Entrepreneur School (In the AI Era)

Entrepreneur School in the AI Era is a podcast for experienced business owners who’ve already built something meaningful and are now figuring out how to work in a world where AI is suddenly everywhere. Hosted by Kelly Sinclair, award-winning marketer turned AI platform co-founder, the show explores how to integrate AI in practical, human-centred ways without sounding like a robot, losing touch with your unique gifts, or dismantling the business you’ve already built. Kelly originally adopted AI to elevate her work in marketing and visibility but quickly realized it was reshaping far more than she ever expected, ultimately transforming her entire business. This podcast is about navigating that reality together. Because AI isn’t a one-time upgrade. It’s an ongoing shift, and there’s both a right way and a very wrong way to use these tools. Expect strategic conversations, AI-forward guest spotlights, and honest perspectives on how to evolve with intention, protect what matters, and stay grounded as the way we work continues to change.

Entrepreneur School (In the AI Era) is a business podcast hosted by Unknown Host, with 192 episodes on record and a Required Pod Score of 80. PitchCentric scores this show on Booking Probability, Listen Score, and live audience signals refreshed every 24 hours.

Unknown Host hosts Entrepreneur School (In the AI Era), a business show with 192 episodes published.

Our AI reads these to draft pitches. Use them as grounding for a pitch that cites a real guest and a specific topic.

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  Episode #192

  The AI Opportunity Most Experts Are Missing

  Sep 8, 202644 minS1

  Most experts are thinking about how AI can make their content faster. I’m far more interested in what happens when AI helps your clients actually use your expertise. Today, you’re hearing me on the other side of the microphone. This conversation originally aired on Ellen Yin’s Cubicle to CEO podcast, where we unpacked the accidental series of coffee dates, custom GPT frustrations and client implementation gaps that eventually became wAIv. We also got into a much bigger question: What happens to the value of your intellectual property when someone can feed your course materials, worksheets and best ideas into generic AI? You’ll learn: The critical difference between generic AI and expert-backed AI Why online courses can teach people how to think, but AI tools let them use your thinking The security and access problem creators encounter when sharing custom GPT links How Bot Squads combine custom AI tools, shared context and orchestrated workflows Why “give away your best stuff” deserves another look in the AI era How a hybrid human-plus-AI model can create better client results without replacing the expert CHAPTERS 01:01 A little role reversal 04:33 The rise of expert-backed AI 06:30 When strategy never gets implemented 09:06 The custom GPT security problem 13:11 Is wAIv replacing ChatGPT? 16:42 Bot Squads around the boardroom table 19:30 When three AI tools have a baby 24:05 Removing friction for your clients 27:33 Should you still give it away? 32:30 Why the hybrid model wins >CONNECT WITH ELLEN Website: https://www.ellenyin.com/ Cubicle to CEO: https://cubicletoceo.co/podcast Instagram: https://instagram.com/cubicletoceo >Introducing wAIv This episode is brought to you by wAIv—our brand-new platform built for online experts who want to securely build and sell AI tools powered by YOUR thinking, YOUR frameworks and YOUR methodology. wAIv helps you create Bot Squads—a suite of AI tools that work together to help your clients implement your expertise faster and with better results than ever before. >Your Next Steps: Build your own AI tool using Claude (in under 2 hours) with the AI Product Build Lab. Podcast listeners save 98%: https://graviastudio.com/build/?code=podcast1 Follow our new Instagram account @joinwaiv: https://instagram.com/joinwaiv >Thanks for Listening! If you enjoyed this episode, please help us share it by: Following the show—this helps you stay updated and supports us! Leaving a positive review—this boosts our ranking and helps more entrepreneurs find the podcast. -------------------------- Entrepreneur School is proud to be featured on the Feedspot list of 30 Best Canada CEO Podcasts! https://blog.feedspot.com/canada ceo podcasts/

