Aggressively Human: Online Business in the Age of AI, Algorithms & Automations Leaving the Casino: The Origin Story
Oct 23, 2025
Jessica Lackey, author and consultant, shares her insights on practical business strategies for solo and small business owners. Frustrated with empty motivational advice, she created a systems-based framework in her book, emphasizing context over cookie-cutter tactics. The conversation highlights the pitfalls of popular business books, the myth of scaling as the only path, and the importance of ethical pricing. Jessica's goal is to provide actionable guidance that respects the unique challenges faced by individual entrepreneurs.
43:36
Books Often Lack Practical How-To
- Jessica Lackey found most business books inspirational but practically hollow and misaligned with solo practitioners' needs.
- She wrote Leaving the Casino to offer concrete, repeatable guidance instead of motivational promises.
Tactics Don't Fit All Business Models
- Many online programs push one-size-fits-all tactics that don't fit all business models, like launches for fractional services.
- Lackey highlights the mismatch between taught tactics and real soloist workflows.
Adjust Financial Frameworks To Fit You
- Don’t apply generic financial frameworks without adjusting for your business type and margins.
- Rework Profit First percentages to fit craftsman soloists and creator businesses before spending.
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Intro
00:00 • 1min
Why Jessica Wrote Leaving the Casino
01:06 • 2min
Misfit Tactics for Different Business Models
02:41 • 1min
Reading the Business Canon and Finding Gaps
03:55 • 4min
Why Popular Frameworks Don't Fit Soloists
07:26 • 5min
Adapting Financial Frameworks for Craftsman Soloists
12:11 • 3min
The Book as a Synthesis and Critique
14:49 • 4min
Testing Ideas Across Business Roles
19:13 • 1min
Translating Frameworks into Visuals and Chapters
20:36 • 14sec
Addressing Privilege and Context in Business Advice
20:50 • 4min
How the Casino Metaphor Shaped the Book
24:31 • 2min
Responsibility as a Business Decision Lens
26:03 • 3min
Pricing, Boundaries, and Operating Ethos
28:38 • 3min
Archetypes Over Memoir for Practical Guidance
31:47 • 35sec
A Textbook Approach to Business Advice
32:22 • 2min
Who Books Are Written For and Market Realities
34:11 • 2min
Balancing Manifesto and Practical Guide
36:14 • 1min
Plans for Promoting and Distributing the Book
37:35 • 1min
Toolkit and Free Resources for Readers
38:40 • 2min
Acknowledgements and Community Contributions
40:50 • 2min
Outro
42:29 • 59sec
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Leaving the Casino
Stop betting on tactics. Start building a business that actually works.
Jessica Lackey
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
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