Archive for the ‘fear of not succeeding’ Category

You miss 100% of the shots you don’t take

December 15, 2009

Something I have just loved about being in the venture capital business is the people I’ve met, running businesses I did not fund.  And of those there are a few I found so relevant to my own interests, and with founders who had such passion and integrity, that I continued to meet with them well after saying “no.”  Trying to be a productive sounding board, making introductions, passing along knowledge or experience where it seemed helpful.

It’s always been such a pleasure to get the updates from these CEOs, they arrive when you least expect them and it’s exciting to see how things are developing, where the connection is no longer the possibility of financing, but a genuine interest in the business and a relationship with the CEO/team.

Dustin Hubbard of Paperspine is one of these.  His company offered a subscription service for books.  Physical books.  He  had the idea for his company after finishing a book, and having no room for it in his already jammed bedside table.  So, he planned and planned, left his job at Microsoft, started and ran Paperspine out of his garage.

Paperspine worked really well, and solved problems that people cared about.  It probably saved my family hundreds of dollars, just with my 16 year-old daughter, a voracious reader, and who routinely dropped tens of dollars at bookstores, only to read the books once.  She loved Paperspine.  She was on a five book out at once subscription at one point, and it enabled more massive reading without bankrupting her.

And while Dustin had gotten Paperspine off the ground with funding from friends and family, he couldn’t raise his next round of financing – in a market where raising money is almost impossible anyway.  But he applied himself to solving this problem with every ethical means imaginable.  Cut costs to get to break even, went back to work at Microsoft, tried to expand into ebook rentals.

Dustin and I spoke every 45-60 days, where he would walk me through his latest set of challenges, his ideas to address them, and we’d then spend the next hour testing his assumptions, plans, and brainstorm solutions.  But he always arrived prepared and ready to dive into a meaningful discussion, and sometimes I could help, other times I think he just valued the opportunity to have someone outside the company to run his thinking by.

But for many reasons, some within in his control, many outside it, he was unable to get his next round of financing.  And he seemed to be reaching the limit of how much this business was encroaching on his life, quality of life, and family.

So, last night I was truly saddened but not necessarily surprised to receive an email from Dustin, saying that he was closing the doors.  I can only imagine how hard this was for him, how heartbreaking.

And he closed off his dreams for Paperspine with the kind of grace and thoughtfulness that we should all take note of, and admire.  You should read his final blog entry, a real fitting testimonial to a worthy business, and an incredibly decent founder.  And you can see pictures of his “warehouse” in his garage, and learn more about how he took his idea and brought it to life.

His wife framed this so well, reminding him that “you miss 100% of the shots you don’t take.”

That phrase captures the essence of what it means to take an idea that crossed your mind, and have the courage to start a company to bring that idea to life.  And you bring it to life focused on why it will and should succeed, while also keeping, in a separate place, the knowledge that there are many reasons why it could fail.

Dustin, you should be very proud of what you accomplished and learned these past two years, but you should also be very proud of how you ran your company, and how you finished.  Well done, not painless, but well done, indeed.

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Startup advice brilliance

October 21, 2009

A friend pointed me to a superb summary of advice for startups, specifically calling out the ways that advice can be flawed, along with some perceptive insights into how to identify advice that’s actionable and useful.  The post is by Eric Reis, and is appropriately titled The 10 Ways Startup Advice is Flawed

Eric’s pov is appropriately snarky, and at a macro level he calls out various ways that being lucky and being smart are frequently confused with each other.  Snarkiness aside, the really valuable point he makes is how important it is to be a critical thinker, in general.  The value of making your own assessment of the information you’re consuming, and not just accepting it.

I especially liked his point #6: Maybe the thing they did used to work, but it doesn’t anymore

I think about that a lot in my own context.  I was at RealNetworks back when it truly was pioneering this new phenomena of sending audio and video over the internet, and we owned that market.  In public we said we had 85%+ share of the market, but in reality it was closer to 95% for a good long time.

