The Garage

Slack vs Microsoft

Founding story, key facts and history — side by side.

Slack
A failed multiplayer online video game that accidentally turned corporate communication into an addictive, multi-billion dollar chat factory.
Founded2013 (Metamorphosed from Tiny Speck, origins from 2009)
FoundersStewart Butterfield, Eric Costello, Cal Henderson, Serguei Mourachov
HQSan Francisco, California
SymbolCRM
VS
Microsoft
Started with a lie. Built the world's most used software. Bet everything on AI.
Founded1975
FoundersBill Gates, Paul Allen
HQRedmond, Washington
SymbolMSFT
The Story — Side by Side
Slack
2013
The ashes of Glitch and the accidental enterprise communication breakthrough
Slack's origins trace back to Tiny Speck, a company built by Flickr co-founder Stewart Butterfield to launch an eccentric, non-violent web-based multiplayer game called Glitch. The game flopped catastrophically and was completely shut down in late 2012, forcing Butterfield to lay off almost his entire staff. However, the engineering team realized that the highly customized internal IRC chat tool they had built to communicate across different cities was incredibly fast and addictive. They pivoted the remaining capital entirely to commercialize the tool, launching it as Slack (Searchable Log of All Conversation and Knowledge).
2016
The arrogant New York Times open letter to Microsoft Teams
When rumors surfaced that tech giant Microsoft was planning to launch a competing enterprise chat tool called Teams, Slack executed a notoriously arrogant, highly public marketing stunt. The company bought a full-page open letter advertisement in The New York Times, condescendingly welcoming Microsoft to the market and bragging that building a deeply loved communication tool required a level of craft they couldn't easily copy. The public stunt completely backfired as Microsoft aggressively weaponized its pre-existing enterprise Office 365 bundling advantages, launching a massive existential assault that quickly eroded Slack's market share growth.
2020
The defensive $27.7 billion Marc Benioff Salesforce acquisition lifeline
Confronted by the unstoppable, hyper-aggressive distribution power of Microsoft Teams during the remote-work boom, Slack realized it lacked the enterprise sales muscle to survive as a standalone entity. In December 2020, Marc Benioff orchestrated a historic $27.7 billion cash-and-stock acquisition to absorb Slack directly into Salesforce. The massive transaction provided Slack with an immediate enterprise sales pipeline while giving Salesforce a modern, collaborative user interface layer to tie its diverse CRM software products together.
2023
The sudden founder exodus and the aggressive Salesforce operational alignment
Within two years of the acquisition closing, almost the entire original creative leadership of Slack, including visionary founder Stewart Butterfield and co-founder Cal Henderson, abruptly exited Salesforce. Benioff replaced the independent product-focused management team with hard-nosed Salesforce veteran Lidiane Jones, who immediately realigned Slack's internal culture. The new regime slashed operational overhead, initiated aggressive price increases across historical customer tiers, and restructured the product to act as a primary dashboard for Salesforce data workflows.
2026
The complete AI workflow integration and the omnipresent corporate hub
By mid-2026, Slack Technologies functioned as the central operating hub for the broader Salesforce ecosystem, deeply integrated into multi-billion dollar enterprise software rollouts. Under the expanded Salesforce framework, the platform deployed advanced Slack AI features, allowing corporate employees to instantly generate conversational summaries of complex multi-channel discussions and automate repetitive corporate workflows. The addictive chat layout successfully maintained its status as the default digital workspace for knowledge workers globally.
Microsoft
1975
The deal that didn't exist yet
In January 1975, Paul Allen showed Bill Gates an issue of Popular Electronics featuring the Altair 8800. Neither of them had written a BASIC interpreter for it. But Gates called MITS and told them Microsoft had a working version ready. They then had eight weeks to actually build it. It worked. Gates was 19.
1980
IBM, DOS, and the deal of the century
IBM approached Microsoft in 1980 to write an operating system for its new PC. Microsoft didn't have one. Gates bought QDOS from a Seattle programmer for $50,000, renamed it MS-DOS, and licensed it to IBM — while retaining the right to license it to other manufacturers. IBM thought hardware was the business. Gates understood it was software. The decision made Microsoft the most powerful company in computing for the next two decades.
2014
Satya Nadella saves the company
When Satya Nadella became CEO in 2014, Microsoft was widely regarded as a company that had missed mobile, missed search, and missed social. Nadella pivoted to cloud computing, transformed Microsoft's culture from internal competition to growth mindset, and repositioned Azure as the foundation of the enterprise. The market cap tripled in his first five years. The transformation is studied in business schools as one of the greatest corporate turnarounds in history.
2023
The OpenAI bet pays off
Microsoft invested $10 billion in OpenAI in January 2023, securing exclusive access to GPT-4. Within months, "Copilot" had been embedded in Word, Excel, Teams, GitHub, and Bing — repositioning Microsoft as the leading AI company in enterprise software. By early 2025, Microsoft's AI business had crossed $13 billion in annualised revenue, growing 175% year-over-year.
2026
$37 billion in AI revenue and the Copilot empire
By Q3 fiscal 2026, Microsoft's AI business had surpassed $37 billion in annualised revenue — growing 123% year-over-year. Azure revenue grew 40%. Microsoft 365 Copilot had over 20 million paid seats, with the number of enterprise customers deploying more than 50,000 seats having quadrupled year-over-year. Cloud revenue crossed $50 billion in a single quarter. Microsoft had extended its OpenAI partnership, securing a 27% stake in the company and cementing its position as the most important distribution partner for large language models in enterprise software.
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