I’m Too Sexy For This (Enterprise) Startup

Everyone is talking about the enterprise being “sexy” “again.”  VCs are urging entrepreneurs into enterprise battle.  Quora-ians are trying to figure out how to get more people into enterprise startups.  People are actually describing entire data centers (usually unmarked white concrete buildings) as sexy.  Kevin Rose digs it.  Apparently there is even a beauty contest for “sexiest enterprise startup.”  Heck – while everyone else has a man or woman-crush on Jack Dorsey, Jack’s now in love with enterprise file sharing startup Box’s CEO Aaron Levie:

My reaction: WTF (as in World Trade Foundation).  Is everyone crazy?  Sexy?  Are you serious?

Sure, technically there have been 56 IPOs with more than $1 billion in value in the last 10 years, includingWorkday, Service Now, Splunk, Jive and Palo Alto Networks.  And pundits claim there is a strong pipeline of upcoming enterprise public offerings like Box, Marketo, Zuora and others.  And maybe there are a few hundred billion dollars or something of revenue at old incumbents waiting to be disrupted.

But like a club party that’s gone on too long in the dark, let’s turn the lights on and see if enterprise still looks so hot:


Palo Alto Networks founder Nir Zuk, recently remarked at TechCrunch Disrupt:

I say, the opposite.  Solving hard technical problems, creating important value for customers, leveraging new computer science algorithms – anyone can do that.  Deciding whether to use a Lyft or SideCar ride share to get to work, finding the best place to sit at The Creamery to hear M&A rumors, figuring out how to transform yourself from a programmer to a brogrammer – these things test what you’re truly made of.

How do enterprise entrepreneurs even sleep at night?  I mean I know they probably sleep on mattresses filled with $1000 bills.  But isn’t that uncomfortable?


Enterprise companies are really struggling.  While Instagram is putting up 100 MM customers on the board, the supposed success story Salesforce.com only had a piddly 90,000 at their most recent conference.  Even the iPhone Vuvuzuela app has more users than that – I think.

Enterprise companies will tell you their customers actually pay them – a lot, but that’s no excuse.

And these sucker companies actually have to talk to their customers.  They travel on planes.  They eat at airport Applebees.  They go to places like Pittsburgh, PA.  Or even San Jose.  Some of these places don’t even have Uber, if you can believe it.  And no, TaskRabbit won’t meet your customers for you… yet (business opportunity!).

Sales People

Consumer startups are often smart enough to avoid hiring sales people altogether – or at least they banish them to some godforsaken place like New York City.  In enterprise startups, the sales people are everywhere.  They’re on the phone.  They’re in your inbox.  They’re even under your desk – watching your every move.


Ask an enterprise entrepreneur what her DAUs or MAUs are and you’ll get a blank stare.  She’ll confuse you with “vanity metrics” like “revenue” and “profit” and throw made up acronyms at you like “EBITDA” to hide the real truth – that the business is a house of cards with nothing keeping it up except amazing financial performance.


Start a consumer tech company and you can have so many exits.  You can pivot.  You can have a soft landing.  Of course you can be acqui-hired.  Heck – I’m pretty sure we’ll see an acqui-contractor-ed or acqui-unpaid-intern-ed exit before the end of the year.  The possibilities are endless.  And if you don’t like the exits in front of you, simply run your startup from Hawaii.

Enterprise exits?  They literally haven’t innovated in years – still stuck with tired, huge acquisitions and aforementioned cliched IPOs.  Out of ideas, enterprise guys and gals?  Too busy counting your billions to get creative?

Movies, Tigers and Islands

Consumer startups have Oscar-winning movies made about them, Bravo reality TV shows profiling them and caged-tiger-parties celebrating them.

Enterprise startups?  They’re so lame that most enterprise entrepreneurs cry alone on their own islands.

Longing For the Days

Let’s turn back the clock – back to a stronger, smarter startup world before all of this madness.  Where $3.4 billion enterprise acquisitions are rightfully written off as “boring.”  Where famous bloggers call out enterprise startups for being the snooze-fest / goldmines that they are.  Where Michael Arrington yawns at all of this uncool stuff.  Wait, that last one was just a few months ago.  Thank goodness for Arrington – keeping it real.

Wake up, enterprise.  Until you have your own Gangnam Style video, you’re sexy-dead to me.  At least Box’s Aaron Levie got the message.

* Actually I used to be too sexy for enterprise.  Now I’m just sexy enough, which is to say, not at all.

Nick Mehta

As a huge sports fan, Nick thinks of his job as being like that of a head coach. His role is to help bring the right people together on the team and put them in the best position to win for our customers, partners, employees and their families. He’s a big believer in the Golden Rule and we try to apply it as much as we can to bring more compassion to our interactions with others. And he talks way too fast and overuses the word awesome like it’s going out of style. Before coming to Gainsight, Nick was the CEO of awesome leading Software-as-a-Service E-Discovery provider LiveOffice through its acquisition by Symantec and prior to that was a Vice President at VERITAS Software and Symantec Corporation.