Last week was Salesforce and Slack acquisition speculation, and today, direct from The New York Times, Salesforce to Acquire Slack for $27.7 Billion: “Salesforce on Tuesday said it would buy the workplace software company Slack for $27.7 billion in cash and stock, the latest in a wave of deals as the coronavirus pandemic boosts demand for tools that enable people to work remotely.” But more importantly, “Other firms focused on workplace collaboration products, including Airtable, Asana, Box, DocuSign, Dropbox and Smartsheet, may also be potential targets as highly valued software companies look to roll up the fragmented market for collaboration tools.” Are WordPress websites “workplace collaboration products?” The question is hugely important to ask because Automattic is already a recipient of Salesforce Ventures largesse with a $300 million investment just one year ago.

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If Salesforce is interested in acquiring Automattic, then the Automattic IPO question becomes very interesting. With an IPO, there would be an immense amount of capital injected into Automattic for growth (and a great exit for Salesforce Ventures), but what if – a big what if – Salesforce wants to have a a huge influence on a SaaS based internet with a WordPress foundation? They certainly wouldn’t want to pay IPO prices for a privately held company. Could this happen in 2021?

And I thought 2020 was an interesting year.

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