Episode 771 | What Changes As You Grow, AI Agents, Patents, and More Listener Questions (with Craig Hewitt)

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Apr 22, 2025

Craig Hewitt, founder of Castos, shares his experiences in scaling a SaaS company while maintaining culture and brand identity. He discusses the challenges of transitioning from a startup to a multi-million dollar business and the survival of SaaS amid AI agents. The conversation dives into the impact of AI on SaaS platforms and the complex nature of patents for bootstrapped firms. Hewitt emphasizes the importance of community engagement and strategic hiring to sustain values during growth, providing invaluable insights for tech entrepreneurs.

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ADVICE

Leverage Strong Brand and Ambassadors

Leverage your strong brand as a top player in your niche to gain advantages over competitors.
Use community or brand ambassadors to monitor mentions and engage your audience consistently.

ADVICE

Use Financial Leeway to Experiment

Use your financial leeway at $200K+ MRR to take marketing and sales bets.
Test asymmetric bets like sponsorships or YouTube ads to discover scalable growth opportunities.

ADVICE

Preserve Startup Culture Deliberately

Maintain startup culture by owning your small business roots and modeling company values daily.
Culture is best defined by founder behavior rather than prematurely codifying it when growing a small team.

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Can SaaS companies survive the rise of AI Agents?

In episode 771, Rob Walling is joined by Craig Hewitt to answer listener questions. They discuss the changes that happen while transitioning from a small startup to a multi-million dollar SaaS, competing against larger competitors, and maintaining startup culture as teams grow. They also share thoughts on AI agents in the SaaS space and the relevance of patents for bootstrapped businesses.

Episode Sponsor:

This podcast is brought to you by Mercury. I've been banking with Mercury for years and whenever I set up a new account, I'm reminded why traditional banking feels stuck in the past.

When our previous bank faced solvency issues, we needed to spin up new accounts quickly that could handle millions in funds across multiple businesses. Mercury had us up and running almost immediately.

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The interface is elegantly simple for daily banking, paying invoices, and sending and receiving international wires, yet powerful enough to handle the multi-step approval processes we needed to put in place when funding founders with large transfers.

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Mercury is a financial technology company, not a bank. Banking services provided through Choice Financial Group, Column N.A., and Evolve Bank & Trust; Members FDIC.

Topics we cover:

(2:41) – Marketing and sales strategies while scaling
(9:31) – Keeping the startup culture through growth
(14:50) – Can SaaS survive autonomous agents?
(21:03) – AI wrapper tools
(25:15) – Patent strategy for startups
(29:30) – Competing against VC-backed companies

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If you have questions about starting or scaling a software business that you’d like for us to cover, please submit your question for an upcoming episode. We’d love to hear from you!

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