How to Piss Off Investors

+ weekly list of handpicked startup events for founders and investors in London

Author

Vasily Alekseenko
May 08, 2025

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How to Piss Off Investors

Let’s face it — every founder thinks they’re special. We kind of have to. A little bit of delusion is a survival mechanism in this game. Otherwise, we’d all give up before the first rejection email.

But there’s a difference between being ambitious and being careless. And way too many founders go full “spray and pray” with their outreach — which not only doesn’t work, but ends up doing more harm than good.

I’ve invested in a few startups myself, and running Rare Founders means I’m constantly speaking to other angels, VCs, syndicate leads, and accelerator partners. The feedback is always the same. Founders keep making the same mistakes — and they’re turning potential allies into very annoyed people.

So if you want to avoid becoming that founder, read this 👇

🔴 Don’t add investors to your update list without asking.

I’m not the only one who gets this — every investor I know is spammed daily with random “investor updates” from founders they’ve never spoken to. Guess what we do with those emails? Mark as spam. Every time.

Not only does that annoy investors, but it damages your email deliverability — so even the right people will stop seeing your updates. Just ask. If someone wants to hear from you, great. If not, save yourself the hassle.

🔴 Stop sending cold messages without checking relevance.

Most investors clearly state their criteria — on LinkedIn, websites, even Twitter/X bios. But founders still ignore it and send pitch messages that have nothing to do with what that investor actually backs.

I’ve had this happen, and so has every investor I know. If you can’t be bothered to read a LinkedIn profile or Google a thesis, don’t expect a reply. Straight to spam or ignore.

🔴 Don’t pitch 2 seconds after connecting on LinkedIn.

Again — this isn’t just me. Ask any investor and they’ll tell you: nothing screams “I don’t respect your time” more than an instant cold pitch right after the connection is accepted.

What works? Personalised messages. Something like: “I saw your comment on X,” or “I’ve been to your event — it really helped me,” or “I loved your blog on Y.” These always stand out. The rest? Delete.

🔴 No reply after 3 messages = move on.

This applies to all outreach — email, LinkedIn, whatever. Most investors are overwhelmed with messages and pitches. If someone hasn’t replied after a couple of follow-ups, take the hint. It’s not personal. Move on and try again in 6-12 months if it makes sense.

🔴 Read the damn investment criteria.

This is probably the most common complaint from every VC, accelerator, and pitching competition I’ve spoken to. Founders apply without checking if they’re even a fit.

All the info is public — stage, sector, cheque size, region. But too many founders just assume “maybe they’ll like us anyway.” No. They won’t. You’ll just come across as sloppy and unprepared.

🔴 Don’t send generic messages. Ever.

Mail merge and automation tools are tempting — but it’s obvious when you’re using them. Every investor I know can spot a generic message a mile away. If you’re not putting in the effort to personalise, don’t expect effort in return.

Use tools like ShipShape.vc if you need help — but at the very least, read someone’s damn LinkedIn before hitting send.

This stuff isn’t just about “best practice.” It’s basic respect for people’s time and attention. You’re not just hurting your own chances — you’re making it harder for every other founder who does take the time to do it properly.

So be the founder who stands out — in a good way.

🗳️ Be honest — which of these have you done before? 😅

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Tue 13 May, 16:00 - 21:00 GMT

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EF

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Vasily Alekseenko
Founder
@ Rare Founders

Rare Founders - building the bridge between founders and investors via regular in-person and online events, meetups, conferences.

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