Business, Bourbon & Cigars

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

18 min · 7 de may de 2026
Portada del episodio Why Do Winning CEOs Make Choices That Always Seem to Blow Up Later?

Descripción

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/workbook [http://meplusultra.com/workbook] Apply for the Me Plus Ultra Mastermind to connect with elite entrepreneurs who solve real problems together: https://MePlusUltra.com [https://MePlusUltra.com] Subscribe so you don't miss any episodes: Apple Podcasts: https://apple.co/3SN2fHn [Apple Podcasts: https://apple.co/3SN2fHn] Spotify: https://open.spotify.com/show/74bfJL9J2fjevQEvi17ekU [about:blank] YouTube: https://www.youtube.com/@MePlusUltraNetwork/ [about:blank] Connect with Me Plus Ultra: https://www.instagram.com/me_plus_ultra/ [https://www.instagram.com/me_plus_ultra/] https://www.facebook.com/MePlusUltra/ [https://www.facebook.com/MePlusUltra/] https://www.facebook.com/groups/1011061052968028/ [https://www.facebook.com/groups/1011061052968028/] https://x.com/Me_Plus_Ultra/ [https://x.com/Me_Plus_Ultra/] Connect with Scott Joseph: https://www.linkedin.com/in/ScottJoseph [https://www.linkedin.com/in/ScottJosephhttps://www.instagram.com/scotttjoseph/https://www.facebook.com/ScottTJoseph/https://x.com/ScottTJoseph1] https://www.instagram.com/scotttjoseph/ [https://www.instagram.com/scotttjoseph/] https://www.facebook.com/ScottTJoseph/ [https://www.facebook.com/ScottTJoseph/] https://x.com/ScottTJoseph1 This episode was produced by Podcast Boutique https://www.podcastboutique.com [https://www.podcastboutique.com]

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Working Harder Than Ever and Loving Every Minute: Here Is What Actually Changed

That ceiling you've hit even after years of success? It's usually not your strategy. It's the gap between the version of you that built your last chapter and the one that's supposed to build the next. You'll learn why the outreach you'd delete might be the one your next chapter depends on, how to tell when you've outgrown the version of yourself your business was built on, and four moves to close it, from separating identity from accomplishment to protecting your first three hours each day. Working harder isn't the problem. Working harder as the wrong version of yourself is! Topics discussed: The kind of growth that has nothing to do with revenue or headcount (00:00) The signal success can quietly mask (02:19) How almost deleting a LinkedIn message can cost you (03:38) Why you're the last to see your own blind spots (05:25) The buried beliefs and assumptions steering your decisions (06:30) What becomes possible when you build from who you actually are (08:08) Why the right work feels lighter even when it's harder (08:43) Step #1: separate what you've achieved from who you are (11:49) Step #2: name the assumptions you've been avoiding (13:11) Step #3: write your personal mission in terms of impact (14:35) Step #4: protect the first three hours of your day (15:47) Tired of feeling stuck? Download our FREE Limitless Growth eBook for strategies for continuous improvement, time management, and leadership skills that make an impact: https://meplusultra.com/growth/ [https://meplusultra.com/growth/] Apply for a Me Plus Ultra Sessions observer seat and watch a real working session before you decide if it's the right fit: https://meplusultra.com/hotseat [https://meplusultra.com/hotseat] Subscribe so you don't miss any episodes: Apple Podcasts: https://apple.co/3SN2fHn [https://apple.co/3SN2fHn] Spotify: https://open.spotify.com/show/74bfJL9J2fjevQEvi17ekU [https://open.spotify.com/show/74bfJL9J2fjevQEvi17ekU] YouTube: https://www.youtube.com/@MePlusUltraNetwork/ [https://www.youtube.com/@MePlusUltraNetwork/] Connect with Me Plus Ultra: https://www.instagram.com/me_plus_ultra/ [https://www.instagram.com/me_plus_ultra/] https://www.facebook.com/MePlusUltra/ [https://www.facebook.com/MePlusUltra/] https://www.facebook.com/groups/1011061052968028/ [https://www.facebook.com/groups/1011061052968028/] https://x.com/Me_Plus_Ultra/ [https://x.com/Me_Plus_Ultra/] Connect with Scott Joseph: https://www.linkedin.com/in/ScottJoseph [https://www.linkedin.com/in/ScottJoseph] https://www.instagram.com/scotttjoseph/ [https://www.instagram.com/scotttjoseph/] https://www.facebook.com/ScottTJoseph/ [https://www.facebook.com/ScottTJoseph/] https://x.com/ScottTJoseph1 [https://x.com/ScottTJoseph1] This episode was produced by Podcast Boutique https://www.podcastboutique.com [https://www.podcastboutique.com]

