One of the best-kept secrets in the start-up world is that you can access almost anyone you want to with a great cold email. Well, almost anyone… see more below.
CEOs are remarkably accessible and easy to reach.
Most CEOs and VCs personally read every well-formed email they get, even if they don’t know the sender. This means that if you send a great cold email to your favorite CEO, chances are it will get read.
If you don’t know the CEO’s email address, it’s easy to guess. The email address of 90% of company executives follows the company’s normal email convention. If you wanted to guess the CEO of Apple’s email address, for example, you could start with [first initial]firstname.lastname@example.org and iterate from there.
When I was in college in the 1990s, I would send cold emails to people like Steve Jobs, then the CEO of NeXT, and Steve Ballmer (then #2 at Microsoft). Both of them would reply within hours… to a college student. And if you’re wondering, yes, I would usually send them from my berkeley.edu email address at 3 am while in the computer lab waiting for a program to compile.
But just guessing someone’s email address does not make your email worth sending.
If you want to start a meaningful conversation with the person you’re trying to reach, you need to write a great cold email.
There are three things you need to do to write a great cold email:
- Personalize and send it to the right person.
- Emphasize how responding will benefit the reader.
- Make it short and clear.
That’s it. That’s all you need to do.
Personalize and send it to the right person.
This is the first rule of cold emails. If you’re not sending it to the right person, there’s no hope of getting a response.
For example, if you are looking for funding for a SaaS business, don’t send the email to the biotech investor. Send it to the SaaS investor. Sounds obvious but you’d be surprised how often this one simple thing does not happen.
The email has to make a clear connection between the subject and why it’s relevant to what the person does on the day-to-day.
If you are looking to sell HR software, don’t send an email to the CEO of General Electric. Send it instead to people in the organization who WANT to get your email because what you’re offering could make their lives easier.
It also helps to personalize the email by connecting to something specific about the other person or their work.
If you are reaching out to a VC, you could mention some of the companies she’s invested in that you admire (and most like your company). People love to talk about things they love. If you tell a VC how much you love a business they also love, you’ve greatly improved your odds of getting a response.
Emphasize how responding will benefit the reader.
Imagine that you are sending an email you would love to receive. What kind of information is so intriguing that you wouldn’t be able to ignore it?
Make it immediately clear why you are emailing the person and how they will benefit from engaging with you. You need to provide value.
In a great cold email, the person receiving the email should benefit far more than you from a potential exchange. That’s how you can pique their interest and improve your chances of a response.
If you don’t have something that will benefit the person you are sending the email to, you are better off waiting to send it until you do. You only have one shot to send someone a cold email. If they don’t think your first email is relevant to them they may reflexively not read your future emails.
Make it short and clear.
Before the reader even gets to the body of the email, it should be immediately transparent that it comes from you. It should also have a very clear subject line, like: “Invite to DaaS dinner on April 2 in SF”.
Regarding the body of the email, people have little time – especially CEOs. No one is going to read a giant block of text that takes three minutes to scroll through. Your email needs to be short, clear, and well-formatted. This means short paragraphs and lots of white, empty space.
You want people to be able to quickly grok an email while reading it on their phone in the elevator (or the toilet). The person receiving the email might take a peek at it while she is at a meeting or on a conference call. You need to make sure in that 3-second peak, the person understands why you’re reaching out and why it benefits them.
A short email does not mean hastily written. Put time and effort into it and choose your words carefully. It’s also good to be enthusiastic and passionate about what it is you are pitching. Enthusiasm around specific things that genuinely get you excited is contagious.
You also need to lay out exactly what the next steps are for moving the conversation forward. Are you looking for a ‘yes’ or ‘no’ via email? Are you hoping for a phone conversation to really make your pitch? Or are you asking permission to follow up with your deck if the person is interested?
Avoid ambiguity at all costs, and tell the person exactly why they will benefit from the next steps. You can even provide a time-frame for a response if necessary.
If your email fits the three rules above, then send it. If it doesn’t, then don’t send it.
… now that you know how to write a great cold email, here are some things you should absolutely avoid…
Do not ask to grab “coffee” or ask for general career advice.
This is a waste of time for both of you. It is too ambiguous.
Instead, offer to give advice.
For example, don’t email someone for advice on how to write a blog post. Email the person and tell them that you went through their last 10 blog posts and edited them for clarity and made them better with illustrations, graphs, etc. And then ask them if they want to see your work.
You will have a 2000% better response rate and you will be immediately adding value.
Don’t ever say “I hope you are well.”
“I hope you are well” is the most overused and under-impactful email phrase. Especially when it is being sent to someone you don’t know.
When you have the urge to use this phrase, hit the ground and do five push-ups … and then eat some spicy hot peppers … then punch yourself in the face … and then just don’t do it because it’s a terrible opening.
There are some people who are NOT good targets for cold emails.
Super famous people often have a secret email address. You likely will have trouble cold emailing sports stars, national politicians, movie stars, etc.
For instance, if you want to reach out to your U.S. Senator (let’s say her name is Jennifer Marks), her public email might be email@example.com but her real email could be firstname.lastname@example.org … which you would only know if she told it to you.
The same thing is true for a movie star (like Tom Cruise). Emailing email@example.com will likely end up with an automated response, or will be potentially read by a low-level PR flak. His real email could be something unguessable like firstname.lastname@example.org (Cruise’s birth name is Thomas Mapother IV).
Of course, if his real email was made public, Cruise would change to a new secret email in an hour and alert the core people he cares about. Many celebrities change their personal email yearly.
What would you do if you want to reach a very famous person?
If you wanted to reach LeBron James, you would have a lot more luck reaching out to his agent. James’s agent is Rich Paul who runs Klutch Sports Group. My guess is that his personal email is much easier to access.
Remember, you can reach out to everyone.
Great cold emails work, but only if you know how to write them.
I’ve received hundreds of cold emails that have turned into business relationships and great friendships. In fact, I met many of our SafeGraph employees after receiving cold emails from them.
Here is a cold email (actually a cold Quora in-mail) sent to me in 2016:
When I received this outreach from Ryan, I had just left LiveRamp and was figuring out what to do next.
Ryan’s note is a great cold email. It’s personalized, short, and benefited the receiver.
I definitely want to meet amazing data scientists, especially one that has a background in neuroscience and also loves to write on Quora. In fact, after getting this message, I spent over an hour reading his fantastic Quora answers.
Nine months later, Ryan was employee #1 at SafeGraph. I still work with him today. And yes, I had a typo in my response (sorry Ryan!).
Great cold emails work, but only if you know how to write them.
Here is a message I sent to Jason Cook in August 2016:
I didn’t know if Jason remembered me from when I interviewed him a few years before, so I made sure to craft an email I thought he would likely respond to. Jason did respond, and I still work with him today.
Ben Casnocha has been a great friend of mine since 2003. We built that friendship via a cold-email he sent me when he was just 14 years old! He was running a super cool start-up so we met up for lunch. I’m so glad Ben took the time to reach out to me as his friendship has been dear to me over these years.
My secret dinner party invitations.
I personally love one-conversation dinners (or lunches or breakfasts). These are hosted dinner parties where I invite a small group over to discuss interesting topics. Sometimes I invite people I know, but often I invite people I have never met before. Today, some of my closest friends are people I cold emailed and invited to dinner. (and yes, I do Zoom dinner parties too).
So if you are reading this and want to invite me to a one conversation dinner (5-12 people), I’ll respond positively.
I used to do monthly dinners with Peter Thiel. The deal was that Peter would supply his home and his chef and I would invite the participants and moderate the dinners. Besides being a blast, the conversations were always interesting (Peter is the smartest person I have ever met).
Peter would have an idea of something he wanted to discuss over dinner (like understanding energy production) and I would invite 6-8 experts. After the 8th dinner we did together, Peter asked: “Auren, how do you know ALL these people?”
I answered: “I actually never met any of the people before the dinner. I cold emailed all of them.”
You don’t need to know anyone to invite them to an interesting dinner. Of course, you will have a much higher response rate when you cold email people and ask them to come to dinner with Peter Thiel … but you can still have a good response rate without the draw of a world famous entrepreneur.
Today, I still cold email at least one new person a day (and usually many more). It is the single best way to reach out to someone (and usually much better than getting a warm introduction).
That’s the power of writing a great cold email that will actually get a response.
P.S. Here’s a fictional cold email I would love to receive from you:
John Malone is in town next week and he asked me to put together 6 people to learn more about how to become a life-long learner. I thought you would be great to add to the discussion.
We’ll be doing it at my house in SF on Wednesday at 7:30 am, can you make it?
(I need to know by tomorrow. There will just be seven of us.)
– Your name
Special thanks to Thomas Waschenfelder for his help and edits.
P.P.S. This is a random email I once sent to Steve Ballmer: