Entrepreneur School

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.
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.
Let’s talk about monetization with AI—without the overwhelm, the jargon, or pretending you’re suddenly a coder. In this episode we break down three clear paths to monetizing with AI that don’t require you to build a tool, start a tech company, or even understand how ChatGPT works behind the curtain. You’ll discover how to: Save hours (and reclaim your evenings) by using AI to streamline the behind-the-scenes work Enhance your client delivery so every touchpoint feels high-touch—without adding more calls to your calendar Productize your expertise into AI-powered experiences that sell while you sleep You’ll hear real-world examples, including how I turned my proprietary frameworks into tools like Brenda (the BrandCalibrator™) and Valerie (the Visibility Auditor)—and how these tools create scalable, on-brand experiences that feel personal and profitable. Plus, I’ll walk you through the #1 mistake most creators make when building GPTs and how to protect your intellectual property before you put your methods into AI. This episode will spark ideas for how you can work less, earn more, and serve better using AI in your business—no tech degree required.