In a nutshell, the podcast show aims to step into the shoes of real-life startup founders and talk about their success and failures, as well as what it is like to be an entrepreneur in today's fast-paced world.
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Startup Playground Podcast

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Startup With Kids Podcast | Parenting | Entrepreneurship | Side Income | Business
Startup With Kids Contributors: Online Entrepreneurs, Marketers, Bloggers, and Business Strategists
Telling the stories, strategies, and successes of parents doing business. Hosted by StartupWithKids.com contributor Dan Cumberland, the Startup With Kids Podcast is a playground at the intersection of business ideas, inspiring stories, and practical help for raising kids and launching businesses at the same time. Join us as we explore together. If things go as planned, you’ll find yourself with a growing business, more family time, more freedom, and having a lot of fun along the way.
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Streamlined Solopreneur: Helping solopreneur parents stop checking email at the playground
Joe Casabona — Business Systems Architect
You didn’t start your business just to work through bedtime and answer emails at the playground. But if you're a solopreneur parent, that’s probably what it feels like. Imagine actually being present during family time. Picture taking real vacations without your laptop, making it to every school pickup, and having your business run smoothly while you focus on what matters most. I’m Joe Casabona, and I help solopreneur parents run their business in less time—without sacrificing quality or bur ...
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"Lex Fridman Podcast of AI" is a forward-thinking podcast dedicated to exploring the latest developments and innovations in artificial intelligence. Each episode delves into a variety of AI-related topics and news, offering listeners insights into the ever-evolving world of technology. The show provides in-depth analysis and discussions on how AI impacts industries, society, and the future. In the same style of your favorite Lex Fridman interview tune in for a comprehensive understanding of ...
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Love Your Work is the intellectual playground of David Kadavy, bestselling author of three books – including Mind Management, Not Time Management – and former design advisor to Timeful – a Google-acquired productivity app. Love Your Work is where David shows you how to be productive when creativity matters, and make big breakthroughs happen in your career as a creator. Dig into the archives for insightful conversations with Dan Ariely, David Allen, Seth Godin, James Altucher, and many more. ...
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Banking on Grok's AI Companion has become a trending question in the tech economy. The product is raising eyebrows with its monetization model, shifting how people think about artificial intelligence and revenue. Its approach may change how tech firms build profitable AI-driven tools in the future. Try AI Box: https://aibox.ai/ AI Chat YouTube Ch…
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Understanding Anthropic's New Usage Limits
12:02
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12:02Understanding Anthropic's New Usage Limits has become a pressing concern for many users. The new policy is influencing AI access, with ripple effects across the AI community. As limits reshape expectations, users are reevaluating how they interact with the platform. Try AI Box: https://aibox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@J…
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DuckDuckGo has decided to bans artificial content from its platform. This move is part of its initiative to ensure real results in search results. It reflects a growing trend toward responsible tech use and ethical content delivery. Try AI Box: https://aibox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Com…
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Loveable Secures $200M in Fresh Capital at $1.8B Valuation
7:10
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7:10Investors are buzzing after Loveable securing a $200M investment. The funding has propelled the company’s valuation to a remarkable $1.8 billion. This marks a pivotal moment in Loveable’s growth journey. Try AI Box: https://aibox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.com…
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Decoding Growth: high-performance innovation techniques
9:32
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9:32Take a closer look at how Perplexity's unique growth philosophy is enabling future-ready strategies. This episode delves into the core of Perplexity AI’s methods, revealing strategies you won’t find in typical playbooks. These insights show how smart innovation is leading the AI transformation journey. Try AI Box: https://aibox.ai/ AI Chat YouTub…
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Breaking Down Unprecedented Tech Innovation with Mistral's Deep Research
12:02
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12:02In this episode, we’re discussing unprecedented llm development from the perspective of Mistral's Deep Research. Discover how this work is driving the next wave of innovation and setting a new standard for innovation in AI. We’ll break down the most important insights, explore real-world implications, and share why this matters now more than ever. …
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Unpacking Revolutionary OpenAI Experiments
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12:02In this episode, we’re unpacking revolutionary openai experiments—handling real-world tasks. Try AI Box: https://aibox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.com/aihustle/about
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I just updated my /now page for the first time in a while, and it’s become much more comprehensive than before. I walk through all the new sections I’ve added - from current projects and media consumption to streaming services and personal details. There’s also a fun revelation about my five-CD changer playlist that’s surprisingly close to what I a…
