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Smooth sailing is a myth—real business is built in headwinds.

In this episode, we get practical about what actually breaks companies (and how we fix it). We start where most founders stumble: the “unknown unknowns.” Frozen cash, stalled deals, and messy hiring aren’t flukes—they’re normal. So we pull apart the moments where plans fail, decisions stall, and people problems masquerade as process problems.

We talk action over theory. Books and YouTube help, but nothing replaces getting in the arena. That’s why we use the 40/70 rule: less than 40% info is guessing; waiting for 100% is paralysis. At 70%, we move—then let feedback sharpen us.

From there, we build what actually scales: playbooks, clear ownership, and simple guardrails. Not corporate fluff—step-by-step systems anyone can run at 10 p.m. on a Friday. We get into culture that’s both human and high-standard, accountability without ego, and the “vacation test”: can the business run the same (or better) with us gone for three months?

This is straight talk for owners who want freedom, not just a fuller to-do list.

📌 Key Topics:
✅ The myth of smooth sailing—and why chaos is normal
✅ “Unknown unknowns” and making decisions with imperfect info (40/70 rule)
✅ Action > theory: learning by doing without burning the house down
✅ Building playbooks: turning emergencies into repeatable steps
✅ People vs. process: how to diagnose the real issue fast
✅ Ownership of results (not tasks) and tiered decision authority
✅ Culture with a spine: standards, empathy, and clear expectations
✅ The vacation test: designing a business that runs without us

If you want more freedom, start here: document one messy task today, hand it off tomorrow, then measure what breaks—and fix that next.

Chapters:

00:00 The Illusion of Smooth Sailing in Business

05:01 Navigating Unknown Unknowns

09:49 The Importance of Action and Experience

15:03 Building Systems and Processes

19:59 Managing People and Expectations

25:04 Creating a Culture of Accountability

29:56 The Role of Systems in Business Success