Couverture de Entrepreneur School (In the AI Era)

Entrepreneur School (In the AI Era)

Entrepreneur School (In the AI Era)

De : 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 Direction Economie Management et direction Marketing et ventes Parentalité Relations
Épisodes
  • I Don’t Sell AI Skills. Here’s Why
    Oct 27 2026

    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 inspect
    • Why an expert’s learned method is valuable in the AI era
    • The context you cannot control when a skill runs in a client’s AI environment
    • My “recon skills” approach: help people see an opportunity without giving away my entire method
    • Why an installed skill is a snapshot that you cannot update for that buyer
    • When a bot squad and ongoing access may fit the result better
    • Questions 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=PODCAST1
    • wAIv:https://graviastudio.com
    • Episode 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/

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    20 min
  • The hidden cost inside your AI tool
    Oct 20 2026

    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't
    • The utility meter running behind every AI tool
    • How wAIv pricing ties to your growth

    CHAPTERS

    0:00 Somebody pays for every AI tool

    1:40 What it means to be the tech engine

    3:23 Inference cost in plain English

    4:09 Why your custom GPT felt free

    6:13 Question 1: how long should access last

    8:27 Question 2: can a low-ticket offer carry AI

    10:29 What we landed on for wAIv

    12:00 Questions 3 to 5: before you build

    13:10 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/

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    17 min
  • Stop Dickin’ Around with Your Messaging
    Oct 13 2026

    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 else
    • Jen's "say it ugly" rule for getting to your real message
    • How she uses AI to break her own bad writing habits
    • The signs your messaging is the problem, before you blame your logo, offers or pricing
    • Why your audience needs specifics now, and why feelings alone won't land
    • Where 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 JEN<<

    Jen Liddy helps course creators, coaches and expertise-based entrepreneurs stop dickin' around with their messaging, so they get it right whether they're using AI to help them write or not. After watching AI change how her clients approached their own brand voice and messaging, she shifted her focus to messaging diagnostics. Now she shows people how to find the gaps in their messaging that no amount of bot training can fix.

    >CONNECT WITH JEN<<

    Website: https://jenliddy.com

    Instagram: https://instagram.com/heyjenliddy

    Grab Jen's resource

    Why You're Getting Seen But Not Chosen is a private podcast that runs under 20 minutes. It covers how to evolve your messaging so all that visibility work actually lands. It also includes a self-audit of your messaging patterns and an AI writing checklist you can give your favourite robot so it calls you out when you slip: https://jenliddy.com/evolve

    >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 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/

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    41 min
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