5. Crisis simulation (quarterly)

Pick one scenario and run it as a tabletop exercise with your team:

  • Client worth 30% leaves tomorrow.
  • Your primary bank account is frozen.
  • Your top engineer quits with two weeks’ notice.

Walk through: What breaks? Who does what? What’s the timeline?

Document the answers. Improve the weak spots.

6. Maintain the “Emergency Kit”

Every founder should have a simple folder (digital + hard copy):

  • Emergency contacts (lawyers, bankers, advisors).
  • Backup banking/logins.
  • Crisis playbooks (client communication templates, press responses).
  • Personal well-being plan (who covers you if you’re offline).

7. Review & update regularly

Risks shift as you grow. A 5-person team’s biggest threat is dependency on one client.

A 50-person team’s is misaligned management and cashflow complexity.

Quarterly review:

  • Remove obsolete risks.
  • Add new exposures.
  • Update the matrix and buffers.

Risk management is not paranoia. It’s operational maturity.

It’s the difference between a founder who prays the plane comes back — and a founder who designs it to withstand real fire.

When you ready, that’s what I help with founders in the Ops-On-Demand™ Sprint.

And one more thing.

A quick video I made on the topic. Might be useful.
That’s all for today. See you next week.
- Eugene

Whenever you’re ready, there are 3 ways I can help you:

1.  Reply or DM me — and I’ll help.

That’s where I offer the Ops-On-Demand™ Sprint to founders who are ready to step out of daily chaos.

2. Founder Resources (free)​

My ebook Business Black Box Unpacked, the 5‑Day Ops Setup email course, and mini tools to simplify your operations.
→ Explore Founder Resources​​

3. Private Strategy Call (premium)​

A 60-minute 1:1 session for founders ready to fix operational bottlenecks.
You’ll leave with a clear diagnosis, practical system improvements, and specific ideas for automation, delegation, and simplification.
→ Book a Strategy Call

Join the “most offbeat” Businessletter on entrepreneurship.

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Autjor avatar

Hi, I’m Eugene.

Strategist, operator, and product builder helping founders escape operational chaos and build businesses that work without them.

Over the past 20+ years, I’ve grown an international agency from one-person freelance to a multimillion-dollar business. I’ve led teams, scaled systems, burned out, rebuilt, and learned (the hard way) what it really takes to run a business that doesn’t consume your life.
Today, I work with small business owners and independent founders who’ve outgrown hustle advice and need practical structure.

I help them make sense of complexity, design simple systems, and create the kind of business they actually want to run.

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