Archive for the ‘fear of not succeeding’ Category

There is no “career path,” just a network of relationships

March 30, 2018

And how you get from one adventure to the next

A few weeks ago I was asked to give a talk at the University of Wisconsin-Whitewater College of Business and Economics, on the subject of career paths. And the title of my talk was “There Is No Career Path.”

I wasn’t all that that creative. Steve Jobs made this point in his Stanford Commencement speech in 2011, six years before he died. His point was that a career path is only visible in hindsight. The “path” is produced by following your interests and talents. But I want to take that a step further.

My observation is that your career is a product of the relationships you develop along the way in your job along with following your interests and your talents. Notice I didn’t say college alumni networks. One of the points I made to the UWW students was I attended two of the top five universities in the world (Berkeley and MIT), and my alumni networks have produced zero jobs for me.

Networking

But the relationships I developed at LSI Logic, at C-Cube Microsystems, at RealNetworks, and as a venture capitalist at Frazier Technology Ventures have produced six incredible jobs, and have formed the foundation of my career.

When you unpack “relationships” there’s a lot to examine. For me, relationships are formed by establishing trust and credibility with the people you work with and for. And you do that by doing what you said you would do. By speaking your mind. By being honest. By acting with integrity. By being in a culture that aligns with your values.

Your network of relationships is fundamentally about about your personal brand.

That’s right, your personal brand is made up of the people you work with. How well you communicate to them. How well you support others. And that all involves . How you treat them. Those experiences, those memories persist. They’re your personal brand.

Finding the next adventure

And here I am, at another juncture where I am about to move to my next adventure. I left my role as CMO at SPS Commerce in early January, to return to Seattle. Family reasons draw us there, and I really wanted to get back to my roots – building category-creating technology companies.

And it’s this network of relationships that is guiding me. Which made me think of another set of conversations I’ve been having with folks I know – about how instrumental these relationships are to discovering your next adventure.

I’ve been employing the method that has propelled me to where I am now, and which I know will get me to where I want to be next. It involves four activities:

Hone your story – What this means is having clarity about what it is you want to do and what you’ve done to prepare you for this, and it’s being sober and humble about what you’re really good at. And finally, it’s about being compelling about why this next adventure is right for the role and for you – and for whoever it is you will work for.

“Your story” is what you say after you meet someone, you exchange pleasantries, and there’s a pause. You then tell the story. Why you’re there with them, why there is context, and you paint a picture of your future that they might be able to help you with.

Lots of conversations – This is the foundation of the process. This is where you start speaking to lots of people who might be able to help sharpen your focus, sharpen your story (you’ll be telling that to them), and who might know someone else who you might meet. But fundamentally you are asking someone to spend time with you. To help you.

It’s awesome your contact will meet with you, so be considerate of their time. Thank them. And make sure you see if there’s anything you can do to help them. It will make you feel less bashful about asking for feedback, or to be connected to someone else.

Considerate networking – Expect and insist on “double opt-in introductions” – this means the person connecting you someone needs to check with that person to confirm they’re interested BEFORE making the introduction . Only after that person agrees to be introduced, then expect the introduction. This means there’s mutual interest in the conversation.

This also introduces an obligation to responsiveness on your part. That means as soon as you see that email connecting you to the other party, respond promptly – before the other party has to. Your contact is doing you a favor, so demonstrate grace by making it easy for them for them to find a time and place to meet. And while you’re at it, be considerate of the person who made the introduction. In your reply, move that person to the bcc line of the email. That way they will see that the connection has been made, but they are not burdened with seeing the 7+ email exchanges that went into finding a date and place to meet.

Let go of the outcome – This is the hardest part. The only part of this process you can control is your ability to meet with people, tell your story, and explore where this all takes you. What it won’t do is provide a linear path to an awesome next role for you. But enough of these sincere conversations, where you’ve been considerate and forthcoming, will produce a conversation, at some point, that will point to a person or a role, that is exactly what you’re looking for.

It’s that simple. I can tell you every one of the awesome opportunities I am exploring right now have followed these four steps. And it has had nothing to do with where I went to school.

And like with you career – there is no deterministic path you can see stretching forward. Just a network of relationships guiding you down the road.

 

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Why video games are awesome preparation for life, and careers. By Peter Zaballos

March 23, 2018

And why adults get video games wrong

Recently, my world has been totally rocked with the multi-player game “7 Days to Die” which is a zombie apocalypse game that my children and I play together, even when scattered across the country. Sunday at 7 is our time, and we generally play with me in one city, each of our kids in other cities, and some of their friends in other cities as well.

