Having raised a number of VC rounds personally and observed many more as an investor or friend, I’ve come to think there are a set of dominant best practices that entrepreneurs should follow.
1. Valuation: Come up with what minimum valuation you’d be happy with but never share that number with any investor. If the number is too low, you’ve set a low ceiling. If your number is too high, you scare people off. Just like on eBay, you only get to your desired price by starting lower and getting a competitive process going. When people ask about price, simply tell them your last round post-money valuation and talk about the progress you’ve made since then.
2. Never tell VCs the names of other VCs that are interested. Reasons: 1) if you are overplaying your hand that could send a negative signal. Most VCs know each other and talk all the time. 2) it is possible they’ll get together and offer a two-handed deal in which case you have less competition.
3. I think the optimal number of VCs to talk to seriously is about 5. That is usually enough to get a sense of market but not so much that you get overwhelmed. You should pick these VCs carefully – this is where trusted, experienced advisors are critical.
4. If there is a VC you really like, have a “buy it now price” and if they hit that valuation (and other terms are clean) do the deal. Otherwise, say you’d like to “run a process” and include them in it.
5. Try to set timelines that are definite enough that investors feel some pressure to move but not so definite that you look dumb if you don’t have a term sheet by then. (Investors have an incentive to wait – “to flip another card over” as they say – whereas entrepreneurs want to get the financing over with asap). Depending on where you are in the process, say things like “we’d like to wrap this up in the next few weeks.”
6. Once you start pitching, the clock starts ticking on your deal looking “tired.” I’d say from your first VC meeting you have about a month before this risk kicks in. You could have a great company but if investors get a sense that other investors have passed, they assume something is wrong with your company and/or they can wait around and invest later at their leisure.
7. The earlier stage your company is the more you should weight quality of investors vs valuation. For a Series A, you are truly partnering with the VCs. You should consider taking a lower valuation from a top tier firm over a non top tier firm (but probably any discount over 20% is too much). If you are doing a post-profitable “momentum round” I’d just optimize for valuation and deal terms.
8. Term sheets: talk about terms in detail over the phone. Only accept a term sheet once you have decided that if it matches what was described you are prepared to sign it. After sending a term sheet VCs get worried you’ll shop it and usually want it signed in 24 hours.
9. Get to know the VCs. Talk to their other portfolio companies, read their blogs, call references, etc. You will be in business with this person for (hopefully) a long time.
10. Timing. While it’s ideal to raise money once you hit the milestones you set out initially, you also need to be opportunistic. Right now, for example, seems to be a really good time to raise a VC round. You could make a ton of progress over the next 6 months but the market could tank and end up in a worse place than you would be today.