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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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/

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