I now write on Medium here. You can find some of my old essays below.

Why They Don't Answer Your Emails

Occasionally, people don't answer my emails. Realizing that this is a fact of life -- and an inevitable part of being an entrepreneur -- has been one of the toughest things to wrap my mind around. When I was getting started, it was an insult. I came straight from a world (college) where people received possibly twenty relevant emails a day, and not answering any one of them was an intentional slight. But realizing that the startup world simply doesn't work this way this was step one.

Step two -- which is still in progress -- is figuring out why people don't answer my emails. That's what this post is about.

(Step three, for the curious, is not answering all of my own emails. I'm really sorry.)

These are observations I've made from years of "warm" emailing acquaintances, potential partners, investors and people I met at conferences. This isn't about cold emailing or email campaign optimization. I assume those people don't email you back because they don't know who the fuck you are. As always, your mileage may vary.

Finally, "Busy" is not a sufficient reason for the purposes of this list. Everyone is busy.

1) They're embarrassed. I think this is the single least-understood reason why people don't answer their emails. I do this a lot, and I know a lot of people who fall victim to the same pattern. If I've been bad at responding to someone, and I've sat on an email for three weeks, the chance that I'll respond with each passing week grows smaller and smaller. If I email them, I'll simply remind them of how long it took me to respond. Allie Brophy mentions this in her latest wonderful post.

The Fix: Push them. I've found that this is often an ideal situation to suggest an in-person meeting. Coffee or drinks can be scheduled well in the future, and removing the tension of a broken line of communication may actually re-open the dialogue in the meantime.

2) They don't want to deliver bad news. Saying "no" sucks and -- in many situations -- little is gained by doing it. Turning someone down is difficult, which is why many people make their assistants write those notes. If someone doesn't have an assistant or simply doesn't care what you think, the rejection email isn't getting sent.

The Fix: There's often nothing that can be done here. Gentle reminders can get you to a clear "no", but identifying this situation early and taking the hint can save you time. That said, I think many entrepreneurs greatly overestimate how often this is the reason for a non-response. Many people assume that someone isn't interested when in fact one of the other reasons on this list is delaying the response.

3) They're preserving option value. This is a corollary to (2) and is very applicable to VCs, but it requires a different response tactic. This is one of the most annoying things that VCs do, but it's actually much more common than getting a simple "no". VCs' reactions to most pitches fall somewhere between "I'm writing the check now" and "security will escort you from the office". For these median cases, they'll only write the check when they see a term sheet from Sequoia, but they'd like to preserve their ability to invest in case Sequoia actually gives you a term sheet.

The Fix: Convince them that the train is leaving the station -- they should make a decision or forever hold their peace. Investors are coming in, a strategic is interested, the round closes on X date, etc. This is hard to do but is really the only way to get out of this hole. But do it quickly or else the deal will get stale.

4) There isn't a clear ask. I occasionally get messages that I'm not sure what to do with. Am I supposed to respond to this? Forward it? RSVP to an event? Help me out here. If I'm not sure what I'm supposed to do, I'm probably not going to do anything.

The Fix: Clearly state what you want in the first 1-2 lines of the email. It's really that simple.

5) There's no value proposition. Some people will do things out of the kindness of the hearts, especially for people they've met. Others won't.

The Fix: I always try to tie my emails back to some kind of benefit the recipient could see down the road if they respond to my email. There are pluses and minuses to doing this -- some people are more willing to help you for the sake of helping you than enter into some kind of vague trade -- but in all I think it's a positive.

6) Politics. Sounds weird to an entrepreneur, but responding to emails at-will is politically difficult in a lot of organizations. A low- or mid-level employee could get in a decent amount of trouble by even hinting at something that may not happen, whereas they probably won't catch any flak by simply not responding.

The Fix: This is the toughest to overcome. Often it means you are approaching the wrong person in the organization, or you need to approach multiple people. Or perhaps there's nothing you can do and you should just wait. It really varies based on the organization and situation.

Any others I'm leaving off? Why don't you respond to emails, fair reader?