We called the shots, named the prices, dictated terms.  We muscled into and out of markets we cared about, aligned ourselves with titans of the technology landscape.

And then Microsoft showed up and we fought them tooth and nail.  It was a hard and ugly fight, which they eventually won (once they started paying attention).

Well, they won, sort of.  It was epic, and in a start-up kind of way, it was epic fun.  I remember picking a big fight with the Windows Media team on an internet media list-serve, where I’d just published some user research showing how people preferred our new video to Windows Media’s.

And Microsoft’s head of a/v technology posted to the list, accusing us of fluffing up the research, and he included a three page outline of the ways you could falsify/skew consumer surveys.  And it was so much fun to respond to the list , asking “how was it that Microsoft knew of so many ways to distort research?”

But I digress.

We each became so obsessed with each other we quit paying attention to what Macromedia was doing with Flash and what Apple was doing with the tight coupling of iTunes and the iPod.  So, while we were both wrestling in the mud pit, Apple and Macromedia left the building and started more interesting and lucrative businesses elsewhere.  And until that point the thing we did at RealNetworks really did used to work.

Eric’s “ten ways” are simple and insightful.  The hard part is putting them into action, in the moment.  My experience at RealNetworks is valuable to the startups I work with and talk to if and only if both of us are cognizant of its context.  And it takes discipline and a good dose of humility to walk the talk Eric is alluding to.

I know there’s a ton of stuff I did that was a product of luck and timing, and a lot that was a result of deliberate hard work and applied intelligence.  The hard part is being honest enough with myself to examine where those boundary lines are, to strip out the specific circumstantial knowledge from the generalized, truly durable knowledge.

So, let’s all get a good laugh out of Eric’s list, but also remember how hard it is to actually do what he’s suggesting.

Offsite complete, re-entry, hiatus

September 3, 2009

Well, my adventure came to a rather fitting and comfortable close on Monday August 24th, at about 10:45 in the morning, when I arrived at the Onion Valley trailhead, and met my longtime friend, Miles, who graciously spirited me away to one of his relatives’ condos at Mammoth Mountain, so I could take a well deserved, and very much needed hot shower.  We then spent the next eight or so hours catching up as we made our way back to San Francisco, where I caught a flight back home on Tuesday morning.

The trip was just spectacular.  No disappointments really, of any kind.  An enormous number of small and large pleasant surprises along the way, and a steady stream of incredibly kind and generous people I met along the trail.  I ended up doing about what I had set out to do, mileage-wise (170+ miles, 60,000+ feet of climbing and descending), but had to adjust both the beginning of the trip (started a few days later than I had planned) and the end (decided not to do the 28 miles in two days to Shepherd’s Pass, and left the trail at Kearsarge Pass instead).

I began the trip with two close friends from high school (Ernie and Duane), and was able to end the trip meeting three other close friends from high school and college (Brian, Steve, and Mark)…all of whom I’ve been backpacking with in much of this same country for many years.  And in between I had plenty of time on my own, some days not seeing a single person on the trail, and camping at some lakes where I was the only person there – and perhaps for many miles around.  But I was never lonely, or lacking for something wonderful to look at, think about, or explore.

Two people I met really made warm and lasting impressions.  The first was Patt, the 81 year-old woman who ran the Muir Trail Ranch backpacker resupply station, and whose heart was both huge and warm.  She was charmed with what my thirteen year-old, Ben, wrote on the outside of my resupply package (actually a 5 gallon plastic bucket):  “By opening this bucket, you hereby agree to buy your thirteen year-old son a kitten”.  Ben loves cats, and she and I had a nice long laugh about his wit and seemingly foolproof plan.  Ben, sorry, that contract was not binding in California.

