44 | How Bootstrapped Software Founders Build a Company Worth Buying (with Greg Head of Practical Founders) episode artwork

EPISODE · Sep 15, 2026 · 21 MIN

44 | How Bootstrapped Software Founders Build a Company Worth Buying (with Greg Head of Practical Founders)

from The Path to Exit · host Vista Point Advisors

For founders who built a software company without big venture rounds, the exit playbook looks different. Raising little or nothing keeps your options open, but it also means you have to build a company worth buying without the fuel VC-backed peers spend on sales, marketing, and product. In this episode, Mike Lyon sits down with Greg Head, founder of Practical Founders, to discuss how bootstrapped SaaS founders keep their optionality, why AI is shifting the calculus for smaller and middle-market software companies, and the specific steps to prepare for a transaction on your own terms.Vista Point Advisors is a boutique sell-side investment bank providing unconflicted M&A and capital raising advice to founder-led software, AI, and internet businesses. We partner with entrepreneurs of growing businesses to help them understand their options in the marketplace so they can maximize business value, leverage their options, and realize their ideal outcomes. Securities offered through Vista Point Advisors, member FINRA/SIPC. This has been provided for informational purposes only and should not be considered as investment advice or a recommendation. It is not intended to address all circumstances that might arise. The views expressed herein may change at any time subsequent to the date of issue. Opinions contained herein should not be interpreted as a guarantee of future results. Outcomes will vary depending on individual circumstances. Any examples used in this material are generic, hypothetical and for illustration purposes only. Testimonials from past clients may not be representative of the experience of other clients and there is no guarantee of future performance or success. Clients are not compensated for their comments. 

Episode metadata supplied by the publisher feed · Published Sep 15, 2026

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For founders who built a software company without big venture rounds, the exit playbook looks different. Raising little or nothing keeps your options open, but it also means you have to build a company worth buying without the fuel VC-backed peers spend on sales, marketing, and product. In this episode, Mike Lyon sits down with Greg Head, founder of Practical Founders, to discuss how bootstrapped SaaS founders keep their optionality, why AI is shifting the calculus for smaller and middle-mark...

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44 | How Bootstrapped Software Founders Build a Company Worth Buying (with Greg Head of Practical Founders)

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