Entrepreneur School (In the AI Era)

Kelly Sinclair
  • 5.0 (20)
  • Entrepreneurship
  • 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. 2d ago

    200 Episodes Later: The Business I Never Saw Coming

    This one's for you if you've been building something for a few years and you keep measuring it against numbers that never feel like enough. I recorded episode 200 and almost didn't mark the occasion. Before I hit record I went looking for the stats: just about 22,000 downloads, over 100 guests, almost four years of weekly episodes. My first instinct was that it wasn't enough. So I used the episode to look at what's actually changed. The show started as a place to talk about building a life-first business as a parent and an entrepreneur. That goal hasn't moved. Everything about how I'm chasing it has. I went from brand and visibility work to co-founding an AI company, and I still walk my kids to school, which was my definition of success from day one. I also tell the story of a cold guest pitch I'd normally have passed on, the episode it became, and how the momentum from it ended with me on stage at the Ryman in Nashville. The bigger question underneath all of it: what are you measuring, and is it the thing you actually said you wanted? We'll get into: Why the download number is the wrong first question to ask about your own workHow a goal can hold completely still while the method changes beyond recognitionWhat I was navigating when I started this show that nobody was talking aboutThe cold pitch I almost deleted and where it took meWhy "monetize your podcast" was never the point for meWhat I'd tell you about starting something before you know where it ends MENTIONED IN THIS EPISODE Episode 49, Redefining Success with Multimillionaire Keaton Hoskins: https://entrepreneurschool.ca/captivate-podcast/redefining-success-with-multimillionare-keaton-hoskins/AmplifYou, the team who produces this show: https://amplifyou.com/The AI Product Build Lab: 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: 🤖 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/

    200 Episodes Later: The Business I Never Saw Coming

  2. Oct 27

    I Don’t Sell AI Skills. Here’s Why

    I don’t sell AI skills. Sometimes, I wish other people would stop selling them. Skills are easy to install, people seem to be buying them and it can feel like you need to make one to keep up. But what if the method inside that downloadable file is the very thing that makes your work valuable? I’ve built more than 60 skills to run processes in my own business. In this episode, I explain why I don’t sell those proprietary processes as skill files, how I’ve found a different role for skills in my customer journey and why the environment where a client uses your tool matters as much as the instructions you wrote. This is a nuanced business decision. Some experts are comfortable sharing their methods, and I welcome that perspective. I want you to consider your own IP, the result you promise and whether a downloadable tool will still serve your client as your field changes. We’ll get into: What a skill file contains and what someone can inspectWhy an expert’s learned method is valuable in the AI eraThe context you cannot control when a skill runs in a client’s AI environmentMy “recon skills” approach: help people see an opportunity without giving away my entire methodWhy an installed skill is a snapshot that you cannot update for that buyerWhen a bot squad and ongoing access may fit the result betterQuestions to ask before you build or buy a skill CHAPTERS 00:00 My controversial opinion on selling AI skills 01:02 What a skill file is 02:11 Why protecting expert IP matters to me 04:10 The pressure to build what seems to be selling 05:38 Will the skill deliver a good client result? 06:05 The AI environment you cannot control 08:22 A collaboration that made me rethink skills 10:19 How my “recon skills” work 13:17 A skill as the first step 14:02 Why a downloaded skill gets out of date 16:01 Questions for creators and buyers MENTIONED IN THIS EPISODE The AI Product Build Lab:https://graviastudio.com/build/?code=PODCAST1wAIv:https://graviastudio.comEpisode 198 on the ongoing cost of AI tools:https://entrepreneurschool.ca/captivate-podcast/198 >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/

    I Don’t Sell AI Skills. Here’s Why

  3. Oct 20

    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

  4. 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

  5. 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

  6. 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?

  7. 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

  8. 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
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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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