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After a recent project, I’ve been thinking a lot about the subject of preparing a smaller company for a successful founder’s exit. In larger firms there is a robust process and standard options for how this typically goes down (IPO or mainline M&A activity), complete with an entire multitrillion-dollar industry — investment banking — largely dedicated to it. But what about smaller founder-run companies (say, under $10MM in revenue), particularly those with with decades of tenure? Boomers are squarely in the standard retirement range right now, but sadly most Boomer-owned companies probably won’t sell. What will happen to them? If

This material is excerpted from the introduction to Bots in Suits: Using Generative AI to Revolutionize Your Business, a practical demonstration of how to converse with a generative AI chatbot (like ChatGPT) for business use. Because generative AI operating at the level of ChatGPT is so new, you need to tread lightly. It would be a dire mistake to read this book and go, “Wow, now I don’t need to pay all these lazy employees/contractors/vendors anymore! You guys are all outta here!” and start upending major parts of your business with layoffs and restructuring. If that’s your approach, you will

Let’s talk about the wave of layoffs in the news. It’s become a common sight over the years to see poorly run, highly funded startups (usually in tech) resort to mass layoffs in knee-jerk fashion. That’s no surprise, as many of those companies aren’t really differentiated on product and don’t even need a path to profitability in order to be considered a reasonable funding bet for many VCs. The common VC model only looks for a small handful of true winners, followed by some break-evens or small losses and the rest as total failures with 100% loss of capital. If