Startups For the Rest of Us

Snapshot · Startups For the Rest of Us

Episode 845 | Lifetime Deals Revisited, Building is Not the Hard Part, and Confirming an Idea is Worth Paying For (Rob Solo)

Explore episode Aug 11, 2026

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Customer Agreements and M&A Due Diligence

At 15:10 · chapter starts 14:00

Johannes from Sweden, a longtime listener and MicroConf regular who runs SQL Spreads, submits a detailed audio question about whether and how rigorously he should review the custom agreements his enterprise customers ask him to sign. He's particularly asking about acquisition context: how deeply do M&A buyers examine these documents at the $1–2M ARR stage, and what can he do now to avoid problems later? Rob's response is practical and layered. First, he flags a cautionary tale about a man who used ChatGPT as a de facto lawyer, shared incriminating things in the conversation, and saw those transcripts subpoenaed and admitted as evidence after the court found no attorney-client privilege applied. The lesson: AI is a useful first-pass tool, not a legal advisor. For substantive contracts, Rob recommends having a contracts attorney review the most onerous ones by the time you're doing $1–2M ARR. In a perfect world, a lawyer reviews everything — but that's not realistic for most bootstrappers, and Rob admits he didn't do it consistently himself. What matters most during due diligence: uncapped liability clauses (which expose the acquirer to unlimited risk) and any clause where you've given away IP rights, since those directly undermine the value of what you're selling.

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