Entrepreneur School (In the AI Era)

Kelly Sinclair
  • 5.0 (20)
  • ENTREPRENEURSHIP
  • UPDATED 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. [Encore] Expert-Backed AI Is the New Online Course

    6D AGO

    [Encore] Expert-Backed AI Is the New Online Course

    We're living through another gold rush moment in the online space, and most people don't even realize it yet. Between 2019 and 2021, the online course market exploded from $45 billion to $165 billion. Early movers captured 70% of that market just by being first. But by 2022? The market hit saturation. Course completion rates dropped to 20%. Content fatigue set in. And honestly? I've got my own course graveyard collecting dust on Google Drive. (I know I'm not alone!) But here's what's happening now: Expert-backed AI is creating an entirely new category and it's not just a trend. It's a fundamental shift in how we deliver transformation. In this episode, I'm breaking down what expert-backed AI actually is, why it's different from just using ChatGPT, and how it's changing the monetization game for coaches, course creators, and service providers. This isn't about replacing you. It's about extending your brain into tools your clients can access 24/7 so they get faster results, you have deeper conversations, and everyone wins. In this episode, you'll learn: Why expert-backed AI is NOT the same as a generic large language modelThe shocking stats behind the online course boom—and bustHow AI completion rates are 3–5x higher than traditional coursesWhy "time to first result" has dropped from 4–6 weeks to 2–5 daysThe difference between teaching people how to think vs. letting them use your thinkingHow supplementary AI tools are elevating coaching sessions (not replacing them)Why your old worksheets should probably become interactive botsWhat the $50 billion AI Education Tools Market means for creators in 2025How to pair your expertise with AI without losing the human touchA sneak peek at Project Vault and what we're building for expert-backed AI monetization The Big Idea: Courses teach others how to think. Expert-backed AI tools allow others to use your thinking. It's like having a little clone of you—or a brain extension—that your clients can access whenever they want. And that? That's a game-changer for implementation, impact and income. >>Your Next Steps:🤖See what an AI tool built on your expertise actually looks like. Explore wAIv 🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™ Follow our new Instagram account @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!

    24 min
  2. We launched a new AI platform!

    APR 21

    We launched a new AI platform!

    Okay, I'm finally spilling it. After months of being *annoyingly* coy about "the platform," I can officially tell you what Andrew and I have been building—and what it's called. Meet wAIv (yes, spelled like that—lowercase w, capital AI, lowercase v). It's an AI platform designed to help expert creators like you build, protect, and *monetize* your knowledge through custom AI tools we call bot squads. In this episode, I'm taking you behind the scenes of our launch—how we named the company (pizza + whiteboards were involved), why we're doing this, and what makes wAIv different from anything else out there. I'll also share: The origin story of wAIv and Gravia Studio (and why naming a company is WAY harder than it should be)What a "bot squad" actually is—and why it's like a custom GPT, Claude skill, and workflow all rolled into oneHow we're protecting creator IP in a world where people are already feeding your worksheets into ChatGPT (yep, it's happening)Why we believe in *human-first AI adoption*—and what that means for your businessA sneak peek at our beta program and how creators are already rethinking their entire delivery modelsHow you can try the **AI Tool Launch Playbook** and experience what wAIv does firsthand This isn't just another AI tool. It's a philosophy shift. It's about enhancing your expertise, not replacing it. It's about helping your clients get results faster while deepening the work you do together. If you're a coach, course creator, or consultant who's ever thought, "I wish my clients could access my brain when I'm not there," this episode is for you. >>Your Next Steps:🤖See what an AI tool built on your expertise actually looks like. Explore wAIv 🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™ Follow our new Instagram account @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!

    25 min
  3. How to Stay Grounded When AI Is Moving Faster Than You Can Process

    APR 7

    How to Stay Grounded When AI Is Moving Faster Than You Can Process

    I didn't sleep last night. My brain wouldn't shut off—and it wasn't my kids, my snoring husband, or even my senior dog waking me up at 2 a.m. It was the relentless pace of AI news, the fear of falling behind, and the pressure of building in this space while trying to make sense of it all. So I figured if I'm feeling it, you probably are too. In this episode, I'm getting real about what it actually feels like to be a business owner right now—when AI is moving faster than most of us can process, when the headlines are loud, and when you're trying to figure out what actually matters versus what's just noise. I'm sharing: How to filter out the AI noise without missing what's actually importantThe difference between excitement and overwhelm—and how to move forward with intention instead of panicWhy chasing every shiny object means building nothing sustainableMy own struggle with staying focused while building a platform in the AI space (spoiler: I'm figuring it out in real time too)The mantra that's keeping me sane: What am I protecting? What am I building toward? What's one step forward right now?A sneak peek at our platform reveal happening April 16th (and why I'm nervous and excited in equal measure) If you've ever felt that low-level hum of "Am I keeping up? Is this going to change everything? What am I even supposed to do with this?"—this episode is for you. Because here's the truth: Your expertise is real. Your relationships with your clients are real. And the value you create is real. AI doesn't change that. It just changes how you deliver it, scale it, and protect your time while doing it. So let's take a breath together and figure out how to move forward with clarity instead of chaos. >>Your next steps📋Get on the waitlist for our new platform 🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™ 🔹Check out my Interactive AI Starter Kit to see how worksheets can become bots 🔹Let’s talk Bots for your business! Book a coffee chat 🔹 Connect on Instagram >>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!