7DTD is a game where every seven nights (in game) a zombie horde attacks, and the rhythm of the game is to spend your time between hordes preparing. It’s all about cooperating, and dividing up the work – where the work can be scavenging supplies, making building materials and tools, crafting weapons and ammunition. And developing a plan to defend ourselves. We all log on, and setup a group phone call, and there’s a constant stream of updates, suggestions, and help.

Here’s the base we’ve created. My main skill is converting rocks and sand into concrete. You can see how we put that to use. BTW, this base was shredded later that night (horde night). We survived, but the base took tremendous damage. Which caused us to assess what had gone right, wrong, and what our next defense setup would need to look like. We figure out what’s working, what’s not, and adapt. This is what I do at work every day. Except for the zombie horde. At work it’s competitors.

7DTD base

It’s an easy way to spend five hours without even realizing it. And it is a rock solid environment to hone the kinds of skills any of us needs to get through life, and succeed in our careers.

But every week it’s the same focus. We develop a plan to build defenses, a plan for how we’ll cooperate and support each other because we all have different skills and resources. And like all plans, they become obsolete the moment the zombie horde arrives. Here we are at night, my avatar’s name is RaceCondition (inside computing joke there) and the view is from one of my son’s avatar. We’re all so relaxed because since hordes swarm every seven days, and it’s day 58, we can more easily gather like this at night (in this shot we’re at an abandoned city looting).

7DTD crew

But before going on, let me tell you about how my children (and their friends) and I got here.

It may be that our family is unique, but I really doubt it. Our kids grew up playing video games. Freddi Fish was a big hit when they were little. They played them on the desktop computer we had way back then.

But even then the play had a strong social component to it, since we had four kids in five years, there was lots of group play involved. Two or three of our kids would be crowded around the monitor watching the other play, and there’d be banter throughout the game.

When the subject of getting a video game console came up, my wife and I proceeded cautiously. We’d “heard” so many scary stories about them. About how people’s kids would disappear for hours/days/weeks into a basement TV room and waste away there, living this solitary existence staring into a screen.

What we got wrong about video games is how incredibly social they are. And how much the games foster problem solving and collaboration.

We started slowly, with a Nintendo Wii. And it was fun. Mostly family fun. And soon the topic of an Xbox surfaced. Their friends had them, and over time we reluctantly agreed. There we some conditions, the biggest was that the kids would need to pay for it themselves, along with the games they wanted. So they saved, and did.

What ended up happening totally surprised us. This was full-on social pandemonium. There’d be upwards of a dozen kids at time in our basement – some playing – but most watching the others play. And the conversations, laughter, and screams of delight that grew and grew as the games progressed could be heard throughout the house.

We also witnessed our kids spending so many hours playing with all their friends and spending those hours talking…about the game, about life, about anything and everything. And there’s a growing amount of research showing video game play does create better career skills.

Which is why I was so touched when our youngest child, four years ago, suggested I learn to play Halo. He was patient, it took me literally almost a year before I didn’t feel completely incompetent. But we played through Halo 2, then Halo Reach (as far as our children are concerned, the franchise effectively stopped there). Eventually I would even get invited down when all the other friends were there and play with them, and hold my own.

I went on from that to play through Portal, Portal 2, and Bioshock Infinite. All three of these are phenomenal problem solving games with awesome story lines. Portal 2 is worth playing just to experience Stephen Merchant as the voice and personality of Wheatley – likely the single best voice performance in a video game, ever..

The more I observed how our kids played these games with their friends the more it looked like the environment I like to foster on my teams at work: goal-focused, team-oriented, sharing data to make better decisions. The more it looked like the environment I strive to live up to in my User Manual.

So of the many good decisions my wife and I made as parents, one was being open minded about video games, and trusting our children to make good decisions about how to embrace video games. We learned a lot as a family there, that has helped prepare our children for career success.

Why conversion rate optimization is the most important role in marketing. By Peter Zaballos

February 26, 2018

And it’s as important as your product

Why? because conversion rate optimization is the function that reveals the truth of your brand, your product, your business. Holistically.

It’s where you have to think deeply about the problem your customer or prospect has, and the information path they will follow to find a solution. But it doesn’t stop there.

Many marketing orgs look at “conversion” as the final step. But it’s really the beginning of the customer journey. It’s when all that carefully crafted terminology has to be aligned to what the customer experiences with the product you just sold them. The customer journey is about delivering value. And having a happy customer come back. And bring their friends and colleagues.

analytics-ss-1920

I was having a conversation with a senior exec at a successful cloud application provider last month, and they mentioned that they were having a hard time converting free trial users to paid subscribers. They were asking my opinion about what communications strategies I’d used in the past to boost these.

