| Hi everyone, it's Nico Grant. Black Friday is a great time to go shopping for new technology. Just ask Marc Benioff. In the coming days, Benioff's Salesforce.com Inc. could announce a mega-deal to acquire workplace chat app Slack Technologies Inc., people familiar with the matter have said. Slack's current market cap, $23 billion, would make the purchase Salesforce's largest deal ever—a significant milestone for a tech giant with an acquisitive streak. One of Benioff's favorite pastimes as Salesforce chief executive officer has been snapping up other companies. Salesforce has bought more than 60 in the last 21 years—some of them significant, publicly traded businesses, including Tableau and MuleSoft. Benioff has said that he has a vision for his business, which sometimes includes combinations, and that Salesforce has done a better job of integrating acquired companies than most anyone else. "There's not a lot of other software companies who have this kind of track record," he told me last year. On a call with investors, Benioff said he thought his 2019 purchase of Tableau would prove to be "the best acquisition ever done in the history of the software industry." Yet just three months ago, Benioff suggested Salesforce might scale back. After spending more than $20 billion in less than two years, the CEO explained that he was now focused on execution. "We're not in a good M&A environment. I just don't see it," he said. "This isn't part of our plan right now." Then Benioff saw Slack, a rare flashy company in the dry realm of enterprise technology. Not only is Slack growing quickly, it would give Salesforce another opportunity to compete fiercely against Microsoft Corp. Salesforce is already up against the company in sales-tracking software and analytics, while Slack is challenging the Microsoft Teams communications tools. Not everyone thinks a Salesforce-Slack tie-up is a good idea. Salesforce's stock fell as much as 5% on Wednesday following headlines about the acquisition talks. Kirk Materne, an analyst at Evercore ISI, called the deal "not the right target, nor the right time" for Salesforce. He also said that many investors would view such a deal as a way to buy growth, and that there was doubt about Slack's long-term prospects. "Even with Salesforce's heft in the enterprise market, competing with Microsoft Teams in its core market is going to be extremely difficult," Materne said. That may not matter much to Benioff, who has long dreamed that his company would become a big player in the communications market. He infamously tried to buy Twitter Inc. in 2016, before Salesforce shareholders balked at the prospect. Salesforce also spent a decade pitching a workplace communications and collaboration tool called Chatter. The company went to such extreme lengths to make the product a success that it bought a 2011 Super Bowl ad starring Will.i.am to get businesses to adopt the app. All these years later, Chatter hasn't made much of a mark. Slack, with its millions of users and fans, would reverse that legacy virtually overnight. Benioff knows what any Black Friday shopper could tell you: It's the sentimental purchases that mean the most. —Nico Grant | 
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