Effective cold emailing for founders and VCs
10 rules when reaching out from NYT Editor and Pulitzer-Prize winning editor Glenn Kramon
Do you start your emails with “Hope you are well”?
If so, yikes! But you’re not alone.
When you’re a founder emailing an esteemed investor like a16z’s Marc Andreessen in the hopes of getting a meeting, good luck — Marc receives about 1,300 emails a day. Getting him to open your message, let alone respond, is a tough task. But it’s not impossible.
In our first GSB Impact Fund training session of the ‘24-’25 year, New York Times Editor, Pulitzer-Prize winning editor, and GSB Lecturer Glenn Kramon delivered a master class on effective cold outreach and emailing.
Venture investors often receive hundreds, if not thousands, of emails a day. Similarly, strong founders can receive numerous messages from investors eager to get into a hot or oversubscribed round (don’t forget, VC isn’t one-sided; founders pick their investors too!)
To help cut through the noise, Glenn shared his battle-tested, time-worn tips for what works in cold outreach.
Glenn Kramon’s 10 Rules of Reaching Out
First, the cardinal rule:
To make yourself one in a million, make them feel like one in a million.
Rule 1: Know something about the person to whom you’re writing, and exploit it. With LinkedIn and a few internet searches, it’s easy to find a few details about that person’s backgrounds or interests to personalize the message. Dig deep.
Rule 2: Clear, personal subject line indicating urgency. Personalize the subject line so it doesn’t read like spam. Bad subject line: “A possible investment.” Good subject line: “Can we work together on a deal?”
Rule 3: Start fast. Get to the point quickly, not at the end. In the military they call this BLUF, bottom line up front. In journalism, this is NOT burying the lede. In any case, your reader’s attention drops off quickly after the first few lines, so get to the point quickly.
Rule 4: Begin with something she doesn’t know, not with something she does know. Suppose you’re emailing Jeff Bezos. A bad intro line: “You have transformed industry after industry by changing how people interact with and receive traditional services.” A better line: “I can help Alexa with patients needing personalized follow-up care.” In any case, be original.
Rule 5: Name someone you know whom the person you’re writing about also knows (and respects). Or, have that someone introduce you two. Glenn is a proud Stanford alum, and a fervent fan of Cardinal Football. His idol, therefore: Bryce Love. Mention Bryce Love in an email to Glenn, and you’ll get his attention. Everyone has a Bryce Love.
Rule 6: Try to compare yourself to the person you’re writing to. Example: “Like you, I decided my strength was in early-stage startups, not working for large mainstream businesses…” Or mention something you’ve learned from that person by researching them.
Rule 7: Can you tell a story you know will make that person smile, even laugh? A bit of warmth or humor always goes a long way. No one’s ever been offended by humor (unless distasteful, of course). If you can’t find a way to do it in the body of the email, you can always utilize the P.S. effectively.
Rule 8: Keep it short. Make sure there’s an “ask” or next step. And keep the ask as small as possible. Make it easy to say yes. We’d like to think people are intrisincally good and inclined to help — it also makes them feel better about themselves. So make it easy for them to do so.
Rule 9: Offer something in return. Maybe you know something, or someone, that she doesn’t. It could be as simple as attaching a research report. Demonstrate usefulness and that the relationship won’t be a one-sided request.
Rule 10: Check for accuracy, then check it again, before sending. Nothing kills an message faster than a typo or mis-addressed title. With new AI tools like ChatGPT, Claude, or Grammarly, there’s no excuse to make a rookie mistake.
