Business Etiquette Advice for Would-Be Entrepreneurs

Paco Xander Nathan
4 min readApr 21, 2019

This story was written as a capsule of advice to send to those who need it the most.

Scenario: you’ve just arranged for an important introduction through email. Something like:

well-connected VC:
Hi XYZ, meet Joe. Can’t say enough great things about Joe. You two need to talk soon, I’m sure there’s so much you could do to help Joe.
Joe: XYZ is a luminary in the emerging ecosystem of ____ with way too many notable accomplishments to mention. This relationship will be an amazing boost to your venture.

The next step is crucial. Far too often, inexperienced people fumble with replies such as:

Thanks well-connected VC, moving you to BCC:
Our venture is a world leader in the emerging ecosystem of ____.
XYZ, I’m copying my administrative assistant to schedule us for a call.

Let’s break that down, in terms of Business Development 101. People who are accomplished and expert in matters that are in demand (XYZ above) tend to be busy. Quite busy. Already. Moreover, they must contend with thousands of people like you (Joe above) every year. They tend to develop great BS-detection skills as a result. Undoubtably they have better things to do — perhaps spends a few spare moments with friends and loved ones in-between professional responsibilities — instead of pouring through yet-more-email from strangers.

Attempting to schedule someone’s time without first stating your intent or finding out anything about their interest and availability is arguably akin to a microaggression — where the stigmatized group is just anyone Joe tech bro feels a need to co-opt. That act makes you (Joe above):

  • appear inexperienced and ineffective in business (likely outcome)
  • give others a strong signal that you’re probably a jerk (also quite likely)

People who are experienced in business will tend to guess that both of the above are more true than not, and ignore you (Joe above).

A more effective approach— given how you’re already using a media channel to communicate — is to state your intentions, needs, etc., briefly up-front, then inquire about XYZ’s availability and interest. Politely. Perhaps they aren’t available, but they could redirect you (Joe above) to someone who’ll become a key customer lead. Or something.

Don’t screw up your opportunity here. Don’t attempt to posture as if you’re some proverbial unicorn-builder, quoting entire passages from Tim Ferris and Steve Blank while moving faster and breaking more things than any other entitled tech bro in the seven hills.

Instead be real, and civil.

Also, when you (Joe above) use an “administrative assistant” to respond to a cold intro and schedule your meetings… that’s bad form. Unless you’re leading an organization of a few hundred people or more, that approach makes people guess that you (Joe, above) are:

  • probably a privileged cis-male tech bro (likely)
  • probably an idiot (also likely)
  • probably a complete douche (statistically, almost certain)
  • probably not someone to add to your contact list, ever
  • probably someone to be avoided or redirected in earnest
  • in general, probably all of the above

BTW, if that “assistant” happens to be a chat bot then you can go 10x all of the above, especially the second point.

Another common failure is to reply with something along the lines of:

Dude, let’s get coffee in SF.

Okay, by the numbers… The point of assuming that tech luminary (XYZ, above) is based in SF provides a dead give-away that you (Joe, above) are:

  • mostly indistinguishable from a privileged cis-male tech bro (likely)
  • biased that San Francisco is the center of the world (it’s not)
  • someone who does not have much going on, nor likely ever will
  • someone who has no clue about conducting business
  • ibid., complete douche
  • probably all of the above

Rhetoric matters in media. It’s how people make judgements based on the actions of others when there isn’t much other information available. The sample message above demonstrates a rhetorical posture that will tend to make people delete your email. And perhaps message back privately…

Hey well-connected VC, WTF?
PS: you *owe* me.

Signal was built for that kind of messaging.

Among the people I know who (a) reside in SF, and (b) are highly influential in technology businesses … they don’t spend much time in SF. They are active out in the world. Unlike you (Joe above). And that’s the point: they go to great lengths to be unlike your ilk. Caveat stultus.

For those who reached the end of this article after receiving its link as an email reply, (a) you probably fumbled your response to an email intro which prompted this exchange in the first place, and (b) now you have advice about how to improve your approach.

Got it?

Paco Xander Nathan

evil mad sci, ; lives on an apple orchard in the coastal redwoods; board member;