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On the show
From 17 epsHost
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Recent episodes
How to Scale Your Expertise Without Burning Out (Using AI)
Jun 23, 2026
Unknown duration
Why We Refused to Launch Our Software the Normal Way
Jun 16, 2026
Unknown duration
What Happens When You Train AI on Your IP
Jun 9, 2026
43m 32s
Two Skills That Actually Matter With AI
Jun 2, 2026
22m 03s
Free Info Is Dead (Here’s What Replaces It)
May 26, 2026
16m 36s
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| Date | Episode | Topics | Guests | Brands | Places | Keywords | Sponsor | Length | |
|---|---|---|---|---|---|---|---|---|---|
| 6/23/26 | ![]() How to Scale Your Expertise Without Burning Out (Using AI) | What if you could have a PR expert on call 24/7 — one that already knows your story, your angles, and your voice?That's exactly what Nicole Pearl built. And I got to watch it happen in real time.Nicole is a journalist and PR coach with 25 years of media experience, and she's one of the founding creators on wAIv. What she built there, the Pearl Pitch Desk, is one of the clearest examples I've seen of what expert-backed AI actually looks like in practice. Not generic. Not a shared ChatGPT link. A full bot squad designed to get her clients onto TV shows and podcasts using Nicole's exact frameworks, journalist eye, and hard-won industry knowledge.It even landed her a TV segment that had a producer saying “this is the best segment idea ever!”This conversation gets into the real difference between AI-generated pitches (which, yes, major PR agencies are sending and journalists are immediately flagging) versus pitches built on actual expert thinking. We also talk about why this approach is helping Nicole prevent burnout, serve more clients, and create a delivery model that grows with her business instead of threatening to replace her.What you'll learn in this episode:Why AI-generated pitches are getting founders blacklisted, and what to do insteadHow Nicole designed a six-bot squad that takes clients from intake to finished pitch without losing her personal touchThe difference between using a generic LLM and using expert-backed AI to produce client workWhy building on a single LLM was keeping Nicole stuck, and how wAIv changed thatHow expert knowledge embedded in AI actually removes client objections to doing the workWhy the "choose your own adventure" approach to a bot squad creates a better client experience>>Meet NicoleNicole Pearl is a journalist, PR coach, and on-air professional with 25 years in media. She helps small business founders land TV and podcast features through relationship-led pitching, her signature media messaging framework, and the Pearl Pitch Desk — a wAIv-powered bot squad built entirely on her expertise.Connect with Nicole:@NicolePearlBeautyGirl on Instagram (DM for her PR tips close friends list)Pearl Pitch Desk: https://nicolepearl.comFree AI Media Matchmaker: Grab it here>>Resources MentionedBot Squad Bootcamp (doors close June 28, kickoff July 6): https://graviastudio.com/bootcampBook a 20-minute fit call with KellyAnother case study of wAIv with Dr. Michelle MazurQuestions? Email kelly@graviastudio.com>>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🤖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! | — | ||||||
| 6/16/26 | ![]() Why We Refused to Launch Our Software the Normal Way | Here's a confession: I've bought at least a handful of softwares in my life that I've literally never logged into. Not once.So when it came time to launch wAIv to the public, every coaching instinct in my body refused the traditional software playbook. Open the doors, run ads, free trial, hope they convert? Absolutely not. I've watched too many entrepreneurs buy a thing that just sits there, and Andrew and I did not want to build a company on people not using the thing.Instead, we built something I'm calling the most coach-brained software launch you've ever seen: Bot Squad Bootcamp. This episode is the full tour.In this episode, you'll learn:Why the traditional software launch playbook was a hard no for us (and what we designed instead)What a bot squad actually is, and why your bots get noticeably smarter the moment they share contextThe duct tape problem: why your clients shouldn't be the connective tissue between your AI toolsThe real risk of housing your frameworks and IP on