The Bootstrapped Founder

Hello everyone,

Welcome to the Bootstrapped Founder podcast.

My name is Arvid Kahl, and I talk about bootstrapping, entrepreneurship, and building in public.

This episode is called How NOT to Use Twitter DMs.

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Now, let's get started.

Too many founders use Twitter like they'd use Google. They find someone they'd like to talk to, send them a Direct Message, and never receive a reply.

The culprit?

Usually, the message itself.

When it comes to DMs that do the job, you want them to be warm, low-effort, and short. Yet, in reality, most DMs sent by eager Twitter users are the exact opposite.

Let's dive into why so many entrepreneurs write DMs that fail at establishing relationships with their prospects.

## The Freezing DM

When you send a message to someone you've never interacted with, it's considered a cold DM.

And for many Twitter beginners, those DMs turn out to be freezing cold.

Imagine walking up to a stranger in a supermarket and asking them, out of the blue, for their favorite food. How many people would give you a straightforward answer? Most will look at you and —depending on the average levels of politeness in your culture— tell you to get lost or just ignore you. Then they'll walk away. You'll be standing there, between the aisles, without an answer, having made the person you wanted to talk to very suspicious of why you asked them about food.

They might even leave the store.

For some reason, people have no problem repeating this very interaction a hundred times in a Twitter DM. They are oblivious that just because you *can* ask someone a question without any prior interaction, you might not want to.

Here's the thing: trust is everything. I won't do business with someone I don't trust. And to trust them, I need to know that their intentions aren't going against mine.

Now, why should I reply if you ask me about my preferences without telling me who you are?

Give people a reason to trust you when you reach out to them.

Don't pretend to know them more than you do. This is a great opportunity to check yourself for a potential [parasocial relationship](https://thebootstrappedfounder.com/parasocial-relationships-imaginary-friends-of-the-social-network-age/). People are weirded out by strangers that act like they are good friends. Instead, be your likable, authentic self.

Ideally, your DM is following a lengthy and personal prior conversation. That conversation can happen in public, as an interaction between you and the person you're reaching out to. If you're building a business to serve specific customers, you've likely been doing your due diligence on your prospect. You know what they work on and how you can help them.

The trick to building trust is that there is no trick: it's built slowly, one interaction at a time. Be there to cheer on the people you want to help succeed. When they ask for opinions, share yours. When they need reach, retweet their questions. In every interaction, work for them and with them to help them achieve your goals.

And slowly, over time, your relationship will turn from glacial frozen to a much warmer connection. Give without asking, and then —much later— ask them to reciprocate.

## The Big Ask

But even those who engage intentionally for a while often fail to get a response once they start asking.

Usually, that's happening because they ask for too much. Here's an example of a founder who reached out to me recently, telling me that even though they had been chatting with their prospects on Twitter before their DM, they haven't seen any responses.

When I read through their DM copy, their last sentence immediately rang my alarm bells: "Do you have time in the next couple weeks to chat?"

Asking for a chat is a big ask. I hate scheduling a block of time on my calendar, but I have no problem writing a 1000-word email on the spot. The call is daunting; writing a lengthy response is not.

I recommended rephrasing this cold DM approach into something even more personal. Here's what I suggested:

Envision their business and where they might struggle already, come up with three or so potential problems, and then ask them to tell you which one of those they struggle with most. It's all about slowly opening up communication channels. Right now, you're essentially asking someone who you just met to go on a 2-week vacation with you starting tomorrow. That's a bit much.

It's that much because you ask them to jump straight from an asynchronous Twitter DM into a synchronous chat. That's a huge jump. I personally keep talking to people in Twitter DMs once I establish the initial relationship. The cold DM is not the hook to get them off Twitter. The cold DM serves as a nudge to keep them on Twitter and talking to you more and more. Eventually, you might source a few calls from this. But for now, I'd just keep having chats where they have an easy time replying. This works best if you give them topics and easy response patterns like "which one of these three things bothers you the most" or "if you'd have to choose, where in your business would you spend a windfall of $2000?"