The second was a 20 year-old Cal Poly junior, Ryan, who I crossed paths with for two days, as he was on his way to attempting the entire John Muir Trail (all 221 miles), in nine days.  Ryan has maturity and ambition beyond his years, and carried a good dose of humility as well.  He had failed to do this same adventure in June, went home, figured out what had gone wrong, and came back to do it again.  Meaningful failure in action.  He posted a comment here on my blog when he returned, letting me know he did in fact finish in nine days.

I collected a set of photos and made an online slide show of my trip (using some slick web technology from our company, Smilebox), and it should be on this side of not too long and hopefully not boring:

Click to play this Smilebox slideshow: JMT slide show
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Thanks to so many of you for your encouragement and support.  I am deeply grateful I had this opportunity, and appreciated as well as valued every moment I was in the Sierras.

And as some of you may have noticed, I have changed the masthead photo, to one I took of Upper Kearsarge Lake on August 24, in the early morning.  A fitting photo, and it will be nice to have this frame my blog for the coming year.

It’s been a challenging “re-entry” process getting back up to speed on life at home and work, and I wanted this post to also let you know that I will be taking a hiatus from posting here, to focus attention on these areas.  I hope to resume again later in the fall.

My John Muir Trail adventure

August 8, 2009

Many of you know I’m about to make my trek down most of the John Muir Trail, and that I will be “off the grid” from today (August 8th) and on the trail until I emerge at the Symmes Creek Trailhead (near Independence, CA) on Monday August 25th.

This is a trip I’ve been planning for the better part of a year, and has been a life-long goal of mine.

Thanks to the generosity of some dear friends from high school who I bacpack with every summer, I will be carrying with me a “FindMeSpot” GPS unit, which will transmit my location to a google map embedded in a web page, so you can track my progress along the way.

The device is setup to broadcast my location every ten minutes, so you really can follow me as I go – think of it as a back-to-nature variant of twitter.

There will also be a little footprint corresponding to where I pressed my “update” button each day, which you can click on to get the time stamp and GPS coordinates.

You can check my progress and see where I am along the way.

That said, for those of you who know me well, I might end up forgetting to make a daily update, so if you don’t see an update on any one day, don’t assume something dire has happened. This GPS device also has a button I can press to summon the rangers, so it will also serve as an emergency beacon if I need it to, but we all know I won’t.

I may be able to update my blog when I resupply on the 14th or 15th, but am not counting on it.

Look for an update for sure sometime after I complete my trip, on the 26th or 27th.

Thanks everyone for your support and enthusiasm, I have much to reflect on, especially recently, relating to the core theme of this blog – meaningful failure.

I will surely have a wonderful experience, and am deeply grateful for the opportunity to make this journey.

Posted from my iPhone, at 7,800 feet near the Red’s Meadow trailhead. Updated from ‘small un-named lake’ next to the John Muir Trail, at 9,260 feet, where for good or bad, I have 3G reception.

Preparation for a long offsite

July 23, 2009

I’ll be hiking the John Muir Trail in the Sierra Nevada mountains in California next month, which is something I’ve wanted to do my entire adult life.  The Sierras and backpacking really took root with me in high school, where a core group my friends went every summer, and continued through college and a few years beyond before losing the thread to careers and starting families.

Three years ago we restarted these annual trips, and about then I realized how much I enjoy being up in the mountains, away from all forms of electronic communication, as a way to get some perspective and some balance.

So this year I leave on August 4, and my friends and I will start down the John Muir Trail, five days later they’ll leave the trail at Red’s Meadow, and I’ll resupply there and continue on, on my own.  I’ll finish near Mt. Whitney, two weeks and 170 miles later.

And I’ve been doing a lot of reading to prepare for the trip.  Mostly trail guides, even a book on the geology of the Sierras (ensuring I will be the most boring person at the next cocktail party I go to).  But one that’s proven particularly helpful is a book called High Sierra by Phil Arnot, and it’s been great at providing detail on side trips I can make along the way.

