“One of three things were happening. One, I was being sold a bunch of bogus things to do to grow my business by the online entrepreneurship system. Two, I was realizing how disconnected all the strategies were across B2B and B2C, and then third, I read every single business book I could get my hands on. And every one of them sort of laid out the strategies for maybe why you wanted to be a company of one, or how to think about marketing, but none of them actually told you what to do or why.”
What happens when every business book tells you what to think—but never explains what or how to do it?
In this episode, Meg interviews Jessica about her new book, Leaving the Casino: Stop Betting on Tactics and Start Building a Business That Works. The conversation traces how the book came to life—from frustration with hollow business advice to the creation of a grounded, systems-based framework for experts who want to stay small, sustainable, and sovereign.
Jessica shares how she read her way through the entire business section—books that were motivational but hollow, all premise and no practice. Some were thinly veiled sales funnels; others were memoirs pretending to be manuals. None answered the questions solo business owners actually ask: How do I make better decisions? What kind of business am I running? What’s enough? And how do I make this sustainable?
They explore what’s missing from most business books, the trap of “CEO-energy” culture, and the myth that scaling is the only path forward. Jessica shares how years of client work, research, and teaching evolved into a practical field guide for soloists who want to build differently—without gambling their time or integrity.
Get the details behind Leaving the Casino!
Why Jessica wrote Leaving the Casino after realizing most advice ignores context
How the online business world sells tactics that don’t fit most experts
Why many books are either memoirs or funnels to a paid program
How Jessica went from consulting to creating and publishing the book
The limits of frameworks like Profit First, Traction, and Essentialism
The risks of outsourcing sales, marketing, and finance too early
Responsibility, enoughness, and right-sized growth as operating principles
How privilege and life circumstances affect what “success” looks like
Why the book blends manifesto and textbook—both call-to-arms and manual
Jessica’s hope that it becomes a long-term reference for expert entrepreneurs
Resources
Leaving the Casino: Stop Betting on Tactics and Start Building a Business That Works
Connect with Us
Connect with Meg and Jessica