platforms you don't controlThe week-by-week build path inside Bot Squad Bootcamp, from gathering your materials to graduating with a live, sellable squadExactly who this is for, who it's not for and a transparent breakdown of what wAIv costs after your first three months>>Resources MentionedBot Squad Bootcamp (doors close June 28, kickoff July 6): https://graviastudio.com/bootcampBook a 20-minute fit call with KellyLast week's episode with Dr. Michelle MazurQuestions? Email kelly@graviastudio.com>>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.We're currently rolling out in beta, and you can join the waitlist now to access our AI Tool Launch Playbook, which walks you through exactly how to start thinking about your first Bot Squad—what to put in it, what it will solve for your clients, what to name it, and exactly how to build it.Head to https://waiv-ai.com to get on the list.>>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! | — | ||||||
| 6/9/26 | ![]() What Happens When You Train AI on Your IP✨ | AI in coachingexpert-backed AI+3 | Dr. Michelle Mazur | Expert Up ClubMoxie | — | AI toolscoaching+5 | PodcastPODCAST70 | 43m 32s | |
| 6/2/26 | ![]() Two Skills That Actually Matter With AI✨ | AI skillscommunication+3 | — | Wave | — | AIcommunication+3 | PodcastPODCAST70 | 22m 03s | |
| 5/26/26 | ![]() Free Info Is Dead (Here’s What Replaces It)✨ | knowledge economyAI impact+5 | — | — | — | AIknowledge economy+8 | — | 16m 36s | |
| 5/19/26 | ![]() How AI Is Changing Your Business Model (And What to Do About It)✨ | AI in businessbusiness model transformation+4 | — | — | — | AIbusiness model+5 | — | 25m 52s | |
| 5/12/26 | ![]() Life Is Lifing: How AI Became My Family Command Center✨ | AI in family logisticsentrepreneurship+4 | — | WaveSocial Media Marketing World | — | AIfamily logistics+6 | — | 26m 19s | |
| 5/5/26 | ![]() 3 Entrepreneurs Share How They’re Making Money with AI✨ | AI monetizationentrepreneurship+4 | Maddie Van PattonEmma Tiegan+1 | — | Anaheim, CACalifornia | AI toolssmall business+4 | — | 13m 17s | |
| 4/28/26 | ![]() [Encore] Expert-Backed AI Is the New Online Course✨ | AI in online coursesexpert-backed AI+3 | — | — | — | online course marketAI completion rates+3 | — | 24m 27s | |
| 4/21/26 | ![]() We launched a new AI platform!✨ | AI platformcreator monetization+4 | — | AI Tool Launch PlaybookChatGPT+2 | — | AI platformcreator IP protection+4 | — | 25m 18s | |
Want analysis for the episodes below?Free for Pro Submit a request, we'll have your selected episodes analyzed within an hour. Free, at no cost to you, for Pro users. | |||||||||
| 4/7/26 | ![]() How to Stay Grounded When AI Is Moving Faster Than You Can Process✨ | AIbusiness ownership+4 | — | — | — | AI newsbusiness owner+5 | — | 18m 53s | |
| 3/31/26 | ![]() Why Your Human Work is Now More Valuable than Ever✨ | AI strategysales systems+3 | Prerna Malik | Content BistroProfitably Yours+3 | — | AIsales+5 | — | 34m 17s | |
| 3/24/26 | ![]() Expert-Backed AI Is the New Online Course✨ | AI in online coursesexpert-backed AI+3 | — | Google Drive | — | online course marketAI completion rates+3 | — | 24m 27s | |
| 3/17/26 | ![]() The QuitGPT Movement: What It Means for Your Business✨ | AI toolsbusiness strategy+4 | — | OpenAIAnthropic+1 | — | QuitGPTAI tools+6 | — | 20m 14s | |
| 3/10/26 | ![]() How I Built a Marketing Team Out of Bots✨ | AI toolsmarketing team+4 | — | — | — | AImarketing+3 | — | 18m 12s | |
| 3/3/26 | ![]() The AI Shift That Changes How You Lead✨ | AI collaborationleadership+3 | — | — | — | AI toolsmarketing plan+3 | — | 15m 58s | |
| 2/24/26 | ![]() Should You Sell AI? The Answer Might Surprise You✨ | AI adoptionbusiness strategy+4 | — | BrandCalibrator™Year of the Bot Bundle | — | AIbusiness+6 | — | 25m 07s | |
| 2/18/26 | ![]() How to Set Up ChatGPT Projects That Work✨ | ChatGPT ProjectsAI organization+3 | — | OpenAI | — | ChatGPTAI projects+3 | — | 26m 35s | |
| 2/10/26 | ![]() Five Real Ways I Used AI This Week (Steal Them)✨ | AI integrationbusiness strategy+3 | — | — | — | AIbusiness+3 | — | 17m 06s | |
