Monthly Archives: August 2012

It’s time for me to confess…

I think enterprise software is sexy as hell.  There, I said it. I think creating value that customers will pay for is extremely hot. A recurring revenue stream makes me giddy.  And nothing, absolutely nothing, turns my head more than profitability.

Why is enterprise boring by definition?  How can improving or changing the way people do business not get you fired up?   Even when I was a noob to the Valley, I still preferred business over consumer. Maybe it’s just because I don’t understand consumers or I don’t want to fall prey to their fickle nature.  Maybe I really am just old and boring and can’t accept it.  Or maybe it’s because I grew up in the age of SaaS.  At my first startup in 1998, we didn’t even know what to call it. We said, “Um, it lives in your browser.” [Blank stare.]  “You can log in from any computer, even from home.” [Furrowed brow.]  Our incumbent competitor wasn’t just premise-based, but kiosk-based, so it was a mind-bending concept for our prospects to grasp. At some point these magical services became ASP, then on-demand, then SaaS, and now we’re all happily living in the cloud – until the next rebrand.

The inspiration for this blog came after reading a great article in TechCrunch where Alexander Haislip explains that the model to follow is not Instagram, but companies that have “real intellectual property, obvious monetization and a plethora of cash-rich potential acquirers.”  I loved Alex’s contrast on the statistical exit probability and valuations of consumer and enterprise markets…. but it was the reader comments that hooked me. It was a lively debate and I’d wager I could guess the age of each commenter within 5 years.  And then I found the one that struck a nerve, “God in Heaven, I don’t know ONE techie who WANTS to build that crap!”

Crap? Really?

As I sat ranting in my head about how these SoLoMo app building, Red Bull drinking, freemium loving, hoodie wearing twentysomethings don’t have a freakin’ clue, it hit me – I am a complete hypocrite.  I cannot count the number of times I’ve turned up one side of my lip while emitting an audible sound of disgust at the thought of working for a global, lumbering, legacy enterprise like Oracle or Cisco. How could that enterprise be my enterprise?   I realized that, just as the newest generation of entrepreneurs and enthusiasts have little understanding of what’s come before them, I’ve completely failed to pay homage to all that came before me. … and what those companies did to empower our generation to build the next great thing on top of their achievements.

When I joined the “dotcom” ranks, we were revolutionizing the world with “the Internet,” turning tradition on its ear, changing the way the world communicated, and had zero respect for anything that got in our way.  In hindsight, it’s clearer to me that while all of that is true, we owed that opportunity to the trailblazers that made our revolution possible.  Without the on-premise and client-side software providers, what improvements would we have had to offer with our fancy new SaaS-iness? Without the hardware, database and communications infrastructure, what would we have built upon? The big boring behemoths are behemoths precisely because our world can’t run without them.  Remove that infrastructure and our apps, enterprise or otherwise, grind to a screeching halt.

I’d also venture to say that this generation’s arrogance is completely justified.  Social and mobile are absolutely revolutionizing how the world connects and interacts.  It did, however, take a lot of once-alluring hardware innovation and uber-sexy enterprise (and consumer) software to get here.

Thankfully Aaron Levie has declared enterprise is sexy “again” (twice!). And even if Dustin Moskovitz and Drew Houston haven’t explicitly declared their infatuation they (along with others) have certainly done it in deed. Yes, fanboys, someone can voluntarily leave Facebook for enterprise without dying of boredom. And just for the record, I love SoLoMo apps, Red Bull and hoodies.  Just don’t get me started on freemium unless you’re ready for an earful. It’s a topic for an upcoming blog.

Here’s my point: From mainframes to mobile, everything that has value was sexy at some point, even if that’s no longer the case.  This blog will feature interviews and guest posts from everyone along the way.  Tales from the trenches, lessons learned, and a timeless perspective on who and what has contributed to creating the industry I love.

Wanna share your sexy story through a guest post or interview?  Let me know in the comments or connect with me on Twitter.

Special thanks to David “The Punctuation” Gleason for his Wikipedia mind, colorful insight and masterful editing prowess.

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