300+ pages of detailed route descriptions, elevation changes, permit locations…in short a bunch of data and information about as “touchy feely” as the phone book.  It even has a section on “Hiking Solo” with a set of very pragmatic preparation guidelines regarding safety.   But then it went in a direction I didn’t expect, with the following passage:

“So, in a way the wilderness experience may be catalytic in bringing us to face, really face, the most important questions we can ever ask ourselves:  Am I really living the life I want to live?  Am I fulfilled in my work?  Are my relationships based on sharing and intimacy or are they primarily obligatory?  What do I really want to do with my life?”

Well, for those of us who love backpacking and being in the mountains, that set of questions told me the author truly knows his subject.  For me, these are the questions my mind gets drawn to when my “job” for the day is to traverse six or eight miles (or more) of trail at 10,000 feet, and what separates you from the beginning and end of the hike is a lot of time to walk and think.

Take the “fulfilled in my work” question.  That one’s easy.  I love my job as a venture capitalist.  I love that it requires that you think hard about strategy and equally hard about operations and execution.  You’re on a constant learning curve looking at new businesses and needing to quickly get to their essence to make a funding decision.  And when you find a business you want to fund, you get to go deep with it, for years, to help it (hopefully) succeed and grow.

But that’s the “work” part of this, and what makes my job truly fulfilling is who I work with.  Through equal parts self-selection and deliberate effort, my partners and I have created the kind of transparent, friction-free, trust-based working relationship that up until this point I had only read about.

The fact that we had all worked together before getting into this business helped, but over the past five years we’ve had to make our way through uncomfortable, difficult conversations that required egos to be set aside, and personalities to be parsed from the logic and data.  Everybody talks about this, it’s the first time I’ve experienced it first-hand.

That’s great, but actually making money in this business is getting incredibly hard.  The whole industry is in a state of transition and transformation.  Fred Wilson has done a good job explaining this, but in short, it’s taking longer to get companies sold, the IPO market is dead, and the median valuations at sale have been declining for years.  In order to generate the returns institutional investors need, you’ve got to as a firm perform well above median.

It’s daunting.  We’re doing well as VCs, but looking at the whole industry it gives you pause.  This business will be getting smaller before it gets larger, and as I’ve written in an earlier post, the old stuff gets broken faster than the new stuff is put in its place in industries who are in a state of transition.  And this is an industry in transition.

But that’s where the exciting part of this job is.  Transitions create no shortage of opportunity, and challenge.  I’m grateful I have the chance to put some more thought into this, during my long offsite.

Between now and when I “go off the grid” on the 4th, I’ll be posting on some related topics.

The collateral damage of a missed opportunity

May 21, 2009

Sometimes life just steps right in and provides an illustration of a key principle, almost as if on cue. My apologies for the length of this, but the topic merits it.

For those of you who have read my bio, you know that I work in Seattle but commute from a small town in the Midwest. There’s a separate blog post needed to explain why, but the town I live in is small enough for us to know everyone, and be very actively involved in our community.

Last week someone at our high school wrote racist comments, a death threat, and the names of a number of the black students at the school on a stall door in one of the boy’s bathrooms. No ambiguity here. Horrible, fundamentally unacceptable, reprehensible thoughts. Scary too.

How the school responded to this presents a crystal-clear example of how ambiguity + fear of failure = colossal missed opportunity for a community and for its students. And it offers a heartbreaking follow-up to my post last week about ambiguity and alignment of your principles and ethics.

Here’s what happened:

  • A death threat naming six of the high school’s black students was discovered on a bathroom stall door at around 2:30 pm last Thursday.

Here’s what was done:

  • The six students were pulled from class that same day by the administration, informed of this, asked if they knew of anyone who might have done this.
  • The next day the police department was pulled into this, and spent the day at the school investigating the incident.
  • This same day – the day after the discovery – the administration met with the six children’s parents.
  • A letter was finally sent home to students this past Tuesday, identifying this as a student safety issue, and stating that “racist or threatening behavior will not be tolerated.” You can see it here.

