A great founding engineer may not be the right person to be CTO of a larger team. Recognizing this misfit can lead to a mutual, amicable departure where the exiting co-founder retains their fully vested equity, preserving the relationship and acknowledging their early contribution.
After raising at a peak-market valuation, Lawmatics navigated the downturn by raising several small, unannounced Series A extensions and a small 'non-Series B' round. This strategy added capital and runway without the public pressure of a large round at a potentially flat valuation, preserving optionality.
For vertical SaaS, niche industry conferences where customers get continuing education credits are a powerful growth channel. Lawyers attend events like the ABA Tech Show to fulfill requirements, creating a captive audience and a great sponsorship opportunity for early-stage companies.
Simply adding a generative AI co-pilot is now table stakes for SaaS companies. The founder argues the next evolution is 'agentic AI' — systems that don't just provide insights but autonomously perform tasks and make decisions for the user, like qualifying and actioning a sales lead.
Instead of raising prices on its entire customer base, the company rewards its earliest adopters by letting them keep their original, deeply discounted price ($60-80/mo). This builds extreme loyalty, even as new customers pay 5-7x more ($400-500/mo) for the same platform.
When an experienced founder starts a new venture based on their own vision, the equity split doesn't need to be 50/50. By framing it as 'my deal,' the primary founder can retain a supermajority (e.g., 80%) while giving a technical co-founder a smaller but still meaningful stake.
After seeing his first company's value explode post-acquisition, this founder now prioritizes partial exits (recaps with equity roll) over all-cash deals. This strategy allows him to de-risk while retaining significant upside for future growth, a stark lesson from his first exit.