How Many Investors Should Actually Be in Your Pipeline?

One of the most common questions I get from founders we work with is some version of:

"How many investors should we actually be reaching out to?"

And almost every time, they fall into one of two camps.

Camp 1: The founder who has a list of 5-10 investors they "really like" and want to have deep, meaningful conversations with each one.

Camp 2: The founder who blasts 5000 investors with a templated email and hopes something sticks.

Both of these are usually wrong.

The first approach is too narrow. You're putting all of your eggs into a handful of baskets and praying that one of them writes a check. If those 5 conversations don't convert, you're starting from zero again - except now you've burned 2-3 months.

The second approach is noise. No personalization, no targeting, no understanding of what that fund actually invests in. You might book a few meetings, but they're going to be with the wrong people.

So what's the actual answer?

It depends on a few things, but here's the framework we use at Breakout.

Start with your round size and work backwards.

If you're raising $5M, you're likely looking for a lead check of $2-3M and a few follow-on checks to fill out the rest.

That lead check is the hardest part of the raise. Everything else gets easier once it's in place.

To find that lead, you need to be having real conversations with 30-60 qualified, relevant investors who have a track record of writing checks at your stage, in your sector, at your check size.

Not 500. Not 5. Somewhere in between - but only if they're the RIGHT ones.

You are going to need to talk to more investors than you think.

Are there exceptions to this? Of course.
Could you find your lead after 2-5 conversations? Yes.

But it is rare, and it is not a strategy we recommend leading with unless your product has an Open AI-level of disruption and demand.

Most active funds are reviewing hundreds, sometimes thousands, of deals per quarter. Your email is landing in an inbox next to 50 other founders who are also raising, also have traction, and also think they're the best opportunity in the market.

That's not a reason to panic. It's a reason to be realistic about the math.

Even if your company is strong, your story is tight, and your metrics are solid - a lot of the investors you speak with are simply not going to be the right fit. Wrong stage. Wrong sector focus. Wrong timing in their fund cycle. Already allocated to a competitor.

None of that is personal. But all of it means you need more at-bats than you originally planned for.

This is why we say the investor pipeline should be treated like a sales pipeline.

You need volume at the top, qualification in the middle, and conversion at the bottom.

You need enough at the top to give yourself real options at the bottom. And you need every single one of those investors to be targeted, relevant, and contacted in a way that actually gets a response.

A good fundraise is a living pipeline. You're adding new investors weekly. You're following up with warm leads. You're cutting dead weight. You're getting intros where they make sense and going direct where they don't.

Thanks for reading as always,

Ryan Bryden
Breakout Capital Group

If you have a customer LTV > $50k and want to unlock 6-7 figures of sales pipeline from a new acquisition channel before you make a sales hire, check out our Revenue Advisory Offer

If you're raising $2-50M in the next 6 months and want guaranteed access to investors who can fill your round, check out our Capital Advisory Offer