Here’s the issue. With one exception, what they did wasn’t wrong, it just could have been a whole lot righter. And bolder. And more educational, for everyone.

The one thing they did wrong? Waiting until the following day to tell the parents. My heart goes out to the parents of those six children when those kids came home and told them what had happened at school that day. How alone they all must have felt. I don’t need to dwell on the tragedy here, the local Fox affiliate got there way before me.

So, the police got called in to investigate, and a letter went out to the students and parents. A safety issue. My daughter summed this up well by saying it screamed ‘this is not our fault.’ I was profoundly let down, feeling decisions were guided by a desire not to fail, not to make a mistake, and to minimize the visibility of this incident.

Retreating to this being primarily a safety issue is a red herring. This is unequivocally a racism issue. And it’s not about the high school. It’s about the entire community. Whoever wrote these threats does not live at the high school. Any one of us may be running into this kid on a ball field, in a supermarket, anywhere. The school provided the medium for the expression, but those racist thoughts leave the school ground at 3:05 and go somewhere.

The school administration got the whole visibility opportunity wrong. They claimed raising visibility would satisfy “that person’s need to do it and maybe there is more that will happen.” Huh? I can’t think of a better way to ensure this doesn’t happen again than getting the entire school and community to get out in public, now, and express their opposition to this kind of behavior.

And “out in public” is where the six students and their families need to feel supported, and safe. These six children and their families should feel comfortable knowing more than the school and the police are looking out for them. Worse, time matters here, a lot. These children and their families needed that support the moment this was discovered. Importantly, the opportunity for members of the community to show their support in a timely manner was also taken away too.

What if the actions were guided by a fear of not succeeding? Success is not about catching whoever it is who wrote the graffiti. It’s about demonstrating unambiguous intolerance to racism, in the school system and community as a whole.

How could this have been handled differently?

  • They could have held a school-wide assembly to inform the students not of the threat as much as of the intolerance of racism. Of the vigilance to eradicate it.
  • They could have called a joint City Council-School Board emergency public meeting to shine a bright light on these two institutions’ intolerance to racism and vigilance to eradicate it.
  • They could have held a community-wide rally to ensure no one missed an opportunity to show support for these children and their families.

Hiding this or minimizing its visibility means that if whoever it is who made these threats is never caught, then he or she or they will have won. Even if caught, the legal process will be conducted in rooms, in buildings, away from the community.

What a spectacular opportunity to bring the community together and shine a big, bright light on this. And what a colossally great learning opportunity, missed. My daughter is taking a “Race, Prejudice, and Intolerance” class in that very school, right now. Holy cow, why not get the entire student body in on a real-time lesson. How many people can say they’ve taken part in an anti-racism activity, as a student, in their own school?

And that list I came up with about how this could have been handled differently? It can all still be done too.

And this isn’t personal or about the people involved. It’s about the direction they chose. I know the school principal and many of the school administration and teachers. These are smart, caring, very hardworking people. People that make you proud that they do what they do to provide a great education for our kids. That’s why it’s so heartbreaking to witness the straightforward, sensible path that produced this missed opportunity.

A fear of failure produced this. Nothing done wrong, but plenty of collateral damage, and six students, their families, and the community poorer for the experience.

Ambiguity and alignment

May 13, 2009

My last few posts have been very much “inside the world of vc and high tech” and I wanted to get back to the broader theme that underpins this blog – meaningful failure and what you can learn from failure.

I had one of those wonderful experiences last week where a friend connected me to a friend, and I subsequently found myself deep into a conversation I hadn’t expected.  In this case, I was on the phone with a former technology executive who left his career to pursue his passion for poetry.  There we were, getting to know each other, locating some common ground in our shared interests of startups and writing.

One of the subjects we lingered on was how whether you’re at work or at home, you’re the same person deep inside.  And that the converse is perhaps more interesting: what happens when you’re a different person at work than you are at home?  I was thinking alignment of values and areas of ambiguity.  This sent me in an interesting arc.

