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.

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.

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.

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.

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.

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.