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  Episode #191

  Coaches Need to Know This About AI

  Sep 1, 202632 minS1

  Jasmine Jonte runs CRE8TION, a done-for-you program design agency that's built 160 programs and reached more than 100,000 students.This whole conversation revolves around one question: now that anyone can generate a course outline in ten minutes, what are people actually paying for? Her answer is that they were never paying for the information. The passive income promise sold to experts in 2020 was a marketing lie, and AI didn't break the model so much as make the crack impossible to ignore. She walks through where her clients use AI inside a program build, where they deliberately don't, and what the standard looks like now that buyers know what good feels like. What you'll learn: Why the barrier to entry keeps dropping while client expectations keep climbing The $7,500 program that showed her experts know what they know but can't teach it What her clients are replacing workbooks and calculators with The one thing she says AI can't be coded with How to talk about AI use with clients who have friction around it The closing line about lifetime value that reframes your whole delivery model CHAPTERS 01:05 Meet Jasmine Jonte 02:05 From Teacher to Agency 03:52 AI Raises the Bar 06:58 New Client Expectations 09:00 Beyond Information Dumps 12:03 Personalization at Scale 15:08 How Much AI to Use 17:23 Positioning and Disclosure 22:53 Case Studies in Action 28:02 Make Results Easy 29:28 Where to Connect >MEET JASMINE Jasmine Jonte is the founder of CRE8TION, a done-for-you program design and client experience agency for established experts and thought leaders. Her team builds the program architecture, client experience, and delivery systems so founders scale on their expertise instead of managing chaos. CRE8TION has built 160 programs and reached more than 100,000 students using transformation-based learning, NLP, and AI. A former Detroit classroom teacher and Teach For America alum, Jasmine believes in transformation over information. >CONNECT WITH JASMINE Website: https://www.cre8tion.co Instagram & Threads: @jasminejonte Grab Jasmine's resource 10 Strategies to Make Your Course as Binge-Worthy as Netflix. It's a free playbook plus CourseFlix AI, a tool trained on all 160 programs her team has built that tells you which strategies apply to your specific program in about 60 seconds. https://cre8tion.co/netflix >Introducing wAIv This episode is brought to you by wAIv—our brand-new platform built for online experts who want to securely build and sell AI tools powered by YOUR thinking, YOUR frameworks and YOUR methodology. wAIv helps you create Bot Squads—a suite of AI tools that work together to help your clients implement your expertise faster and with better results than ever before. >Your Next Steps: Join me live at the AI Product Build Lab on October 8 and build your first squad using the new Claude connector. $1 with code PODCAST1: https://graviastudio.com/build/?code=PODCAST1 See what an AI tool built on your expertise actually looks like. Explore wAIv: https://graviastudio.com/waiv Follow our new Instagram account @joinwaiv: https://instagram.com/joinwaiv >Thanks for Listening! If you enjoyed this episode, please help us share it by: Following the show—this helps you stay updated and supports us! Leaving a positive review—this boosts our ranking and helps more entrepreneurs find the podcast. -------------------------- Entrepreneur School is proud to be featured on the Feedspot list of 30 Best Canada CEO Podcasts! https://blog.feedspot.com/canada ceo podcasts/

