💃 The One That Got Away🕺

Good morning, Salesforce Nerd! Every fisherman has the story - the monster that hit the line, fought for an hour, and slipped the hook at the side of the boat.

Marc Benioff's monster was LinkedIn. Spring 2016, two whales circling the same fish, and the biggest miss in Salesforce history was decided by tackle, timing, and one email that arrived after the boat had already left the dock.

And the one who reeled it in was CEO Satya Nadella, grinning 😀 from a boat called Microsoft.

Ten years later, that fish is still sitting in Microsoft's cooler... barely touched 😬.

TWO BOATS, ONE FISH

How did Salesforce lose LinkedIn to Microsoft?

February 2016 | Satya and LinkedIn CEO Jeff Weiner sat down for a quiet dinner about a potential merger. By March, Benioff caught wind and requested his own meeting with Weiner. The race was on.

Both suitors opened at $160 per share 💰. Microsoft brought an all-cash offer, clean and simple. Salesforce brought a cash-and-stock blend, which sounds creative until you realize it's the dating equivalent of splitting the check on Valentine's Day 💔.

Then Salesforce's stock popped 10% over twelve days in mid-May, juicing their offer to a notional $200 per share 📈. Microsoft panicked, bumped to $196 all-cash 📈📈, and LinkedIn's board chose the certainty of cold, hard cash over Salesforce's stock-flavored promise. On June 13, 2016, Microsoft landed the $26.2 billion catch.

Benioff later told Reid Hoffman he would have bid "much higher." The fish was right there. The line just wasn't strong enough.

🤦‍♂️

STAR CROSS’D

The One That Got Away

Here's what makes this loss sting - LinkedIn wasn't just a good target. It was THE target.

🎯 LinkedIn generates 80% of all B2B leads from social media.

🎯 Four out of five members drive business decisions at their organizations.

🎯 1.2 billion professionals updating their own records, voluntarily, every single day.

🎯 Job titles, company sizes, industries, seniority levels, buying signals... all self-reported, all structured, all clean.

For a CRM company, that's the holy grail.

Imagine Salesforce owning that graph. Every lead, every contact, every account enriched with live professional data. Sales Cloud goes from tracking relationships to predicting them.

Now add the AI layer 🤖. Salesforce is betting the farm on Agentforce and Data Cloud. Both are starving for structured, trustworthy data. LinkedIn's professional graph would be the richest training set in B2B.

AI agents that know who just got promoted, who changed companies, who's hiring, who's buying... all flowing natively into your CRM. Back to the lake: that's a fish that feeds the entire village.

Instead, Salesforce pays for a LinkedIn connector. A third-party integration. They're renting a rod on a lake they should have owned 😩.

CATCH AND RELEASE

The Biggest Digital Professional Network on Earth, Microsoft Edition

Microsoft caught the fish of a lifetime. Then they stuck it in a tank and forgot to feed it.

😩 LinkedIn's organic reach has dropped 25% year-over-year.

😩The feed is a wasteland of motivational posts, engagement bait, and "I'm humbled to announce" cringe.

😩Spam messages are up 200%.

The platform that was supposed to be the professional internet became a content mill with a recruiter problem.

Revenue? Sure, LinkedIn brings in about $4.6 billion a quarter. But it's buried inside Microsoft's "Productivity and Business Processes" segment, lumped in with Office and Dynamics.

☹️ No standalone P&L.

☹️ No visible strategy.

☹️ No killer CRM integration that would justify the premium.

Microsoft bought a fishing boat and uses it as a storage shed.

Meanwhile, Benioff is building AI agents that need exactly the kind of data LinkedIn has. The irony is thick enough to cut with a Flow trigger.

AI is only as good as the data they swim in, and most CRM data is a stagnant pond.

Linkedin is a self-updating, self-improving database where the data sources (Linkedin users) are incentivized to maintain high-integrity information!

Agentforce sitting on a living professional graph would know who just got promoted into budget authority before your rep finished coffee. That's the moat Benioff was casting for. Microsoft owns it and uses it as a job board with a newsletter problem 👎.

FINAL THOUGHTS

Takeaway

Salesforce losing the Linkedin bidding war was a tough pill for Marc to swallow a decade ago.

Today that pain is like 1st gen Pokemon card collection your parents threw out when you were 12 years old 😭. Generational riches gone.

Salesforce + Linkedin + AI would be the end-all, be-all CRM.

And for Microsoft…WOW, what a coup to steal Linkedin away from Salesforce. And clearly not because of what they’ve done with it, but solely by keeping it out of Salesforce’s hands.

It’s just the cherry on top, for Microsoft, that they’re content with Linkedin being the Portland Trailblazers of professional communities 💀.

SOUL FOOD

Today’s Principle

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