Entrepreneur School

Kelly Sinclair
  • 5.0 (16)
  • ENTREPRENEURSHIP
  • UPDATED WEEKLY

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.

  1. The Messy Middle of Mom Life & Business

    18H AGO

    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
  2. The Messy Middle of Mom Life & Business

    18H AGO

    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
  3. How Can You Budget Without Feeling Limited?

    DEC 16

    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
  4. How to Reinvent Your Business for 2026

    DEC 9

    How to Reinvent Your Business for 2026

    Ever felt the itch to change everything — but also felt paralyzed because you’ve built a community, payroll, and a reputation on the “old thing”? I sat down with Tracy Matthews,  a serial reinventer who’s survived bankruptcy, built and rebuilt seven-figure creative businesses, and now runs a program called The Art of Reinvention. This episode is a masterclass in doing the pivot work without burning it all down (unless you actually want to). We get honest about the messy middle: burnout, descaling, the loneliness of leadership, and the brutal clarity that hit after 2008 when Tracy’s jewelry company imploded. If you’re tired of launching the same thing in different packaging, or you’re stuck between keeping a legacy brand alive and chasing a new north star, this episode will give you permission, structure and a shove. What we unpacked  Why reinvention is not flaky — it’s how you stay relevant, wealthy, and inspired.  How Tracy rebuilt after bankruptcy and turned custom relationships into a new, profitable model.  The emotional and financial reasons founders resist “hard pivots,” and how to descale with dignity.  When community becomes the thing that holds you back and how to bring people along ethically.  The 3-step Art of Reinvention framework: Clarity → Create → Cultivate (and what each step actually looks like).  How to write a vibrant, visual vision (not a boring sentence) that consistently pulls you forward.  Why creativity is the business life force — and how to find it again when you’re burned out.  Practical product strategy: one core offer that serves beginners through scale-ups.   You’ll walk away with A clear first action if you think you need a reinvention but don’t know where to start.  Language to explain a pivot to your team and community without sounding flaky.  A refresh checklist for deciding what to keep, what to kill, and what to consolidate.  The emotional permission to “work yourself out of the business”  and why that might be the boldest move you make. >>MEET TRACY>CONNECT WITH TRACY>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...

    32 min
  5. You Might Be Doing This Wrong With Your Audience

    DEC 2

    You Might Be Doing This Wrong With Your Audience

    We’re not easing into this one. We’re going straight to the soapbox. In this conversation with marketing strategist and host of Marketing Unfiltered, Sophia Parra, we get real about AI, the “trust recession” online, and why your nurture strategy probably isn’t actually nurturing anyone. Sophia shares why “I’m just not going to use AI” is no longer a viable business stance, how AI has quietly devalued traditional coaching in your clients’ minds, and what that means for your offers and messaging going forward. We also dig into her wildly effective Q&A Day strategy—a simple, unscalable-on-purpose nurture event that’s converting 90%+ of participants into paying clients, all rooted in actual conversations instead of algorithm chasing. If you’ve been feeling like your sales are slower, your webinars aren’t filling, and your people are more skeptical than ever… this episode will help you understand why and what to do about it. We’ll unpack: Why “I’m not going down the AI track” is quietly putting a nail in your business coffinHow AI has changed your buyers’ expectations (even if you don’t use it yet)The trust recession: why so many buyers feel burned by coaching and online programsThe real definition of nurturing (hint: it’s not “I post every day and send a weekly email”)Sophia’s Q&A Day Party strategy that turned casual subscribers into paying clientsHow she uses those Q&A days for market research, content ideas, and offer developmentWhy you should stop obsessing over scalability and start doing the unscalable things firstHow to think about AI as support, not a replacement, inside your business and your offers This one is equal parts ranty, honest, and super practical. You’ll walk away with one big mindset shift and a very tangible way to deepen relationships with your audience. >>MEET SOPHIA>CONNECT WITH SOPHIA>Your Next Steps: Let’s chat about your custom visibility plan: https://tidycal.com/ksco/discovery-call 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. ...

