Winning the Week

The podcast

The intersection of technology, culture, and well-being. Every Thursday morning. No ads: Value for Value.

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The catalog

Oct 29, 2026

Episode 72: The Job, Not Feeling Model for YouTube Titles

Strangers search for a job to be done, not for your feelings or your inside jokes. This week Scott walks through Rob the Maritimer's plan for a new channel's first 10 videos, the AI channel comparison that led to his "job, not feeling" model, the four prompts he uses for topic…

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Oct 22, 2026

Episode 71: How to Get Found by People Who Never Heard of You

Your YouTube titles might be the reason strangers never find you. This week Scott shares his "the job, not the feeling" packaging rules he came up with after comparing his channel to a bigger one, the four prompts he now uses for topics, titles, thumbnails, and descriptions, a…

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Oct 15, 2026

Episode 70: The Intersection of Technology, Culture, and Stress

The intersection of technology, culture, and well-being. For Gen X and Boomers who are done being talked down to about the modern technical world. Phones, AI, streaming, privacy, outrage media, podcasts, the tools that were supposed to make life easier and often don't. We sort…

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Oct 8, 2026

Episode 69: This is what's going on - all at once!

The intersection of technology, culture, and well-being. For Gen X and Boomers who are done being talked down to about the modern technical world. Phones, AI, streaming, privacy, outrage media, podcasts, the tools that were supposed to make life easier and often don't. We sort…

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Oct 1, 2026

Episode 68: This Is What Fred Found Out

The intersection of technology, culture, and well-being. For Gen X and Boomers who are done being talked down to about the modern technical world. Phones, AI, streaming, privacy, outrage media, podcasts, the tools that were supposed to make life easier and often don't. We sort…

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Sep 24, 2026

Episode 67: Own the Feed - You're Already Making a Podcast and Don't Know It

YouTubers: did you know you can turn the videos and livestreams you are already making into a podcast you actually own? I'm going to talk about getting your existing content into every podcast app on a feed that YOU control - without starting from scratch. I'll talk about why …

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Sep 17, 2026

Episode 66: You Don't Have to Fear Artificial Intelligence

💯🌍 Wednesday Night Livestream: https://www.youtube.com/@WinningTheWeek/streams • Podcast: https://podcast.winningtheweek.org • Free Stickers: https://forms.gle/nzmtKyfnUhFvP3Dh9 • Mission: Embarrassment" Experiments: https://www.youtube.com/watch?v=t4Nt3o4-McQ&list…

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Sep 10, 2026

Episode 65: A Change Is In The Wind

I want to change the world one person at a time, but I don't want to change just ONE person. Eventually I will speak on topics adjacent to my main theme, things like being a contrarian thinker and recognizing the value of our place in the universe, but for now I am just re-int…

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Sep 3, 2026

Episode 64: Is YouTube Telling Me It's Over?

Be more confident in public, defeat social anxiety and be the winner you were created to be! This is a Value for Value Channel. Please support at https://donate.winningtheweek.org

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Aug 27, 2026

Episode 63: Let's Get Unembarrassable

The intersection of technology, culture, and well-being. For Gen X and Boomers who are done being talked down to about the modern technical world. Phones, AI, streaming, privacy, outrage media, podcasts, the tools that were supposed to make life easier and often don't. We sort…

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Aug 20, 2026

Episode 62: Beach Embarrassment

The intersection of technology, culture, and well-being. For Gen X and Boomers who are done being talked down to about the modern technical world. Phones, AI, streaming, privacy, outrage media, podcasts, the tools that were supposed to make life easier and often don't. We sort…

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Aug 13, 2026

Episode 61: Time For a Change!

The intersection of technology, culture, and well-being. For Gen X and Boomers who are done being talked down to about the modern technical world. Phones, AI, streaming, privacy, outrage media, podcasts, the tools that were supposed to make life easier and often don't. We sort…

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Aug 7, 2026

Episode 60: Looking Foolish

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Jul 30, 2026

Episode 59: Dancing In Public

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Jul 23, 2026

Episode 58: Humiliating Myself ON PURPOSE Again! | RIP JCD

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Jul 16, 2026

Episode 57: "Putting Myself Out There" - Embarrassing Myself ON PURPOSE

This Week: 🌟 The Cool Kids' Table ( Pre-show, come early!) 🌟 Commenter and Encourager of the Week! 🌟 Scenes From a Mall (PYOT) 🌟 Memberships Update 🌟 Producer Shout-outs WINNING THE WEEK LIVESTREAM: WEDNESDAY NIGHTS 8PM EASTERN https://live.winningtheweek.org FR…

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Jul 9, 2026

Episode 56: The End of Memberships?

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Jul 2, 2026

Episode 55: I'm Out of Peace!

Let's spend some time together and talk a little bit about how easy it is to get "out of peace" ... I'm here for it, let's have a heart to heart. Let's figure this out together. I'm all about peace, motivation, optimism, comfort, positivity, love... but is it enough? This Week…

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Jun 25, 2026

Episode 54: What's So Funny About Peace, Love and Understanding?

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Jun 18, 2026

Episode 53: Feel the Love

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Jun 11, 2026

Episode 52: Who Is It For, What Can They Expect?

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Jun 5, 2026

Episode 51: Walk With Me This Week

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May 28, 2026

Episode 50: Something Has to Change!

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May 21, 2026

Episode 49: My YouTube Channel Grew After I Started Livestreaming

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May 19, 2026

Episode 48: Your Inner Circle Is a Garden - You Have to Weed It

🪑 Welcome to the Cool Kids' Table. I saved you a seat.

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May 18, 2026

Episode 47: Forget FOMO, Try JOMO! - The Fear of Missing Out

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May 15, 2026

Episode 46: They're Trying to Kill Podcasting!

Big tech platforms like YouTube, Spotify, and Apple are undermining traditional podcasting by hosting shows that they market as "podcasts" but which lack open RSS feeds, thereby centralizing control, bypassing the decentralized distribution model, and eroding the free-speech p…

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May 14, 2026

Episode 45: A Man of Culture

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May 13, 2026

Episode 44: Transactional Friendships

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May 12, 2026

Episode 43: Welcome to Winning the Week - Contemplating Channel Identity & Branding Ideas

The inception of Winning the Week

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