Bootstrapped : The Lighter Side - The Podcast For B2B SaaS Founders

What SaaS Founders Get Wrong About Growth and Funding - A Candid Conversation With Greg Head of Practical Founders

April 6, 2026·40 min
Episode Description from the Publisher

In this episode, Melissa Widner sits down with Greg Head, founder of Practical Founders, to explore a different path to building successful software companies—one that doesn’t rely on venture capital or “grow fast or die” pressure.Greg shares insights from over 30 years in the SaaS world, working with founders who are building valuable, sustainable businesses through bootstrapping and non-dilutive funding. Together, they unpack what defines a “practical founder,” why most exits don’t make headlines, and how founders can retain control, optionality, and long-term upside.They also dive into the metrics that truly matter—CAC, LTV, and net revenue retention—and how AI is reshaping growth strategies for modern SaaS companies. Plus, Greg offers candid perspectives on venture capital myths, exit timing, and why many founders are better off playing a different game entirely.If you’re a founder weighing funding options, navigating growth decisions, or thinking about your eventual exit, this conversation offers a grounded, real-world perspective on building a company your way.

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