https://www.cnbc.com/2025/04/28/box-ceo-i-once-turned-down-big-offer-to-sell-startup-now-worth-billions.html?utm_campaign=trueanthem&utm_content=main&utm_medium=social&utm_source=linkedin
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That’s not even the half of it. 20-20 hindsight, here we come.
At the time, Citrix was in the running to buy VMware but would lose out to EMC who bought it for $625M. Rumor had it that EMC had outbid Citrix by offering a price Citrix wasn’t willing to pay. That was 2003-2004 and to be fair the X1 project was in full-force and it would another 3 years before Citrix hit $1B in gross revenue. What a goal for a up-and-coming software company: $1B in gross revenue and not make life-altering software, disrupt, invent sh-t mankind has never seen before, etc.
By 2007, Citrix was able to pay $600M for Box, and wound up paying ~$500M for XenSource - to own it without actually owning it not to own it, but to… just have something in the virtualization space.
The team around XenSource stuck around (by contractual obligation) and, after a couple of years, moved on to do whatever (golf, walks on the beach in Spain - that was F-U money!!!). I cannot recall if any one of them lingered beyond their contract date, and if they did, it wasn’t for long.
Bottom line was that Citrix didn’t (maybe couldn’t) go big when it had the opportunity to (buying VMWare). Having done so would have changed the whole trajectory of Citrix’s outcome.
The other takeaway - when you purchase a company for (what was at the time and for a company the size Citrix was at the time a HUGE investment) that much money, you shouldn’t be interested in just buying the tech, but you should also be interested in acquiring and retaining the talent that created the tech.
XenSource and Box were dev projects with a tiny core of people while VMWare was an entire company (albeit a fraction of the size of Citrix at the time, if you can believe that). I’m certain the effort was made to retain those folks and incorporate them into a corporate fabric blah blah blah — but ask yourselves where Microsoft would be if they let Mark Russinovich go instead of incorporating him into Windows Dev and eventually Azure?
$2T in market cap instead of $3T - that’s where.
Joking aside, imagine having brought in the VMWare talent and worked and possibly might have become the world’s first Cloud Provider in the present sense? Then again, Citrix woulda found creative ways to alter that outcome too.
Thank you for reading.
Another acquisition company Citrix could have destroyed.
We can’t even make our home grown products work properly without taking on stuff we know nothing about.