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Turning Strangers into Supporters
CEO Briefing #80

Turning Strangers into Supporters

Turning Strangers into Supporters
Short answer

Cold outreach to investors works when it does not feel cold. Even top investors miss breakout founders, so founders should add push to pull. A strong cold message opens with why this investor is relevant, says in one sentence what you build, explains why now, and attaches a deck that is easy to skim.

Cold Outreach That Actually Works: Turning Strangers into Supporters

Most founders dread cold outreach.

It feels awkward. Low odds. Low dignity.

But here’s the truth: Cold can convert – if you understand how to make it feel warm.

In last week’s FundraisingCOUP call, we unpacked exactly that. And if you get this right, you’ll never again hesitate to DM a VC.

1. Great investors miss great deals – unless you show up

You can’t rely solely on the idea that “if you’re good, they’ll find you”. As I explain in my free FundraisingColdstart Course, there is a lot you can do to be discovered by VCs. But don’t rely only on “Pull” – add “Push”.

Even top-tier investors miss breakout founders – because they’re overwhelmed, distracted, or optimizing for deal flow from known sources.

Cold outreach is not desperate. It’s disciplined.

And if you really don’t have anyone who could connect you with an investor or simply don’t have the time to wait for intros, it might be the only way to get on the radar of someone who would otherwise never see you.

2. Cold works when it doesn’t feel cold

The goal isn’t to be slick. It’s to be clear.

Here’s what strong cold outreach includes:

  • 1st line = why them / relevance: Mention something specific – a recent investment, a shared thesis, something they said.
  • 2nd line = what you’re building: 1 sentence, no buzzwords. What do you do, for whom, with what momentum?
  • 3rd line = why now: Fundraising status, round size, timeline. Give them a reason to open the deck now, not later.
  • Deck: Make it easy to skim.

3. Cold outreach isn’t just about the reply rate – it’s about the breakthrough

Sure, most won’t respond. But one strong connection can change the entire trajectory of your round.

And not all VCs are allergic to cold per se. They’re allergic to irrelevant, bloated, or unclear.

You’re not asking for a favor. You’re offering a high-potential, time-sensitive opportunity.

Treat it that way.

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Episode page with show notes on id.vc

Frequently asked questions

Does cold outreach to VCs work?

Yes, if it doesn’t feel cold. Even top-tier investors miss breakout founders because they are overwhelmed or focus on deal flow from known sources. Without intros, cold outreach may be the only way to get on an investor’s radar.

What should a cold email to an investor include?

A first line on why this investor is relevant, such as a recent investment or shared thesis. A second line on what you are building, in one sentence without buzzwords. A third line on why now: fundraising status, round size and timeline. Plus a deck that is easy to skim.

Why do VCs ignore cold emails?

Not all VCs are allergic to cold outreach as such. They are allergic to messages that are irrelevant, bloated or unclear.

Iskender Dirik
About the author

Iskender Dirik

CEO advisor for fundraising, exits and executive branding. Venture Partner at EQT Ventures, previously led the global Gen AI practice at Samsung NEXT and was Managing Director of Microsoft ScaleUp. Host of DEALMACHER, the podcast with the dealmakers who sat at the table when big capital moved.

EQT VenturesSamsung NEXTMicrosoft ScaleUp
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