Entrepreneur School

I can't remember what work was like before AI. And honestly? I don't want to go back. This episode is a little different—I'm pulling back the curtain and showing you exactly how AI showed up in my business this week. Not in theory. Not aspirationally. But in real time, messy and strategic and ridiculously helpful. Because here's the thing: AI isn't showing up in just one way for me anymore. Sometimes it's a thinking partner, helping me clarify what I actually need before I talk to a human. Sometimes it's a task doer, handling the stuff that used to drain my brain. And sometimes? It's just making my personal life easier—like planning a Vegas trip to see the Backstreet Boys without spending three hours Googling speakeasies. I'm sharing five real examples from my week—some played out over multiple days like a diary I kept coming back to, and others were quick, one-and-done moments that saved me hours. If you've ever wondered how to integrate AI into your business in a way that feels aligned and not robotic, this is for you.
I just got off a panel talking about AI for experts who don’t want to sound like robots, and the conversation was so good I had to bring it straight to you. Let’s be real: there’s a lot of pressure to go all-in on AI. But there's also this voice in the back of our heads asking, "Am I about to automate myself out of a job?" After spending years honing our craft, the idea that a robot could do it in seconds feels… well, a little offensive. I’m a firm believer in keeping a human in the loop. But that doesn't mean we should ignore AI. It means we have to be intentional and draw our own lines in the sand. This episode is your guide to figuring out exactly where those lines are for YOU. Forget the hype and the “shoulds.” We’re talking about how to use AI to free up your time for the deep, human work that only you can do—the stuff that makes you truly valuable.
BIG NEWS: Entrepreneur School is officially stepping into the AI era! I know, I know. I’m a PR and branding person, not a tech bro. Stepping into this role has been a journey full of imposter syndrome and "what the hell am I doing?" moments. But after diving deep into AI, co-founding an AI platform, and seeing its power to give us back our time and humanity… I knew I couldn't ignore it. And neither can you. This episode is your official orientation to the new Entrepreneur School. I’m pulling back the curtain on why this change is happening now, what it means for you, and how we’re going to navigate this new world together—without the hype, hustle, or losing ourselves in the process. If you’re ready to build a business that feels like you in a world that’s changing faster than we can keep up, you’re in the right place.
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.
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.