    45 min
  6. 3 AI Predictions That Will Redefine 2026

    NOV 24

    3 AI Predictions That Will Redefine 2026

    The Year of the Bot Sale is here Nov. 24 - Dec. 1, 2025! ________________________________________________ It’s the end of November, and I’ve been thinking a lot about how I want next year to feel. Not just in my business, but in my actual life—the pace, the white space, the energy I want to bring in, and the things I’m done with. So today, I’m sharing my 3 predictions for 2026—and why I’m calling it The Year of the Bot. These aren’t just tech trends; they’re clues to how we can finally run businesses that feel lighter, more human, and more aligned. Here’s what we’ll unpack: Why 2026 is the Year of the Bot—and why AI is no longer optional.How implementation (not more strategy) will set leaders apart.Why the next era belongs to the ones who know how to human.How AI can give you back your time, creativity, and white space.A behind-the-scenes look at my Year of the Bot Sale—five Human-First AI offers designed to make 2026 your most spacious year yet. My favorite takeaways:"AI isn’t replacing us. It’s releasing us to do the work only humans can do.""2026 belongs to the implementers—the ones who bridge great ideas and real follow-through.""The next era belongs to the ones who know how to human.""We don’t need to be busier. We just need to be braver." >>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

    21 min
  7. The Trust Recession: Why Coaches Must Sell Differently in 2026

    NOV 18

    The Trust Recession: Why Coaches Must Sell Differently in 2026

    If you’ve been side-eyeing social media, this one will feel like a deep exhale. Amanda Walker—“the coach that coaches coaches” with 25+ years of experience—breaks down how to get clients in a skeptical market by building trust that sticks. We talk about why posting more isn’t the answer, what RGAs (revenue-generating activities) actually look like, and how small-buy offers + radical transparency speed up buying decisions. She also shares the real story behind taking 55 days off social while bringing in $52K, and why you’re only ever 80% certain—so ship the B+ work and move. We’ll unpack:Why social is a nurture channel—not your primary client sourceThe trust recession (and how to sell with transparency)RGAs: the under-the-iceberg moves that actually create revenueHow small-buy offers accelerate trust + conversionsMessaging in 2025: hyper-specific who + problemThe mindset reframe: you’re only ever 80% certain—decide and move >>MEET AMANDA>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

    34 min
  8. How to Stop Outsourcing Your Self-Trust

    NOV 11

    How to Stop Outsourcing Your Self-Trust

    Ever feel yourself outsourcing your power to the next course, coach or hack? Same.  In this conversation with certified coach Carly Clark Zimmer, we dig into how to rebuild self-trust so you can make clear, grounded business decisions without the constant second-guessing. We unpack why overthinking drains you more than doing, how parts work (IFS) creates internal harmony, and the simple (not easy) practice that unlocks clarity: spaciousness. You’ll hear real talk on comparison traps, sunk-cost stubbornness, and how to know when to keep going vs. pivot.  Plus, Carly’s free tool—the Five-Minute Laser Coach—to spark a quick breakthrough. We’ll Unpack:Why entrepreneurs outsource self-trust—and how to take it backThe difference between thinking about doing vs. doing (and why thinking is often more exhausting)Parts work/IFS in plain English: letting every “instrument” in your inner orchestra be heardA simple decision filter: priorities, capacity, contextWhen to stick with a strategy vs. press pause on what isn’t convertingPracticing intuitive decision-making (yes, even on “what’s for dinner”) >>MEET CARLY>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: img role="img"...

    42 min
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Trailer

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About

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.

Information

  • Creator
    Kelly Sinclair
  • Years Active
    2023 - 2025
  • Episodes
    159
  • Rating
    Explicit
  • Copyright
    © Copyright 2025 Kelly Sinclair
  • Show Website
    Entrepreneur School

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