What's up, it's Zayd.

When I was raising money, I learned a lesson that has almost nothing to do with raising money and everything to do with selling.

The first fundraising call you take is always the one where someone asks the question you did not prepare for. You stumble through a half answer, you feel it land badly, and you spend the rest of the call trying to recover. (Now replace those You’s with…I). We all do it. The instinct is to start with your dream investors so you can lock them in early. If you take one thing away from this letter. Just. Please. Don’t. Do. That.

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The lesson I learned the hard way (and what I tell anyone selling into a market they have not cracked yet), is to start with your tier-four prospects. These are the accounts that would be nice to clinch, but that you are not emotionally attached to. The ones where, if the conversation goes to shit, you just take the L and move on.

On a fundraising call, that means going on “practice” dates. Test your material and work out the kinks with the tier-four investors. Every question they ask that you didn’t expect goes into a question bank to prep for and practice later. By the time you reach the investors you actually want, you’ve mastered all the easy parts, so you can focus on objection handling and company specifics, because those are the only parts still capable of surprising you.

Same goes for selling. The first time you call into a new segment, you don’t really know which objections are real and which are reflexes. You don’t know which line in your pitch made people lean in and which one made them open UberEats under the table to order lunch. The fastest way to stop guessing is to spend your low-stakes calls collecting the answers.

A rough call that feels awkward and halting and like you’ve both never had a social skill in your lives is…draining…but it’s also just inventory. Every objection that catches you flat is a gift, because it is going to come up again, and now you have a chance to build a clean answer before it costs you a deal you can’t afford to lose.

For the answers themselves, the biggest advice I can give is don’t “doth protest too much” (or whatever the phrase is). There’s nothing more off-putting than getting defensive on a call. Objection handling should be short and succinct. Just give a very direct reason why the concern is not true, or a concrete way you will prove it is not true in the future without any fanfare. When a prospect says “can you actually do this,” the strongest answer is some version of “yes, it is one of the things we are best at,” followed by the proof. You turn the question into a strength (classic interview “what’s your biggest flaw"” “I work too hard,” rules apply). You can’t do that live if you’ve never heard the question before.

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Founders and reps both make better decisions when they’re not afraid of the next sentence. You’re supposed to be able to move forward with about 60 percent of the information. That is much easier when you have already metabolized the questions that used to scare you. The C-tier calls are how you buy down that fear cheaply, on accounts where the cost of a mistake is close to zero.

Everybody has a plan until they get punched in the face. This metaphor sounds masochistic, but I’m standing by it. Choose to get punched by people who can’t really hurt you, so that by the time it matters, you have already learned to keep your hands up (there’s some joke to be made about my last name being, Ali. I’ll think of it three days late, for sure).