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The Hidden Cost of Switching Tools (It's Not What You Think)
25:00
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25:00My dad's furious "never again" phone call to some faceless company stuck with me for decades. Fast forward to last weekend: I'm rage-quitting Dropbox after a seemingly small slight. Sound familiar? If you're a chronic tool switcher like me, you know that moment when you've had enough. But here's what nobody talks about—switching tools isn't just ab…
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Nvidia Returns to China’s AI Market boosts China's access to powerful AI infrastructure despite previous restrictions. From Washington to Shenzhen, this decision is already rippling across tech and politics. Try AI Box: https://aibox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool…
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Steering AI in the Right Direction raises urgent questions about alignment, autonomy, and unintended consequences. Join us as we analyze real-world examples of AI misalignment—and what went wrong. Try AI Box: https://aibox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.com/aihust…
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Hello, It’s Google’s AI Calling is aiming to replace traditional phone reps with scalable AI systems. It’s a glimpse into a future where machines speak on behalf of companies. Try AI Box: https://aibox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.com/aihustle/about…
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Rebuilding the Cloud: Meta’s AI Push represents Meta’s commitment to leading in infrastructure, not just algorithms. We unpack how Meta’s infrastructure philosophy is evolving with the AI boom. Try AI Box: https://aibox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.com/aihustle/…
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Debuting Voxtral—Mistral AI's latest innovation in voice technology. It's being positioned as next-gen audio intelligence. We analyze where Voxtral fits into the rapidly evolving landscape of multimodal AI. Try AI Box: https://aibox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.…
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Learn how cognitive cooperation encourages machines to learn, adapt, and grow together. It’s a critical discussion at the intersection of intelligence and collaboration. Try AI Box: https://aibox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.com/aihustle/about…
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Am I messing up not having a community? [Audio Note]
5:03
5:03
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5:03I’m wrestling with a realization from Justin Moore’s 10K Brand Challenge - I don’t have a place for my audience to hang out and connect. I’m exploring options like Slack, Discord, and Circle, but feeling stuck on which platform makes sense for parent solopreneurs and my “chaos to clarity” framework development. This is a raw, unresolved brainstorm …
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Stop Explaining What You Do and Start Showing It with Charlotte Crowther
45:46
45:46
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45:46Picture this: you're on a discovery call, your kids are making noise upstairs, and you're trying to explain what you do while mentally juggling dinner plans. Sound familiar? You're not alone—and there's a solution that goes way beyond just "trust me, I'm good." I sat down with Charlotte Crowther, the mastermind behind some of the most recognizable …
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Why I’m Making My Podcast the Linchpin of Everything [Audio Note]
9:17
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9:17I’m done letting AI dictate my content strategy and worrying about episode number parity while my downloads tank. After months of overthinking tactics, I’m simplifying everything by making my podcast the center of my content universe. Here’s how I’m cutting through the decision fatigue and getting back to what actually works: showing up generously …
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How to Keep Up With AI Without Losing Your Mind with Charlie Guo
53:08
53:08
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53:08Remember when ChatGPT first came out and it felt revolutionary? Well, that was just the beginning. Things are moving so fast in the AI world that by the time you figure out one tool, three new ones have launched. That's exactly why I brought Charlie Guo on the show—he's an AI engineer who actually understands this stuff and can explain it without m…
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Am I Outsourcing My Brain to AI? [Audio Note]
7:12
7:12
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7:12I’m wrestling with whether I’m becoming too dependent on AI for critical thinking, especially after it helped me create an entire quiz for my business. While I don’t use it for actual writing, I’ve noticed I’m defaulting to AI for brainstorming, research, and problem-solving more quickly than I used to. I’m exploring the line between helpful automa…
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When AI Writes Your Code: Success, Horror Stories, and What's Next with Susan Boles
20:42
20:42
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20:42Remember when coding meant years of computer science classes and debugging late into the night? Well, things have changed. I recently sat down with Susan Bowles, founder and fellow solopreneur, to dive into the world of "vibe coding" — essentially describing what you want to AI and having it write all the code for you. While I had a nearly flawless…
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How Google Workspace Saved my Life with FamousAshley Grant
49:24
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49:24I always say to use what you’ll actually use. For Famous Ashley Grant, that’s Google Workspace. And today, she’s telling us all about how she uses it to manage literally everything in her life – from client work to meal planning. Ashley's story hit home for me. Before implementing her system, she was constantly working too many hours, missing deadl…