    19 min
  4. Why Your Human Work is Now More Valuable than Ever

    MAR 31

    Why Your Human Work is Now More Valuable than Ever

    Today, I sat down with Prerna Malik, an AI strategist, sales expert, and conversion copywriter behind multiple seven-figure launches for clients like Pat Flynn, Amy Porterfield, and Copyhackers. Prerna is co-founder of Content Bistro (soon to be Profitably Yours), and she blends AI, buyer psychology, and conversion science to help entrepreneurs build people-first, profit-rich sales systems. This conversation is a masterclass in using AI intentionally and keeping the "you" in your business. In this episode, you'll discover: The two things Prerna will never let AI do—and why her boundaries might surprise you (especially if you think AI can do "everything")How to know if your AI output is actually good enough to send—hint: it's not about the tool, it's about what you know before you hit generateWhy people are paying more for certain kinds of tools right now—and what that means for how you position your expertise in an AI-saturated marketThe sneaky way Prerna stress-tests her copy before it goes live—and how it's saved launches from floppingThe question every entrepreneur needs to ask before using AI for anything—because "faster" doesn't always mean "better"Why some clients are still paying full price for human-written copy—and what that tells us about where this is all headingThe one thing that makes an AI tool worth buying—and it's not the tech itself >>CONNECT WITH PRERNA>Your next steps📋Get on the waitlist for our new platform 🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™ 🔹Check out my Interactive AI Starter Kit to see how worksheets can become bots 🔹Let’s talk Bots for your business! Book a coffee chat 🔹 Connect on Instagram >>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!

    34 min
  5. Expert-Backed AI Is the New Online Course

    MAR 24

    Expert-Backed AI Is the New Online Course

    We're living through another gold rush moment in the online space, and most people don't even realize it yet. Between 2019 and 2021, the online course market exploded from $45 billion to $165 billion. Early movers captured 70% of that market just by being first. But by 2022? The market hit saturation. Course completion rates dropped to 20%. Content fatigue set in. And honestly? I've got my own course graveyard collecting dust on Google Drive. (I know I'm not alone!) But here's what's happening now: Expert-backed AI is creating an entirely new category and it's not just a trend. It's a fundamental shift in how we deliver transformation. In this episode, I'm breaking down what expert-backed AI actually is, why it's different from just using ChatGPT, and how it's changing the monetization game for coaches, course creators, and service providers. This isn't about replacing you. It's about extending your brain into tools your clients can access 24/7 so they get faster results, you have deeper conversations, and everyone wins. In this episode, you'll learn: Why expert-backed AI is NOT the same as a generic large language modelThe shocking stats behind the online course boom—and bustHow AI completion rates are 3–5x higher than traditional coursesWhy "time to first result" has dropped from 4–6 weeks to 2–5 daysThe difference between teaching people how to think vs. letting them use your thinkingHow supplementary AI tools are elevating coaching sessions (not replacing them)Why your old worksheets should probably become interactive botsWhat the $50 billion AI Education Tools Market means for creators in 2025How to pair your expertise with AI without losing the human touchA sneak peek at Project Vault and what we're building for expert-backed AI monetization The Big Idea: Courses teach others how to think. Expert-backed AI tools allow others to use your thinking. It's like having a little clone of you—or a brain extension—that your clients can access whenever they want. And that? That's a game-changer for implementation, impact and income. >>Your next steps📋Get on the waitlist for our new platform 🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™ 🔹Check out my Interactive AI Starter Kit to see how worksheets can become bots 🔹Let’s talk Bots for your business! Book a coffee chat 🔹 Connect on Instagram >>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!

