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.

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.

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.