TL;DR: optimize only for monotonically increasing, vanilla terms for 24 months runway at a time. As a VC and an entrepreneur, various times over the last 19 ye

TL;DR: optimize only for monotonically increasing, vanilla terms for 24 months runway at a time. As a VC and an entrepreneur, various times over the last 19 years, I will say this to entrepreneurs in good faith: 1. Your core competency is company building, not fundraising. (There are exceptions, but you're not one of them.) Just get enough money to company-build for the next 18-24 months on plan. 2. The primary (only?) thing to optimize for in valuation is "monotonically increasing over time." All of the pain (for founders, early investors, et al.) is when you have flat-to-down rounds. That's when you REALLY get diluted, and I don't mean like "geez 30% sucks" I mean like "let's build in a new 20% option pool because then founders are now down to 5% each" kind of dilution. 3. The other thing to optimize for is keep your overhang (liquidation preferences) manageable. The bigger the prefs, and the bigger the post, the worse your options are for an earlier founder-friendly exit. 4. Finally, as a sandpaper-the-edges kind of thing, remember that terms tend to get more investor-friendly over time, even for good (but not phenomenal) performers. So all in all, choose smaller rounds and lower valuations provided you get vanilla terms (meaning no multiple prefs or strange dividends etc.) because subsequent investors will insist on same-or-better sweeteners, which can bite everyone down the stack. 5. Really finally -- remember that for all of the seeming insider sharkiness of VCs, they all have to see each other in polite company again. Meaning, they're the devil you know. The real rapacious problem terms come from non-VC participants who don't mind slashing and burning -- be most cautious of those.