I was thinking about what questions I would ask if I were raising venture capital. Funny thing is that I often think about what to ask entrepreneurs when deciding whether to invest in them. I've told entrepreneurs often enough that they should ask their VCs just as many questions. I have never really clarified, though, what they should ask. My bad. So, to be fair, here is what I would ask a VC if I was interviewing one for the highly coveted opportunity to invest in my business (note the satire).
1. Who Is Responsible for Your Track Record?
The boring question would be, "What is your track record?" This doesn't address what you need to know, plus you'll get the most personal marketing B.S. Finding out who the VC's go-to people are is probably more important. How will he get you in the door of where you need to be pitching? Has he opened doors in the past that led to revenues, partnerships, mergers, acquisitions, exits? Does he just pay lip-service to everything he can do for you, or does he actually execute? No one works alone in the VC business. VCs should have a strong network of people on whom they can not only call but depend. I answer this question as honestly as possible when asked. I know when I can and -- more importantly -- can't help you. I'll tell you openly when I can't add value to your venture.
2. How Involved in My Company Do You Plan to Be?
This is a double-edged sword. The answer will range between, "I'll just be a board member" to "I'll call you every day to see how things are going." Be afraid of both! Having someone who only comes to board meetings but is otherwise completely unreachable really sucks. But having someone on your back every day takes up too much of your time. If you need your VC by your side every day, you're not good enough to run the company anyway.
3. How Much Vacation Do You Take Each Year?
No, seriously, ask this. Some hardcore VCs out there work night and day. You'll also find race horses out to pasture, VCs who were once superstars but are now just "doing it for fun." If they're accessible, nothing beats the latter. However, those ones do tend to take month-long "trips," during which time they have no interest in business, phone calls, interruptions, or anything of the sort. Ask them. It may mean the difference between getting the advice you need in a crunch and having to figure it out on your own once again.
4. Will I Have Access to Your Partners?
I have really smart guys working with me. I often ask for their help, advice, and insight. Why shouldn't you? Ask the partner you are dealing with if you will be able to access his or her partners in times of need, and ask how they might fill in the knowledge gaps so that your business can succeed.
5. What Is the Process for Follow-On Investment, and How Much Capital Will You Reserve for This?
People are usually so focused on getting the first round that they forget the rest. Ask about the process for follow-on investment. Will a whole new due diligence process be required? Will the VC have to prepare a whole new investment proposal? Who will determine whether to inject additional capital? How long would that take? Most important, will there be enough capital for a follow-on investment? Sure, you're probably saying in your pitch that this round will take you to an exit or the break-even point. But why not plan for rainy days? Ask what would happen... just in case!
6. What Stage of the Fund's Life Cycle Are You in?
Remember, as VCs, we invest other people's money (as well as our own). Every fund has a life cycle (which I won't get into here, but you can find out more here). The companies we look for near the end of an investment fund's life cycle tend to be different than the ones we look for at the beginning of a cycle. Sure, exceptions can be made, and we make them often, but asking doesn't hurt.
I'm sure there are more and better questions, but these are the ones that sprang to mind as I thought about the process of raising VC money. Feel free to add your own in the comments if I've missed any.