How to Decide How Much to Ask Investors For:The Chain

Decide how much to ask investors for by working backwards from a milestone. Pick the specific milestone that makes the next conversation easy, work out how many months it takes, and price those months. A number chosen because it sounds normal tells them there's no plan.

How to decide how much to ask investors for, from the milestone back

"How much are you raising and what will you do with it?"

That question is asked in every single meeting. And in most of them it's answered vaguely. A round number, a hopeful shrug, a list of things the money will "support". You can see the investor's attention drift.

Here's why it matters more than it sounds. The question isn't really about the number. It's a test of whether there's a plan behind it. The investor is checking one chain: this amount buys this many months, which reaches this specific milestone, which makes the next conversation straightforward.

That chain is what's actually being assessed when you work out how much to ask investors for. Not the figure. The chain.

So a number picked because it feels normal for your stage does the opposite of what you want. It signals the plan doesn't exist. Whereas a modest number with a visible path behind it reads as someone who knows exactly what they're doing.

How much to ask investors: the chain, link by link

Build it in this order. Don't skip ahead to the amount. The amount is the last thing you get to write.

Read the right-hand column again before you settle how much to ask investors for. Every defensible answer is specific and checkable. Every weak one is a mood.

The milestone is the hard part, and it's the one most people skip. Choose it by asking what the investor after this one will need to see. Not what you'd like to build. What would make a stranger say "yes, that's worth a conversation". Work backwards from there.

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Before the number: should it be a number at all?

Stop. You run a one-person business. You currently own all of it and answer to nobody. So before you price a raise, price the alternative.

Ask what capital would let you do that revenue and evenings can't. Be specific. "Move faster" is a real answer, but weigh it against what you'd hand over: ownership, control, and an obligation to chase an outcome big enough to return someone else's fund.

Then notice what this does to the amount. If the honest answer to "what would the money buy" is "one specific thing, worth this many months", you can price it. If the honest answer is "I'm not sure, but raising seems to be what people do", you can't. You've found your answer before you've touched a spreadsheet.

This is a legitimate trade in both directions. Raising isn't a graduation. It's a choice with a cost. The number you ask for is just the price tag on that choice, so make sure you want the thing it buys. What investors look for in a pitch explains why they'll test your answer to this harder than any slide.

Name the risk the money is buying down

Every deal has one dominant risk. Yours is one of four: market, execution, distribution or technical.

Your ask should read as a plan to shrink that risk. Say it out loud: "The main risk is this. Here's what I've done about it already. Here's what this money buys in further reduction."

That sentence turns the amount from a request into a trade. They aren't being asked to fund your hopes. They're being shown exactly which uncertainty their money removes. It's the cleanest argument you have, and it costs nothing to write.

People worry that naming the risk creates it. It doesn't. They'll find it within two meetings anyway. The only variable is whether they hear it from you with a plan attached.

The mistakes this avoids

Get the chain right and several expensive errors disappear.

• Asking for the typical amount. A figure taken from "what people raise at this stage" has no plan under it, and they can tell.
• Asking for too little to reach anything. If the money runs out before the milestone, you're back in the market weaker than you left it.
• No slack. Your runway has to allow this to take considerably longer than you expect. Raises always do.
• A vague use of funds. A list of categories isn't a use. A milestone is.

Note that second-to-last point. The guide is blunt about it: make sure your runway allows the process to take considerably longer than you expect. A raise is a pipeline, and pipelines drift. How to keep it moving is in how to run an investor process.

How to say it in the room

When the question lands, answer in one breath. Amount first, then the chain.

Something like: "We're raising this much. It covers this many months, and it gets us to this milestone, which removes this risk." Four beats. Then stop talking.

That silence is where you earn trust. You gave a number, a timeline, a goal and a risk, and nothing in it was an adjective. Compare that with the usual answer, a round figure followed by a spray of things the money will "support". One is a plan. The other is a wish list.

Practise it until it takes less than a minute. It belongs in your short version of the pitch, the one you'll use most. And write the same chain into your notes after every meeting, because the answers you get back will tell you whether the milestone convinced anyone.

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A smaller ask can be the stronger one

You might think asking for more shows ambition. It doesn't, not on its own.

What shows ambition is a milestone that matters and a path to it that holds up under questions. Pad the amount and you add a number you'll have to defend, with nothing behind it. Trim it to the cost of reaching the milestone and every euro of it has a job.

There's a second reason. The more you take, the more you hand over and the bigger the ending you owe someone. You currently own all of it. Every extra euro you ask for is something you'll pay for later in ownership and control. So ask for what the milestone needs, not for what looks impressive. And if the milestone could be reached from your own revenue and evenings, say so to yourself honestly before you pitch anyone.

What if you can't defend the path?

Then you've learned something cheaply.

Maybe the milestone is fuzzy. Maybe you can't say how many months it takes, because you haven't done the work to know. That's the finding. A plan you can't walk through isn't ready to be funded, and it's far better to discover that in your own notes than in the middle of a meeting.

Some people find this is exactly why preparing to raise was useful, even when they never did. It forces you to state, in public, what you believe about your economics and your path. The audience is adversarial and informed, which makes it more clarifying than private planning. You find the missing middle of your plan early.

If the number only works with assumptions you can't back up, adjust the plan, not the story. And remember that all this prepares the case you'll later make in your deck. What goes in a pitch deck shows where the ask slides in.

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Do this before your next conversation

1. Write one milestone. A single result that makes the next investor's decision easy. If you have three, you have none.
2. Write the risk it shrinks. Pick the dominant one. One.
3. Count the months, then cost them. Do the runway arithmetic honestly, line by line.
4. Add slack. Then add a bit more. It will take longer.
5. Say the chain out loud. "This amount buys these months, reaching this milestone." If you stumble, find the weak link.

Do that and how much to ask investors stops being the dreaded question and becomes the easiest one in the room. You won't be defending a number. You'll be reading out a plan.

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Frequently asked questions

Is there a standard for how much to ask investors at my stage?

There is usually a typical range, but picking from it is the mistake. A number chosen because it sounds normal signals that no plan sits behind it. Start from your milestone and cost the months it needs.

What should the money buy?

A specific milestone that shrinks the dominant risk in your deal, whether that is market, execution, distribution or technical. Say what you've already done about the risk, and what this amount does in further reduction.

How much slack should I build in?

Enough that your runway allows the raise to take considerably longer than you expect. The guide gives no figure, because it depends on your costs. Write your own number from the runway arithmetic and then add to it.

What if I can't justify any amount?

That's useful. It usually means the milestone is unclear, or capital isn't what you need yet. Fix the plan before you pitch. Remember too that not raising is a fully legitimate outcome when you own everything today.

The full method, with the checklists, is in The Pitch Playbook, a free 23-page playbook.