Mark Suster has another excellent post on the VC business and how it can affect entrepreneurs. This time the subject is investing across funds. The only thing I would add is that, as Mark Suster points out, at the time of the initial investment you can, and should, try to make sure that the fund, or funds, that are investing in your company have both the resources and the longevity to themselves support follow-on rounds. If they don’t then the VC can face the issues that Suster points to. One of these is if the B round is a down round, how do they explain to fund 1 investors that fund 2 investors are diluting them? However, once you get past round 2 and you have multiple VCs with multiple agendas each of whom has made investments after yours (thereby changing their overall fund availability), there is just little you can do. If the end of fund problem strikes, you are going to have to rely upon the investors to work it out.