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This podcast is available on 10 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.

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No, this podcast does not typically feature guests.

Entrepreneur School

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by Kelly Sinclair

5.0(34 reviews)

187 episodes

Updated Daily

Accepts GuestsHas SponsorsLocation 🇨🇦

Podcast Authority

Beta

GoodBased on show quality, social media presence, reviews, charts, and more

Quality79

Social94

YouTube68

Engagement77

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Podcast Overview

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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Publishing Since

1/14/2023

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🇺🇸 Charts #3

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Spotify 827

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Podcast Authority

Beta

GoodBased on show quality, social media presence, reviews, charts, and more

Quality79

Social94

YouTube68

Engagement77

Learn more

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Recent Episodes

July 28, 2026

Are you accidentally giving your IP away to AI?

Holly Haynes built seventeen AI bots for her signature program. Then she almost didn't share them.Here's what stopped her. When you package your expertise into a shareable AI skill, you have to hand over everything inside it. The transcripts. The client Q&As. The framework you spent years refining. Holly had poured all of Anti-Social School into hers, and when it came time to pass it to a client, she got nervous. Not because she was hiding anything, but because she knew exactly what it was worth.That's the conversation I wanted to have with her. Holly's a business strategist with a corporate tech background who's now baking years of experience into AI tools her clients actually use. She's one of our founding creators at wAIv, and she's doing the thing I think most expertise-based businesses are going to have to figure out.How do you use AI to get your clients better results without giving away the thing that makes you valuable, and without turning your program into a course full of videos nobody watches.What I love about her answer is how unglamorous it is. Her bots don't replace her. They handle the blank page so her clients show up to calls with ten options instead of "I don't know where to start." WHAT YOU'LL LEARN:<ul><li>Why "micro" is the whole trick with AI tools, and what happens when you ask one bot to do too much</li><li>The IP problem hiding inside every AI skill you share, and what it actually costs you</li><li>How Holly's clients get through homework faster and go deeper on calls because of it</li><li>Why a structured input beats a rich chat history, and what that means for your brand context</li><li>How to decide what AI belongs in your business without doing everything on day one</li></ul> >MEET HOLLY<<Holly Haynes helps women build businesses that fit their real lives, without the pressure to post daily or hustle 24/7. A former Fortune 500 strategist, she grew her company while working full-time and raising twins, then retired herself and her husband in under two years. She's the founder of Anti-Social School™, host of the top 100 Crush the Rush™ podcast, and creator of systems that have helped thousands of women grow without the scroll. >CONNECT WITH HOLLY<<Website: <a href="https://www.hollymariehaynes.com" rel="noopener noreferrer" target="_blank">https://www.hollymariehaynes.com</a>Instagram & Threads: <a href="https://instagram.com/thehollymariehaynes" rel="noopener noreferrer" target="_blank">https://instagram.com/thehollymariehaynes</a>Podcast: Crush the Rush >GRAB HOLLY'S RESOURCE<Holly runs a private podcast called The Anti-Social Shift that goes behind the scenes on how she built her bot squad and why. There's a full episode in there on how she leverages the bots to scale both her clients' companies and her own, so if this conversation made you want to see the mechanics, that's where they are.<a href="https://www.hollymariehaynes.com/shift" rel="noopener noreferrer" target="_blank">https://www.hollymariehaynes.com/shift</a> >Introducing wAIvThis 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: See what an AI tool built on your expertise actually looks like. Explore wAIv: <a href="https://graviastudio.com/waiv" rel="noopener noreferrer" target="_blank">https://graviastudio.com/waiv</a><img role="img" class="emoji" alt="🤖" src="https://s.w.org/images/core/emoji/17.0.2/svg/1f916.svg"> Train AI to sound like you (in under 2 hours) with BrandCalibrator™: <a href="https://ksco.ca/brandcalibrator/" rel="noopener noreferrer" target="_blank">https://ksco.ca/brandcalibrator/</a>Follow our new Instagram account <a href="https://instagram.com/joinwaiv" rel="noopener noreferrer" target="_blank">@joinwaiv</a>: <a href="https://instagram.com/joinwaiv" rel="noopener noreferrer" target="_blank">https://instagram.com/joinwaiv</a> >Thanks for Listening!If you enjoyed this episode, please help us share it by:<img role="img" class="emoji" alt="⭐" src="https://s.w.org/images/core/emoji/17.0.2/svg/2b50.svg"> Following the show—this helps you stay updated and supports us!<img role="img" class="emoji" alt="⭐" src="https://s.w.org/images/core/emoji/17.0.2/svg/2b50.svg"> 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! <a href="https://blog.feedspot.com/canadaceopodcasts/" rel="noopener noreferrer" target="_blank">https://blog.feedspot.com/canada</a><a href="https://blog.feedspot.com/canadaceopodcasts/" rel="noopener noreferrer" target="_blank">ceo</a><a href="https://blog.feedspot.com/canadaceopodcasts/" rel="noopener noreferrer" target="_blank">podcasts/</a>

July 21, 2026

Are You Actually Ready to Sell AI Products?

Host [Host Name] guides listeners through five readiness markers to determine if they are truly prepared to build and sell AI products to clients.

July 14, 2026

AI commoditized information. Sell this instead.

Host [Host Name] interviews [Guest Name] about leveraging expert-backed AI to sell unique knowledge in an information-saturated market.

187 total episodes available with 29 transcripts

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What is Entrepreneur School?: 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.
How often does this podcast release new episodes?: This podcast updates daily.
Where can I listen to this podcast?: This podcast is available on 10 platforms including Apple Podcasts, Spotify, and more. You can also use the RSS feed directly.
Does this podcast accept guests?: No, this podcast does not typically feature guests.

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