One Cold Email Changed My Life
Everything good in my professional life has come from cold email or some other form of cold outreach.
New job opportunities. New sales opportunities. New customers. New friends. New experiences.
So many adventures sit on the other side of a simple ask or connection request.
So why don’t more people do it?
Because humans are herd animals. We hate rejection. We fear separation from the herd.
We take it personally when someone ignores a text message or well-thought-out cold email.
But if you can push through the fear of rejection, you will find that you can get access to just about anyone in the world through cold outreach.
That’s been my experience, anyway.
Let me tell you how a single cold email led me to a job opportunity and an adventure that changed the course of my life.
Selling flip-flops from a van
I was like most entrepreneurs when I was a kid. I had lemonade stands. I wanted to make money.
Throughout high school and early college I held a series of hourly-wage jobs.
I was a bus-boy at the neighborhood Italian restaurant. I cooked crawfish, crabs, and shrimp at a seafood market (I grew up in New Orleans). I worked in the bag room at the local country club. I waited tables. I bartended.
I also had side hustles to make more money. I wrote term papers for other classmates. I bought used textbooks at the end of the semester and sold them on eBay or to the university Co-op.
But no matter how hard I worked, I wasn’t really getting ahead. I wanted more.
One spring day in 2009 I was working counter at the City Park Golf Course pro shop. at the across an article in the New Orleans newspaper about local an entrepreneur Kyle Berner who started a flip-flop company. 19-year-old me was enamored by the idea of a flip-flop company. Sounded like exactly the thing I would want to work on.
The problem is, I didn’t know the founder personally. So I wrote him this email:
I’m cringing as I re-read the email.
My writing has certainly improved in the last 15 years. But the bones of this email are good!
The context is relevant, I mention his recent newspaper article. I offer to help with no string attached.
Kyle did respond to this email and in just a few months we were traveling across the country in a mini-van selling Feelgoodz flip-flops to Whole Foods and other retailers.
We worked together for the next two years and built Feelgoodz from a fledgling startup to a national footwear brand.
That experience set me on a path for building a scaling businesses that would change the rest of my life.
And it all started from a cold email.
15-years into the journey and I still use cold outreach every day to connect with new people.
I hope that this essay inspires you to take action today and reach out to someone that can influence your life in a positive way.
Why people don’t respond to cold email
Most people don’t send cold email because they are afraid of the rejection.
They don’t want to take a chance and look foolish or feel embarrassed.
It’s natural to feel this way, and you only get used to the feeling with experience.
When you send a cold email and don’t get a response, your mind is flooded with negative thoughts.
“They must think I’m stupid, that’s why they didn’t respond.”
This is so far from the truth.
There’s a laundry list of reasons why people don’t respond to your cold outreach:
- People are busy. They saw your note and meant to respond but forgot.
- You sent a message through the channel that they don’t use. Maybe they don’t check their Twitter SMs that often, so they didn’t see it.
- Your message didn’t resonate. No call to action. Unclear context. AIDA framework
- Your message didn’t stand out in the sea of notifications. Your message is competing with 1,000 other messages vying for attention: Work email, Personal email, Twitter, Slack, Teams, Text, Phone, LinkedIn, Instagram, Discord, WhatsApp, it’s never ending.
- You didn’t follow up.
The rejection is easier to swallow when you know what you are up against.
Cold outreach works when you are highly targeted, relevant, and timely with your message
When you are reaching out cold to someone, you are in a position of low leverage.
There has to be a compelling reason for them to want to connect with you.
A couple of warnings before you send your message:
- Don’t reach out to “pick their brain” or “buy them coffee”. This is a fools errand. The person you are reaching out to doesn’t want to some random person to hijack their afternoon. This kind of outreach gets ignored.
- Don’t use AI to automate your cold outreach. People are good at detecting authenticity. They can smell a generic, AI generated message from a mile away. And they won’t respond.
Instead, think about how you can be of value to the person that you are reaching out to.
Successful, ambitious people want to surround themselves with people like them. Regardless, of age.
They want to meet other people who are doing interesting things, or who want to do interesting things.
You can’t fake this, it has to be sincere.
Ryan Holiday explains this concept well in The Canvas Strategy for cold outreach:
“In other words, discover opportunities to promote their creativity, find outlets and people for collaboration, and eliminate distractions that hinder their progress and focus.”
That’s how you do it. Find ways to provide value and you will get a response.
If the person is active on social or if they have a podcast, go read what they are writing and saying. You will find countless topics that you can use to engage your future friend.
Once you connect with them, you have to show up with the goods. You need to be the person that they are expecting from your message, this is why it’s so important to be authentic.
Use multiple mediums at the same time when you really want to get their attention
The salesperson in me knows that getting someone’s attention requires two things: reach and consistency.
For reach, you can use one of the many mediums available to you:
- Email is probably easiest, if you have their email.
- Text is best if you have their cell number, but this can come off stalker-ish if you don’t have permission to text or a connection in common.
- Sending DMs on social platforms like Instagram, LinkedIn, Twitter, or TikTok can work well if the person uses those platforms regularly. Pro tip: go look at what they are posting, liking, and sharing. Reference this in your outreach.
For my first cold outreach, I like to send on at least 2 platforms at the same time. For example, if they are regularly posting on LinkedIN, I’ll send them a DM through the platform and send them an email at the same time.
This increases the chances that they will see your message.
You have to follow up
Once you send your cold outreach, prepare to follow up within 24 hours. Expect that they are not going to respond. That’s the norm.
I have received roughly 2 responses in the last 10 cold outreach attempts.
If the person is quality enough, keep following up. Some of the best connections in my career have come after 5+ attempts to connect with the person.
Don’t worry about bothering them as long as you are focusing on delivering value in every cold message. If they really don’t want to connect, they will tell you that they are not interested.
Give them something to believe in
Cold outreach works because people naturally want to grow their network.
People want to believe in something. They want to surround themselves with other people like them. They want to meet younger people who are working on cool stuff. They want to meet older people who have lived a life of experience. They want new and exciting relationships.
When you reach out cold to someone, you are giving them a blank canvas that you both can paint on together. What An amazing opportunity for all of us to connect with the people that inspire us to be better and go farther.
So here’s the call to action, send a message today to one person that you could learn from. Push through the fear of rejection. Make the message compelling and hit send.
Who knows… it could change your life.