| 2/3/26 | ![]() Where Does AI Belong in Your Business (and Where Doesn’t It)? | I just got off a panel talking about AI for experts who don’t want to sound like robots, and the conversation was so good I had to bring it straight to you.Let’s be real: there’s a lot of pressure to go all-in on AI. But there's also this voice in the back of our heads asking, "Am I about to automate myself out of a job?" After spending years honing our craft, the idea that a robot could do it in seconds feels… well, a little offensive.I’m a firm believer in keeping a human in the loop. But that doesn't mean we should ignore AI. It means we have to be intentional and draw our own lines in the sand. This episode is your guide to figuring out exactly where those lines are for YOU.Forget the hype and the “shoulds.” We’re talking about how to use AI to free up your time for the deep, human work that only you can do—the stuff that makes you truly valuable.In this episode, we’ll unpack:The critical difference between a task that needs your unique lens and one that’s just a supporting function (and how to tell them apart).My “redeployment of capacity” concept—a mindset shift to see AI as a tool that enhances your human touch, not erases it.The 4 questions you MUST ask yourself before outsourcing any task to AI.Why emotional intelligence is still your greatest asset (and something a robot can’t replicate… yet).The mic-drop line my own AI came up with that perfectly summarizes where your true value lies.This isn’t about becoming a tech wizard. It’s about creating your own rulebook for the AI era so you can stay in control, protect your expertise, and get a strategic edge.🔹 Grab the FREE Year of the Bot Bundle with 50+ AI tools for your business (available until Feb. 15/26)🤖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. | — | ||||||
| 1/27/26 | ![]() 3 Years In: What’s Changing on Entrepreneur School | The Year of the Bot Bundle is available for FREE until Feb.15!____________________________________________________________________________BIG NEWS: Entrepreneur School is officially stepping into the AI era!I know, I know. I’m a PR and branding person, not a tech bro. Stepping into this role has been a journey full of imposter syndrome and "what the hell am I doing?" moments. But after diving deep into AI, co-founding an AI platform, and seeing its power to give us back our time and humanity… I knew I couldn't ignore it. And neither can you.This episode is your official orientation to the new Entrepreneur School. I’m pulling back the curtain on why this change is happening now, what it means for you, and how we’re going to navigate this new world together—without the hype, hustle, or losing ourselves in the process.If you’re ready to build a business that feels like you in a world that’s changing faster than we can keep up, you’re in the right place.In this episode, we’re unpacking:The new mission: How we’re using AI to build more human-centered businesses, not less.What you can expect from the show moving forward (think real-time strategy, AI-forward guests, and behind-the-scenes looks at my own founder journey).My personal story of going from a communicator to co-founding a tech company (it’s a wild ride).Why this isn't a pivot away from the show's core values, but a deeper commitment to them in a new context.The one belief that’s guiding this entire next chapter: avoiding AI doesn't protect you, but being intentional about it does.>>Your Next Steps🔹 Grab the FREE Year of the Bot Bundle with 50+ AI tools for your business (available until Feb. 15/26)🤖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! | — | ||||||
| 1/13/26 | ![]() I Quit Social Media and My Business Got Better | What if the key to your next level of success wasn't hustling harder, but quitting the one thing you think your business can't survive without?This conversation with Ash McDonald is one for the books. She’s a therapist and business mentor who came on the show and dropped so many truth bombs I’m still cleaning up the mess. We start with her "soapbox" moment—why she permanently quit social media—and the immediate, visceral impact it had on her energy and well-being. (Spoiler: After just two days back for a quarterly check-in, she felt like crap. Relatable.)But this isn't just a chat about logging off. Ash takes us on her incredible journey of selling everything she owned to travel the world with her three young kids. We get into how this radical leap redefined her as a mother, an entrepreneur, and a woman. She gets brutally honest about the trauma that surfaced after her most successful year in business—a half-a-million-dollar year on less than 10 hours a week—and how it led to total burnout.This episode is a masterclass in untangling