In my experience, terms with lots of if-then conditionals are the most common flag. The last "messy" term sheet I saw had an unusually long diligence period. Predictably, the investor "found" a bunch of problems at the 11th hour and pulled out, leaving the startup in a financial lurch.
Anything that differs from standard docs should be _highly_ suspect, assuming you can get ahold of some.
As a lower bound, I've never seen terms presented on Shark Tank that weren't off-the-wall insane. :D
> How would a first time founder tell the difference?
By talking to other founders, advisors, and their attorneys. This book was useful when I was approaching the first term sheets I ever saw: http://www.amazon.com/Term-Sheets-Valuations-Intricacies-Big...
I 100% agree with you (and I have such contacts to help me out), but I lament the fact that many founders will lack such contacts to give them a sanity check. Perhaps one can reach out to people about it, but without a preexisting network to tap, I am afraid that many will simply accept the bogus terms rather than deal with the discomfort of reaching out for help.
As an aside, I think it's really hard to get clean terms when you're outside silicon valley... I had a friend raise money in Utah recently and he was saddled with all sorts of strangeness. (board for a $200k seed investment, etc.)
Another startup hub advantage.
Which is the whole point. I was told point blank by Cooley that no one outside of the valley will ever do SAFE because it is different.
They also will never do post money options pools which are what YC seems to push for.
So good luck everyone else (myself included).