How Many Different Directions Are Too Many?

I’m a serial entrepreneur at heart.  An idea guy.  An angel investor.  I love diving into new things.  I guess you could say I have Entrepreneur ADD.  I just can’t help myself sometimes.  A constant in my life since 2000 has been CustomScoop. But I have had other companies that I have started and sold off (for modest amounts) or shut down.  I have helped other companies grow, some successfully and some less so.

In With the New…

And now I’m in a phase where I have several different ventures percolating.  A new media company featuring niche online properties relying on my theory of converged media that I described in The New Media Cocktail.  First out of the gate will be StartRocket, a web site focused on Internet entrepreneurship with an “East of the Rockies” perspective.  Then I have a fine dining property in the works called Cork & Knife (more on that to come in due course) that will likely exist under the same company banner.

But I also have an inkling for a couple of other companies that are more application oriented.  One is a quick, fun application that I think would have real potential viral appeal.  It would likely take off or not and wouldn’t require a ton of work unless it does (but then could be all consuming to make sure it could handle the load).  Another application I’m musing about has more lasting appeal and would actually nicely complement some of the things that the new media company I’m starting will do.

…While Hanging on to the Old

Of course, I’m remaining as CEO of CustomScoop, too.  In fairness, though, years ago I got out of the day-to-day management of the company and I play more of a strategic role while serving as the public face of the company — probably Chairman or possibly hyper-active Chairman is a more accurate depiction of my role.  And I still have this blog and my podcast (both of which have been suffering of late as I have been gearing up the new venture and writing an e-book).

Not to mention speaking engagements, conference commitments, serving as a columnist for Mass High Tech magazine, and writing numerous one-off articles for various publications.

So How Much is Too Much?

I’m fortunate in that I have a great team with me at CustomScoop that enables me to roam free.  I also have a solid team of business partners who help make these things possible through things like our angel investing outfit.  I have had the good luck to assemble thoughtful outside advisors who are always there to have their brains picked.  And, of course, an understanding family that tolerates seeing me on the road half the year and buried in work at home when I’m not in some hotel somewhere.

From time to time over the past decade I have realized that I was going in too many different directions at once and everything was suffering.  Ironically, sometimes it was only two things that had my attention.  At others, I have been able to juggle as many as five ventures simultaneously without too many ill effects.

I guess it’s one of those things that you can only define when you see it — and hope that you do see it before it is too late.  Many successful entrepreneurs juggle more than one serious thing at a time — look at Kevin Rose with Digg and Pownce.  Or even Bill Gates with Microsoft and his foundation.  Obviously, the key is to define one’s role appropriately, surround yourself with real talent, and avoid over-committing. 

It will be interesting to see if I succeed at that concept this time around.