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

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🔹Let’s talk Bots for your business! Book a coffee chat

🔹 Connect on Instagram

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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

• 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.

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Entrepreneur School is proud to be featured on the Feedspot list of 30 Best Canada CEO Podcasts!

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

🤖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

If you enjoyed this episode, please help us share it by:

⭐ Following the show—this helps you stay updated and supports us!

⭐...

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

🤖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

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...

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:

1. How to embrace flexibility as a superpower when your schedule is dictated by sick days and nap times.
2. Why working with your unique brain (procrastination and all) is more effective than forcing someone else’s systems.
3. The truth about comparison culture and how to put on “blinders” to stay on your own path, at your own pace.
4. How to redefine your value beyond the dollar amount you bring in (because your contribution is so much more than that).
5. The strategic power of starting small to build a sustainable foundation without burning yourself out.
6. 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

🤖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

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

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:

1. Why money problems aren’t about overspending… they’re about disorganization
2. How to set up a one-page budget that mimics your real life
3. Why separating accounts is the key to reducing stress
4. How automation replaces willpower
5. What entrepreneurs especially need to understand about stabilizing income
6. The 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.

Budget 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<<

🔗 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)

🤖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

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<<

Tracy Matthews — founder, speaker, author, and creative reinvention expert. Tracy launched and scaled multiple jewelry brands, survived a market crash and bankruptcy in 2008, built Flourish & Thrive Academy (14 years, multiple seven figures, 9,500+ creatives served), authored The Desire Brand Effect, and now teaches founders how to reconnect with their creative life force and pivot with strategy. She’s launched The Art of Reinvention program and a private podcast called Reinvention Season to help founders navigating change.

>>CONNECT WITH TRACY<<

• https://reinvent.tracymatthews.com/next-chapter
• Instagram
• LinkedIn

🤖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

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 coffin
• How 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 programs
• The 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 clients
• How she uses those Q&A days for market research, content ideas, and offer development
• Why you should stop obsessing over scalability and start doing the unscalable things first
• How 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<<

Sophia Parra is a no-fluff marketing strategist, creator of Pocket CMO, and the unfiltered voice behind the Marketing Unfiltered Podcast. She helps coaches and online business owners ditch the performative content hamster wheel and build marketing that actually nurtures, converts, and feels good to run.

>>CONNECT WITH SOPHIA<<

• Listen to Marketing #Unfiltered
• Grab the private podcast For the Love of Marketing: https://www.gotocoach.club/fortheloveofmarketing
• Follow Sophia on Instagram

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

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.

...