Entrepreneur School (In the AI Era)

Kelly Sinclair
  • 5.0 (20)
  • Entrepreneurship
  • Updated Weekly

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.

  1. 3d ago

    The Hidden Cost Inside Your AI Tool

    Every time someone uses an AI tool you built, somebody pays for it. If you sell courses, programs, memberships or templates and you're thinking about putting AI inside them, this episode gives you five questions to answer before you do. After our live AI Product Build Lab, the same pricing questions kept coming up, and we made some big pricing decisions at wAIv that week. I walk through the questions I asked myself, starting with the cost most creators never see: custom GPTs hid it, and a tool people access directly puts it on you. The bigger question for you: if AI is part of what you deliver, have you decided what it costs, or is it just happening? The 5 questions to ask before you sell AI: How long should someone have access to your offer?Can a low-ticket offer cover its own AI usage?What happens when the access window ends?Which of your offers need AI inside them at all?What happens when your heavy users show up? Also in this episode: Why your custom GPT felt free and your next tool won'tThe utility meter running behind every AI toolHow wAIv pricing ties to your growth CHAPTERS 00:50 Somebody pays for every AI tool 02:30 What it means to be the tech engine 04:20 Inference cost in plain English 05:05 Why your custom GPT felt free 06:45 Question 1: how long should access last 09:20 Question 2: can a low-ticket offer carry AI 10:55 What we landed on for wAIv 12:45 Questions 3 to 5: before you build 14:05 Decide on purpose >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: Come build one live. Get into the AI Product Build Lab for a dollar 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 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/canadaceopodcasts/

    The Hidden Cost Inside Your AI Tool

  2. Oct 13

    Stop Dickin’ Around with Your Messaging

    If you're letting AI write your emails, posts and sales pages and wondering why nothing's landing, this one's for you. Jen Liddy is a messaging diagnostician and former English teacher. She's spent years helping experts find their voice, and she's watched AI change how her clients write. We talk about why you need to know your own voice before you can push back on a robot. We also cover why she stopped building $6,000 messaging guides and the signs that your messaging is the real problem. The bigger question for you: can you say what you want to say before you ask AI to say it for you? WHAT YOU'LL LEARN: Why AI copy sounds "pretty good" to you and flat to everyone elseJen's "say it ugly" rule for getting to your real messageHow she uses AI to break her own bad writing habitsThe signs your messaging is the problem, before you blame your logo, offers or pricingWhy your audience needs specifics now, and why feelings alone won't landWhere to start when a full messaging overhaul feels like too much CHAPTERS 01:35 The bio that says what it means 03:39 The hill Jen will die on with AI 07:03 You have to be able to validate the output 10:58 When AI beats saying nothing at all 12:15 The therapist who stopped trusting her voice 16:50 Say it ugly, then make it better 18:16 Using AI to break your own bad habits 24:26 Why she stopped selling $6,000 messaging guides 29:31 How to know you have a messaging problem 34:11 Start with your website header >MEET JENCONNECT WITH JENIntroducing 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 first protected AI product. Join the AI Product Build Lab for just $1 with code PODCAST1: https://graviastudio.com/build/?code=PODCAST1&price=1 See what an AI tool built on your expertise actually looks like. Explore wAIv: https://graviastudio.com/waiv >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/canadaceopodcasts/

