OnStartups

First off, I’d like to say that I’m not particularly fond of the term “serial entrepreneur”.  The only other context that I’ve seen the term “serial” used to describe something in mainstream language is “serial killer”.  Interestingly, even “Repeat Entrepreneur” doesn’t quite work because it reminds me of “repeat offender”.  Oh well.

Semantics and phrase associations aside, I’d like to take a look at the idea of being a “parallel entrepreneur” which I would define as having more than one entrepreneurial effort going on at any one time.  In my experience (and I’m guessing there are others like me), life doesn’t always work out so cleanly.  Though it would be ideal to wrap one thing up, put a nice little bow on it, and then start the other – it doesn’t seem to work out that way in real life.  As I’m in the process of winding down one thing, new opportunities come to mind.  Sometimes, I’ll end up in “parallel” mode whereby I wind up with multiple initiatives going on simultaneously. 

Thoughts On Being A Parallel Entrepreneur
 

1. Don’t Ride Two Horses:  There are any number of metaphors (or is it analogies?) that explain why you shouldn’t try to do multiple things at once.  Though I’m not one for clichés, I must say that this one is true.  It is hard and often highly ineffective to try and do multiple “big” things at once.  Heck, it’s even hard doing one big thing at once and getting it right.  So, my first piece of advice, is to do your best to not get into parallel mode with two major initiatives.  It’s asking for trouble.  I’ve done it, and it’s not fun.

2. Having A Day Job:  The above is not as dangerous if what you’re doing is keeping your day job (and a steady paycheck) while you explore a new entrepreneurial opportunity.  This is not being a parallel entrepreneur (because you’re not juggling multiple entrepreneurial initiatives).  Of course, you need to take appropriate measures to ensure that your “outside work” activity does not conflict (legally or otherwise) with your new startup.  Tread carefully here.

3. Starting One, While Stopping Another:  This is one of the most common causes for parallel entrepreneurism.  You’re in the process of winding down one initiative (sale of the company, shutting down a failed business, new management, etc.) and starting up another.  I’m not sure if this is the same for everyone, but in my experience, winding something down takes much longer than you thought it would, and starting something new up consumes much more energy than you thought it would.  As such, where possible, it’s best to try and finish up the first before starting the second.  

For example:  I was in the midst of negotiating the sale of my first company (Pyramid Digital Solutions) to a large multi-billion dollar technology company.  By this point, I had really strong management in place so my day-to-day involvement in the company was minimal anyways (as an aside, I’d also joined a graduate program at MIT, but that’s a story for another day).  Based on my expected “closing date”, I kicked off things with a new startup.  As it turned out, getting the M&A deal done took much longer (12+ months) than I had ever expected.  Thankfully, I didn’t take any big steps, like building the early team, with the new startup during that time (though I was tempted to).  If I had to do it over again, I’d wait to finish one thing up before kicking off the next.  Entrepreneurs tend to over-value the “window of opportunity”.  There’s usually more time to get the new thing kicked off than they realize.

4. Are You Hedging Or Leveraging?  One big question is, do you have two things going on at once because one is a “hedge” against the other, or is each initiative bringing value to the other?  Only you can really figure out the true answer to this.  (Though, it’s often tempting to rationalize something as being “leveraging”, when deep down inside, you know it’s a hedge).  If you are hedging, you may find that there is more risk in trying to do two things at once – and hence doing neither particularly well.  It’s hard to be equally passionate about two things at once and commit the necessary energy to both.  If one helps the other, great.  I’d also advise making one of the two initiatives the “primary” one.  It should always trump the other when things get tough (which they will).

For example:  I’m in currently in the process of building HubSpot, a new software startup.  We’re still in the early stages, so things are chaotic, exciting and lots of fun.  Simultaneously, I have OnStartups Enterprises (which is what operates this website).  I would label this more as “leveraging” vs. “hedging”.  The reason is that OnStartups, though operated as a business, does not make any direct revenue.  HubSpot is never competing for my time or energy with OnStartups (HubSpot always wins).  Finally, HubSpot does benefit from the existence of OnStartups as it is a great vehicle to find early clients and members for the HubSpot team.  Case in point:  I’m in discussions with an exceptionally talented individual right now that I’m hoping to bring on board full-time.  We connected via the OnStartups community and would likely not have met otherwise.

Summary of My Point:  With rare exception, it’s important not to try and have two (or more) initiatives going on that compete for your passion and energy.  Being a parallel entrepreneur with more than one equally exciting idea is a recipe for failure.  Pick one that you’re the most excited about and run with it.  If you do have multiple things going, make sure you’re honest with yourself and those around you as to what each opportunity represents and why they won’t conflict.