One of the things you have to be really careful about as a new business raising money is VC's who are probably just jerking you around. I've unfortunately seen too much of this over the past few years for my liking. I am seeing a strategy firmly take hold where a VC will screen an entire market segment, basically listening to any pitch he can get at to determine what the market looks like. Granted, this is smart business on the side of the VC but you as the struggling business with minimal resources will probably get screwed. You'll be led to believe for quite a while that you have a valid chance of raising money and you will waste time and resources delivering all the information to said VC.
We try to quickly determine whether we want to invest in a business at my firm. If we know in the first meeting that the chance of investment is zero, we'll tell you so. Further, if after the first meeting or two we sour on the deal, we'll break off the process. I firmly believe in not wasting other people's time. Sure, I could take the shortcut of having you educate me on the market but I just don't believe this is good business practice. Keeping you on the back-burner for the option of investment just in case we missed something is not our style.
To hopefully save you some grief when raising capital, here are a couple of ways to determine whether you are being strung along or whether the VC truly wants to invest.
1. First and foremost, a partner will be involved very early in the process. If you have multiple meetings and calls without even knowing which partner from the firm is on the deal, be very weary. Initially it's normal to speak with Analysts/Associates/Investment Managers but ultimately the decision is being made at partner level if you are getting financed or not. Make sure one is involved, you've met them and they are your internal deal champion.
2. A term-sheet has been discussed (note I did not say finalized as some VC's do this early and some late in the process). You may not necessarily have one on the table but you've talked about terms. If you are more than two meetings in and haven't discussed terms/valuation/amount of financing to some extent, be concerned. Again, just as a good salesman would do, make sure the buyer is looking to buy and has the money and authority to do so.
3. The VC has indicated interest in doing reference calls. For some reason, once a VC is doing reference calls, he's much more committed to a deal than when just talking to you. If you have great customer references, gauge the interest of the VC early on to make sure he wants to talk to them. Sure, we as VC's also like to call people whom you did not prepare for the call but generally we will speak to at least one or two references you give us.
4. A pitch to the partnership has been scheduled. If you are forever in due diligence mode and the investment manager or partner have not indicated that you will soon pitch the partnership, worry. For final approval on a deal, you have to convince all the partners. They decide as a group. If you haven't received a firm commitment to a date where you can pitch and it's been many meetings at this point, start asking questions.
5. You've provided enough market material and research to fill a library. Seriously, you probably have some lazy investment manager on the other end letting you do all the work he should be doing. If it just seems like endless requests for more info keep coming and points 1. through 4. above haven't been fulfilled, you're being jerked around. Start asking when next steps will take place and indicate you are weary of providing info non-stop without knowing where the process is headed.
6. Finally, the VC in question has already started talking to your other investors if you have them. It's highly unlikely you are a serious target if the new investor hasn't asked to speak with your current investors. I would never move forward on a deal early on without speaking to the other investors. If this hasn't yet taken place and you're deep into the process, you're being strung along or major negotiation issues lie ahead in your future.
VC's rarely back out of deals very late in the process. If the due diligence has been done, you've pitched the partnership and have a term-sheet, you're looking good. This isn't a thorough list but should give you an idea nevertheless of things to watch out for. Sure, each VC has his or her own process but be very aware of competitive intelligence research. Don't worry as much about your information being shared with your competitors. That would hurt you far less than simply losing all the time and resources feeding a VC with information without investment at the end of the process. You could have spent your time with someone who really does want to give you money.