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  Episode #190

  OpenAI Just Cancelled Custom GPT Building. What This Means

  Aug 25, 202618 minS1

  If you're a business owner who's built custom GPTs to share with your clients or sell as a product, listen in. On August 16th, 2026, OpenAI stopped letting personal accounts create or publish new custom GPTs. That covers the Free, Go, Plus and Pro tiers. Existing GPTs still work. Editing an existing one still works with an eligible subscription. Creating a new one to share is what's gone. There was no email about it. I found out from some buzz online and went and checked my own account. In this episode I walk through what actually changed, what I found when I tested it, and the bigger question underneath it all. What does this mean for you if your methodology is sitting inside a tool on somebody else's platform? What you'll learn: What OpenAI changed on August 16th, in their own words, and what still works My take on why this happened now, and what an 852 billion dollar valuation has to do with it The backup habit to start this week for your GPT instructions, knowledge files and settings Why custom GPTs were never designed for what we've been using them for What multi-tenant access, data privacy and gated delivery mean for a non-technical builder How a bot squad differs from a single GPT, using Nicole Pearl's Pearl Pitch Desk as an example CHAPTERS 0:00 What OpenAI changed without telling you 00:45 The exact wording of the new rule 01:40 What still works, and what doesn't 03:10 The IPO theory nobody's saying out loud 05:25 Back up everything you've built 06:35 You built something OpenAI never intended 10:13 What a bot squad actually looks like 11:50 The part vibe coders forget about 12:55 Claude and wAIv, the wedding of the century 16:40 No need to panic, but do decide --- >Mentioned in this episode The AI Product Build Lab, Friday August 28, 11 a.m. to 1 p.m. MDT. Podcast listeners get in for $1 with the code PODCAST1, and the link below applies it automatically. Can't make it live? Register anyway and you'll get the replay, plus an invite to the next live session. https://graviastudio.com/build/?code=PODCAST1 --- >Introducing wAIv This episode is brought to you by wAIv—our brand-new platform built for online experts who want to securely build and sell AI tools powered by YOUR thinking, YOUR frameworks and YOUR methodology. wAIv helps you create Bot Squads—a suite of AI tools that work together to help your clients implement your expertise faster and with better results than ever before. --- >Your Next Steps: Join me live at the AI Product Build Lab on August 28 and build your first squad using the new Claude connector. $1 with code PODCAST1: https://graviastudio.com/build/?code=PODCAST1 See what an AI tool built on your expertise actually looks like. Explore wAIv: https://graviastudio.com/waiv Follow our new Instagram account @joinwaiv: https://instagram.com/joinwaiv --- >Thanks for Listening! If you enjoyed this episode, please help us share it by: ⭐ Following the show—this helps you stay updated and supports us! ⭐ Leaving a positive review—this boosts our ranking and helps more entrepreneurs find the podcast. -------------------------- Entrepreneur School is proud to be featured on the Feedspot list of 30 Best Canada CEO Podcasts! https://blog.feedspot.com/canada ceo podcasts/

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  Episode #189

  Is ManyChat Killing Your Sales?

  Aug 18, 202633 minS1

  I've been pretending my ManyChat is set up for about two years now. Here's my actual system: someone comments the keyword, I see it, and then I manually DM them the next day like it's 2016. So when Angelica Pompy came on the show and dropped a plot twist about ManyChat in the first ninety seconds, I was already leaning in. Angelica generates about 65% of her revenue from Instagram. She's not anti-automation. She just knows exactly where it belongs and where it quietly costs you money. She sold a $3,400 VIP day in the DMs with no sales call, no funnel, no link. Just a video message and a few voice notes back and forth. And the story she tells about the event she wanted to attend but never bought a ticket for, because the host never followed up, is the most useful thing I've heard all month about why your launches underperform. We're all so busy automating the top of the funnel that we've automated away the part where someone actually decides to buy. What you'll learn: The exact moment ManyChat stops helping and starts costing you sales Why a $3,400 offer can close faster in the DMs than through a full email sequence The follow-up gap that makes you think nobody's interested when they actually were How Angelica labels and tracks leads in Instagram, and why that system breaks after 30 days Her three-post rotation and why she never sells in every post What "success" on social actually looks like when a viral post isn't the goal CHAPTERS 02:30 The ManyChat plot twist 03:38 When ManyChat actually earns its place 04:13 The New York event she refused to automate 06:05 A $3,400 VIP day closed in the DMs 06:56 The follow-up that lost her sale 09:24 Labelling leads before they disappear 12:11 The video message that got an instant yes 17:18 Where 65% of her revenue comes from 20:41 Building a lead system the algorithm can't erase 27:56 The three post rotation she teaches >MEET ANGELICA Angelica Pompy is a business coach, speaker, and marketing strategist helping women build profitable businesses with more clarity, confidence, and visibility. Through Angelica Pompy Education, she teaches money making marketing strategies, better systems, and simple sales that help women grow without losing their mind, time, or magic. She's also the founder of Pompy Portraits, a Jacksonville-based photography studio specializing in bold boudoir photography. Whether she's coaching clients, speaking on stages, or behind the camera, Angelica is known for her bold energy, no-fluff approach, and passion for helping women show up unapologetically in life and business. >CONNECT WITH ANGELICA Website: https://www.angelicapompy.com Instagram & Threads: https://instagram.com/angelicapompy Grab Angelica's resource Angelica's Instagram Secret walks you through how she turns Instagram conversations into paying clients without a sales call. https://angelicapompy.com/instagram-secret >Introducing wAIv This episode is brought to you by wAIv—our brand-new platform built for online experts who want to securely build and sell AI tools powered by YOUR thinking, YOUR frameworks and YOUR methodology. wAIv helps you create Bot Squads—a suite of AI tools that work together to help your clients implement your expertise faster and with better results than ever before. >Your Next Steps: See what an AI tool built on your expertise actually looks like. Explore wAIv: https://graviastudio.com/waiv Train AI to sound like you (in under 2 hours) with BrandCalibrator™: https://ksco.ca/brandcalibrator/ Follow our new Instagram account @joinwaiv: https://instagram.com/joinwaiv >Thanks for Listening! If you enjoyed this episode, please help us share it by: ⭐ Following the show—this helps you stay updated and supports us! ⭐ Leaving a positive review—this boosts our ranking and helps more entrepreneurs find the podcast. -------------------------- Entrepreneur School is proud to be featured on the Feedspot list of 30 Best Canada CEO Podcasts! https://blog.feedspot.com/canada ceo podcasts/

