Special: Slack + Salesforce Emergency Pod with Packy McCormick of Not Boring

The emergency discussion begins only hours after Salesforce announces its $27.7 billion agreement to acquire Slack, with Slack expected to remain independent under CEO Stewart Butterfield pending shareholder approval. Packy McCormick arrives with mixed feelings: his bullish thesis had recently argued that Slack's business was stronger than its public-market narrative, but he had hoped the company could keep compounding on its own. The hosts frame the deal as a major software acquisition and compare it with other large technology-company purchases, while positioning the central strategic question as Slack's relationship to Microsoft.

The announced price was $45.86 per share, roughly split between stock and cash, representing a 55% premium to Slack's pre-leak trading price and an 85% premium to its post-earnings decline in September. Packy says he had expected more upside: at the time, Slack traded in the mid-$20s, and a comparison with other top-quartile cloud companies suggested to him a price in the low $50s. At the same time, he describes the transaction as a strong outcome for readers who bought after his bullish article. The conversation keeps both points in view: the premium is substantial, yet Packy believes the deal may cap a company that could have grown further independently.

Packy identifies Microsoft Teams as the main reason Slack's stock had been discounted. Microsoft publicly named Slack while reporting Teams usage, reinforcing a narrative that the bundled competitor would overwhelm it. Yet Slack's reported metrics remained strong: Packy describes it as one of the better SaaS companies across growth, retention, and margins, with growth of 49% compared with Zoom's 300%. He argues that this comparison can mislead because Zoom is simple to adopt for a one-off meeting, while Slack requires an organization to set up workspaces and integrations. Those setup costs may slow initial adoption but deepen use over time; the hosts note that Slack is less naturally useful to people outside a company, while Zoom has broad personal use.