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

22/09/2025 26 min

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

Episode Synopsis

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/wbetiagoLinkedin: https://www.linkedin.com/in/tiago-ferreira-48562095/Timestamps by PodsqueezeIntroduction 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)

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