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

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.—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.—CONNECT WITH JESSICA LACKEY: Website: https://www.deeperfoundations.com/LinkedIn: https://www.linkedin.com/in/jessica-lackey/Book: https://www.deeperfoundations.com/casino—SUBSCRIBE TO THE NEWSLETTER: Subscribe to the Creator Alchemy Newsletter for exclusive content and unlock the Psychology of Success Masterclass for free.Go to https://www.creatoralchemy.com/—JOIN THE COMMUNITY:The Creator Alchemy Lab is a community for ambitious creators taking bold action to transform their businesses, their lives, and themselves.Go to https://www.creatoralchemy.com/lab now to join.—TIMESTAMPS:00:00 Why Building an Online Business Feels Like a Gamble08:10 When the Math Doesn’t Math13:37 Understanding Your Business Model39:04 Common Pitfalls of Early Entrepreneurship51:10 Languaging, Frameworks, and Resonating with the Right Audience56:33 The Power of Curiosity and Conviction01:16:22 Leaving the Casino of Business01:25:47 Creating an Impact with Your Work01:36:14 Dealing with the Fear of Ridicule01:40:45 The Harsh Truth About Building a Business01:59:35 Advice on Building a Successful Business02:05:09 Final Thoughts—SOCIAL LINKS:Website: https://coreywilkspsyd.com/YouTube: https://www.youtube.com/@coreywilkspsydSubstack: https://substack.com/@coreywilkspsyd LinkedIn: https://www.linkedin.com/in/coreywilkspsyd/Twitter: https://x.com/CoreyWilksPsyDInstagram: 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.