    Stop Dickin’ Around with Your Messaging

  3. Oct 6

    This AI Tool Led to a 28% Conversion Rate in 24 Hours

    If you run a membership, course or coaching program and want AI to help your clients actually implement, this one's for you. Nadine Nethery, a customer experience and retention strategist, joined me to walk through the AI tools she's built into her membership and workshops. She shared three of them. The first is a survey builder that packages 10 years of her framework. The second powered an interactive workshop that converted 28% of live attendees within 24 hours. The third is a roadmap builder that gets new members committed to a six-month plan on day one. The bigger question for you: where could an AI tool clear the friction that stops your clients from doing the work, and where do you want your own perspective front and centre? WHAT YOU'LL LEARN: Why a ChatGPT-built customer avatar makes a risky foundation for your marketingHow Nadine turned a done-for-you service into a tool her members run themselvesThe workshop format that had attendees diagnosing their own gap live, then buyingThe virtual scratchie card idea for adding loyalty rewards without a full rewards programWhy course sales are slowing and what Nadine's turning hers intoHow to decide where AI should touch your business first CHAPTERS 00:00 AI that puts more of you into your programs 04:19 A survey builder trained on 10 years of frameworks 07:21 The danger of ChatGPT-made customer avatars 10:14 The webinar that converted 28% in 24 hours 12:37 Loyalty gaps and the virtual scratchie card 15:09 Protein, macros and the objection AI erases 19:14 The roadmap builder that kills overwhelm 21:35 Why course sales are slowing down 23:06 Courses teach thinking, AI tools apply it 30:12 Why she built for clients before the back end >MEET NADINECONNECT WITH NADINEIntroducing 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 first protected AI product. Join the AI Product Build Lab for just $1 with code PODCAST1: https://graviastudio.com/build/?code=PODCAST1&price=1 See what an AI tool built on your expertise actually looks like. Explore wAIv: https://graviastudio.com/waiv >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/canadaceopodcasts/

    This AI Tool Led to a 28% Conversion Rate in 24 Hours

  4. Sep 29

    Goodbye Custom GPTs. What’s next?

    This episode is the practical guide to planning your Custom GPT migration. Your custom GPTs have a deadline. Your IP shouldn't be the thing you give up to meet it. OpenAI is retiring custom GPTs, and enterprise workspaces lose theirs on December 11. If you built GPTs for your clients or your audience, you need a plan, and the most popular option right now asks you to hand over everything inside them. What you'll learn: The three piles to sort your GPTs intoWhat to do with internal versus free or paid custom GPTsWhat to tell your paying clients before December (even if you haven't decided yet)What someone gets when you hand them a skill file, and why that matters for your paid programsWhat hosting a free bot costs, and when it's worth it CHAPTERS 01:07 The decision you need to make before December 11 01:44 Where custom GPTs started and what frustrated me 03:07 What OpenAI just announced 04:15 Sort your GPTs into three piles 05:53 What to do with paid program GPTs 07:09 What you hand over with a skill file 08:50 Why your IP still matters 10:15 The mixing problem nobody's talking about 13:45 AI options for your free GPTs 16:29 Where wAIv fits Resources mentioned: OpenAI's custom GPT retirement FAQ: https://help.openai.com/en/articles/20001519-custom-gpt-retirement-and-migration-faq Email me: kelly@graviastudio.com >>Your Next Steps: Bring your custom GPT to the AI Product Build Lab on October 8. Get your seat for $1 with code PODCAST1, plus a free two-week wAIv trial: https://graviastudio.com/build/ See what an AI tool built on your expertise looks like. Explore wAIv: https://graviastudio.com/waiv Follow our new Instagram account @joinwaiv: https://instagram.com/joinwaiv >>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. >>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/canadaceopodcasts/

    Goodbye Custom GPTs. What’s next?

