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

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

Update: 2025-09-22
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Description

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 )

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

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

Tiago Ferreira