My first thought was, “you may be too late to do a whole lot about it.” If the content path that caused someone to find your solution – all those carefully crafted conversion junctures – did not line up with the first experience of the product, then you’re stuck.

No amount of in-app or email or chat communications will fix that. You might make the bad situation a bit better, but you really need to see this as a continuum of your brand promise. It’s what creates the words that draw a prospect in, and the experience they have with your product.

Like with almost everything today you get one shot at establishing trust and a relationship. Whether you’re a marketer or a product manager. And as a marketer you’re ultimately marketing a product experience. So there’s got to be tremendous coherence and alignment between what you market and what happens the very first time that former prospect becomes the user of your product.

Activation is different from retention. Retention looks past that first experience and presumes activation. Activation is converting the promise of a solution into…an actual solution to a problem. Retention is ensuring that the solution is durable, compelling, and lasting.

So if I were to pick one discipline that a marketing org should master it’s conversion rate optimization. Above any other. It’s the moment of truth for your business. It’s measurable. It quantifies your ability to deliver value to your customers.

And this is why it’s awesome to be a CMO and to be responsible for Product and Marketing. Because you are accountable to the business for ensuring the brand promise gets delivered. Everywhere. Every time.

CRO

 

Category creation – Why a messaging pivot is frequently essential. By Peter Zaballos

February 19, 2018

Part Three: The fallacy of “Everything is working, we just need to tell the story better”

So your CEO has articulated a bold vision of what is possible for your customers. Fundamentally different from what they have today. A change so dramatic they can’t imagine it. But you can.

This all got written down. And these words matter. A lot. They didn’t come easily or quickly. At the beginning they were directional, not precise. Intensive scrutiny and many iterations produced the exact set of words that describe the change you envision, and the category you’re creating.

Now you shift your focus to putting those words into action. And those words will inform and bring to life the go-to-market orchestration that will position you as the leader, the creator of this new category. They will inform the demand generation, the events, the company communications and training, and most important, the experiences customers have when they use your product. Let’s call this your category story.

The category story is the collection of words and visualizations that tell the market, your customers and prospects, and critically your employees about your role in bringing the bold future to reality. It’s the core creative idea that fuels any of the forms of the media you will deploy.

A SpaceX Falcon Heavy rocket lifts off from the Kennedy Space Center in Cape Canaveral

The story can and should live in lots of people’s hands. It’s what gets amplified through marketing. Evangelized through events and workshops. It fuel’s the virtuous circle of adoption. It informs every step of the buyer’s journey. It creates the triggering events that makes someone open to switching from what they’re using now, to the future you inspire them to join.

The reality is that a lot of companies formalize their category vision after they’ve shipped their product. After they’ve sold it. After they’ve figured out how to create demand.

When I was a venture capitalist, I lost track of the number of Series B and Series C financings I was pitched where the CEO would sheepishly admit that they’d “shipped their demo.” It worked well enough to get traction and funding. And that part of the next financing was to finish and fix what had gotten them started.

So a lot of companies need to make this pivot to build their category while running their existing business. With demand gen working. Salespeople selling. Customers using the product. Going back to what I wrote in Part One, category creation is for the bold and means you’ll need to make some pretty scary choices to leave the familiar past behind to realize the category’s potential.

It’s crucial that you amplify the category value proposition. Not the tactical value prop that got you here. The chief warning sign that’s you’re falling into that trap is believing…

“Everything is working we just need to tell the story better.” 

But that’s the wrong story. The old story is made up of well thought through campaigns and tactics, but without the purpose of creating your category dominance. The old story may produce near term success, but it sure won’t build your category.

This is the “make or break” juncture for the business. You can certainly amplify the tactics that got you to where you are today. Increase the paid search budget targeting potential buyers of today’s tactics. Scrape for more organic visitors by tuning the search performance of your pages to the value prop of today. Train your salesforce to sell what got you to where you are today.

You’ll just dig the hole you’re in a lot deeper. You’ll acquire customers and partners who aren’t aligned to your category vision. Who won’t evangelize it’s potential for you. Whose product and service feedback will be a distraction from your category progress.

So when I’m asked by executives and CEOs about how to scale their growing business and how build awareness of the role their solution plays in the market, I always go back to “what is your category and how is that aligned with your growth campaigns?”

This is where the CMO’s marketing organization needs to carry the responsibility to transform words into bold actions. If you start from anything else, you’re applying bandaids to a wound that won’t heal, and will instead get worse. And more bandaids won’t fix that.

