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Entrepreneur School (In the AI Era)

Entrepreneur School (In the AI Era)

By: Kelly Sinclair
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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.Copyright 2026 Kelly Sinclair Economics Leadership Management & Leadership Marketing Marketing & Sales Parenting & Families Relationships
Episodes
  • Coaches Need to Know This About AI

    Coaches Need to Know This About AI
    Sep 1 2026
    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 modelCHAPTERS01:05 Meet Jasmine Jonte02:05 From Teacher to Agency03:52 AI Raises the Bar06:58 New Client Expectations09:00 Beyond Information Dumps12:03 Personalization at Scale15:08 How Much AI to Use17:23 Positioning and Disclosure22:53 Case Studies in Action28:02 Make Results Easy29:28 Where to Connect>MEET JASMINEYour 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=PODCAST1See what an AI tool built on your expertise actually looks like. Explore wAIv: https://graviastudio.com/waivFollow 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/
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    32 mins
  • OpenAI Just Cancelled Custom GPT Building. What This Means

    OpenAI Just Cancelled Custom GPT Building. What This Means
    Aug 25 2026

    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/canadaceopodcasts/
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    18 mins
  • Is ManyChat Killing Your Sales?

    Is ManyChat Killing Your Sales?
    Aug 18 2026
    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 salesWhy a $3,400 offer can close faster in the DMs than through a full email sequenceThe follow-up gap that makes you think nobody's interested when they actually wereHow Angelica labels and tracks leads in Instagram, and why that system breaks after 30 daysHer three-post rotation and why she never sells in every postWhat "success" on social actually looks like when a viral post isn't the goalCHAPTERS02:30 The ManyChat plot twist03:38 When ManyChat actually earns its place04:13 The New York event she refused to automate06:05 A $3,400 VIP day closed in the DMs06:56 The follow-up that lost her sale09:24 Labelling leads before they disappear12:11 The video message that got an instant yes17:18 Where 65% of her revenue comes from20:41 Building a lead system the algorithm can't erase27:56 The three post rotation she teaches>MEET ANGELICAYour 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/canadaceopodcasts/
    Show More Show Less
    33 mins
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