Q: What was the biggest acquisition failure or missed opportunity by a company?

It’s hard to really force rank a list, especially of deals you don’t know about. And it’s easy to be an arm-chair quarterback on all this.

Still, my partial list in Cloud/SaaS:

  • Google letting Microsoft buy / outbid for Github for $7.5b. If you want to own the developer relationship, you own Github. Microsoft knew this. Google could have easily paid more.
  • Salesforce and Everyone Else letting Microsoft buy / outbid for LinkedIn at $26b. LinkedIn for $26b was a steal. Salesforce knew it, and did everything possible to win the deal, but their market cap and resources at the time were just not big enough. Owning the employee graph is a once-in-a-generation opportunity. Everyone in tech of scale should have tried to outbid MSFT here.
  • Oracle and Cisco Not Buying Salesforce When They Had the Chance (Multiple Times). Both had their chance, and passed over valuation. Bad call. Instead, they for the most part bought aging SaaS products that did not move the needle.
  • HP Buying Autonomy for $11.7 Billion. A $12b failure to get into SaaS that accomplished nothing but lawsuits. HP is a non-player in SaaS after $12b. More here: Why did the former CEO of HP pursue such a shoddy deal for Autonomy? | SaaStr
  • Possibly, SAP and Qualtrics for $8 Billion — But Only Due to CEO Change. This is a good deal — don’t get me wrong. But with the CEO of SAP moving on almost immediately after the deal, it could become an orphan and a missed opportunity to leverage Qualtrics to drive Cloud change at SAP. Priorities change when CEOs change.
  • Salesforce buying Assistly instead of Zendesk. Zendesk is at $1b in ARR today. Assistly ended up becoming Help. com and then being shut down. Still, Service Cloud is huge so in the end, Salesforce built an epic business here in the enterprise segment. But they should have just paid a little more for Zendesk over Assistly.
  • Microsoft and Everything in Mobile — Danger, Nokia, etc. Didn’t work.
  • Ebay and Skype. Microsoft and Skype. No synergies, and in the end, stagnation. Skype had an incredible run but in the end did not leverage its lead and keep up.

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