SmoothSpan Blog

For Executives, Entrepreneurs, and other Digerati who need to know about SaaS and Web 2.0.

My Startup Track Record

Posted by Bob Warfield on March 22, 2010

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

17 Responses to “My Startup Track Record”

  1. Alexander Ainslie said

    Whatever you decide to do next, good luck with it!

    Alexander (@AAinslie)

  2. Zoli Erdos said


    Without knowing anything definite, I’m sorry to hear the (implied) news.

    And the selfish guy in me is happy to (re)gain an excellent blogger. The plan to share your startup learnings shows courage, I can’t wait to read your stream of consciousness.

    And I know you’ll be back in business soon. 🙂

  3. […] My Startup Track Record […]

  4. benkepes said


    Sorry to hear.. well some implied sad news. Like Zoli you’re a person I have a huge respect for and I, for one, am looking forward to seeing your next move


  5. billodell said


    As always, you summed up my own feelings about start-ups and Helpstream very well. I too have had my share of Successes and of Failures – one IPO, two acquisitions – so I guess I could claim a good batting average as well. I have always thought one can not be in the start-up game without an overabundance of optimism and of competitiveness. Its the latter I think that makes the Failures most hard to swallow. We just hate losing.

    Take heart though, as I do, that from any Failure comes great learning and even greater strength. I look forward to continuing on the journey and most certainly to tracking your adventures in the future.

    It was a good ride my friend.


  6. […] My Startup Track Record Success.  Success.  Failure.  Success.  Failure. […]

  7. […] My Startup Track Record Success.  Success.  Failure.  Success.  Failure. […]

  8. lovedrums said

    Whoa Bob, sorry for the news. I’m sure you will land on your feet and meanwhile provide us with more insights and knowledge about this crazed business. I’ve made some in acquisition scenarios, but zero via IPO. Some were significant, some were basically high tech garage sales. Some just faded away, some were like missiles flaming out on descent. But it is entertaining all were learning experiences.

    – Ray

  9. mikecichon said

    Hi Bob,

    I think it’s a bit of a stretch to say you failed at Helpstream. Knowing a bit about the company, it seems to me that despite a lot of hard work the business model failed and while the vision seemed real, it fell short and the market figured it out. Clearly financial success is way more gratifying and fun to talk about than financial failure, but was this success ever possible for Helpstream? Inquiring minds want to know. (In other words, you tell me.)

    Look at it this way. Would you rather have had a 9-5 job? Silicon Valley has always and probably will always be about innovative people who are not afraid to work hard and propose new ways to solve problems. Adversity doesn’t change this, it just makes those who learn from it stronger. You know, the “that which doesn’t kill me, makes me stronger” thing? Winning and losing can be so temporary anyway. Sure it’s good to be competitive, but sometimes it pays to have a short memory too. You know, the “get back in the saddle” thing?

    As always, creative destruction is alive and well in Silicon Valley, and I hope to see you in the mix of something new very soon. God Speed my friend!

  10. schlafly said

    At least you know that it was a failure, and you can move on. Good luck with your next startup.

  11. smoothspan said

    Thanks for all the great comments, folks!

    To be clear, I appreciate the pep talks, but I do understand that this really is part of the startup game and it isn’t the first time. I also accept it as a personal failure, whether or not I can see something I should have done differently. I think that is a pragmatic way of looking at it, much like judging in terms of the monetary return, simply because others will look at it that way. That’s fine, and I am again, comfortable with that.

    It’s time today to write a Learnings post. I think I’ll start with Freemiums and SaaS.

  12. […] Comments smoothspan on My Startup Track Recordschlafly on My Startup Track Recordlovedrums on My Startup Track RecordHelpstream CEO […]

  13. […] of SaaS OperationsMemcached: When You Absolutely Positively Have to Get It To Scale the Next DayMy Startup Track Record Salesforces Switches to Dell/Linus. What's Next, MySQL Over Oracle?Freemiums for SaaSWhy Do SaaS […]

  14. […] people I know whose Smoothspan blog provides refreshingly frank insights from the position of one who has been both incredibly successful and not so successful. Anyone trying to understand this market will find plenty to think about at Bob’s place. Most […]

  15. […] people I know whose Smoothspan blog provides refreshingly frank insights from the position of one who has been both incredibly successful and not so successful. Anyone trying to understand this market will find plenty to think about at Bob’s place. Most […]

  16. […] Mon…andrewnadeau on Why Do SaaS Companies Lose Mon…More on free and coi… on My Startup Track RecordMore on free and coi… on Minimizing the Cost of […]

  17. […] Comments ajaydawar on References and Pricing for Saa…My Startup Track Rec… on References and Pricing for Saa…smoothspan on References and Pricing for Saa…den on […]

Leave a Reply

%d bloggers like this: