How NOT to Send a Cold Email: Bullshit Sincerity

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If you’ve done just a bit of research into writing better cold emails, you’ve probably come across the advice to “compliment the person you’re emailing and express sincerity.”

This makes sense at first glance. People like to be complimented. You’ve probably been drawn into talking to a canvasser on the street (one of my favorite analogies for cold emailing) because they complimented something you were wearing and instinctively said, “thanks!”

The difference between the canvasser and the cold emailer, though, is that the canvasser can see you and choose something on the spot. The cold emailer can’t see you and has to choose something specific to compliment you on going into the email.

This does not mean just saying, “I appreciate what you’re doing in your industry!” Without specific evidence to show that you didn’t just run a mail merge and send the same email to everybody on your list, the reader assumes you are just bullshitting with them and everybody else on the list.

Fake sincerity executed well is worse than real sincerity poorly executed.

There’s something about fake sincerity that makes it insulting. I received a spam email last week that started like this:

I looked at it, grimaced, and turned to a colleague and pointed out how, for some reason, this is more annoying than an email that would have skipped the attempt at a compliment and gone right into pitching me on an ICO. I don’t do anything in the crypto industry. A short Google search of my name shows this. The closest was a talk I gave in 2015 about decentralizing education. Hardly “doing in crypto industry [sic].”

(I’ve torn down ICO emails already here and here.)

She agreed.

Fake sincerity is a bigger turn-off than poorly-attempted sincerity. She compared the above email with one where somebody reached out and complimented her on her career path. The email wasn’t formatted particularly well and could have been written better, but the fact that the sender actually did research on her gave her enough reason to keep reading.

Don’t Bullshit: How to Do Sincere Compliments the Right Way

“Does this set off my bullshit alarms?”

That’s the question you should ask yourself before sending a cold email to a stranger.

(It’s also a question you should ask yourself any time you put big, lofty claims in an email, a cover letter, or your resume.)

If it sets off your bullshit alarms — if it makes you feel insincere and like you’re lying — it might set off theirs. The people you email are not stupid. They are Very Busy People who protect their time and will respect you more for doing a little bit of reading on who they are instead of just making stuff up and insulting their intelligences.

To get past the bullshit alarms, do some work.

Do The Work.

A good cold emailer will do research on the person they’re emailing before sending the email. This means:

  • Listening to or reading interviews
    • Searching YouTube or the Podcasts app for interviews with the target
  • Looking at the target’s personal website
  • Looking at the target’s LinkedIn
  • Looking at the target’s company website
  • Searching the target’s name on Google News for recent accolades

Does this mean that the good cold emailer will send fewer emails than the bad cold emailer. Probably — but what you’re trying to get aren’t necessarily opens or responses, you’re cold emailing for a specific purpose or outcome. You’re emailing to get the meeting, the interview, the endorsement, or the advice. You’re not emailing just to get an open or a reply. You want a reply that results in your desired outcome.

This is why I am never impressed when I hear somebody say, “I send 1000 cold emails every three days!”

Really? How many sales/meetings/interviews/calls/endorsements/whatever did you get from that?

“Oh, well, 10.”

So, if I sent 25 emails in that same time period that were better-written or researched and got 10 meetings, we’d be at the same place, no?

“I guess that’s right.”

Doing the Work When Getting Started: Sincerely Compliment and Solve Problems


When I got started in doing cold emails seriously, I was the first Director of Business Development at an education & apprenticeship startup. Nobody had ever heard of us and I had a weird pitch for business owners, founders, and investors: let us send you college and high school dropouts to work in jobs that require degrees.

I could blast out tens of thousands of emails (and dabbled in doing so, with poor results). Or I could pump what little network I had (mostly absorbed from the founder of the company) and send strategically placed cold emails.

This worked wonders.

1. Have Something Your Recipient Wants (Solve a Major Pain Point)

The first thing I did was find companies for whom we could solve a problem. This meant companies we could send great talent to at low cost and who were in a position to try out something new to solve the staffing problem. I mostly used the Inc 5000 Fastest Growing Companies list. Companies growing quickly need new talent and they need it yesterday. These companies were usually still run by the founders (which is important for points 2 and 3) and often needed the kind of talent we could provide.

You could write the best cold email in the world but if the person you are emailing doesn’t need you/your product/your service, you’ve wasted your time.

2. Do Research on Them and Their Organization

Actually do some research on the person you’re emailing. If they’re actually a decision maker, they receive so many un-researched outreach emails every day. If they see one that actually acknowledges them and the work they’ve done, they’re more likely to read past the first few sentences.

It helps if you’re sincerely interested in the people you’re talking to. In my business development job, I loved talking to entrepreneurs and investors. I loved learning about them, their industry, and why they decided to get started. This made the research enjoyable.

If you aren’t in a place where you love researching these people, try going a step deeper. Are you interested in where they went to school and what they majored in (check LinkedIn for this)? What about where they’re originally from? What the company produces? Find something you can find interesting.

3. Open the Email with Short-But-Detailed Reference to What You Find Interesting

You are fighting for every second of their attention. They’re happy to give it to you if you prove that you won’t waste their time. One way to signal that you won’t waste their time is showing you’ve already spent time thinking about them.


“Hi Zak,

I really appreciate what you’re doing in the crypto industry.”


“Hi Zak,

My name is [name]. You don’t know me but I came across a talk you gave about decentralizing education in 2015 at d10e. I really liked the point you made about the degree simply being a signal and that it’s the job of new organizations to create new, stronger signals. I’m emailing you because…”

Which of these expresses sincerity? The second one (and it would have likely garnered a response from me).

The key here is to make the reference to something that’s one or two levels deeper than an article headline or a talk title. You want to signal that you did more than just Google the person’s name and decide to reference the first article about them that came up.

If you’ve followed these steps and you’re still struggling to find something interesting about the person, defer to what you find interesting about their industry, business, or even the city they’re in.

(“I’m putting together a trip to Phoenix and your company came up in my research as one to reach out to because of your recent growth. I’m always astonished by how beautiful the Phoenix area is. I’m jealous you can call it home.” is better than nothing.)

If your BS alarms still go off, move on to a new person. Better to get the same outcome out of somebody you find interesting than kill yourself over somebody you don’t.

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