The Worst Business Advice I Ever Gave My Wife

Years ago, I gave my wife business advice that made perfect sense.

It was logical.It was strategic.It worked.

And it led her to build a business she didn’t actually want.

In this episode, Ray unpacks what really went wrong — not the strategy, but the lens it came through. The advice was filtered through his definition of success, his bias toward scale, and his belief about how businesses “should” grow.

But her definition of success was different.

If you’re an entrepreneur, operator, or spouse giving business advice inside a relationship, this episode will help you think more clearly about how bias shapes advice — and how defaulting to scale can quietly pull you away from what you actually want.

What You’ll Learn in This Episode:

1. Why good business advice can still be wrong when it’s filtered through someone else’s bias
2. How “you should scale this” often reflects the advisor’s definition of success — not yours
3. The danger of defaulting to growth, hiring, and systematization as the automatic next step
4. Why different people can look at the same opportunity and want completely different outcome
5. How to filter advice from your spouse, mentors, or peers before building something you don’t actually want
6. The discipline required to define success for yourself — especially when external indicators say “go bigger”

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This podcast is where Ray thinks through hard decisions — especially when the usual playbooks stop working.

If that approach resonates, that’s what you’ll find more of here.

New to the show? The “Start Here” playlist outlines what the podcast is about and how to approach it: https://player.captivate.fm/collection/a7577a6f-15da-4521-b214-35e4e47f320b