But with a free tier to push the business, perhaps too many users were free and not enough were in the paying category. It seems that the writing might have been on the wall last June when the company announced it was laying off 14% of its workforce.

But Slack’s struggle to succeed as an independent company sadly mirrors that of many one-time innovators in enterprise productivity. Mailbox died and Acompli sold to Microsoft, where it became the mobile Outlook app. Evernote is a pale shadow of its former self. Of that early cohort, only Box and Dropbox became — and still remain — public companies... See more

It's hard to get around that, but the way you can do it is if you build in utility. And I think that is largely because advertising was a hell of a drug for these companies for so long. That is why all these big internet advertising platforms were slow to become marketplaces, because it would have a temporary negative financial impact. Th... See more