Here’s one that has always amused me to some extent. Rarely have I met an entrepreneur who was not obsessive about confidentiality. I understand the need to keep a lid on good ideas, but let’s think about this unemotionally for a minute. Most ideas are variations on a theme, often times without any truly new or proprietary elements. How critical is it to keep such ideas under tight wrap? I typically err on the side of being open with my ideas, at least with people I know through one or two degrees of separation – it’s far more important that people know what you’re up to, than that you compulsively force everyone to sign an NDA (non-disclosure agreement). Again, this is not an argument against NDAs, it’s an argument against becoming so obsessed with confidentiality that you lose sight of the big picture – it’s unlikely that you will succeed in any venture unless the people who can help you know what you’re up to. Remember too, very few VCs will sign NDAs, so don’t push them too hard on it, at least at the beginning stage, or you will give yourself away as an amateur. It’s also important to keep in mind that with VCs, strategic investors, potential partners, and others, you are in control of how much information you disclose, and perhaps more importantly, at what stage of the conversation you disclose it. Only when you get to the point that you feel uncomfortable that you are about to disclose something proprietary that could harm your success in the marketplace, should you pull out an NDA..