Most business owners are making decisions every day but how many of those decisions are actually built to last? Dawn K. Kennedy, author of Before You Decide: The Field Manual for Durable Decisions Under Pressure, joins me on the Interview Connections podcast to talk about why so many businesses fail not because of a bad idea, but because of how decisions get made (or avoided) along the way.

Dawn brings a uniquely grounded perspective to this conversation. She's a business law attorney, a former Army Capabilities Developer and Fortune 500 Intelligence Analyst, and the co-owner of a family coffee roastery, giving her real skin in the game across both service-based and product-based businesses. Her book is not a fluffy entrepreneur read. It's a field manual, and it shows.

In this episode, we cover:

  • Why the 50% business failure rate at five years hasn't moved since the 1980s and what's actually behind it
  • The difference between micro-decisions you make on autopilot and high-stakes decisions that require deliberate thought
  • How our hardwiring for certainty pushes us to make decisions before we're ready
  • Why "move fast, break things" works for VC-funded startups but can quietly destroy a small business
  • The pendulum problem: how market shifts catch business owners off guard, and what to do when the strategy that was working stops working
  • Why second and third-time business owners succeed at much higher rates and what first-timers can learn from that
  • The real cost of "bootstrapping" that nobody talks about
  • Why we pick the decision that relieves pressure instead of the one that keeps us moving forward


Resources mentioned:

Before You Decide: The Field Manual for Durable Decisions Under Pressure by Dawn K. Kennedy — available on Amazon now.

Unreasonable Hospitality by Will Guidara — recommended by Dawn as a companion read on staying true to your original purpose as a business evolves.

Free resources and guidebooks available at DawnKKennedy.com.

Want to make smarter decisions about how you're growing your business through podcasting? Join me at the free Podcast Guesting Masterclass, where I walk you through exactly how coaches and thought leaders use podcast guesting to build authority, reach new audiences, and attract clients. Register here: interviewconnections.com/masterclass-2026

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