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Ask Me Anything: Automation Questions Roundup
14:30
14:30
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14:30It’s an Automation AMA! From scheduling social media content to making kids' lunches (yes, really), fellow solopreneurs shared their biggest time-wasters. I ended up creating custom automation solutions for everything from podcast guest research to email management. Special thanks to Kit for letting me record in their Studios! I highly recommend th…
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My 4-App Travel System That Saves Hours of Trip Planning
17:50
17:50
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17:50I'm recording from Kit Studios in Boise while attending conferences, which got me thinking about something crucial to my business success—my travel system. As someone who travels frequently for networking and conferences, I've developed a streamlined approach that keeps me organized and stress-free on the road. My system revolves around two essenti…
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This episode examines how AI is reshaping the music production landscape. We dive into how generative AI is enabling new forms of musical expression. We break down the capabilities and creative potential of the model. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https…
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Discover how these innovations could affect jobs, safety, and efficiency. Hear insights into the tech behind Amazon’s latest robotic advancement. Discover how these innovations could affect jobs, safety, and efficiency. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: htt…
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This episode unpacks what this deal means for the future of data and AI. This podcast looks at the synergy between Neon's innovations and Databricks’ goals. Learn how Neon’s technology fits into Databricks’ larger platform strategy. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle C…
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OpenAI Boosts Tech Use with Smarter Problem Solving
10:16
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10:16We discuss how OpenAI continues to evolve its tools for professional use cases. We discuss how OpenAI continues to evolve its tools for professional use cases. This podcast unpacks the technical edge GPT-4.1 adds to ChatGPT. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community…
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I've been on a mission to use my phone way less this year, sparked by reading The Anxious Generation and that magical Disney World trip where I barely touched my phone. The solution? iPhone focus modes - my secret weapon for controlling the fire hose of information instead of letting it control me. Think about it: you finally sit down to get some r…
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Crown Prince Leads Crown Prince’s AI Venture
8:25
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8:25Learn how this AI initiative could shape the region’s tech future. We analyze the global implications of this Middle Eastern AI startup. We examine how this launch positions Saudi Arabia on the AI world stage. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.s…
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We explore Google's latest venture into AI-focused investments. We examine the tech giant’s approach to fostering the next wave of AI development. Discover the sectors and technologies this fund aims to support. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www…
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Trump Admin Alters AI Regulation and Chip Strategy
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12:50We discuss the Trump administration’s latest moves on AI-related policies. This episode investigates the policy battles shaping the future of American AI. This episode explores changes in AI copyright laws and semiconductor strategy. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle …
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Disrupting Search with Google with Revolutionary Pricing
10:19
10:19
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10:19Hear about the tech specs and market strategies behind ZeroSearch. This episode breaks down how Alibaba's innovation could disrupt the search engine market. Discover how Alibaba plans to challenge Google with a cost-effective alternative. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hu…
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OpenAI’s Surge vs Google’s Decline Big Tech Competitors
9:32
9:32
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9:32Hear real-world examples of enterprises making the switch to OpenAI. Hear real-world examples of enterprises making the switch to OpenAI. Discover the reasons why companies are shifting to OpenAI solutions. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skoo…
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Utilizing OpenAI for International Financial Strategies
8:03
8:03
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8:03Explore how countries are leveraging AI to secure funding from global institutions. This episode uncovers the role of AI in economic development and international finance. We analyze how OpenAI impacts the strategies behind national fundraising initiatives. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSc…
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Amazon Introduces Affective Robot and Machine Learning Coder
9:23
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9:23A new kind of emotional robot was just introduced by Amazon. Alongside it, a smart AI coder has been announced to automate programming tasks. This dual launch marks a major leap in AI evolution. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.com/aihust…
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Anthropic Contends with Google with Progressive Online Query System
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8:04Anthropic's new tool puts pressure on established search leaders. It redefines how AI understands user intent online. This marks a turning point in AI-based internet services. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.com/aihustle/about…