    24 min
  6. The QuitGPT Movement: What It Means for Your Business

    MAR 17

    The QuitGPT Movement: What It Means for Your Business

    I couldn't stay silent on this one. If you've been watching the drama unfold between OpenAI, Anthropic, and the U.S. Department of Defense and seen the uprise in the #QuitGPT momevent… yeah, it's a lot. And if you're feeling stuck, confused, or even a little trapped by your AI tools right now? You're not alone. I think we need to talk about what's actually happening, what it means for online business owners like us, and what your real options are when it comes to using AI tools that align with your values. I'm not here to tell you what to think about the whole situation. I'm here to help you navigate what it means for your business—especially if you've been building custom GPTs or relying heavily on ChatGPT to run your content, your programs, or your client delivery. Here's what we're unpacking: A neutral recap of the OpenAI vs. Anthropic conflictWhy so many creators feel "trapped" by ChatGPT right now—and what's really keeping you thereWhat it actually takes to migrate from one AI platform to another (spoiler: it's way easier than you think)How I experimented with Claude this week—and what I learned about switching toolsWhy you DON'T need to port over 3 years of ChatGPT conversations to use a different model effectively I’m also announcing we are opening our waitlist for our AI Creator Platform (name to be released at launch). It’s a place where you can build AI bots and multi-agent squads, choose your own models (OpenAI, Claude, Gemini, Perplexity, and more), and share tools with clients without being locked into one provider. If you've been wrestling with this decision, feeling stuck, or just wanting more control over how you use AI in your business, this episode is for you. >> Mentioned in this Episode: New AI Creator Platform Waitlist (brought to you by my new company, Gravia Studio)The Artificial Intelligence Show Podcast. Catch up on the “Pentagon vs Anthropic” issue in episodes 200&201. >> Your Next Steps: 🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™ 🔹Let’s talk Bots for your business! Book a coffee chat 🔹 Connect on Instagram >>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!

    20 min
  7. How I Built a Marketing Team Out of Bots

    MAR 10

    How I Built a Marketing Team Out of Bots

    You've got AI tools that are more powerful than entire creative teams from a few years ago… and yet you're still doing manual labor. I'm talking about the endless copy-paste shuffle. The re-explaining your business to every new bot. The feeling that you're supposed to be the one stitching all your tools together when they should be working for you. If that hits home, this episode is for you. I'm introducing you to the Bot Squad—and no, it's not a metaphor or a productivity hack. It's a fundamentally different way of using AI where your tools actually collaborate instead of working in isolation. I walk you through: What a Bot Squad is and why it changes everythingThe frustration of using custom GPTs that don't talk to each other (hello, copy-paste hell)How I built my own "Pod Squad" to plan, promote, and produce my podcast—without losing contextWhy this matters for both your internal workflows and your client deliveryA real-time example of how I'm using this system to launch our new platform (yep, this episode was created WITH my Bot Squad) If you've been feeling like you're close to something powerful with AI but still doing too much heavy lifting, you're right. And you're exactly who we're building this for. This is recorded in real-time on March 5th, 2026, as we're heading into our beta launch. Translation: this tech is happening now, and I can't wait for you to see what becomes possible when AI stops being a collection of disconnected tools and starts being an actual system. 🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™ 🔹Let’s talk Bots for your business! Book a coffee chat 🔹 Connect on Instagram >>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!

    18 min
  8. The AI Shift That Changes How You Lead

    MAR 3

    The AI Shift That Changes How You Lead

    There's this moment in your AI journey when everything shifts.You stop thinking, "I should run this through AI," and start thinking, "How can I co-create with AI?" That shift—from AI as an assistant to AI as a collaborator—is your competitive advantage. It changes how you work, how you lead, and how you help your clients get better results. In this episode, I'm unpacking that exact moment of recognition. I'll walk you through what it looks like when you've made the shift, what it unlocks for you, and how you can help your clients make the same leap so they can truly leverage the tools you're building for them. I share a real example from my own week: building a launch marketing plan for our new platform (coming soon!). Old me? Would've opened a Google Doc and started writing goals, objectives, milestones, strategies, tactics, timelines—all the things. New me? I opened my AI tool and verbally dumped all my ideas: launch party details, mystery clues in emails, podcast roadmaps, collaboration timelines. Within an hour, I had a fully fleshed-out marketing plan that didn't just tell me what to do—it started writing the emails, outlining the podcast episodes, and structuring the launch event. That's not just efficiency. That's a fundamental shift in how I think and create. And if you're building AI tools for your clients, this shift is everything. Here's what we're covering: ✅ The two distinct phases of AI use (and why most people don't realize when they've crossed from one to the other) ✅ How to recognize you've made the shift—and why it matters ✅ The 3 key advantages of becoming an "AI-first thinker" ✅ Why this isn't about replacing your expertise—it's about multiplying it ✅ How to help your clients make the same shift so they get exponentially better results from your tools 🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™ 🔹Let’s talk Bots for your business! Book a coffee chat 🔹 Connect on Instagram >>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!

    16 min
See All (173)

Trailer

5
out of 5
20 Ratings

About

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.

Information

You Might Also Like