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  Episode #188

  Why Your Affiliates Go Quiet and How AI Fixes It

  Aug 11, 202644 minS1

  If you host collaborations or work with affiliate partners, you know the drill. You build the swipe file, you send the Drive link, and half the people who said yes never actually promote. Dr. Destini Copp fixed that. She has Claude read a partner's own emails and website, learn how that person writes, then build them a personalized page in their voice with their coupon code and copy they can paste in as-is. One affiliate used just the PS and made six sales. This isn't an AI-for-speed story. It's AI used to make something more personal than she could have made it by hand, which is a use case almost nobody's talking about. What you'll learn: The affiliate setup that turns a "hard no" ask into an easy yes Why she built the first page manually and never had to build another How to use AI for customization instead of volume The anatomy of a free event that brings in $30k to $50k Where an AI power user still insists on a human, every time CHAPTERS 01:15 Two businesses, a full time job, and AI 04:27 The affiliate page that changed everything 09:43 Six sales from a single PS 11:04 What she was doing before this 14:20 The Claude skill that builds the whole package 19:30 How free events pay contributors twice 24:49 Where the revenue lift actually showed up 29:32 Inside the $37 to $50,000 funnel 32:11 The one job she won't give to AI 34:48 The 1% better rule >MEET DESTINI Dr. Destini Copp is a digital product strategist, MBA professor, and host of the Creator's MBA Show. She's the founder of two brands, HobbyScool and Creator's MBA where she helps digital product business owners build predictable revenue using her Creator Growth Flywheel framework. She's spent 25+ years in marketing and 7+ years running her own digital product businesses, and has taught more than 12,000 students. Her focus now: using AI to run lean while protecting the human judgment AI can't replace. >CONNECT WITH DESTINI Website: https://www.destinicopp.com/ Instagram & Threads: https://www.instagram.com/destinicopp Podcast: Creator's MBA Show Skool community: Creator’s MBA Boardroom >>Grab Destini's resource Destini's giving away Creator's Daily Focus, a free Claude skill that runs every morning and tells you the one thing to work on to actually move your business, plus what to skip. https://lab.destinicopp.com/daily-focus >Introducing wAIv This episode is brought to you by wAIv—our brand-new platform built for online experts who want to securely build and sell AI tools powered by YOUR thinking, YOUR frameworks and YOUR methodology. wAIv helps you create Bot Squads—a suite of AI tools that work together to help your clients implement your expertise faster and with better results than ever before. >Your Next Steps: See what an AI tool built on your expertise actually looks like. Explore wAIv: https://graviastudio.com/waiv Discover what AI tool you can build and sell by going through the AI Product Playbook: https://graviastudio.com/playbook Follow our new Instagram account @joinwaiv: https://instagram.com/joinwaiv >Thanks for Listening! If you enjoyed this episode, please help us share it by: ⭐ Following the show—this helps you stay updated and supports us! ⭐ Leaving a positive review—this boosts our ranking and helps more entrepreneurs find the podcast. -------------------------- Entrepreneur School is proud to be featured on the Feedspot list of 30 Best Canada CEO Podcasts! https://blog.feedspot.com/canada ceo podcasts/

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