A FIELD GUIDE FOR ENTREPRENEURS COMMITTED TO SUSTAINABLE GROWTH
Leaving the Casino
Stop betting on tactics.
Start building a business that actually works.
Download the sample chapter
“You have written a book that both discourages and shows the pitfalls of the “quick fix” solutions, which can be so tempting because they offer potential relief from real business woes, and *also* you have written a book that offers another way: REAL relief to common business woes, the answers to which will be different for every business owner.”
- Catherine LaSota
When you play by their rules, the house always wins.
“Charge your worth!”
“Turn on your marketing funnel!”
“Hire before you’re ready!”
“This one tool saved me 10 hours a week!”
“Launch your course and make money while you sleep!”
You’ve heard this advice from the Entrepreneurial Casino - an industry built to sell you promises of quick and easy success.
But most of that advice leads you toward someone else’s vision: performative marketing, overbuilt systems, and a business that doesn’t actually work for you.
And we’re the ones left paying the price.
Leaving the Casino: Stop Betting on Tactics and Start Building a Business that Works is a guide for expertise-based business owners—coaches, consultants, creatives, and service providers—who want to build a real business rooted in values, sustainability, and intentional growth.
Through practical frameworks and grounded guidance, you’ll learn how to:
→ Navigate trade-offs about business growth with clarity, not confusion
→ Define what enough looks like for your business
→ Make pricing, marketing, hiring, time management, and offer decisions that align with your business values and vision
→ Reclaim your time, energy, and cash from bad-fit tactics so you can grow with intention
→ Apply foundational strategies—not just stories of what worked for me—so you can design a business built for you
If you’ve ever been burned by the marketing bros, exhausted by B2B marketing hacks, or underwhelmed by “just manifest it” advice, this book is for you.
About the author
A business strategist, former McKinsey consultant, and founder of Deeper Foundations. She helps expert entrepreneurs build sustainable, values-aligned businesses through strategy, structure, and systems.
Jessica Lackey
Choose your Package
Package 1: the book, the workbook & the exclusive video classes
The Compass Bundle
Package 2: the book & the workbook
The Reflection Bundle
• Signed hardcover of Leaving the Casino
• Digital e-book
• Printed workbook + digital workbook
• Shipping included
Turn insight into action with this book + workbook set.
For those who want to move from reading to implementation.
This bundle pairs Leaving the Casino with the companion workbook, designed to help you reflect, assess, and apply each chapter to your own business.
The Essentials
Just the book—clear, focused, and ready to shift how you see your business.
For the reader who wants the core message without the extras.
This edition includes both the hardcover and e-book versions of Leaving the Casino, so you can read at your own pace and revisit it whenever you need a reset.
Package 3: the book
• Signed hardcover of Leaving the Casino
• Digital e-book
• Shipping included
STANDALONE EDITIONS
• Paperback book on Amazon, Bookshop, Barnes Noble
• Buy the digital workbook
• Signed hardcover of Leaving the Casino
• Digital e-book
• Printed workbook + digital workbook
• Shipping included
• 10 video chapter debriefs
For those who want more than just the map—this is the conversation that helps you navigate it.
Includes the book, the workbook, and exclusive video classes that offer deeper dialogue on each chapter.
Designed for entrepreneurs who want not just frameworks, but guidance on how to think through the trade-offs and apply them with nuance.
The FREE tools to help you build a business that works for you.
FREE LEAVING THE CASINO COMPANION RESOURCES:
• Business Stage Quiz and Guide
• Survive / Sustain / Strengthen and Serve Calculator
• 5 Pricing Approaches Worksheet
• Map Your Marketing Grid
• Process, Prune, Prioritize Worksheet
• The Hiring Matrix
• Repeatable Processes Worksheet
Use these tools to map your own way forward—not another coach’s recycled “playbook.”
Join the Book Club
Each month, we’ll have live discussions and prompts related to each chapter of the book.
WHY I WROTE THIS BOOK
I was trapped in the Entrepreneurial Casino too.
In my own journey—from life coach to Fractional COO to course creator—I’ve experienced the full spectrum of what entrepreneurs are sold: the high-ticket blueprints, the viral content formulas, the endless programs that promise “proven secrets” but left me with outdated tactics. I know what it feels like to follow all the advice and still wonder why it’s not working.
So I put my skills to use.
Redefining how business gets done
I took what I learned at McKinsey, Harvard Business School, and Nike—systems thinking, strategic decision-making, and operational design—and turned it toward a deeper exploration of how business really works when you’re building something rooted in expertise, not algorithms.
I’ve worked across B2B, B2C, B2SMB, B2B2B, and B2GOV. I’ve supported hundreds of entrepreneurs—coaches, consultants, and service providers—who wanted to build businesses that are profitable, sustainable, and actually aligned with their values.
Leaving the Casino is the book I wish I had when I started: not a one-size-fits-all roadmap, but a practical guide to making clear, grounded decisions for a right-sized business.
Now it’s yours.
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“The biggest mistake business owners make is listening to the lies they’ve been sold.”
We’ve all seen the ads. Promising to solve lead generation and 10x our revenue in 30 days (or our money back!). Leaving the Casino makes clear that if you don’t know your business model and the business model of the help you hire, you’ll waste time and money that could be better spent elsewhere. Jessica’s critique of the Entrepreneurial Casino is apt, timely, and has taught me more than any other business resource. I can’t recommend this book enough—it’s an essential read for all coaches, consultants, and creators looking to build sustainable, profitable businesses without selling their soul.
— Dr. Matthew Jones, Co-Founder Clarity
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“Jessica’s book is the business education I didn’t know I needed.”
This book is clear, generous, and deeply useful. As someone who never wanted an MBA and never dreamed of being a founder, I was able to build the systems and structures to make my work actually work. Jessica offers the kind of operational clarity that makes vision possible, and sustainable — she respects the heart of your work while strengthening its spine. The book is perfect for people building businesses with care, integrity, and no interest in hustle culture.
— Shivani Mehta Bhatia, Tulsi Studios
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![Amelia Hruby - Owner of Softer Sounds and host of Off The Grid Podcast]()
“Jessica looked ‘under the hood’ of my business and was able to quickly and accurately assess what was going well and where I was out of alignment (with myself, my clients, my goals.)”
I now know where my business is going and how to get there. And I feel like I understand the financial big picture better than I ever have.
— Amelia Hruby, Owner of Softer Sounds and host of Off The Grid Podcast
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![Julie Morris - Persona Media]()
“Just because you can grow a business doesn’t mean you can successfully operate it.”
Jessica brought her skills and expertise to pragmatically solve the organizational mess that a brilliant marketer like me needed. I wanted to solve all the problems in our organization but had no clue which angle to attack from. She’s realistic and an absolute genius and gets into the details with you.
— Julie Morris, Persona Media
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![Jennifer Bower - Fortuna Money]()
“After my work in Deeper Foundations, I’m seeing consistently higher revenue, and I have a realistic plan for long-term growth.”
— Jennifer Bower, Fortuna Money
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![Kelley Bonner - Burn Bright Consulting.jpg]()
“I was able to systematize [my business], versus trying to find an additional stream of income.”
— Kelley Bonner, Burn Bright Consulting
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![Linda Rhyne - Linda Rhyne Consulting.jpeg]()
“You’re really clear on keeping the human aspect of work and business in the center. I truly believe my business would not be where it is today without her support.”
— Linda Rhyne, Linda Rhyne Consulting
Need 30+ copies?
Bulk orders for speaking and keynotes
Discounts are available for orders of 30+ books, whether they are for your event, team, clients, students or something else.
Email jessica@deeperfoundations.com for a quote.
