Why to cold email

• Because it can potentially open doors for you in a way that vastly accelerates things, especially if you're looking to do sales, fundraising or job hunting

Who to cold email

• Anyone you want to talk to. It never hurts to ask. You'd be surprised at the lack of correlation between status vs. responsiveness (in other words, people you think are out of reach are often not that hard to reach!)

Cold email vs. finding an intro

• Find an intro if the person making the intro is someone who can really vouch for you. Do NOT ask for an intro from someone who's an acquaintance or loose connection. It's much better to control the conversation by reaching out directly than for someone to make a weak, watered down intro for you that fails to paint you in a flattering light.
• Also, the dynamic THEY have with that person is also important. I've found that people who are professionally "higher status" are often comfortable making many intros for even people they've just met and their intros get a high response rate because they have clout with the person on the other end and don't have to worry about risking reputation or "social capital"
  • In other words, you never know who will be willing to drop some 🔥 intros for you if you just ask, even if they don't know you that well — because it all comes down to who they know and how confident they are that people will be willing to do them favors

Cold email copywriting

• Keep it short. PLEASE keep it short. Big blocks of text are overwhelming, unnecessary, and signal that you're not considerate of people's time, which does not bode well.
• Craft an email with the goal not of convincing them to buy/invest/whatever the end objective is, but with the short-term objective of getting them on a call or in a meeting. This is why you don't need to tell your entire life story or resume story or startup story in five paragraphs. You just need to give them a teaser compelling enough for them to want to say yes to a synchronous conversation.
• Keep it professional but human. I won't say "casual" but don't sound stiff. I personally avoid "Dear Sir/Madam" or such nonsense, and find that an easygoing but respectful tone (maybe even with a light joke thrown in there) can perform really well.
• Check your mindset. If you're selling or pitching, chances are you're offering something that could potentially be a win-win (and if that's NOT the case, you have a much bigger problem and need to go back to the drawing board). This means that the goal of your conversation is to qualify if they are the right customer/investor for YOU and if they ARE, then it's to explain how you can make THEIR lives easier or better or more successful in some way. Basically, know your worth and truly embody that confidence so your writing, your tone, and your behavior are confident vs. needy, respectful vs. obsequious, curious vs. desperate. Good writing comes from the heart (cheesy but true), and your heart needs to be in a calm and sincere place, not a frantic or fearful place.
• Make a very clear and reasonable ask.
• If you're asking for advice, be specific (but not too detailed) about why you want to talk to them.
• For the love of God, don't say you want to "pick their brain."

Cold email etiquette