- Small holes have a way of widening when you push a few zeros through them; and
- When a contract is being negotiated, founders are focused on the marriage. Their lawyer is (or should be) focused on the divorce.
Founders, for personality reasons, often pride themselves on being “closers” and able to accept levels of risk that others aren’t willing to tolerate. They’re “upside” people. That’s generally a great thing, but seasoned negotiators know how to play off that tendency to their advantage. This happens all the time:
Background: A draft’s been delivered and negotiated back and forth a bit. Then, right before signing, the other side’s counsel drops in a provision that they say should be uncontroversial – and casually includes a signed signature page, ready to close.
Company Counsel: (speaking to Founder) This provision is problematic. It could lead to X, Y, or Z. I’ve seen it happen before.
Founder: (speaking to lawyer) Ugh, seriously? I just want to close this deal.
:: after discussion, Founder calls Investor to discuss ::
Investor: Your lawyer is being paranoid. There’s no way we’d do that. We’re all aligned here.
Founder: Yeah, you’re right. Damn lawyers.
:: Docs get signed ::
When the Company becomes more valuable, X, Y, or Z ends up happening.
Founder: F***ing S****!@#
Paranoid? No, Experienced.
Why do good startup lawyers see red flags where founders just see corner cases holding up deals? The answer is simple, and it’s not risk-tolerance. It’s volume. This is often the founders’ first VC deal, or at least they’ve never dealt with a fall-out with investors or business partners. This likely isn’t even the lawyer’s 50th rodeo. The lawyer knows that contracts are drafted during the honeymoon, but enforced during the divorce. And holes in contracts have a way of getting bigger when there’s 7+ figures ($) waiting to be pushed through them.
Granted, there are a lot of lawyers who, because of the billable hour (or their own personality issues), do in fact make mountains out of molehills. See ‘When it’s time for your startup lawyer to shut up.‘ But that doesn’t mean that a good lawyer will simply gloss over all issues to keep the business parties happy. Founders need to be prepared when experienced negotiators push the “let’s just get this closed, we’re all aligned here” button to discredit a lawyer’s advice. It’s an old-school tactic.
Good Cop, Bad Cop.
So my advice to founders stuck in this scenario is to go with another oldie-but-goodie: good cop, bad cop. In other words, ask, but blame your lawyer. It goes something like this:
Investor: Your lawyer is being paranoid. There’s no way we’d do that. We’re all aligned here. (replay)
Founder: Yeah, you’re right. He is paranoid. I know you’d never do X, Y, or Z. Lawyers are such a pain in the ass. But can we just make the change so that we don’t have to discuss things with him again? We’re ready to close if you are.
Sidenote: I’ve found joint lawyer bashing to be an essential part of the founder-investor bonding experience. Don’t miss out.
Deal lawyers don’t mind being the bad cop at all. They’re used to it. It works. Well, only if they’re actually your lawyer. See ‘Don’t Use Your Lead Investor’s Lawyers.’ You preserve your image as a closer, but still avoid the landmine pointed out by your “damn lawyer.”
If you don’t trust your lawyer, you should get a new one. And if you say you trust him, you should pay attention when he says that there is a serious problem in a contract. We’re not all risk-averse pedants. We’ve just seen enough divorces to know what “we’re all aligned here” really means.