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14:02 Why a downloaded skill gets out of date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/

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/

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/

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 into
• What to do with internal versus free or paid custom GPTs
• What 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 programs
• What 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/

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 it
• Why validating AI output is the whole job, and how to do it when you're the only expert in the room
• The research AI physically cannot do for you, no matter how good your prompts get
• How to decide whether a platform deserves you at all, including the uncomfortable Instagram question

CHAPTERS

0:00 The hill she'll die on about AI

2:23 Where the AI brand book falls apart

4:08 AI only knows the inner emotions wheel

5:15 Validating output when you're the expert

9:36 The research AI can't go get

12:52 The signals you need to stop and strategize

17:03 Great tactics with nothing connecting them

21:38 A strategy that starts with the founder

27:35 The $7.5 million Instagram story

33:58 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<<

Website: https://www.cheekycopy.co

Instagram & Threads: https://www.instagram.com/cheekycopy

>>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/

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 place
• The advisor agent that started calling Craig out on his own patterns
• How to run the test that shows you exactly where AI can and can't replace what you teach
• Why your customers still aren't asking Claude the thing you're afraid they're asking
• What hundreds of coaching call transcripts can tell you about your ICP that a blank worksheet never will
• The 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 CRAIG<<

Craig Shoemaker is a coach who works with education entrepreneurs to scale their business by exposing the blind spots that sit at the foot of growth. With over 15 years as a course creator and 25 years in big tech, Craig lives at the intersection of AI and online education business.

>CONNECT WITH CRAIG<<

Website: https://craigshoemaker.net

GRAB CRAIG'S RESOURCE

Craig built the Own Your AI Gap assessment to answer the question most experts are avoiding. You take a short quiz based on how you actually work with clients and what you sell, and it shows you how exposed your business is to AI. Then it walks you through having the model teach what you teach, so you can see where it holds up and where it falls apart. He's set up a landing page with everything we talked about in this episode.

https://craigshoemaker.net/r/es-school/

>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/

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/canadaceopodcasts/