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That problem you've been working on for months, the one your advisors keep refining but never quite cracking? The answer probably already exists. It's just not in your circle. In this episode, you'll hear two real Me Plus Ultra moments. A $9M tax liability eliminated over lunch. A $100K decision reframed in twenty minutes. Then four things any operator can do to build the kind of access that compounds. The most expensive problem in your business is probably already solved in someone's head. The only question is whether you're in the room to hear it! Topics discussed: Introduction (00:00) The $9M lunch: how Claudio's client eliminated a tax liability over a meal (02:36) Why John Garcia's question solved what Claudio's standard approaches couldn't (03:31) The 20-minute reframe: Alex Griffiths' $100K decision (05:06) How Overfuel got preferred vendor status overnight (06:49) The mechanic: proximity to people who've operated where you're going (08:13) Step #1: get honest about who's actually in your circle (09:14) Step #2: pursue conversations that reframe, not just answer (10:49) Step #3: treat proximity as a strategic investment, not a social expense (13:35) Step #4: show up to give, not to extract (15:18) Apply for the Me Plus Ultra Mastermind to connect with elite entrepreneurs who solve real problems together: https://MePlusUltra.com/sessions [https://MePlusUltra.com/sessions] Subscribe so you don't miss any episodes: Apple Podcasts: https://apple.co/3SN2fHn [https://apple.co/3SN2fHn] Spotify: https://open.spotify.com/show/74bfJL9J2fjevQEvi17ekU [https://open.spotify.com/show/74bfJL9J2fjevQEvi17ekU] YouTube: https://www.youtube.com/@MePlusUltraNetwork/ [https://www.youtube.com/@MePlusUltraNetwork/] Connect with Me Plus Ultra: https://www.instagram.com/me_plus_ultra/ [https://www.instagram.com/me_plus_ultra/] https://www.facebook.com/MePlusUltra/ [https://www.facebook.com/MePlusUltra/] https://www.facebook.com/groups/1011061052968028/ [https://www.facebook.com/groups/1011061052968028/] https://x.com/Me_Plus_Ultra/ [https://x.com/Me_Plus_Ultra/] Connect with Scott Joseph: https://www.linkedin.com/in/ScottJoseph [https://www.linkedin.com/in/ScottJoseph] https://www.instagram.com/scotttjoseph/ [https://www.instagram.com/scotttjoseph/] https://www.facebook.com/ScottTJoseph/ [https://www.facebook.com/ScottTJoseph/] https://x.com/ScottTJoseph1 [https://x.com/ScottTJoseph1] This episode was produced by Podcast Boutique https://www.podcastboutique.com [https://www.podcastboutique.com]

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

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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/workbook [http://meplusultra.com/workbook] Apply for the Me Plus Ultra Mastermind to connect with elite entrepreneurs who solve real problems together: https://MePlusUltra.com [https://MePlusUltra.com] Subscribe so you don't miss any episodes: Apple Podcasts: https://apple.co/3SN2fHn [Apple Podcasts: https://apple.co/3SN2fHn] Spotify: https://open.spotify.com/show/74bfJL9J2fjevQEvi17ekU [about:blank] YouTube: https://www.youtube.com/@MePlusUltraNetwork/ [about:blank] Connect with Me Plus Ultra: https://www.instagram.com/me_plus_ultra/ [https://www.instagram.com/me_plus_ultra/] https://www.facebook.com/MePlusUltra/ [https://www.facebook.com/MePlusUltra/] https://www.facebook.com/groups/1011061052968028/ [https://www.facebook.com/groups/1011061052968028/] https://x.com/Me_Plus_Ultra/ [https://x.com/Me_Plus_Ultra/] Connect with Scott Joseph: https://www.linkedin.com/in/ScottJoseph [https://www.linkedin.com/in/ScottJosephhttps://www.instagram.com/scotttjoseph/https://www.facebook.com/ScottTJoseph/https://x.com/ScottTJoseph1] https://www.instagram.com/scotttjoseph/ [https://www.instagram.com/scotttjoseph/] https://www.facebook.com/ScottTJoseph/ [https://www.facebook.com/ScottTJoseph/] https://x.com/ScottTJoseph1 This episode was produced by Podcast Boutique https://www.podcastboutique.com [https://www.podcastboutique.com]

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episode How Smart Business Owners Make More Money by Talking Less About Money artwork

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