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Why Do Winning CEOs Make Choices That Always Seem to Blow Up Later? episode artwork

EPISODE · May 7, 2026 · 18 MIN

Why Do Winning CEOs Make Choices That Always Seem to Blow Up Later?

from Business, Bourbon & Cigars

Your dashboards are clean, your reports are thorough, your advisors are sharp. So why don't your decisions carry the same weight they used to?In this episode, Scott Joseph breaks down how the systems you built to give yourself room to think are quietly replacing the thing that made you dangerous in the first place. You'll learn how a $30 million operator lost a multi-million dollar relationship with zero warning, why your dashboard is just a mirror, and the Friday-morning question that pulls senior leaders back into proximity with the work!Topics discussed:Why winning CEOs make decisions that don't carry weight (00:00)The trap: how your systems quietly replace your thinking (01:02)The $30M founder running his company through a screen (03:23)A top-three client walks out with no warning (04:05)Scott's J&L story: when the machine starts running you (05:36)How growth steals back the instinct that built your company (06:39)Data tells you what happened. Thinking tells you what it means. (10:23)The 18-month cost of clean reports and rotting relationships (10:50)The fix: a Friday block and one question (13:01)Why your dashboard is just a mirror (16:36)Turn challenges into measurable results with the FREE Business Bourbon & Cigars Leadership Retreat Workbook! http://meplusultra.com/workbookApply for the Me Plus Ultra Mastermind to connect with elite entrepreneurs who solve real problems together: https://MePlusUltra.comSubscribe so you don't miss any episodes:Apple Podcasts: https://apple.co/3SN2fHnSpotify: https://open.spotify.com/show/74bfJL9J2fjevQEvi17ekUYouTube: https://www.youtube.com/@MePlusUltraNetwork/Connect with Me Plus Ultra:https://www.instagram.com/me_plus_ultra/https://www.facebook.com/MePlusUltra/https://www.facebook.com/groups/1011061052968028/https://x.com/Me_Plus_Ultra/Connect with Scott Joseph:https://www.linkedin.com/in/ScottJosephhttps://www.instagram.com/scotttjoseph/https://www.facebook.com/ScottTJoseph/https://x.com/ScottTJoseph1This episode was produced by Podcast Boutique https://www.podcastboutique.com

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Why Do Winning CEOs Make Choices That Always Seem to Blow Up Later?

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Frequently Asked Questions

How long is this episode of Business, Bourbon & Cigars?

This episode is 18 minutes long.

When was this Business, Bourbon & Cigars episode published?

This episode was published on May 7, 2026.

What is this episode about?

Your dashboards are clean, your reports are thorough, your advisors are sharp. So why don't your decisions carry the same weight they used to?In this episode, Scott Joseph breaks down how the systems you built to give yourself room to think are...

Can I download this Business, Bourbon & Cigars episode?

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