Make sure you help them right there on Twitter by being a sounding board for their ideas. Don't pull them into your own communication channels, but allow them to think and reflect right where they feel safe. Make it easy for them to give you what you need.

I'd recommend something along the lines of the following DM template:

"Hey! I've been following your journey building X for a few months now, and I've been wondering: you've recently built a developer-facing API, a new onboarding sequence, and you've been complaining about EU privacy compliance. Which one of these problems is most pressing for you right now?

I'm trying to make the problems that SaaS founders face less of a pain. I'm just starting out and don't have anything to sell, but I want to make sure I'm building something that actually helps.

I'd love to hear what bothers you the most. Please let me know; I'm eager to help you with that."

There is a point in time when you can pull them into a conversation channel that is more attuned to synchronous exchange. But it's definitely not in one of your first messages.

Now, a few of us like to jump on calls and discuss their issues. Fortunately, they'll tell you about that.

But most founders, creators, and makers are occupied with the things they're working on.

Give them the opportunity to find something valuable even in just answering your question. Make your interaction with them about their problems, not your solution.

There's more value in a warm and trust-based relationship with your prospect than getting them into a call as soon as possible.

## The Wall of Text

And since we're talking about doing something quickly: don't waste people's time by sending them a ten-page essay in your cold DM. If you're embellishing your message to make it feel as if you put more effort into it, consider that you might be causing the opposite of what you want.

People will spend a few seconds reading your message, at most. If they can't find anything useful or intriguing, they'll go to the next message. The shorter your message, the better, as long as your main offer still comes through.

It's a courtesy thing: the less time your prospect needs to sacrifice to see what you have to offer, the better your first DM-based interaction will come across.

Oh, another thing.

Please don't ask people if you can ask a question. I regularly ignore the "Can I ask you something?" messages I get. They signal to me that the person on the other side has not understood the asynchronous nature of the platform. You don't need my permission to ask me something, but you won't get my encouragement either. Ask or don't.

I am guarding my time as much as I can. That means that often, when a DM looks too long or too needy, I will flat-out ignore it. I'm getting dozens of messages any given day, so that's the only way I can get through them.

Don't feel discouraged when your message doesn't get a reply. Your offer might be great, but it likely reached the wrong person or was extended at the wrong time.

Keep building relationships with your prospects and peers. Opportunities will appear over time as you create connections with people by being truthful, courteous, and helpful.

## The Automated Barrage

And one thing that's neither courteous nor helpful is being on the receiving end of a clearly automated (or copy-and-pasted) mass DM. A lot of tools will allow you to send DMs in bulk, which —at first glance— looks like an appealing way to get the max reach with the lowest efforts.

And that's the problem.

I'm not a big fan of full outreach automation. If we operate in a world based on trust and personal connection, then there should be at least a little human touch in each interaction.

I *want* you to put in some effort. If this exchange is about a mutual benefit, we should both have to put in some work. If you don't, the whole conversation is merely transactional, and you signal to me that you don't care about me, just what I can do for you.

And if I know I am one of the hundreds of people who got the same message, I'll skip even reading past the first few lines.

Well, most of the time.

Funny enough, I'll make an exception for the people with whom I have a strong and pre-existing relationship. If you're a fellow founder to who I've been talking many times before, I'll accept that you're trying to maximize your outreach. But even then, I'll be reluctant to fulfill your ask.

If I don't know you at all, look at what it looks like from my point of view: I get a freezing DM that's clearly an automated wall of text with a giant ask. That's four out of four on the Twitter DM bullshit bingo.

Probably not a good idea.

So there you have it.

Keep it warm, keep it low-effort, write your DMs manually, and keep them short.

And don't forget that, even after all looking at all these wrong ways of writing DMs, there are legitimate reasons to send a private message on Twitter.

Don't hesitate to reach out to people who you know could benefit from what you have to offer.

If you do it right —and put in the work— your future customers will thank you.

And that's it for today.

Thank you for listening to The Bootstrapped Founder Podcast.

You can find me on twitter at @arvidkahl. You'll find my books Zero to Sold and The Embedded Entrepreneur and my Twitter course Find your Following there as well.

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Thank you very much for listening, and have a wonderful day. Bye bye.