Don't use caps when reaching out to investors

Don’t use caps when reaching out to investors

Tl;dr: Never use caps when you are communicating professional content. Trying to optimize subject headers is a waste of time. Just do the basics properly

A lady messaged me “Hi Alexander. can we use some words in CAPS in the subject to grab attention?”


Let me explain why.

What is the goal when reaching out to people?

When reaching out to potential clients or investors, the goal is the same: To instigate and then close a deal.

Assuming you are doing cold outreach, the thing that matters the most is establishing credibility.

You’re reaching out to someone you don’t know and asking them to hand over money.

When you pause and think about that, it’s kinda crazy.

If I ask you for $29.99 you’re going to wild out and think before you even do that. And… you’re potentially asking for someone to give you millions?

Really think about that.

It’s A LARGE learning to internalize.

Why will anyone give you a dime, let alone a million?

If you are cold emailing people, think in their shoes.

Optimization is ruining emails

Buzzfeed innovated in headlines, but they’ve now ruined it for everyone. Their innovation has become standard, now permeating who one would think are reputable institutions.

When I see clickbait in Google News, FB, etc, I purposefully ignore it. Just as a FU.

Things work for a while and then become negative.

There are no tricks when you email people anymore. It’s been around 20 years and everyone hates it.

Well, there is… one.

Be a normal person and pass the bullshit test.

Be what an investor expects.

The life of investors

Investors get emails every day from random people, though they would prefer not to.

They know about click-bait and every moron under the sun tries to innovate in outreach in lieu of having built a real business.

I can honestly tell you every time I see a ‘fancy’ attempt at an email it also involves hyperbole that makes my eyes roll.

Seriously… just tell me your numbers. YOU CAN’T SELL ME!

What do investors want?

If you are going to spam investors, communicate how they would like.

There are a lot of people who go for this whole “let me wow you with my story”.

I call BS.

I get interested to allocate time to you on logic, I get swept away by you with a story once it makes sense.

I always teach “I don’t get greedy before I’m not scared anymore”.


The founder thinks using CAPS to highlight something in the subject of the email to an investor (obviously cold spam) might make an impact on the conversion.


The actual issue here is I bet she is going to also use all sorts of lame salesy hyperbole as if she was working at Buzzfeed.

Making up an example here:


What’s actually naïve about this question is that it assumes highlighting words makes a difference. They don’t.

I used super lame words I know founders might use and I bet that they make you cringe? Do you really think someone hasn’t seen this shill stuff before?

The only things you ever want to shout about your metrics. They come in numbers, which in a way are already capitalized.

1, 2, 3 vs. a, b, c

Here is something to shout about, but isn’t in CAPS:

Collaborative SaaS raising S-A. $30m ARR, 26% MoM growth, 2% negative churn

The only words in caps are acronyms, but that is natural.

The other thing to notice is shizzle investors actually care about.

Do you get me?

As a VC, what do I get from the title?

  • Sector: It’s SaaS and the sub-sector is something about collaboration (which I might like or not, but I know what it is)
  • Stage: Raising series-A
  • Size: They’re at $30 ARR so they are at least S-B+
  • Traction: See growth and churn

I have a hard-on for this email.

Yes, I know that is almost no one, but do you see it’s still a normal email, but there are no tricksy tactics needed.

So what is a real example for a normal startup with ‘hopes’?

DEAL FLOW: Collaborative SaaS. $500k seed round. Singapore HQ

If you’re an average startup (With no real traction to show), that’s actually enough. I’ll open that email if:

  • Sector: I invest in SaaS
  • Stage: I invest at seed
  • Geography: I invest in Singapore

The “DEAL FLOW” bit comes my from banking days.

Read this as it’s really useful: Use this banker system so startup emails work for your team

Shite, I just made an exception to the rule for the CAPS writing this blog! ha.

I try to write all emails with what the email is about in CAPS at the start to categorize emails.

Read that blog to learn why.

Let me explain though as I don’t specifically do so in this context.

Let’s say you’re one of my companies and ask me to help you out in meeting VCs. I know my mates hate emails. So I make it easy for them. Let’s categorize my emailing investor friends in two ways in the subject:

  • Social: I write: Yo, Hey, or whatever. They know me so they will open eventually
  • Raising: I write “DEALFLOW: startup description” so they know it’s about a deal and that I do too when they respond

I actually legit do this (To my friends!). You should too.

There are no tricks

I’ve implied it, but let me make it clear. There just are no tricks when it comes to investor outreach other than doing the basics exceptionally well and making it easy for investors to communicate with you.

Optimizing your subject, trying to use NLP in your copy is just a huge waste of time. The best emails to VCs are super short and highly focused on what it is they care about.

All tricks are an attempted hack to make up for the fact that you feel you don’t have the traction needed to get investment and if you “just get in the room, you’ll sell them”. You won’t.

Just focus on the basics buddy. Don’t waste your time thinking about tricks. They don’t work.

Keep hustlin’

If you need help learning how to fundraise the right way, you can book a one on one call with me here.

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