If you have ever tried to raise money, you know the email. You walk out of a meeting that felt good. The investor leaned in, asked sharp questions, told you they would circle back. Four days later: "Really enjoyed this. Probably a little early for us, but please keep me posted." You read it six times, get frustrated it contained no actual words, and either grumble (or scream, depending on how long you'd been raising) about how much you hate fundraising.

While hopefully mine haven't been quite that awful, I have sent that email. I vividly recall the first time I had to send a pass to a founder. I agonized over the wording for over an hour and felt like I was going to puke when I hit send. I have now sent what seems like thousands of these, and I still sometimes get that pit in my stomach when I turn a company down. The email I send is usually vaguer than the one I wish I could send. Some of that is for reasons I will get into. Some is because there are only so many hours in a day.

So this is for the founder staring at that email.

Here is the thing founders get wrong about VC no's: (almost) nobody is trying to be a jerk. As much as I feel like a walking business school ad saying it, we are just trying to get the best returns for our own investors. Once you start to understand how we are thinking, the language of venture gets a lot easier to translate.

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So Why Does Nobody Actually Say No?

VCs are so opaque because we operate in a tightly knit network where optionality, reputation, and conflict avoidance mean survival.

Optionality. VCs never want to be in a position where they can't get access to the best deals. If you turn out to be the hot startup, whether that is five minutes or 18 months from now, the investor who passed wants a way back in. So they say "not now" instead of "no." This is not a hypothetical. I know many, many firsthand stories of investors passing on one round and coming back to lead the next.

Conflict avoidance. Nobody enjoys delivering bad news, and every investor has stories about founders who took a pass badly. It is frustrating for someone who chose to spend scarce time with you and on writing you feedback, and it is memorable in the wrong way. Investors talk (see the Secret VC's recent article on red flags). The odds that the person passing on you knows another investor you are talking to are incredibly high. So to avoid drama and frustration, the safe move, for the VC, is the vague one.

Put those two together and you get the email I mentioned earlier. Interestingly, both of these reasons work in your favor if you handle a 'no' well. The door stays open, and the network hears how gracious you were about it. Handle it badly and they work against you: a tantrum doesn't just cost you that fund, it costs you the others they may talk to. Don't treat every dismissal as a forever no, and don't behave in a way that makes it one.

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The Translation Table

These are the five lines I see founders puzzle over most. Here is what each one usually means when it comes from an investor, and what I would do next if I were sitting in your seat.

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One more move worth keeping in your pocket. When a conversation stalls, meaning slow replies, "reach back out in a few weeks," or a "keep me posted" that has gone quiet, send one follow-up, then what I would call an up-or-out note: "We're continuing our raise and cleaning up our pipeline. I want to make sure I understand whether we should spend more time together. Totally okay if this isn't a fit." Directly asking for a pass sometimes reignites interest, and it often gets you some honesty ("sorry, we're heads-down on another deal right now") that you would not have gotten otherwise.

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So What's Next?

Most of what happens after a no is up to you, not the investor. Use the levers in your control.

Send the monthly update. Same week every month, report out on the same three to five numbers/KPIs, the high and the low, and one specific ask. This is how "keep me posted" turns from a brush-off into a relationship, and where the investors who passed get to watch you do what you said you would do.

Start early with the next stage. "Too early" and "let's reconnect" are an opening if you use them well. I always recommend that founders build relationships with investors at the stage after their current one while not raising. If your seed is 18 months out, take an occasional call with a seed investor now. It is easier when you are not asking for money: you will learn what milestones they care about (which will change, because everything is changing), and if they are on your update list they get to watch you execute, making your eventual, hypothetical investment from that VC faster and easier.

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The No's I Still Can't Give

I try to be direct about why we are passing. These days I try to pass on the first call if I know it is not a fit, which I think is kinder than an email ten minutes later. But there is one "no" I still struggle to deliver: when the founder is the reason. When I don't believe this person can build what they have said they will build, I am not going to say that to their face. Maybe one day I will have the nerve. I am not sure I want to. I try hard to make sure every interaction I have with a founder leaves them and their company no worse off, and I don't know what anyone gains from hearing "interesting idea, but I don't think it's you."

So I will admit it: sometimes I am the obtuse one. In busy seasons I don't always give founders as much detail on a pass as they deserve. What I would ask in return is that founders try to always read these as if they were written with the best intent, because in my experience that is almost always the case.

Then stop waiting for the clear no, because it (almost) never comes. Pull up your investor pipeline. For each conversation, can you name which line in the table you are looking at and what you did about it? If the honest answer is "I'm hoping," send the up-or-out note tonight. The worst case is a no you finally get to hear out loud. And you already know what to do with that.

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Ilana Habib is Principal at Cintrifuse Capital, a venture fund and innovation hub backing early-stage founders and strengthening the Cincinnati startup ecosystem. She’s spent her career in and around the entrepreneurial ecosystem and loves rolling up her sleeves to support founders and operators. She’s also an avid traveller, taking her camera with her to capture some of the most interesting places on earth.