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#36 - Jessica Lackey: How to (Actually) Build a Successful Online Business and Leave the Entrepreneurial Casino

Oct 30, 2025

Guest

Jessica Lackey

In this discussion, Jessica Lackey, founder of Deeper Foundations and author of 'Leaving the Casino,' shares her no-nonsense approach to building successful online businesses. She emphasizes that many entrepreneurs are risking their careers in a gamble, debunking quick-success myths. Lackey advocates for sustainable business models focusing on recurring revenue and community engagement. She stresses the importance of market validation, lived experience in teaching, and the need for genuine conviction and curiosity in driving long-term success.

02:06:42

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insights

INSIGHT

Marketing Sells Dreams, Not Math

Many online business promises sell a seductive image that ignores the underlying economics and effort required.
Jessica Lackey calls this reality a gamble because “the math doesn't math.”

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ADVICE

Validate Before You Build

Know exactly what you're trying to build and how it works before you chase the next tactic.
Validate audience size and product-market fit rather than launching because a course looks easy.

insights

INSIGHT

Teach Decisions, Not Replication

Teaching what you did is different from teaching how business actually works across models.
Jessica emphasizes frameworks for decision-making over prescriptive

Get the Snipd Podcast app to discover more snips from this episode

Why Online Businesses Often Feel Like Gambling

00:56 • 1min

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The Problem with 'Launch a Course' Advice

01:57 • 2min

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Teaching vs. Doing: Credibility in the Creator Economy

04:01 • 5min

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When the Math 'Doesn't Math' (Audience and Monetization)

09:14 • 3min

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Choosing a Marketing Style and Business Personality

12:18 • 1min

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Why Retainer and Recurring Models Reduce Fatigue

13:33 • 3min

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Managing Community Tiers and Veteran Members

17:00 • 1min

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Pricing Realities: Market, Promise, and Audience

18:20 • 2min

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Which Casino Floor Did You Enter? Picking the Right Business Model

20:30 • 2min

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Recurring Revenue Trade-offs and Hidden Costs

22:53 • 4min

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Four Lenses of Responsibility in Business Design

26:35 • 6min

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Should You Offer Monthly or Yearly Community Pricing?

32:44 • 3min

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Designing Your Community's Purpose and Rhythm

35:19 • 4min

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Validate Before You Build: Pre-selling and Market Conversations

39:05 • 3min

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Go Talk to 50 Ideal Clients Before You Create

41:54 • 3min

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Create from Doing: Document and Deliver Value, Not Just Hooks

45:13 • 3min

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Substance Over Packaging: Frameworks Must Be Lived

48:21 • 6min

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The Process of Developing Frameworks and Language

54:14 • 3min

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Curiosity and Conviction: What Sustains a Business Long-Term

57:16 • 5min

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From Curiosity to Conviction: Writing the Book

01:02:21 • 10min

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Pick Your Hard: Embrace the Difficult Parts of Building

01:12:10 • 4min

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The Casino Lures: Quick Fixes and Surface-Level Advice

01:16:23 • 5min

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Meta Creators and Building Education Businesses Ethically

01:21:14 • 5min

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Books, Word-of-Mouth, and Making Something Recommendable

01:26:39 • 7min

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Publishing Fears: Visibility, Criticism, and Identity Risks

01:33:50 • 9min

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Real Work Over Viral Optics: Time Under Tension Matters

01:43:17 • 10min

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Is Your Goal Fame or Transformation?

01:53:19 • 3min

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Be a Business Owner First, Content Creator Second

01:56:04 • 3min

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Book Announcement: Leaving the Casino

01:59:19 • 27sec

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What People Overcomplicate and Underestimate in Business

• Mentioned in 64 episodes

4000 Weeks

Oliver Burkeman

A book about time management and how to live a more fulfilling life.

#3583

• Mentioned in 10 episodes

• Mentioned in 42 episodes

The Pathless Path

Imagining a New Story for Work and Life

Paul Millerd

The Pathless Path by Paul Millerd chronicles his journey from being a high-achieving consultant to embarking on a path of self-discovery and creating a life based on personal values and freedom. The book explores the history of work, the concept of the 'default path' versus the 'pathless path,' and offers practical advice on how to navigate uncertainty, redefine success, and find meaning in one's life. Millerd shares his experiences of living in different countries, facing existential crises, and developing principles that guide him towards a more fulfilling life. The book is an invitation to readers to question their current path and consider a more unconventional, yet meaningful, way of living.

#9926

• Mentioned in 4 episodes

Leaving the Casino

Stop betting on tactics. Start building a business that actually works.

Jessica Lackey

#696

• Mentioned in 35 episodes

Company of One

Why Staying Small Is the Next Big Thing for Business

Paul Jarvis

In 'Company of One,' Paul Jarvis challenges the conventional notion that business growth must always mean scaling up. He argues that staying small can provide more freedom, independence, and a better quality of life. The book offers practical advice on setting up a solo business, determining desired revenues, keeping clients happy, and dealing with crises. Jarvis emphasizes the importance of resilience, autonomy, speed, and simplicity in running a successful 'company of one. ' This approach is particularly appealing to solo entrepreneurs and small business owners who prioritize a balanced and fulfilling life over traditional growth models.

In this episode, I sit down with one of my favorite no-bullshit entrepreneurs, Jessica Lackey, to talk about what it actually takes to build a successful online business. We dive deep into why most entrepreneurs are gambling with their careers and how to build a sustainable, meaningful business based on conviction and curiosity.

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ABOUT JESSICA LACKEY:

Jessica Lackey is the founder of Deeper Foundations, a consulting and training firm that helps expertise-based business owners grow and scale sustainable companies rooted in stronger business foundations. She brings a unique blend of corporate expertise and soulful business building, drawing on an MBA from Harvard Business School, a coaching certification from iPEC, and experience at McKinsey & Company and Nike, Inc. Jessica has supported over 200 entrepreneurs through her programs, blending systems thinking, operational rigor, and deep values alignment.

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CONNECT WITH JESSICA LACKEY:

Website: https://www.deeperfoundations.com/
LinkedIn: https://www.linkedin.com/in/jessica-lackey/
Book: https://www.deeperfoundations.com/casino

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JOIN THE COMMUNITY:

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Go to https://www.creatoralchemy.com/lab now to join.

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TIMESTAMPS:

00:00 Why Building an Online Business Feels Like a Gamble

08:10 When the Math Doesn’t Math

13:37 Understanding Your Business Model

39:04 Common Pitfalls of Early Entrepreneurship

51:10 Languaging, Frameworks, and Resonating with the Right Audience

56:33 The Power of Curiosity and Conviction

01:16:22 Leaving the Casino of Business

01:25:47 Creating an Impact with Your Work

01:36:14 Dealing with the Fear of Ridicule

01:40:45 The Harsh Truth About Building a Business

01:59:35 Advice on Building a Successful Business

02:05:09 Final Thoughts

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SOCIAL LINKS:

Website: https://coreywilkspsyd.com/

YouTube: https://www.youtube.com/@coreywilkspsyd

Substack: https://substack.com/@coreywilkspsyd

LinkedIn: https://www.linkedin.com/in/coreywilkspsyd/

Twitter: https://x.com/CoreyWilksPsyD

Instagram: https://www.instagram.com/coreywilkspsyd/

Disclaimers: The content provided is for educational, informational, and entertainment purposes only. Nothing here constitutes personal or professional consultation, treatment, diagnosis, or creates a professional-client relationship.

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