Email sucks for relationship building

Messaging apps make me a better VC

John Henderson
Feb 4, 2016 · 3 min read

As a VC, I spend my life helping startups. I’m constantly looking for ways to do it more and do it better.

I was giving the White Star team an update on one of our EU portfolio companies recently. In response to a question I began explaining a very specific, technical challenge the company was currently working through. One of my US colleagues turned and asked: “this is great, but how on earth do you know all these details?”.

This question gave me pause. The simple answer was that I have a great relationship with the founder and that we talk regularly (both work and non-work stuff). I knew the details not because I needed to or because he needed help with that issue specifically, but simply because we talk a lot.

Actually, “talk” is the wrong word in this instance. I knew it because we’re in a WhatsApp group together.

That WhatsApp group started out completely non-work related. It has a nonsense title (“pure AI”) and, if you went through its contents, you’d find a bunch of pictures, banter and general naff chat…

Every once in a while we talk about work stuff too. Sometimes it’s triggered by an update email to the board. Sometimes it’s just a seamless and natural part of a broader conversation. But because we’re using a messaging app, “every once in a while” usually means at least once per week.

Contrast this with a typical founder/VC relationship in which the primary communication medium is email. Email isn’t well suited for chit chat. Founder/VC emails tend to concentrate on purely business matters. They are longer, less frequent and more formal.

The medium matters. WhatsApp has helped strengthen our relationship. It helps us talk more often and more casually. There is no pressure or pretence in a WhatsApp message.

More frequent snack sized interactions end up being more valuable to me than long emails, formal 1:1s or board meetings. Without them, my relationship isn’t as tight, I’m not as deep into the details, I miss some nuances and I don’t feel “in the flow”. Email sucks for building a relationship. Without a real relationship, you don’t know as much and it’s harder to be as helpful.

20 short back-and-forth messages is annoying on email. It’s normal on WhatsApp.

This post isn’t meant as an ad for WhatsApp. Pick the medium that works for you. I use Skype messenger with Anthony from Hole19, I’m in WhatsApp groups with Phil from DICE and Mills from ustwo (we Snapchat too, natch), it’s Twitter DM with the founders of a stealth company, and Slack with Jeremy and others from CoinDesk. A hybrid of Slack (being in various company channels) and WhatsApp is probably my favourite combination.

I work with a bunch of other companies too and always help as much as I can, but those are the ones I interact with most frequently. And I’ve come to realise there is a direct correlation between my frequency of interaction and the amount I’m able to help.