You might worry that this could lead to a lot of wasted work, to which I have three responses. First, I wouldn't advise leaving much of anything in your back pocket, regardless of whether or not you're asked. If you're smart about it, you can cleverly find opportunities to proactively slip this work into the dialogue. Done effectively, you can shift the balance of the conversation from the VC saying, "I'm asking you this question because I think it's critical to your business and you better have a great answer," to you saying "I'm sharing this analysis, background research, and insight with you because I know it's what's important about my business."
Second, whether or not you spend time talking about it, much of your work is likely to find its way into an investment memo for my partners. When sponsoring a deal, we allwant our recommendations to be as thorough, thoughtful, and data-driven as possible. If you give us more smart stuff, we'll use it, and be that much better at advocating on your behalf. Make sure that any investor who gets serious about the business gets an invite to that Dropbox.
Lastly, and perhaps most importantly, you should be thinking about this stuff anyway! One real benefit of a well managed financing process is that it forces you to step back and think about the forest for a bit, rather than that tiny piece of bark you've been staring at on that one little tree. If you're thoughtful about which analysis you choose to do, you're going to learn some valuable new stuff from doing the work, whether or not any prospective investor ever asks specifically for it.
A financing process is a high stakes game upon which the future of your business ultimately depends. You can't afford to leave anything on the field. So go into the game with a plan of how to control the discussion. Do so and prospective investors will walk away understanding your business better, and with more convictionthat you are an entrepreneur they want to be behind. And that will lead to a competitive process where you end up holding the cards.
Good luck.
Brad Svrluga is a managing director at High Peaks Venture Partners. Follow him on Twitter, or visit his blog.