With category alignment you can build kickass marketing campaigns. Your events will bring your ecosystem together and send them off evangelizing your value. Your paid search and your organic search will be aligned and fill your demand gen funnel.  The C-suite at your prospects will see the value in standardizing on your solution.

That’s the kind of foundation durable leadership can be built. Category leadership.

Category creation and the value of not listening to your customers. By Peter Zaballos

February 15, 2018

Part Two: Your vision is strategic, your customers’ vision is tactical

In my earlier post on category creation, I touched on how critically category creation depends on a bold strategic vision owned by the CEO. And that vision gets taken to market through a product that delivers a fundamentally different experience and value to customers from what they have today.

This is hard because your customers live in the world of today. With the product you have right now. That’s what your salespeople sell, and your customer success teams support.

But creating a category is about delivering something so much better than “today.” Ambitious, bold companies learn to live with and take advantage of the ambiguity separating today from the bold future you see possible.

Spot Mini opening door

And given the role the product strategy plays in creating a category, a disproportionate responsibility falls on the product and marketing teams. As a result, there are some subtle but critical factors a CMO needs to take into account.

First, do a 12+ month product plan.
Creating a category involves envisioning a future your customers can’t see. But you can. So fundamentally you are creating a product strategy – a framework that extends from today into the not so distant future.

This means, if you’re using Agile, you look out 12-18 months and understand what are the core capabilities you’ll need to figure out and master. How many of those require foundations to be built now? Work back from those to your field of view 6-12 months from now, and the deliverables will be clearer. More specific. The dev and product teams will have a clearer sense of what is straightforward, understood and what is hard, unknown.

Now look at the 3-6 month timeframe. Here you should have a pretty clear sense of scope and difficulty. The iteration in thinking between 3-6 month windows and 7-12 month windows will likely reveal some dependencies and challenges.

Finally, you can think through what the next six sprints need to look like. Here you’re going to be fairly specific about use cases, personas, and technical scoping.

Every two weeks get everyone together and review where you are on the journey. Both with what has shipped, and what customers are telling you. Customer feedback is essential to checking your assumptions on the 3-6 and 7-12 month release plans. This is super important, and plays into the next two sections below.

If you don’t think Agile works this way you’re wrong. Here’s an awesome podcast from Command Line Heroes laying out Agile and why it’s suited for what I describe above. Agile isn’t about two week fields of view. It’s about rigor and discipline about what you’re doing every two weeks, and how you’re doing it. To have working software validate assumptions, or invalidate them.

Second, don’t listen to your customers
Does this contradict what I just said above? No. Your customers are helping you validate assumptions about your vision. What you don’t want to listen to is their long list of things they wish were better with the product you have right now. Category creation is about bringing something fundamentally different to market.

Customers want what they can see in front of them to be better notdifferent. They see what is sitting right in front of them. That’s what your sales people sold them. That’s what your customer success teams support.

When building a category around a bold vision of what’s possible, the sure sign you are losing your way is to devote most of your time into making your existing product better. And if you listen only to that or let customers drive more than 10-20% of your backlog or dev capacity making the product better, well then you’re not building a category.

Worse, driving your product priorities around “better” means you’re ensuring you will be competitively vulnerable. Then you’re really just building a business around your competitors. Because they too can listen to customers about today. About chasing better, not delivering different. If you focus on better, you’re building an product line that is structurally vulnerable to competitors. You’re solving for now. Not the future.

Third, test your roadmap
With the majority of your roadmap devoted to bringing your category to life, you can now devote your customer engagement to testing your category assumptions. Which also means testing whether or not your vision for what is possible is truly compelling.

Testing your roadmap with customers is a way to make sure your 3-12+ month release plan has integrity. It can confirm or question the validity of your core platform and functionality assumptions. It’s about being inherently curious. Being a voracious learner, and where being an optimist and not a cynic finds a comfortable home.

So that means being super hard core about why your roadmap, working all the way back to the next sprint, is creating and testing the building blocks of the future. The different. You may be shipping a “better” feature that customers care about today, but is there a way to build that “better” improvement in such a way that it also helps inform your progress towards “different?”

At every step along the way. From today’s standup to next year’s category-defining product launch has to be threaded through “am I staying focused on different?”

Go into this not being burdened with what you see today, and instead be driven by an optimism of what’s possible.

Your category vision should invigorate you, your team, and your company every single day. Your category vision should invigorate your customers and entice your prospects. Your product strategy brings all of that to life.

That’s the real role of being a CMO. Ensuring your very talented product and dev teams have struck the right balance around delivering on the strategic vision of different and not getting distracted with today’s noise of better.

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.

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.