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The Secret to Digital Success? Break the Law, but Don’t Get Caught…

By Jack Santos | April 18, 2016 | 2 Comments

We’ve had some discussions about the future of organizations in a digital world, and then reflected on key success points: Uber, Google/YouTube, others.  One of the lessons learned, as voiced by a colleague, was “work in the gray areas of regulations”.

Gray Areas? GRAY AREAS???  How about break the rules blatantly, but provide plausible deniability until it’s too late to do anything about it…

Had GREEN cab take market share from YELLOW cab the way Uber and Lyft have done, you can bet  that the regulatory agencies would have been all over it.  What about Google and YouTube – the blatant copying and downloading of copyrighted and protected works is now widely accepted – to a level that even Napster had not foreseen.  The difference between Napster and YouTube?  Plausible deniability.  Report the violation to us – we’ll take it down (putting the onus of discovery on the party whose rights have been violated).

The usual “deniability” claims are centered around “but we’re just the platform” or  “It’s private peer to peer transactions”. That doesn’t hold water.   Like the federal government is “just a platform” to enable citizens to deliver public services. Yeah.

I am, of course, exaggerating the arguments around these issues.   But there is something to be said that in many cases the ability for regulatory and legal frameworks to deal with “The Economics of Connections”, and the scope of internet enabled solutions, has far outstripped enforcement.  And that “address the gray areas for success” is really “find where you can break the rules, yet get away with it until it’s too late to fix the rules – or you have the economic power to fix the rules in your favor”.  If you master that, you are an entrepreneur – in a long line of similar (but not all) entrepreneurs.

I am looking forward to some of this kind of discussion taking place at one of my favorite educational institutions, the annual MIT Sloan CIO Symposium, which this year is entitled “Thriving in the Digital Economy”.  Maybe it should be subtitled “learning to steal markets without getting noticed”.  But that’s what disruption is all about, isn’t it?  Comments for or against welcome…





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  • Haha, love the title of this article. Have you ever been caught Jack?

  • Jack Santos says:

    Rob – I am a boy scout. Which is probably why the startup I was involved with cashed in pennies on the dollar…more evidence for the argument 😉