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Founder-led M&A: Insights from Three-time Exited Founder

Daniel Debow, a three-time exited founder — Helpful (acquired by SHOP), Rypple (acquired by CRM), and Workbrain (acquired by Infor) — offers an excellent, practical guide for founder-led M&A:

Here's a breakdown of some of his insights that resonated:

  • Reframe the M&A Process: Debow emphasizes the need to address core business issues that acquirer executives care about. He succinctly puts it: "it always boils down to you solving a business problem for a business leader at the acquirer."

  • M&A Process as a Job Hunt: Debow recommends treating the M&A process like a job hunt, not a fundraising round. He observes, "VCs tend to have a higher tolerance level for difficult founders..." In contrast, corporate executives are less inclined to deal with "wild cards."

  • Visualizing the Integration: Debow stresses the power of presenting a tangible, integrated future. Recounting his approach with his Salesforce exit, he shares how visualizing Rypple within Salesforce's UX helped make the integration more concrete.

  • Understand the Role of Corp Dev: Recognizing the limitations of a corp dev team is essential. Debow explains, "...very rarely does the M&A team inside a larger organization have the ability to just buy a company... Someone has to put their hand up and say, 'I own this thing.'"

  • Navigating Different Organizations: Finding the right person to connect with in a large organization is a perennial challenge. As Debow points out, "At Shopify, we don't even call it M&A, the team is called 'Product Acceleration'..."

  • Diligence Readiness: Debow advises, "Nothing says 'this is a real thing' more than having a built-out data room and a link the M&A team can click to start doing their evaluations. It demonstrates professionalism while also saving you a month in the process."

Debow's guide is essential reading for anyone running a founder-led M&A process.


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