your worth from your work, chasing the feeling instead of the metric, and building a life that is deeply, personally, and unapologetically yours.In This Episode, We Unpack:The Real Cost of Social Media: How the apps are designed to drain your energy, hijack your emotions, and train your brain for distraction.Permission to Quit: The data-backed audit that proved Ash didn't actually need social media for her business.Alignment vs. Time Management: Why managing your energy—not your schedule—is the key to sustainable success.From Burnout to Barefoot: Ash’s raw story of selling everything to travel the world and redefine her life.The Surprising Trauma of Success: Why a half-million-dollar year can trigger a perfectionism spiral and burnout.How to Avoid the Crash: The secret to building a life you love by chasing the feeling, not the metric.>>CONNECT WITH ASH<<https://ashmcdonaldmentoring.com/Grab Ashley’s FREE 15 minute training on preventing burnout.Shamelessly Ambitious Podcast: https://ashmcdonaldmentoring.com/podcastpage🤖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! | — | ||||||
| 1/6/26 | ![]() Why You Can’t Trust AI with Your Money (Yet) | Have you ever left a meeting with your accountant feeling… kind of dumb? Like you should know more, do more, or just be better with your money? Yeah, me too. It’s this weird, quiet shame that so many of us carry, and we rarely talk about it.My guest today, Serena Shoup, a CPA and bookkeeping CEO, gets on her soapbox about this within the first five minutes—and I was HERE for it. She calls out the condescending, shaming B.S. that can happen in the financial industry and gives us all permission to expect better. (And yes, that includes firing people who make you feel like crap about your business. Mic drop.)This conversation is about so much more than just numbers. We get into Serena’s incredible story of building her firm as a “side hustle to motherhood,” how she accidentally created a second business teaching other bookkeepers, and the market shifts she’s seeing firsthand in her clients’ financials. If you started your business around the 2020 online gold rush, you NEED to hear her insights on what’s actually working now.This episode is a masterclass in stripping away the fear around your finances and learning to see your numbers not as a report card on your worth, but as a powerful tool to help you build a business—and a life—that you actually love.What You'll Learn in This Episode:The #1 reason you feel shame around your numbers (and why it might not be your fault).Why mixing business and personal funds is killing your clarity.How a $27 PDF pre-sold to 50 people launched a whole new business.What's really working in the post-2020 course market (from a CPA who sees the data).Using your P&L as a tool, not a report card, to build a business you actually love.>>CONNECT WITH SERENA<<FREE DIY Bookkeeping Guide!Website: https://www.ambitiousbookkeeper.com/ Instagram: https://www.instagram.com/ofcoursefinancial Podcast: The Ambitious Bookkeeper Podcast >>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! | — | ||||||
| 12/30/25 | ![]() How to Plan 2026 Without a Business Plan | I started 2025 with one rule: “Only if it's a hell yes.” I ended it as the co-founder of an AI company. I didn’t see it coming!This episode is a little nerve-wracking to share, but it’s the real, unfiltered story of my wild ride through 2025. I ditched the 12-month goals, the rigid launch calendars, and all the “shoulds” I’d been forcing for years. As an Enneagram 8 who loves control, this was… uncomfortable.Instead, I followed alignment, curiosity and relationships. The result? A year that was messy, non-linear and more transformative than any I could have meticulously planned. I went from feeling fed up and stuck to building something entirely new that feels more aligned than anything I’ve ever done.In this episode, I’m breaking down the five biggest themes that shaped my year—from micro-experiments that actually worked to the scary-as-hell identity shift I'm still navigating. This isn't a highlight reel; it's a roadmap for your own reflection.What's in this episode for you:The "Hell Yes" Compass: How I ditched control and used alignment to guide every decision, even when it led to some big, scary “no’s.”Micro-Experiments > Master Plans: The power of small, curious tests—including the $1 workshop that sold 135 spots and