From Senior VP to 10% of His Income: William B. Henry on Risk, Failure & Entrepreneurship
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What if the thing everyone else calls failure is actually the beginning of the life you were supposed to build?
In Episode 4 of The Founder’s Backroom, William B. Henry challenges the way entrepreneurs think about failure, security, consulting, and taking the leap into business ownership.
After leaving a senior executive role, William experienced the kind of transition many people would immediately label a failure—earning only a fraction of what he had made the year before.
But his question is simple:
Was it actually failure?
In this conversation, William breaks down why entrepreneurship often requires redefining success, letting go of the security of a steady paycheck, and accepting that the “perfect plan” you are waiting for probably does not exist.
He also shares a different philosophy on consulting.
Instead of creating clients who constantly depend on the consultant, his goal is to teach people how to solve the problem themselves:
“I want to teach you how to build a watch and walk away.”
This episode gets into:
Why failure is often defined too narrowly.
The psychological pull of a predictable paycheck.
Why waiting until you feel completely ready can keep you stuck.
The danger of overplanning in a world that keeps changing.
Why good consultants should build capability, not dependency.
And what it really means to take the entrepreneurial jump before everything feels certain.
Because the reality is, the moment your perfect plan is finished, something has probably already changed.
Sometimes progress starts when you stop waiting for certainty and start moving.