  5. Sep 22

    The Marketing Strategy AI Can't Build for You

    AI doesn't fix a broken marketing strategy. It just breaks it faster. Laura Kendrick and I have been having low-key debates about AI for two years inside a business group we're both in, so I finally just put her on the mic and asked her what hill she'd die on. Her answer was immediate. AI is a genuinely powerful tool with real limits, and it can expand your brand voice and your strategy but it can never build them. What you'll learn: The exact point where an AI-built brand book stops serving you, and what to do when you hit itWhy validating AI output is the whole job, and how to do it when you're the only expert in the roomThe research AI physically cannot do for you, no matter how good your prompts getHow to decide whether a platform deserves you at all, including the uncomfortable Instagram question CHAPTERS 02:02 The hill she'll die on about AI 03:10 Where the AI brand book falls apart 04:30 AI only knows the inner emotions wheel 05:56 Validating output when you're the expert 10:38 The research AI can't go get 13:44 The signals you need to stop and strategize 18:10 Great tactics with nothing connecting them 22:48 A strategy that starts with the founder 28:30 The $7.5 million Instagram story 37:30 Plan it like it's your own wedding Laura Kendrick is an online marketing strategist and the founder of Cheeky Copy. After six years writing copy and building brand voice for online business owners, she now teaches established coaches, course creators, and service providers how to turn scattered marketing into a smarter, more connected strategy that actually leads to sales. Her core belief: you don't need more marketing, you need a better plan. >CONNECT WITH LAURA>Grab Laura's resource Laura made a private podcast called Welcome In, all about folding humanness, hospitality and real care into your marketing whether you're operating at scale or keeping it small. https://cheekycopy.co/welcome-in >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/canadaceopodcasts/

    The Marketing Strategy AI Can't Build for You

  6. Sep 15

    The AI Test Every Course Creator Should Run

    I got pitched by a bot. Then I put the guy on my show. Craig Shoemaker's research agent found my podcast, figured out who I talk to and why he'd be a fit, and handed him the shortlist. Then Craig wrote the email himself. That distinction is the whole episode. He coaches education entrepreneurs, which is my people under a different name, and he's spent 25 years in big tech and 15 as a course creator. So when he says AI has changed this industry forever and also that you shouldn't burn your business down over it, he's earned both halves of that sentence. We got into the seductive part of AI, the part where you feel invincible and start shipping things you haven't thought through. Guilty. My own audit told me my build muscle was strong and my ship muscle wasn't. Craig got the identical result, which made me feel a lot better. The part that stuck with me most was his gotcha moment. If you're the kind of person who listens to a podcast about AI, you're further ahead than you think. WHAT YOU'LL LEARN: Why the value of information dropped and what took its placeThe advisor agent that started calling Craig out on his own patternsHow to run the test that shows you exactly where AI can and can't replace what you teachWhy your customers still aren't asking Claude the thing you're afraid they're askingWhat hundreds of coaching call transcripts can tell you about your ICP that a blank worksheet never willThe difference between scrappy validation and shipping your flagship half-baked CHAPTERS 01:50 Who education entrepreneurs actually are 03:13 What AI has done to this industry so far 05:20 Confidently off in the wrong direction 07:16 The agent that called him out 10:40 Strong build muscle, weak ship muscle 14:09 The Own Your AI Gap assessment 16:20 The gotcha moment nobody mentions 21:10 Hundreds of transcripts beat a blank page 27:28 The niche AI couldn't touch 33:08 Actual intelligence >MEET CRAIGCONNECT WITH CRAIGIntroducing 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/canadaceopodcasts/

    The AI Test Every Course Creator Should Run

  7. Sep 8

    The AI Opportunity Most Experts Are Missing

    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 AIWhy online courses can teach people how to think, but AI tools let them use your thinkingThe security and access problem creators encounter when sharing custom GPT linksHow Bot Squads combine custom AI tools, shared context and orchestrated workflowsWhy “give away your best stuff” deserves another look in the AI eraHow 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 ELLENIntroducing 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/canadaceopodcasts/

    The AI Opportunity Most Experts Are Missing

  8. Sep 1

    Coaches Need to Know This About AI

    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 climbingThe $7,500 program that showed her experts know what they know but can't teach itWhat her clients are replacing workbooks and calculators withThe one thing she says AI can't be coded withHow to talk about AI use with clients who have friction around itThe 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 JASMINECONNECT WITH JASMINEIntroducing 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/canadaceopodcasts/

    Coaches Need to Know This About AI
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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.

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