Chronically Automated - Episode #22 Why “Starting Over” Is the Most Powerful Business Move

This episode was a ride, and a fiery one at that. I dove straight into the chaos and clarity that comes from burning everything down in your business when you know something just isn’t working anymore. You know that moment, when you’ve hit a wall, everything feels misaligned, and your gut is screaming, “Start over!” Yeah, we’ve all been there. But this episode wasn’t about the fire. It was about what happens after the smoke clears. 

I walked through my own process of rebuilding from scratch and why, when you're pivoting hard, speed matters. You’ll hear me unapologetically reject the “move slow and be strategic” advice in favor of my favorite framework: move fast, break things, fix them, and test again. And again. And again. Because the best way to scale something that actually works is to stress-test it in real time.

I also pulled Anthony in to talk about what that rebuild can look like when you’ve got the right tools in your corner, specifically Digital Magic CRM. I don’t just recommend it, I live and build inside it daily. For both of us, having DMC as our foundation means we can pivot quickly, test offers, launch new ideas, and scale without getting stuck in the tech. I helped Anthony build his platform inside DMC, and you’ll hear how he’s been able to evolve it rapidly by using AI, GPT analysis, and feedback loops from real conversations. That’s how growth actually happens.

We also riffed on how GPT has completely transformed the way I do offer development, especially when it comes to testing content, comparing angles, and pulling insights I might have missed. AI isn't just a tool, it's a second brain if you use it right. I shared a few scenarios and walked through how I use GPT to test and validate pivot directions fast, because when it comes to entrepreneurship, momentum is everything.

This episode is for anyone who’s standing in the ashes of something they thought would work but didn’t, and they’re ready to build something bolder, cleaner, and smarter.

If you’re in burn-it-down mode or just itching for a smarter rebuild, this is your playbook. And no, it’s not easy, but I’m not here to sell you easy. I’m here to show you it’s worth it.