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Entrepreneur School

Entrepreneur School

De : Kelly Sinclair
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The Entrepreneur School Podcast shares strategies and stories of being an entrepreneur, and what it takes to run a business while raising a family. Host Kelly Sinclair is determined to change the narrative of what success looks like. Success is subjective here. This is a space where we encourage you to follow your dreams, do the work and acknowledge the challenges along the way. It’s for: → The ambitious mother who wants to create a legacy for her kids. → The goal-oriented parent who values time freedom and flexibility so that they can be there for the school concerts, hockey games and dance recitals. → The woman who’s trying to make it all work without burning out or missing out along the way. Kelly is an award-winning brand and marketing strategist. Visibility maximizer. Small-town Canadian girl. Mom of 2 girls (who couldn’t be more different). There’s more to entrepreneurship than just marketing strategies and business models. You’ll learn all about that here. And, we will talk about mindset, lifestyle tools and habits just as much. This show is all about supporting emerging and early-stage entrepreneurs on the journey from solopreneur to CEO, while wearing all of the other hats in life. It’s for business owners who want to grow their brands online using digital strategies and creating digital products or programs. And most importantly, this podcast is intended to create a movement around pursuing passions, making an impact and finding joy in the journey of raising a family and running a business.Copyright 2026 Kelly Sinclair Direction Economie Management et direction Marketing et ventes Parentalité Relations
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    Épisodes
    • 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. ⭐...
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      46 min
    • Why You Can’t Trust AI with Your Money (Yet)
      Jan 6 2026

      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!

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      40 min
    • How to Plan 2026 Without a Business Plan
      Dec 30 2025

      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!

      ⭐...

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      41 min
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