When I first started thinking about this I thought the issue was more about decency and less about ethics. 

Except people can be incredibly decent, treat others well, communicate compassionately and still be unethical.  They can define “truth” in a way that is not true at all, and exploit this ambiguity motivated by fear, or greed, or insecurity, you name it.  But it means who they are on the outside (defined truth) is different from who they are on the inside (actual truth) 

Which made me think of Entellium.  This is old news, but offers a rich example.

Entellium was a high flying venture capital backed startup in Seattle, where the CEO and CFO created a second set of financial statements that overstated revenue and presented these to their employees, board, and investors. Only these two executives knew about it, and they compartmentalized the truth, keeping it deep inside.  For a long time. 

John Cook of TechFlash summed it up well:  “More than $50 million in venture capital down the drain. Over 200 people out of work. And two Internet executives — both fathers — going to federal prison.”

They didn’t do it because of greed – they didn’t even profit from this deception.  In fact they ended up spurning a $100million offer from Intuit, knowing the fraud would come to light during the accounting review.  

One of the executives admitted the fraud was driven by the fear of failure.  A missed sales objective one quarter and the fear of confronting that caused them to overstate actual revenue.  And then the next quarter of course they were even further behind, and well you know the way these things play out.  So, they lied to their board and employees.

And to their families too, who were blindsided by the fraud.  The police showed up at their houses and took the execs away in handcuffs in front of their wives and children.  Imagine what was going through their heads, and the heads of their families in those moments.   And the comment I kept hearing from people who knew both men was “they were such decent people.”

So I guess you can be decent and have a very ambiguous ethical foundation.  In fact, the belief that your your ethical foundation has ambiguity is the tell-tale that you are no longer behaving ethically.  Entellium was all about the difference between what was true and what could be gotten away with.  There’s plenty of ambiguity to go around in those last six words. 

But deception is a whole number, there are no fractions of it.  There is no ambiguity.  So it’s really not about being a different person at work or home, it’s about always being the same person inside and outside.  Having truth be the connective tissue between the two.

David Foster Wallace said this well in his 2005 commencement speech at Kenyon College “The trick is keeping the truth up front in daily consciousness.”

If it’s up front, then it’s there for everyone to see.  A nice alignment between who you are inside and who you are outside.

A-players hire A-players, B-players hire C-players

April 28, 2009

This is one of those sayings in the startup world that is so accepted that it’s crossed the border of familiarity and become a full-time resident of the land of trite.  

Guess who coined it?  Steve Jobs.  That’s right, Steve Jobs, when he was getting the Macintosh off the ground.  It’s a phrase we used at RealNetworks a lot, and one that my partners and I use as a result. 

But that it’s trite doesn’t mean it isn’t relevant or true.  It is.  Absolutely. 

And it’s a subtle but important concept to really understand.  What do A-players do for you?  Everything.  Most important, it’s the tone they set in the organization and their influence on the behavior and performance of others. The hiring is critical too, but that’s a byproduct of everything else.

  • A-players are at the top of their game.  This means they know the difference between good and great.  In the work they do, and in the standards they set for those around them and those in their organizations.
  • A-players aren’t threatened by someone better than they are.   Rather, they’re relieved.  That stuff they were struggling with?  They’re happy to get that into the hands of someone who can run with it, faster and more nimbly.  How liberating.
  • A-players know what they don’t know.  A corollary to the point above is that A-players know when they don’t know something, and ask questions.  They have the security to not need to know the answer to every question, and know how valuable intellectual curiosity is.
  • A-players can’t tolerate C-players.  So they make sure the C-players are replaced.  And guess what? The rest of the organization is relieved and inspired.  They know who the C-players are, and have felt the drag on performance.  It may sound harsh, but it’s true.

