Entrepreneur School (In the AI Era)

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.

  1. Where Does AI Belong in Your Business (and Where Doesn't It)?

    4D AGO

    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.

    17 min
  2. 3 Years In: What's Changing on Entrepreneur School

    JAN 27

    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!

    20 min
  3. I Quit Social Media and My Business Got Better

    JAN 13

    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>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!⭐...

    46 min
  4. Why You Can’t Trust AI with Your Money (Yet)

    JAN 6

    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>YOUR NEXT STEPS>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!

    40 min
  5. How to Plan 2026 Without a Business Plan

    12/30/2025

    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! ⭐...

    41 min
  6. The Messy Middle of Mom Life & Business

    12/23/2025

    The Messy Middle of Mom Life & Business

    We love a good strategy here at Entrepreneur School, but what happens when the only plan is to just… wing it? Honestly, this is one of the main reasons I started this show—to have real, unfiltered conversations about what it actually takes to build a business and a family at the same time. And let me tell you, it’s never a perfectly executed 5-step plan. Today, I’m talking to Jessica Lamb, host of the Mama Making podcast and founder of Collabs Creative. She’s in the thick of it with a young son, and she gets brutally honest about operating without a roadmap, ditching the comparison game, and redefining what success even means. This episode is a permission slip to let your journey be messy. We talk about everything from leveraging ADHD and procrastination to your advantage, to the complicated feelings that come up when your partner is the primary breadwinner. If you’ve ever felt like you’re making it up as you go while everyone else on Instagram has it figured out, this one’s for you. You’ll learn: How to embrace flexibility as a superpower when your schedule is dictated by sick days and nap times.Why working with your unique brain (procrastination and all) is more effective than forcing someone else’s systems.The truth about comparison culture and how to put on “blinders” to stay on your own path, at your own pace.How to redefine your value beyond the dollar amount you bring in (because your contribution is so much more than that).The strategic power of starting small to build a sustainable foundation without burning yourself out.Why your version of success is the only one that matters—whether that’s hitting seven figures or making it to the school field trip. 👉 MEET JESSICA: Jessica Lamb is the host of The Mama Making Podcast, where real conversations about motherhood, identity, and building meaningful work take center stage. She's also the founder of Collabs Creative, a marketing studio helping small businesses grow with story-first strategy and real-life perspective. Her work is rooted in the belief that you can raise a family and build something that matters - without a roadmap. 👉 CONNECT WITH JESSICA: Listen to the Mama Making Podcast: https://www.themamamakingpodcast.com/  Follow on Instagram: https://www.instagram.com/themamamakingpodcast  >>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...

    22 min
  7. The Messy Middle of Mom Life & Business

    12/23/2025

    The Messy Middle of Mom Life & Business

    We love a good strategy here at Entrepreneur School, but what happens when the only plan is to just… wing it? Honestly, this is one of the main reasons I started this show—to have real, unfiltered conversations about what it actually takes to build a business and a family at the same time. And let me tell you, it’s never a perfectly executed 5-step plan. Today, I’m talking to Jessica Lamb, host of the Mama Making podcast and founder of Collabs Creative. She’s in the thick of it with a young son, and she gets brutally honest about operating without a roadmap, ditching the comparison game, and redefining what success even means. This episode is a permission slip to let your journey be messy. We talk about everything from leveraging ADHD and procrastination to your advantage, to the complicated feelings that come up when your partner is the primary breadwinner. If you’ve ever felt like you’re making it up as you go while everyone else on Instagram has it figured out, this one’s for you. You’ll learn: How to embrace flexibility as a superpower when your schedule is dictated by sick days and nap times.Why working with your unique brain (procrastination and all) is more effective than forcing someone else’s systems.The truth about comparison culture and how to put on “blinders” to stay on your own path, at your own pace.How to redefine your value beyond the dollar amount you bring in (because your contribution is so much more than that).The strategic power of starting small to build a sustainable foundation without burning yourself out.Why your version of success is the only one that matters—whether that’s hitting seven figures or making it to the school field trip. 👉 MEET JESSICA: Jessica Lamb is the host of The Mama Making Podcast, where real conversations about motherhood, identity, and building meaningful work take center stage. She's also the founder of Collabs Creative, a marketing studio helping small businesses grow with story-first strategy and real-life perspective. Her work is rooted in the belief that you can raise a family and build something that matters - without a roadmap. 👉 CONNECT WITH JESSICA: Listen to the Mama Making Podcast: https://www.themamamakingpodcast.com/ Follow on Instagram: https://www.instagram.com/themamamakingpodcast >>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

    22 min
  8. How Can You Budget Without Feeling Limited?

    12/16/2025

    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 again If 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 & Vanessa Master 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>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 a...

    29 min
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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.

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