I Sent 1,952 Cold DMs in 2 Weeks
4 lessons to make your cold outreach less scary and more effective.
My business partner and I almost shut down our company this year.
Six months of burnout, confusion, and zero profit exhausted us.
Then we took off.
What happened?
I started doing cold outreach. 🥶
My virtual assistant sent 1,000 cold DMs (direct messages) on Twitter, Instagram, and Facebook each month. It was tedious to find leads and track everything manually.
Then we started using Drippi — the A.I. service that changed everything for us.
Now it takes one week to reach the same number of people it used to take us one month to find.
A 4x increase in volume. Plus better leads. Done with 1/10th the effort. 🤯
Here are four lessons from sending 1,952 cold messages in less than two weeks.
1) What is a cold outreach “funnel” actually?
A funnel is the journey we take someone on — to transform them from a stranger into a sales call on my calendar.
Ours has four steps:
1) Message sent.
The first DM. I ask if they’re interested in hitting their goals smoother and faster.
If they don’t respond within 48 hours, I send a follow-up message sharing our best results.
If they still don’t respond after another 24 hours, I send this:
You’d be shocked to see how many people finally replied after a second follow-up.
2) Positive reply.
The folks who express interest or curiosity.
Sometimes they ask buying questions — questions only someone considering buying would ask.
e.g.
- “What’s the price?”
- “How does it work?”
- “How long is the program?”
Other times they just send a thumbs up or a simple “interested.”
Then I send them a 90-second video briefly explaining the value we bring our clients and the best results we helped them accomplish.
3) Calendar sent.
If they like the video and are down to chat further, I send them my Calendly link.
I only keep the next four days open. The more time between booking a call and the call itself, the less likely they are to show up.
When they set up a call, they answer a few questions about where they’re at, their goals, and how ready they are to invest in their growth.
4) Call booked.
The end goal of this marketing funnel.
They schedule a call with me to talk about whether or not we’re a good fit.
I want to wake up with as many of these calls on my calendar as possible.
It’s called a funnel because the pool of people shrinks with each step.
Say I send messages to 100 people.
30 reply.
15 are interested.
10 get my calendar.
5 book a call.
4 show up.
1 becomes a new client.
Conversion rate = 1% — we get one new client for every 100 messages sent.
2) Some people will hate your f*cking guts.
Many entrepreneurs are terrified to do cold outreach because they fear annoying or upsetting people.
Here’s how to avoid that:
You can’t.
It’s impossible. If you try to sell or offer anything to a large number of strangers, some of them will despise you simply because you’re trying to sell something.
It makes sense.
We live in the digital age where anyone can sell anything online.
There are scammers and snake oil salesmen out there. People have the right to be on guard when a random dude with a mustache messages them on social media.
We hate feeling sold to. I saw this every day when I did door-to-door sales.
You wouldn’t believe the things people said to me when I knocked on their door. I got treated like scum.
Experiencing that online is way easier for three reasons:
- I’m not standing on their porch
- I’m significantly better at what I do now
- I love and believe in what I’m pitching
Now I just have fun when people are nasty. I send memes. I kill them with kindness.
This guy once wrote an entire tweet thread about me once he found out our service costs money.
I had to block him since he kept messaging me and replying to all my posts.
When someone puts in a ton of time and effort to bash you for building something, the only thing to do is pity them. Their life is so unfulfilling that they must find moments to feel powerful by bringing others down.
I get random messages all the time. Some of them are obvious scams.
It would never occur to me to send them paragraphs in return. But some people have nothing better to do, I suppose.
(I’m not talking about constructive criticism or skepticism. I’m talking about being spoken to like I’m an evil person doing evil things.)
It’s also crucial to not waste time defending yourself.
This guy thought I sent a copy/pasted response.
I didn’t. I typed it out myself.
He also thought our star client bought his subscribers.
He didn’t. I’ve been working with him for three years and witnessed his entire climb from zero.
The photo above is only about 20% of what he sent me. He called me stupid. He promised my business would never succeed.
How did I respond?
Anything else would’ve been a complete waste of my time. His mind is made up. I’m a scumbag.
Haven’t thought about him since.
When people are nasty, kill them with kindness and move on to the next person.
3) Most people don’t reply.
Or they simply say, “No thanks.”
Or they aren’t our avatar — the ideal customer we’re looking for.
Either way, I wish them well.
A little human kindness goes a long way.
Cold outreach always results in lower reply rates than warm outreach (messaging people who know you). Trust is much lower. Walls are up.
But if our reply rate is below 10%, I need to sharpen up the initial message — make it shorter, improve the offer, etc.
4) Some people will thank you for giving them exactly what they need.
Once you get past all the people who:
- don’t respond
- aren’t interested
- say mean things
- aren’t who you’re looking for
- ghost you
There is the tiny percentage of people who are exactly who you’re looking for.
They want what you have. It’s a perfect fit. They’re thrilled to work with you and you’re thrilled to work with them. They pay you for your valuable service.
This is business.
I’ve gotten on calls with some of the coolest and kindest people over the last few months. Many of them are now our clients.
One of the most common phrases I hear on these calls is, “You reached out to me at the perfect time.”
If I have to mildly annoy nine people for a few seconds to get to one who really wants our help…it’s 100% worth it.
You will experience every shape, size, and color response if you send cold messages to lots of people.
Get feedback. Track your progress.
And most importantly, have fun. 🤗
If you want to follow my journey to $50,000/month, get lessons from top 1% creators, and join me as I travel the world with my laptop…
Subscribe to the free Doin’ The Thing newsletter!
(Or just follow me on Twitter / X @dillanroytaylor)
