Deirdre Tshien shares her extraordinary journey from hospitality to SaaS and coaching, revealing the wins, setbacks, and pivots that shaped her career. With experience scaling and exiting seven businesses, Deirdre talks about building CAPShow—an AI-driven content marketing platform for podcasters and coaches—born from her own content burnout. Learn how she achieved a 5x business sale, why market timing matters, and how to design a scalable, sustainable business that works for your life—not the other way around.

Key Takeaways:

• Don’t get trapped by your product—obsess over messaging and market fit instead.
  
  
• Marketing is more important than a perfect product. Visibility is key to sales.
  
  
• Exit ≠ failure. A well-prepared exit can lead to a higher multiple (her business sold for 5x EBITDA).
  
  
• Build systems that support scale: franchise-ready models attract better buyers.
  
  
• Coaches need to create scalable marketing assets without losing their minds—CAPShow does just that.

Timestamps:

00:00 Introduction and Host Greetings

00:12 Star Wars Skeleton Crew Discussion

01:31 Entrepreneurial Journey and Challenges

04:07 Interview with Deidre Chen

06:05 Deidre's Business Ventures and Lessons

12:34 Navigating Business Exits and Setbacks

19:52 Transition to New Ventures and AI Exploration

24:38 Identifying Market Pain Points

28:12 Transitioning to AI in Podcasting

28:43 Overcoming Initial Challenges

29:55 Pivoting to Digital Marketing

31:55 Launching CAP Show

38:27 Navigating Market Changes

43:27 Focusing on Sustainability

49:53 Final Insights and Offers

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