To me the most essential capability A-players bring to an organization is the tone they set for it.  Their definition of “good” is so much greater than a B or a C player’s, it’s as if they’re speaking a different language.  In fact they are, and it’s critical the organization you’re in all speak the same language. 

This is why starting up companies is so liberating for A-players.  I remember when I was at LSI Logic in the early days, fresh out of college with my head spinning in this startup.  The CEO, Wilf Corrigan, made a comment to me once about why he loved being CEO of LSI Logic so much more than being CEO of Fairchild Semiconductor (which he had been before founding LSI).  He said “because I created a company with only people I wanted to have there, not ones I inherited.”  At the time the answer sounded sensible, but now I realize what he meant was he could hire A-players from the start. 

But don’t get me wrong.  A-players are not a homogenous bunch.  There’s a huge, huge spectrum of abilities and characteristics among them.  Some can be incredibly thoughtful and compassionate, others can be intellectual bullies and seemingly heartless.  But the connective tissue that binds them all together?  They know where to set the bar/standard and how to hold themselves and everyone around them to it.

Lots of low cost experiments

April 22, 2009

The really interesting improvements companies make come from takings risks, but in a lot of cases risk-taking can be held hostage by needing data to support every decision.  Being conservative and careful across the board may be safe, but it’s not where breakthrough learning happens.

This is where I see a lot of startups struggle:  confronting the tension that is created between knowing when to apply disciplined fact-based decision making to avoid failure, and when to be disciplined about making decisions where failure is accepted as a likely outcome.

The best companies create a culture that can foster two seemingly conflicting organization abilities: precision and failure.  In fact, you need both to reliably profit from your mistakes.

The key is understanding where in your business you can afford to routinely experience failure, and where failure has more costly significance.  You need internal processes that measure performance, coupled with a culture that has a pretty solid foundation of trust – where anyone and everyone feels comfortable taking a risk, and reporting the results as data.  I wrote on this earlier, it’s a culture where bad news has got to travel faster than good news.

Steve Blank wrote a pithy essay on how to navigate this decision making quandry and I love the quote he referenced from General Patton: “A good plan violently executed now is better than a perfect plan next week.”  This is a variant (or perhaps the inspiration) for another saying “the perfect is the enemy of the good.”

To me they drive home the value of action and experience placed on par with the value of planning and data.  Patton would never go into battle without a well thought through and justified plan, but he speaks to how perfecting the plan is different from winning the battle.

The same is true in startups.  It’s critical that they operate with a well thought through plan supported by data, but it’s equally important that they understand when the plan is no longer as important as what the real world is telling you.  It’s another way of understanding why the numbers in your operating plan are wrong, and is in fact healthy.

Steve talks about a simple heuristic, that decisions have two states: reversible and irreversible.  With the reversible decisions you can liberally experiment, and should.  This is where you can create significant breakthroughs for your company by being highly creative, and surprise yourself by taking risks, and failing, perhaps a lot.  If you’re wrong, re-load and try again.  For me the construct is learning to try “lots of low cost experiments”.

He makes an even more interesting observation about tempo.  It’s not sufficient to be able to take risks with reversible decisions, it’s to do so at a brisk tempo.  Quick, responsive, hungry.

Where this comes in especially handy is with sales and marketing performance and new product development.  In both cases you’re in a race to discover what works, and then what works on a repeatable, scalable basis.  I forwarded Steve Blank’s article to one my CEO’s who is focused on improving her sales and marketing team’s pace and performance.

Jenny Hall also made a similar observation in her post about what she learned as CEO of Trendi.com when it failed.  For her it was “if it won’t matter in three months, don’t spend too much time on it.”

She’s got the necessary ingredients: a culture of trust within the company, data-driven decision making, and performance measurement processes.  When she first arrived, these ingredients weren’t as prevalent, and she worked hard to put them in place, and placed a priority on reducing errors and increasing predictability.  But that was then, this is now, and she’s making the transition to fostering more appropriate risk taking as a way to increase performance.

