I reflect on my recent interview with Craig Hewitt, founder of Castos. I dive into the trade-offs between bootstrapping and raising venture capital. I share my thoughts on how AI is changing entrepreneurship and jobs. I talk about my own experiences with product pivots and tough market challenges. I explain how I use AI to boost efficiency in my startup journey. Building products is easier than ever, but getting distribution right is still the hardest part.

Twitter: https://x.com/wbetiago

Linkedin: https://www.linkedin.com/in/tiago-ferreira-48562095/

Timestamps by Podsqueeze

Introduction and Recap of Previous Episode (00:00:02)

Raising Funds vs. Bootstrapping (00:01:20)

Valuation, Market Size, and Risks of Raising (00:03:59)

Analyzing Competitors and Market Potential (00:09:13)

Calculating Market Size and Revenue Projections (00:10:21)

How Much to Raise and Lessons from Greg Hewett (00:11:32)

Benefits of Not Raising and Work-Life Balance (00:12:54)

AI’s Impact on Productivity and Hiring (00:12:54)

Long-Term Thinking and Consistency (00:13:59)

AI’s Negative Impact on Jobs and the Economy (00:16:25)

Building Resilient Businesses and Diversification (00:18:58)

Turning a Landing Page into a Revenue Stream (00:20:01)

Iterating the Business Model and Monetization (00:21:08)

Distribution as the Key Bottleneck (00:22:15)

Leveraging Distribution Channels for Growth (00:23:20)

Conclusion and Call to Action (00:24:39)

#360 - Bootstrapping vs Raising Funds: How AI Is Changing the Game for Indie Founders