Akash Malik

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From Glitch to Slack, the big pivot to “Plan B.”

Masters of Scale Stewart Butterfield

(Wikipedia) Glitch renamed to Slack Technologies


To Reid Hoffman, entrepreneurship is jumping off a cliff and then building a plane on the way down.

Plan B, “The Pivot,” is having a plan for a parachute.

Slack started as a game, called Glitch.

The idea was a game with no combat, absurdist, “Dr. Seuss meets Monty Python meets something else.”

Not an easy sell to American casual gamers.

Glitch had a small loyal fanbase, but not enough to scale.

They got articles about them written, this that and another, but there was one night Stewart lost faith.

Stewart wrote down a bunch of ideas on a sheet of paper, realizing he had to close this shop.

That is painful to write. How do you tell everyone at work that the party has to end?

To quit everything you were working on, to do this, and ultimately get equity in... nothing.

A company having its second layoffs round in 2023, NYT

Tough conversations with the board, the investors and the staff lay ahead for Stewart.

Management tried placing employees in new jobs. They still had five million in the bank.

They decided, after lots of ideas, that the internal messaging system they built for this game Glitch could become a messaging app now called Slack.

I have used it almost every working day in 2023. They sold to Salesforce for $27.7 billion (NYT).

This chat based communication tool, which they already built for their own needs to transparently communicate with each other, could be useful for other firms.

Then they added a search feature to these messages, because they needed it themselves!

Stewart’s lessons on Slack to Reid:

  • Reframe pivoting and your “backup plans.”

  • These backup plans are built from data and necessity.

  • It is so so so important to have a Plan B.