We live in an era where a significant percentage of new relationships start in writing. Emails, text messages, social media posts and dating apps all serve as jump-off points for real-life relationships.

But it wasn’t always that way.

Back when I was in high school — cough cough 30 years ago — we had pagers but not yet two-way messaging. Email wasn’t mainstream (I didn’t get my first email address until university). And unless you were one of the super-nerdy people experimenting with BBSs (guilty-as-charged), you’d certainly never met anyone over the “Internet”.

In those days, virtually every new relationship — personal or professional — started with an in-person introduction.

Today, the majority of new relationships start in writing. Introductions are made over email and text messages. We meet people in WhatsApp groups and Discord channels, by posting social media comments, sliding into someone’s DMs and “swiping right”. Despite this significant cultural shift, many people don’t consciously think about how they present themselves when they “meet” someone for the first time in writing.

For startup founders, learning to put your best foot forward in writing is one of the most significant ways to increase your success. Improving your written first impression can be a game-changer for sales, fundraising, hiring or trying to get press.

Here are 5 keys to writing for success:

Be Specific

One of the most important things when writing for success is to be specific in your asks. Be up front about why you want to meet this person.

In Canadian culture (and, in fact, in most Commonwealth countries), directness is often seen as rude. We’re taught to dance around our reasons for outreach as though it’s inappropriate to have a specific objective when meeting someone new. This is something that Canadian founders have to unlearn, particularly when entering the U.S. market for sales or fundraising (as American culture values directness in business dealings).

Try to be as specific as you possibly can in your asks:

“I’d like to pick your brain” —> “I’d like to get your feedback on X, Y and Z”
“I’d love to see if there’s an opportunity to collaborate” —> “I’d like to speak with you about our Series A raise”
“I’d love to get your feedback on our deck” —> “I’m struggling with the competition section in our fundraising deck, could you take a look and let me know how it lands with you?”

Be Assertive

When one startup in Panache’s portfolio came out of stealth, a CEO I know pinged me to ask for an intro. He was excited by what he had read online and wanted to talk to them about a trial. I facilitated a double opt-in intro, to which the founder responded with the following:

Thanks Chris (bcc'd)

Hi <redacted>, it's nice to connect! Would love to talk shop when you have time.

While this seems like a reasonable response, there’s no call-to-action. No next step.

In this case, the CEO was a repeat founder himself who often mentors younger founders, so he took the initiative to keep this ball rolling and provide the Panache founder with feedback. Had that not been the case, this hot sales opportunity may very well have died-on-the-vine.

A more effective response would have been something along the lines of:

Thanks Chris (bcc'd)

Hi <redacted>, it's nice to connect! I’d love to learn more about what your pain points are at <redacted> and how we could help. Here is my calendly link to schedule a 30-minute call (or let me know if none of those times work and we can set something up directly).

Just as you do with in-person meetings, make sure your written interactions result in clear next steps and ownership of action items. Don’t be afraid to assert control over the budding relationship’s next steps.

Be Concise

Learning to write concisely is one of the most impactful skills you can learn as a founder.

When it comes to fundraising, being able to concisely convey the key facts about your startup can massively increase your fundraising funnel. You’re trying to convince investors to open your email, then read it, then open your deck and, finally, opt-in to a meeting with you. I find it helpful to think in terms of stages:

A warm introduction and/or good subject line earns you an email open
A well-written, compelling email earns you a deck open
And so on

For the subject line, put one or two key points in there, instead of a generic heading:

“Acme Co Seed Round” —> “YC / $100K MRR / Seed Round” or “Mila Drug Discovery Spinout Seed Round”

For the email body itself, resist the urge to write a rambling, exhaustive email that tries to explain everything about your company. Your goal in the initial email isn’t to try to tell me everything about your startup, it’s to get me to open the deck. That’s it.

I can’t tell you how many founders send me emails that go on for days. If I’ve never met you before, I’m simply not going to read an overly-lengthy email.

In an introductory email, you need to catch an investor’s attention in the first 1-2 sentences. An effective intro email for fundraising is 1, maybe 2 paragraphs total. It uses bullet points to highlight 3-5 key achievements of the startup and immediately hands off to the deck (either as an attachment or a link).

A good rule of thumb: if someone can’t read a initial email in less than 20 seconds, it’s not going to get read.

Be Prepared

Think about how impressed you are when you meet someone in person for the very first time and they’re:

On time (or early)
Dressed and groomed well
Well prepared for the meeting/date/whatever

…and then they kick off the conversation by saying something that demonstrates they’ve taken the time to research you.

Preparing to meet someone for the first time in writing is just as important as it is in person. It’s why writing personalized request-for-introduction emails has such a huge impact on success rate.

Andy McLoughlin of Uncork Capital refers to this as “show me you know me”:

The best advice to remember with a cold pitch is to “show me you know me”. Show the investor that you’ve done the work and this is why you are pitching to them.

When fundraising, too many founders get stuck on quantity-over-quality and send out generic emails or emails where it’s clear that they’ve half-assed the research (or skipped it entirely). Nearly every investor has a lengthy track record available online, including plenty of blog posts, podcasts and videos. If you really want to get their attention, spend the time to look them up and learn something about them.

Does it take time and effort? Absolutely! But good salespeople know that preparation has a massive impact on win rate. You get out of it what you put into it.

(For more on how to write a great request-for-introduction email, check out this post from Arjun Dev Arora.)

Another place where personalization can make all the difference? LinkedIn connection requests.

Don’t Name Drop

This should go without saying, but don’t do it.

When someone walks up to you and says “hey, so-and-so says we should talk,” you immediately know it’s bullshit because that person would have made the introduction directly if they really felt that way.

Guess what? The same thing is true in writing.

One of my team members recently received a cold email from a founder that started off like this:

Hi Tim,
I hope this message finds you well. Found you guys through <redacted> at <redacted>.

The very first thing Tim did? Forwarded the email to <redacted> to fact check:

Hey <redacted> - Hope things are good.
This founder (below) reached out and dropped your name. Wondering if you actually know him? If so, I'll definitely take the call.

It turned out that <redacted> had never heard of this particular founder.

Even if the founder actually knew <redacted>, name dropping almost never works. It immediately shines a light on the fact that the person knows you, yet wasn’t willing to make an introduction — which leaves the recipient wondering “why not?”. You’re better off holding that card to yourself and sending a strong, confident cold email.

How to Write for Success

Be Specific

Be Assertive

Be Concise

Be Prepared

Don’t Name Drop

The Quiet Part Out Loud