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OpenAI Stands Its Ground, Calls Out X.ai’s Model
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14:12Despite criticism, OpenAI is doubling down on its nonprofit mission. Its latest move: calling out X.ai for abandoning ethical safeguards. We explore what this confrontation tells us about the state of AI. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.…
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Beta Playground of AI Box Now Accepting Testers
9:56
9:56
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9:56Beta Playground of AI Box Now Accepting Testers. This marks a major milestone in our journey to deliver interactive AI experiences. Test out new features and give us your feedback as we build together. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.com…
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Anthropic Makes Claude More Capable With App Extensions
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10:40Anthropic Makes Claude More Capable With App Extensions. This new functionality brings automation and transactions into chat. Claude’s expanded integration means more powerful workflows. Try AI Box: https://AIBox.ai/ AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer Join my AI Hustle Community: https://www.skool.com/aihustle/about…
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Last year, my wife and I made the somewhat terrifying decision to skip summer camp for our kids to save $9,000-$10,000 and spend more intentional time together. It wasn't perfect—I gave myself a solid B—but we survived, and more importantly, we're doing it again this year. The financial savings were huge, but the real motivation was recognizing we'…
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I'll be honest—I don't officially do web development anymore. But when a nonprofit asked for help, I thought I could knock out a simple WordPress portal in 25 hours using no-code tools like Zapier and Advanced Custom Fields. Boy, was I wrong. What started as a straightforward project quickly turned into a nightmare of under-scoping and tool limitat…
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The Human in the Loop : AI That Actually Sounds Like Me with Corey Koehler
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55:29When I first started using AI in my business, I was hesitant — it felt like a shortcut that might strip away my voice. But in this conversation with Corey Koehler, I learned that when you set it up the right way, AI can actually amplify your voice and make your work better — and faster. Corey shares how he went from spending hours grinding through …
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Brain Friendly Systems for Professionals who want to Do It All with Skye Waterson
47:05
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47:05My therapist recently asked if anyone had ever talked to me about ADHD. While I've never been formally diagnosed, that question sparked a journey into understanding how our brains work—especially when running a business. That's why I was thrilled to chat with Skye Waterson, an ADHD strategist who helps entrepreneurs build "brain-friendly" systems. …
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One of my favorite things to do at Disney World growing up was get on attractions and press all the buttons. They really made it feel like you were accomplishing things. Maybe that’s why I like the Stream Deck so much. I've been using Stream Decks for about five years now, starting with a 15-key model before expanding to a 32-key XL and adding two …
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How I’m Prepping my Business for Vacation
22:04
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22:04I solemnly swear I’ve never worked on a family vacation. Can you honestly say that? I can’t. From checking emails in Magic Kingdom to recording podcasts at the beach, I've been guilty of putting work before family time, even on vacation. After some not-so-great experiences (including a previous Disney trip that didn't go as planned), I've decided m…
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3 Automations I’m Using in my Business (from Easy to Hard)
20:44
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20:44You’ve probably seen Rube Goldberg machines — those ridiculous setups where a marble rolls down a track, flips a switch, lights a match, and somehow makes toast. They’re fun to watch… but terrible for actually getting anything done. That’s how most automations feel when you’re first starting out: over-engineered, fragile, and hard to maintain. But …
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Preparing for AI Agents: Insights from John Munsell
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45:26AI agents are changing the game, and John Munsell has a plan. He shares how institutions like LSU and companies like Bizzuka are tackling the challenge. Don’t miss these crucial insights. AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer My Podcast Course: https://podcaststudio.com/courses/ Try AI Box: https://AIBox.ai/ Join my AI…
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Living Longer with AI: Blair LeCorte Breaks It Down
44:27
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44:27AI may hold the secret to longer life, and Blair LeCorte is here to explain how. He breaks down the tools driving progress in longevity. The future of aging could look very different. AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer My Podcast Course: https://podcaststudio.com/courses/ Try AI Box: https://AIBox.ai/ Join my AI Hus…
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Altman’s Equity Position Raises Questions at OpenAI
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14:04Sam Altman’s equity stake in OpenAI has become a hot topic. The issue highlights concerns about governance and alignment in the AI space. What could this mean for OpenAI’s direction? AI Chat YouTube Channel: https://www.youtube.com/@JaedenSchafer My Podcast Course: https://podcaststudio.com/courses/ Try AI Box: https://AIBox.ai/ Join my AI Hust…
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