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My Startup Track Record

Success.  Success.  Failure.  Success.  Failure.

That’s it, that’s my story.  It’s been my heartbeat.  I’m a Serial Entrepreneur with a 60% track record, which is comforting, except that I’m coming off my latest failure at Helpstream.  60% is way in excess of what most any VC ever gets.  It’s way better than anyone I know, in fact.  But nothing is ever really very comforting at a time like this. 

What do I mean by “Success” and “Failure” in the first place? 

It’s pretty simple.  For me, a happy return in dollars is a “Success”.  Having no such return is a “Failure”.  One can weasel around, or be difficult about whether money is a good defining characteristic, but in the end I am a capitalist, and I believe the market decides what is Successful and what has Failed.

The Successes involve two acquired startups and one IPO.  Acquired.  Acquired. Failure.  IPO’d.  Failure.  IPO’s are nice to be sure, but I’ve made more money by far off the acquisitions.  That’s a good thing, because in this world we live in today, IPO’s are increasingly hard to come by and acquisitions are the more common exit strategy.  FWIW, the two happy acquisitions were companies I founded.  The IPO I joined in motion, while it was still a startup.  One Failure I founded.  One I joined in motion.  So my track record is better on things I found, for whatever that’s worth.  Probably not statistically significant.

As fun and exciting as the Successes are, its the Failures I take to heart and brood over.   Wasn’t there some way to avoid that Failure?  I’ll be chewing on that bone years later, and I seldom have found a critical change I could have made.  Fine tunings perhaps.  Let’s face it: startups are hard and many will fail.  A fellow executive has a hard time framing what happened at his recent Failure to prospective employers.  He worries about it a lot.  But, he says that for many employers, they look at it as part of the Startup Thing.  Startups Happen.  True Story, that.

What’s next? 

Almost certainly another startup of some kind.  It’s in my blood.  I love startups, though I’ve had a lot of fun at large companies too, particularly the stint I did at Borland back in its heyday as VP of Engineering.  That was a blast. 

I plan to take at least a month off before I start to look in earnest, although I already have calls that I need to take.  I don’t like thinking of my successes as luck (funny, it’s not so hard to put the failures there though!), but the truth is you need a little luck for a great success.  So I can’t afford to be unresponsive lest I let the right deal knock without answering.  Nevertheless, its important to recharge your batteries at a time like this.  Startups proceed at a frantic pace as they must.  It’s part of the joy of a startup, but you have to undertake one in a state of mind appropriate to the pace.  Hence, always recharge the batteries before launching once more unto the breach, dear friends.

Fortunately, the recharge doesn’t take me long.  I get bored easily.  I start talking to people, networking, and pretty soon the Startup Energy is flowing in my veins again.  In the meanwhile, I will have time to be an active blogger once again.  This is a happy synchronicity, because I will have a lot to say.  While it’s fresh, I want to go over my latest learnings from the Helpstream experience.  It’s good therapy for me, and perhaps just a little bit helpful for you, dear reader.  I wanted to pen this initial story for the series on my first work week day of unemployment. 

I am fond of saying you learn a lot more from failure than success.  Call it a consolation prize, but I do learn a lot from the failures, though I also learn from the successes.  Since I am just off a Failure, clearly I have not yet amassed enough learnings to have a perfect picture of how to navigate the treacherous waters a startup sails on to success.   Hence there are new learnings to be discussed.

I’ll walk though it all again in more or less random fashion.  I’m going to write about the signposts that I use to guide my startup decisionmaking and strategy moreso than about the specifics of Helpstream, though I intend to illustrate with examples from Helpstream and the other startups I’ve participated in.  There are definitely some worthwhile new learnings to add, especially in the area of Venture Capital, Mergers and Acquisitions, Product Market Fit, Crossing the Chasm, and Sales and Marketing strategy in general.  Heck there’s even some new learnings on the Technical side, so it’s never too late to teach an Old Dog some new tricks.  Some of the learnings are profoundly new ground, some are refinements of old ideas, and notions made concrete.

I’m not promising any particular schedule for these ramblings, it’s strictly stream of consciousness.  I know when I wake up whether I’m going to pen a missive and what it’ll be about.  By the time I’m out of the shower, I’ve got most of it crafted in my head at which point its just a matter of getting it out via the keyboard.  Please join me for this catharsis.  And by all means, please get in touch to discuss the finer points of Startups.  If we all pool our Learnings, we all Learn.

Postscript:  The Helpstream Learnings Series

Freemiums for SaaS

Minimizing the Cost of SaaS Operations

Three Deadly Sins of a Startup CEO

References and Pricing for SaaS Startups

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