Skiff - Or: Why Venture Capital is Bad for You

/ 24 Pluviose 232
Shavian 4 minutes / 818 words
😵‍💫 Warning: This Diatribe was written in anger, but contains grains of truth

Around a year ago, I decided to shutdown my self-hosted email service after running it for about ten years. My choice in doing such was simply cost related - for the scale of email I was processing, it was not viable to run my own servers to do as such, accounting for time in maintenance and ensuring deliverability. At the time, Skiff mail had been around for around two years, and offered an extremely price competive option for far less than I would be able to setup myself, with more features then I was able to offer, so I made the (incredibly infrastructurly challenging) choice of migrating my mail services over to Skiff.

Anyone who has even worked even adjacent to anyone in Ops or Network Services knows this is not something done lightly. People talk about Skiff as a privacy friendly, fully encrypted email service - which it was, and advertised itself as such, but the truth is that the value of using their services was their system was cheap. I knew they were venture capital backed, but saw the value in their modern, JMAP backed infrastructure which allowed me to run email for a small group of people at around $3 a month.

My thought was that even though the company was venture backed, the technology they were offering was viable enough to generate revenue on its own merits, and as such migrated our services over to them. This was a mistake.

On February 9th1, Skiff anounced that they were “Aquired by Notion”, which the corporate doublespeak hyped up as a very exciting thing. Beyond that though, the reality was simple - Skiff is shutting down in six months, thank you for the money and fuck you.

Six months is not enough time to shutdown a service as critical as email. I will have to haul ass to do a migration (where to? who knows.) In short, Skiff & Notion have accomplished a speed run in burning any good will they had with their customers.

NotesNook wrote a fantastic writeup of the whole fiasco that I highly recommend reading for more information.

What’s the game here?

Notion is a “productivity suite” - they have no interest in runnning an email service and likely never will.

Word on the street is that the main thing they wanted to aquire was its own document and calendar suite, which as a customer of Skiff, I can say isn’t all that and a basket of eggs. Their “pages” service is lacking in comparison to free, open source competitors like Obsidian or Roam Research, the calendar lacks a lot of incredibly basic features like external bookings and meetups, the “Drive” service is so barebones it’s barely worth mentioning - and all of these tools run incredibly slowly compared to even the worst competiors in the space, like Yandex. What is even the point of aquiring skiff? What does Notion have to gain here?

Genuinely beyond me, but even if I could understand it, I swear I will never touch a product by anyone from the Notion Team, or any Skiff alumni.

Venture Capital is Bad for You

This incredible fuck up on Skiffs part gives me space to write about a concept I’ve spoken publicly about for years - Venture Capital is bad for you. There’s basically two paths you can take in building any service, product, or tool:

  1. We are building something that we believe is good, and will be useful
  2. We are building something that we think we can sell

If it is option one, you do not need VC funding to make it happen. It will only hurt you. Yes, VC will allow you to grow much more rapidly then bootstrapping, but at a great cost - your timelines for generating a ROI will be nearly equally as condensed. You will be forced to make choices against your values in order to generate inconsistent short term profit. Your baby will be drowned by vampires to get at the succulent flesh, and there is nothing you can do about it because you sold the baby in a blood pact two funding cycles ago.

Adjust your expectations of wealth, and operate as lean and as small as possible. This is the path to success and happiness.

If you’re starting off as option two you are a blight and cancer on society and I no longer wish to speak to you further.

What am I doing about this?

Obviously, migrating email services. I haven’t chosen yet who to migrate to, but it’ll be a company that’s proven its reliability for at least 10+ years, and likely that metric will be what I use for deciding any network infrastructure service in the future, in perpetuity, forever. Stop breaking my things, move slow, and fix them.


  1. 21 Plu FRC ↩︎