I have sent thousands of cold emails. To investors who had no reason to read them. To potential hires who were happy where they were. To people I admired and wanted to learn from. To strangers whose work I thought might intersect with mine in ways I could not fully articulate yet.
Most cold emails are terrible. Not because people are bad writers — most are perfectly competent — but because they are thinking about themselves when they should be thinking about the reader. This is the guide I wish someone had handed me at twenty-five, before I spent a year writing emails that deserved the silence they received.
Nobody Owes You a Reply
Start here, because everything else follows from this. Your email is an interruption. The person you are writing to was doing something else — something they chose to do — and your message just inserted itself into their day uninvited. That is the reality of cold outreach, and the sooner you accept it, the better your emails will be.
This is not pessimism. It is respect. When you write from the assumption that the reader's time is more valuable than your request, you naturally do the things that make cold emails work: you get to the point faster, you make the ask smaller, and you give the reader a reason to care that has nothing to do with your needs.
The worst cold emails I have received — and I have received many — all share the same flaw. They are written from the sender's perspective. I am building something exciting. I would love to share my vision. I think there is a great synergy between our work. Every sentence begins with I. The reader is not a person in these emails. The reader is an audience.
The Subject Line Is the Whole Email
If the subject line does not earn the open, nothing else matters. You could have written the most compelling pitch in the history of electronic communication, and it will die unread below a subject line that says Quick question or Exciting opportunity or Reaching out.
What works: specificity. A subject line that tells the reader exactly why this email is relevant to them, right now.
Subject lines that got opened:
- "Your talk at TechSparks — question about the pricing model you described"
- "Referral from Meera Shah — re: your open engineering lead role"
- "Read your piece on embedded AI — built something related"
Notice what these have in common. They are specific. They signal that the sender has done homework. And they give the reader a reason to believe the email inside will be worth their time.
What fails: anything clever, mysterious, or urgent. You won't believe this belongs in spam. URGENT: Partnership Opportunity belongs in the trash. And Hey! — a subject line I have received more times than I can count from founders who wanted money — belongs nowhere.
The First Sentence Rule
Your first sentence must answer one question: why should this person care? Not who you are. Not your credentials. Not your company's mission statement. One sentence that earns the right to a second sentence.
Here is an email I sent to an investor in 2019 that got a reply within two hours:
I noticed you led the Series A for [company] — we are solving the same distribution problem for a different vertical, and we are at 3x MRR growth month-over-month with no paid acquisition.
That is the whole first paragraph. One sentence. It tells the reader three things: I know their portfolio, my problem is adjacent to something they already care about, and I have traction. Everything else — who I am, the full story, the ask — can wait.
Here is an email I sent to a writer whose work I admired:
Your essay on decision fatigue in engineering teams changed how I run standups — I stopped asking "any blockers?" and started asking "what is the one decision you are stuck on?" and it transformed our morning meetings.
No introduction. No credentials. Just a specific, concrete demonstration that I had actually read their work and it had affected my behaviour. The reply came the next morning. We ended up having coffee a month later.
How to Ask for Something Without Being Annoying
The ask is where most cold emails collapse. The sender has done everything right — good subject line, relevant first sentence — and then asks for something enormous. Would you be open to a 45-minute call to discuss potential synergies? Forty-five minutes. With a stranger. To discuss synergies, which is a word that means nothing.
The ask should be small, specific, and easy to say yes to. The smaller the ask, the more likely you are to get a yes. And a small yes opens the door to everything else.
Bad asks:
- "Can I pick your brain?" — Vague, suggests an open-ended time commitment, and the phrase itself makes people wince.
- "Would you be open to a call?" — What kind of call? About what? For how long? Too many unanswered questions.
- "I would love to get your feedback on our deck" — You are asking a stranger to do work for you.
Good asks:
- "Would you have 15 minutes on Thursday or Friday to discuss X?" — Specific, bounded, easy to calendar.
- "I have one specific question about Y — if you could reply with even a line, it would be hugely helpful." — Signals that a short reply is welcome.
- "No call needed — I have written up the context here. If anything jumps out, I would value your take." — Removes the scheduling burden entirely.
The Emails That Worked
In 2018, I cold-emailed the CTO of a company whose API we were building on top of. I had no introduction. I had no leverage. I was running a twelve-person startup and they were a publicly traded company.
The email was four sentences. I described a specific technical problem we had solved using their API in a way they had not documented. I included a two-paragraph write-up of the approach. And I asked if their developer relations team would be interested in featuring it as a case study.
He replied in three hours. Not to pass me to devrel — to ask if I wanted to meet when he was in Bangalore the following month. That meeting led to a partnership that was worth more to us than our next two fundraising rounds combined.
What made it work: I led with something useful to them, not something I needed from them. The email was an offer disguised as an introduction.
In 2021, I wrote to a journalist who had covered a competitor of ours. The email opened with a correction — a factual detail in their article that I knew was wrong, and I provided the source. The second paragraph mentioned what we were building. The third asked nothing at all.
She replied to say thanks for the correction. Two weeks later, she emailed me to ask if I was available for a quote on a story she was writing about the sector. That article was the single biggest driver of inbound interest we had that year.
The Emails That Didn't
Failures are more instructive, and I have an archive of them.
In 2017, I spent forty-five minutes crafting what I thought was a masterful email to a well-known angel investor. It was four paragraphs. It covered our market, our team, our traction, and our vision. It was thorough, well-written, and — I can see now — absolutely exhausting to read. It got no reply. Of course it didn't. It was a pitch deck compressed into prose. Nobody wants that in their inbox.
Worse was the email I sent to a potential co-founder in 2019. I was so worried about sounding presumptuous that I hedged everything. I know you are probably very busy. I do not want to take too much of your time. If this is not of interest, I completely understand. Three apologies before I even stated what I wanted. He told me later — after we connected through a mutual friend — that the email made me sound unsure about my own idea. He was right. I was.
The lesson from both: the worst outcome is not rejection. It is an email so forgettable that the reader does not even register it as something worth rejecting. Write something that deserves a no, and you will get more yeses than you expect.