Lots of low cost experiments combined with a brisk tempo supported by a disciplined acceptance of failure.  That sounds like a lot of fun.  Try it.

The iPhone – Virtualizing enterprise market share

April 8, 2009

It’s always good to state the obvious:  there is no way Apple will ever make a dent in overall PC market share, much less get into the enterprise desktop or server business in a way that’s relevant.  The reasons are so obvious most people don’t realize it.

The Mac will never duke it out at the low end, much less hang out with the netbook crowd because the lower margins don’t work with Apple’s business model.  HP, Dell, Lenovo – they get to have all the “fun” sorting out the volume/margin voodoo.  Lucky for Apple there’s a large enough segment that will gladly pay a premium for an elegant, integrated, and stable computing experience. 

And guess what?  Apple gets nicely rewarded:  in the fourth quarter of 2008 Apple’s operating profit was 11% while HP’s was 5% (for their personal systems division). 

But what about the corporate market?  What about all those enterprise customers who you can build lucrative, durable, “sticky” relationships with?  Businesses built from hard-fought battles over market share, premised on whoever sells the most laptops/desktops/servers to corporations reaps the rewards of valuable added services that run on them.  Has Apple really just punted on this?

No, they’re smarter than that.  They’ve realized in a world of cloud computing and web delivered applications, their leverage into this market doesn’t come from desktop unit volume.  It comes from inserting the iPhone into the information flow between businesses and their workers. 

But hasn’t every big mobile device supplier tried this already?  Didn’t Nokia bet a huge part of their farm on this with various “Communicator” handsets? 

What about Microsoft with Windows Mobile?  Wasn’t that supposed to provide the worker/enterprise tether?  It was but it never did.  It neither generates significant revenue for Microsoft, nor has it gotten durable traction with business users.  Dan Frommer of Silicon Alley Insider does a great job explaining why it’s a tweener in the worst way.  I can tell you that my two years using a Motorola Q were the longest mobile “computing” years of my life.  One of my partners compared it and an iPhone to “showing up on horseback (Q) when everyone else is arriving by jetpack (iPhone)”.

And as Network World pointed out, Blackberries are great at corporate email and “legacy” enterprise applications but are not great mobile internet experiences.

These companies forget that it’s not about them and protecting their business franchises, it’s about the user experience.  Apple is the first company to get the complete mobile internet user experience right.  Microsoft, Nokia, even Blackberry/RIM probably have done a better job getting mobile computing right, but in a world of web services, I think the operative term is “internet”, not “computing”. 

So how does Apple become relevant in the enterprise?  By virtualizing its market share.  The battles to be fought in enterprise computing over the next 5+ years won’t be over email and ERP, they’ll be around cloud-based services, web-delivered applications and mobile interactions with them.  Market share leverage will be measured in mobile devices, not desktops. 

And until the iPhone arrived, no one had a compelling mobile internet experience.  Hundreds of millions of other phones shipped, and they all suck at the mobile internet.

In an April 2008 report, Gartner found the iPhone is clearly having an impact on IT strategy.  Of their survey respondents, 65% were responsible for supporting, managing and/or provisioning enterprise mobile solutions.  Of these, 13% said they either currently supported the iPhone or had planned for it, 64% said they were currently researching/evaluating support for the iPhone. 

This is brilliant.  By having major corporations enable iPhone support Apple can get a meaningful share of enterprise users without having to sell a single desktop, laptop, or server:  13% share of mobile support is 10x+ Apple’s share of enterprise desktops.

No one is focused on this, and it makes me wonder if Apple likes it that way.  Keep the “iPhone is a consumer product” head-fake going long enough to get a strong foothold with enterprise users.  And if Apple can instill in those users the loyalty they’ve instilled in consumer iPhone and Mac users, well this could be brand new territory in enterprise business.

The reasons are so obvious most people don’t realize it..