Steve Datnow is a San Francisco Bay Area engineer and entrepreneur. He has been involved in five liquidity events, first as a startup employee, and most recently as a founder. He grew his most-recently acquired company, human resources software maker OrgChart5 Inc., from zero to 1,500 customers by bootstrapping, leveraging his connections, and negotiating well.

In this episode, Steve shares how he learned to prevent surprises by asking those interested in buying his companies the right questions about management structure, financials, and even future plans. We discuss how he navigated a merger with another company, and acquisition by private equity firm Lock 8 Partners, in the same year. Finally, we talk about the three ways to compensate a startup team—cash, stock, or a combination of the two—and the benefits and risks of each.

Like many entrepreneurs, Steve likes to take risks. That’s why as a term of the Lock 8 Partners deal, he chose compensation partially based on future company growth, what he calls the “second bite of the apple.”

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