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Entrepreneur School (In the AI Era)

Entrepreneur School (In the AI Era)

By: Kelly Sinclair
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About this listen

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.Copyright 2026 Kelly Sinclair Economics Leadership Management & Leadership Marketing Marketing & Sales Parenting & Families Relationships
Episodes
  • Where Does AI Belong in Your Business (and Where Doesn’t It)?
    Feb 3 2026

    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:

    1. 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).
    2. My “redeployment of capacity” concept—a mindset shift to see AI as a tool that enhances your human touch, not erases it.
    3. The 4 questions you MUST ask yourself before outsourcing any task to AI.
    4. Why emotional intelligence is still your greatest asset (and something a robot can’t replicate… yet).
    5. The mic-drop line my own AI came up with that perfectly summarizes where your true value lies.
    6. 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!
    1. If you enjoyed this episode, please help us share it by:
    2. ⭐ Following the show—this helps you stay updated and supports us!
    3. ⭐ Leaving a positive review—this boosts our ranking and helps more entrepreneurs find the podcast.

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    17 mins
  • 3 Years In: What’s Changing on Entrepreneur School
    Jan 27 2026

    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:

    1. The new mission: How we’re using AI to build more human-centered businesses, not less.
    2. 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).
    3. My personal story of going from a communicator to co-founding a tech company (it’s a wild ride).
    4. Why this isn't a pivot away from the show's core values, but a deeper commitment to them in a new context.
    5. 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!
    1. If you enjoyed this episode, please help us share it by:
    2. ⭐ Following the show—this helps you stay updated and supports us!
    3. ⭐ 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!

    Show More Show Less
    20 mins
  • I Quit Social Media and My Business Got Better
    Jan 13 2026

    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:

    1. The Real Cost of Social Media: How the apps are designed to drain your energy, hijack your emotions, and train your brain for distraction.
    2. Permission to Quit: The data-backed audit that proved Ash didn't actually need social media for her business.
    3. Alignment vs. Time Management: Why managing your energy—not your schedule—is the key to sustainable success.
    4. From Burnout to Barefoot: Ash’s raw story of selling everything to travel the world and redefine her life.
    5. The Surprising Trauma of Success: Why a half-million-dollar year can trigger a perfectionism spiral and burnout.
    6. 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!
    1. If you enjoyed this episode, please help us share it by:
    2. ⭐ Following the show—this helps you stay updated and supports us!
    3. ⭐...
    Show More Show Less
    46 mins
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