taking the entire summer off social media.Relationship-Led Visibility: Why deepening connections and collaborating in shared rooms will always beat chasing followers or sending cold pitches.When the Universe Screams, Listen: How I recognized the repeating patterns that pointed toward partnership and finally stopped trying to do everything alone.Becoming Before You Declare: The vulnerable truth about the lag between your growth and your identity, and why it’s so damn hard to publicly claim the next version of yourself (I’m right there with you!).Ready for your own reflection?If your year felt non-linear, you’re not behind. Ask yourself this: **What did this year teach me about how I want to move forward?**To help you get started, here are the 5 journaling prompts from the episode. Grab your journal (or your favorite AI tool) and give yourself the space to explore what your year taught you.1. Where did I choose alignment over expectation this year?2. What did I try this year that gave me clarity (even if it wasn't a huge win)?3. Which relationships quietly opened doors for me this year?4. What keeps showing up in my business that I might be meant to approach differently (and not abandon)?5. What version of myself am I already living, but not fully claiming yet?Here's to a 2026 that's led by you, not your to-do list. Happy New Year>>Your Next Steps:🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™ 🔹 Done for you visibility plan by Valerie the Visibility Auditor🔹 Let’s work together: https://ksco.ca/🔹 Get visible without social media🔹 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.⭐ Sharing it on Instagram and tagging @entrepreneurschoolpodcast | — | ||||||
| 12/16/25 | ![]() How Can You Budget Without Feeling Limited? | Today, we’re talking about the other B-word… Budgeting — but before you roll your eyes, stick with me, because my guests Shana and Vanessa (aka the Budget Besties) are flipping everything you think you know about budgets on its head.These two are best friends turned financial coaches who teach ambitious women how to automate their money without shame, spreadsheets, or sacrifice. Honestly? Sign me up. Those are all things I actively avoid.In this episode, we unpack their simple, stunningly effective system that turns your bank into your own personal assistant — so you can pay your bills, enjoy your life, and still splurge on the bougie things without relying on credit cards.They break down why most women believe they’re “bad with money” (spoiler: you aren’t), how modern financial life has become way too complicated, and how a budget — done their way — actually gives you permission to spend.We get into:Why money problems aren’t about overspending… they’re about disorganizationHow to set up a one-page budget that mimics your real lifeWhy separating accounts is the key to reducing stressHow automation replaces willpowerWhat entrepreneurs especially need to understand about stabilizing incomeThe mindset shift that helps you drop shame and start dreaming againIf money has ever felt overwhelming, guilt-inducing, or chaotic, this conversation is going to breathe oxygen back into your confidence.👉 Guest Bio & LinksBudget Besties — Shana & VanessaMaster financial coaches and founders of Budget Besties, helping women automate their money and ditch shame-filled budgeting forever. Their signature method teaches you how to create a simple, separate, automated system so you can enjoy life now and build wealth for the future — without burnout, sacrifice, or spreadsheets.>>CONNECT WITH THE BUDGET BESTIES<<🔗 Podcast: Financial Coaching for Women🔗 Bootcamp: https://budgetbesties.com/bootcamp🔗 Instagram: https://www.instagram.com/mybudgetbesties 🔗 Website: https://budgetbesties.com 🔗Simplified Budget System (affiliate link)>>Your Next Steps:🤖Train AI to sound like you (in under 2 hours) with BrandCalibrator™ 🔹Done for you visibility plan by Valerie the Visibility Auditor🔹 Let’s work together: https://ksco.ca/🔹 Get visible without social media🔹 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.⭐ Sharing it on Instagram and tagging @entrepreneurschoolpodcast | — | ||||||
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![[Encore] Expert-Backed AI Is the New Online Course episode artwork](https://artwork.captivate.fm/7a192e48-7d44-47be-9e53-2b55f96ea036/ESAI173-Encore-Expert-Backed-AI-Is-the-New-Online-Course-Cover.png)















