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James Wedmore16 June 2020

From Broke Bartender to 10 Million Dollar CEO: A Conversation with James Wedmore

5Frameworks
5Insights

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Frameworks in this episode

Self-Mastery5 steps

Belief-to-Result Audit

Trace unwanted results back through behavior to the beliefs producing them.

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Mindset5 steps

From Fighter to Thriving

Retire the identity that requires adversity and adopt a context of support.

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Mindset4 steps

Get the Result or the Lesson

Remove the failure label and turn every outcome into usable feedback.

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Innovation5 steps

Live in the Question

Use outcome-oriented questions to keep possibilities open until answers emerge.

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Strategy5 steps

The Done-Business Method

Define the finished business, identify its behavior, and operate that way now.

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Insights & moments

The myth-busts, hot takes, explainers, and tools worth keeping.

Hot Take· 2

Hot Take33:33

Success Is No Better at Defining You Than Failure

James argues that rejecting failure as an identity requires also refusing to derive personal worth from success. Money, attention, and achievements do not make someone more complete, valuable, or worthy; tying identity to them merely creates dependence on external evidence.

  • Success and failure are both external outcomes.
  • Achievement does not make a person inherently more valuable.
  • Chasing success to feel worthy cannot create stable self-worth.
  • Worth must be separated from performance in both directions.

“Same goes for your successes, your successes don't define you.”

James Wedmore · 34:12

“Whether you have a hundred failures or a hundred successes, and those external things, don't say anything about you.”

James Wedmore · 34:44
#self-worth#success#identity#achievement
Hot Take59:19

School Teaches Permission-Seeking, Not Entrepreneurial Agency

James contrasts the behavioral conditioning of conventional education with the agency required in entrepreneurship. School commonly rewards asking permission, following instructions, memorizing material, and waiting to advance, while entrepreneurship demands independent judgment under uncertainty.

  • Traditional schooling rewards compliance with established rules.
  • Students repeatedly practice asking permission before acting.
  • Entrepreneurs must decide without waiting for an authority’s approval.
  • Old student habits can persist unnoticed inside business decisions.

“You learned to raise your hand, ask permission, do what you're told memorize, take the test.”

James Wedmore · 59:30

“permission to go to the bathroom permission to ask questions, permission to graduate.”

James Wedmore · 59:37
#education#entrepreneurship#agency#decision-making

Explainer· 1

Explainer14:27

Coachability Is Not Being Compliant—It Is Releasing Bad Models

James defines coachability as a willingness to stop defending a model of the world that no longer serves the desired outcome. Jasmine explains that being called coachable was personally significant because she had never recognized that quality in herself.

  • Coachability involves openness rather than passive agreement.
  • Attachment to an existing worldview slows change.
  • A brief piece of accurate recognition can reshape self-perception.
  • Jasmine’s openness helped her change faster than many clients.

“You're not committed to a model of the world that isn't serving you.”

James Wedmore · 15:21

“I am coachable because it was the first time in my entire life that I heard truth about myself with a capital T”

Jasmine Star · 15:01
#coaching#identity#openness#growth

Story· 2

Story00:40

Why Jasmine Star Risked $20,000 on an Internet Mastermind

Jasmine recounts discovering webinars and masterminds for the first time in 2016. Although the $20,000 price initially seemed outrageous, she evaluated whether the program could reasonably help her generate at least that much additional business and submitted the paid application.

  • The mastermind cost $20,000, with $1,000 required to apply.
  • Jasmine initially dismissed the offer as implausible.
  • She reframed the price around its potential incremental business value.
  • Her husband encouraged her to apply and make the most of the opportunity.

“Do I believe that this guide would help me make at minimum$20,000 more in my business, would that investment pay off at minimum of$20,000?”

Jasmine Star · 03:24

“And I thought the answer was yes.”

Jasmine Star · 03:43
#investment#mastermind#mentorship#roi
Story06:26

The Quiet Mastermind Member Who Transformed Behind the Microphone

James remembers Jasmine remaining almost completely silent during her first mastermind retreat and assuming she was simply shy. When she was asked to teach the group, her energy changed immediately and she delivered a presentation that captivated the room.

  • The mastermind used collaborative teaching rather than one-way lectures.
  • Jasmine stayed quiet because she feared revealing that she did not belong.
  • Presenting activated strengths that were invisible during group discussion.
  • James subsequently regarded her as an unusually dynamic speaker.

“And all of a sudden it was like a, a switch just flips.”

James Wedmore · 08:34

“And she goes from this like quiet, you know, silent individual to like, all right, here's the deal”

James Wedmore · 08:38
#public speaking#confidence#mastermind#talent