Every startup fundraising process is influenced by the balance of power between the founder and the investor. When the founder has a company that is doing incredibly well, and is being chased by lots of investors, the founder has more leverage. When the founder is inexperienced, or has a company that hasn't yet gotten a lot of traction, the investor has more leverage.
Often, the output of this shifting balance is reflected in the price agreed to by the two sides. It tends to be higher relative to progress when the founder is stronger, and lower when the investor is stronger. When the two sides are equally experienced, the negotiation is usually “fair” in that both sides know what they are agreeing to. Whether or not they are happy with that is another question.
There are, however, situations that arise in which investors take advantage of inexperienced founders and get them to sign terms that are potentially harmful to the company. Investors that do this want more economic upside and know that they can exploit the founder without the founder even knowing what's happening.
How bad terms can hurt
While I've seen a number of examples of this, there's one I saw recently that was particularly bad. An investor got a first time founder to give them a Right of First Refusal (ROFR) for 2.5x their initial investment on any fundraising that that founder subsequently raised prior to an equity financing round. There are a number of bad things there, but the part that makes this even worse is that the investor has 60 days to say yes or no to the ROFR, no matter what the company does.
Imagine the company were to raise $50k on a 4mm cap safe today, and then 500k on an 8mm cap safe in 55 days - which can be a very long time in the life of a startup - the investor could put in 250k at 4mm! This means that the founders of the company cannot adequately plan out their allocations to new investors, figure out how much dilution they'd be taking, or even know how much money they'd raised until 60 days after the last financing. This kind of uncertainty is terrible for founders and for companies. It is a major distraction and complication at a time when the founder really needs to focus and know what's going on.
This isn't just true about early stage rounds. Founders who are really successful at early stages may find themselves raising late stage rounds where they are again inexperienced. This can lead to founders signing terms that seem good or inconsequential at signing, but lead to really bad things down the road. For instance, a number of founders agreed to ratchets as a trade off against higher valuations in late stage rounds. This is fine if everything goes better than planned, but can hurt the company, founders, and earlier shareholders if things don't go as well as hoped.
Some terms to watch out for
It would be hard to make a comprehensive list of all the bad terms out there, but here are some to watch out for:
- Anti-dilution - where an investor maintains their ownership through subsequent financing without having to invest more.
- Liquidation preferences greater than 1x - where an investor is guaranteed a particular level of return before distributions are made to other equivalent sharelholders in an exit. (http://www.learnvc.com/2008/07/liquidation-preference/)
- Super pro-rata - where an investor has the sole option to increase their ownership at the next round of financing. (http://www.bothsidesofthetable.com/2011/09/25/why-super-pro-rata-rights-are-not-a-good-deal-for-entrepreneurs/)
- Cramming down the pro rata of earlier angels/investors
- Asking for extra advisory shares on top of an investment. This is actually something you might give to incredibly helpful investors who don't have the cash to invest as much as they'd like. It should be your option, though, not a demand.
There's no way to list out all of the bad terms that investors can put into term sheets. There are, however, things that founders can do to stop this badness from hurting them:
- Read every word of every financing that you sign. Make sure you understand each clause, and what that clause will do in the future in different scenarios. If there's anything a doc that you don't understand, don't sign the doc until you do understand those things.
- Get a lawyer that understands startups. It's important to find someone with experience. Not only can a good lawyer explain what's going on with terms of your agreement, he/she can tell you if those terms are standard. Lawyers can also help you negotiate, though this is usually more relevant in priced rounds.
- Be really careful of side letters. If you're using a standard doc, like the YC safe, it's probably already well balanced and understood. When an investor wants a side letter, they want something non-standard. This isn't necessarily bad, but it should make you extra cautious.
- Get help from more experienced founders, particularly ones that have seen multiple financings. They'll be able to give you perspective on what makes sense and what you should push on. They may also be able to help you negotiate.
- Know that, ultimately, if you are desperate for financing, you may have to accept bad terms. While that's suboptimal, it is ok if you understand what you are agreeing to. It's rare that a single bad term you understand will kill your company, though the aggregate impact of terms you don't understand can materially change your outcome.
While these steps can help with future fundraising, there are many founders who have already agreed to bad terms (either through necessity or ignorance), and aren't sure what to do about it. This is tough, because it will depend on whether or not the investor inserted the bad term knowing it was bad for the company, or if they thought it wasn't so bad. As a founder, you should find out, and try to remove it. There's no perfect way to do this, but the first step is to ask the investor to get rid of the term. Say that you were talking to your lawyer or friend and that they pointed out that you signed a term you didn't understand. Ask the investor if you can remove it so that you don't have to worry about it. This will get rid of some portion of these bad terms.
If the investor refuses, your options are more limited. If you have a strong network of other investors or advisers, you can ask them to pressure the investor to change. We've done this a number of times for our companies at YC. Remember that startups, and investing in them, is a long term bet. Reputation matters and smart investors - whether or not they are “good” - will know that screwing a company will end up hurting them down the road. You can make clear that you'll let other founders know about the bad terms you signed. An investor can probably sustain this happening once, but if that investor acted badly towards you, they've likely done it to a lot of companies. If many companies start talking about how bad that investor is, the investor will cease to be able to invest in companies and will have to find a new profession.
The investors that force these terms on unsuspecting founders fail to realize that the big outcomes in investing don't come from clever terms, they come from outliers. Even more than that, asking for these terms is a direct signal that the investors isn't a good investor. I'd avoid those investors asking for these terms, and I tell founders to do the same. In fact, inserting bad terms into funding documents is a good way to limit the number of chances investors have to invest in those black swans because adding those terms will destroy their reputations - it's just a question of how long it will take.
 Here's a good explanation of how this has actually played out recently: https://www.cooley.com/files/TechIPOsTriggeringMore'Ratchets'InShakyMarket.pdf
 This will probably only work for early stage rounds and investors. Later stage investors are more hard nosed, and will hew tightly to caveat emptor.
Thanks Geoff Ralston, Andy Weissman, Dalton Caldwell, and David Tisch for your help on this.