The Case for Cold Contacting
If you’re inundated with cold calls or cold emails (or cold tweets, cold inMail, cold snail mail, cold DMs, cold texts, cold smoke signals…) then you’re probably feeling pretty frigid towards direct outreach. That’s fair. Most cold messages are poorly constructed wastes of time. But it is crucial that we all get better at cold contacting – both sending and receiving. Cold outreach is the only way we will burst the startup/VC bubble and introduce genuine diversity into a historically hermetic system. Personally, I owe a lot to cold messages. I got an amazing job at Collaborative Fund because of a cold tweet. I landed my biggest client ever, a Big 3 consulting firm, because of a cold LinkedIn message. I sold my last company because of a cold email. The email that ultimately led to di8it’s acquisition. Please note the multiple typos. Oof. Do as I say, not as I do. So I’m an ardent advocate of the practical value of reaching out, even when you have precisely zero mutual connections with someone. Yes, it’s more challenging and potentially awkward – I cringe when I think about the first cold messages I sent (see above) – but it can be highly effective, potentially even more so than networking. “Double opt-in warm intros” reign supreme in startup-land, but nothing beats the true passion that emanates from someone who is so invested in talking to you that they can’t delay their outreach a minute – not even to track down a bygone classmate from their MBA program who happens to work with your semi-estranged cousin to make that (luke)warm intro. And that’s essentially what most DOWIs look like. So let’s talk practicalities. I can’t stress this enough: cold outreach is not a numbers game. Five well-considered messages will yield far better results than dozens of Mad Libbed copy & paste hackjobs. While there’s no shortage of articles about how to write cold messages, I’m amazed at how often I still receive lengthy generic emails like this: So I’ll add go-to guidelines to the plethora of online advice: Short: <150 words Personal: references something unique about the person you’re contacting and shows you did research ahead of time Passionate: explains why you’re so excited to chat with them specifically (i.e., why you could not wait) Specific request: ask a clear, direct question. If the request is a follow-up meeting/call, there should be a good reason you can’t do it via email No copy and paste: or, if you must, then be very careful with the formatting in Gmail. It is a clear giveaway I also strongly suggest avoiding cliche phrases like “grab coffee”, “pick your brain”, or “I know you’re busy”, particularly if you’re contacting someone who receives a lot of similar messages. You should not use a template. Every message should be unique to the recipient, situation, objective, and platform (e.g., keep DMs very short!); but here are a couple ideas: I believe guidelines around cold outreach apply cross-industry, but if you’re reading this, you’re probably most interested in the murky world of venture capital and startups. There’s only one non-negotiable rule: send the message. If you’re looking for funding, VCs want to hear from you. That’s their job. If you’re looking to break into the industry, just be prepared that VC hiring cycles are long and unpredictable, but there are ways you can add value in the interim and the generic inbound messages are so common that it’s a low bar to stand out. If you’re looking for advice from a “successful” startup founder/CEO, you may be surprised by how many people genuinely want to help and are just looking for a clear question they can answer or an actionable request. And to VCs, CEOs, or anyone else with cold message fatigue: I feel you, but we all need to suck it up and get better at responding, even to the messages that don’t follow the “rules” and even if only to say “it’s not a great time for me to grab coffee, but let’s see if you can pick my brain over email. Do you have any specific questions I can answer?” People who don’t know the expectations around cold messaging and who don’t have a way to get a DOWI to you are exactly the ones we need to proactively welcome into the fold. Or this bubble is never going to burst.
