When startups are self sustaining and profitable enough to afford an attorney, that is good news. However it also implies that they are also large enough for dire consequences, if something goes wrong. Many small startups work with services like LegalZoom, but others prefer seeking out dedicated legal counsel.
Working with an attorney can sometimes be frustrating, as it seems the default response from him/her is "No! No! Not possible. Not legal. Too risky." After all the purpose of having an attorney is to protect you. The way to get around this is to ask your attorney the "What is the risk of not obeying their recommendation?" Then you can make an executive decision on what to do next.
Let us know about your experiences working with startup lawyers.