New gig

After six months of coffees, breakfasts, lunches and general “Entrepreneur-In-Residence”ing with the good folks at Trinity Ventures, I’ve decided to add one back to the non-farm payroll numbers to help the economy and get a real job again.

As we announced today, this past Monday I joined email archiving and hosting Software-As-A-Service vendor LiveOffice as CEO. I’m very excited about the new role, my new team and the next phase of my career as CEO of a real, profitable company, as you can read here in my new company blog.

Although commuting down to Torrance, CA three days a week will be a challenge, I couldn’t be more thrilled about the opportunity. And last night I went to my first Lakers game (Game 5 against Utah in the playoffs), so I could definitely do this a few days each week.

Career ramblings: Making money in the clouds

I remember running our first website in the mid 1990s during college. In addition to dealing with the hassles of not knowing how to architect properly, program properly, launch properly or run a business properly, I remember how complex it was to simply get the infrastructure up, running and scaled. People who ran websites during that time remember how much downtime the average site faced. I remember when AOL would feature our ad on their homepage, it was guaranteed that our site (and therefore revenue) would grind to a halt. Same with Father’s Day (we were selling golf clubs) and Christmas.  We started thinking of posting a sign like the ones you see in manufacturing floors about safety:

It’s been 2 days since the last website outage.

We were constantly in a rut of buying more colo space, servers and software and yet nothing made things run smoothly.

Given that experience a decade ago, it is with envy and pleasure that I watch the revolution that is cloud computing. Obviously much has been written about Amazon Web Services and the brand new Google AppEngine. And we know that there is much more to come from the large vendors (including Microsoft) as well as the startup community.

From thought experiments to cloud experiments

The most important thing about cloud computing, in my mind, is that it is reducing the cost of experimentation. Starting is a company or launching a product is all about experimentation. Just like in science, as the cost of experimentation goes down, more experiments can be run and we have to rely less on induction and hypotheses and more on empirical evidence. And as failed focus groups and market research (New Coke anyone?) have shown us over time, in the consumer world there is no better way to understand behavior than to actually experiment. Consumers can’t tell you what they want but they know what they want when they see it.  So stop working on the PowerPoint or debating the idea and just build the site!

However, as an entrepreneur spending time in the VC world, I’ve spent a lot of time (with limited progress) thinking about what the disruptive business opportunity is in enabling cloud computing. We know that cloud computing is enabling countless new startup ventures itself but is there is a great startup opportunity around building the infrastructure for cloud computing infrastructure?

This one goes to eleven

To answer this question, it’s useful to get common agreement on what the “stack” for cloud computing looks like. In my mind, it involves the following 11 layers (from bottom to top), with many similarities to the inside of an enterprise data center:

1. Facilities (space, power, cooling)
2. Network
3. Hardware (e.g., servers Amazon EC2 runs or storage Amazon S3 uses)
4. Hardware Virtualization (e.g., Xen for Amazon EC2) - optional (Google supposedly doesn’t use any hypervisor-based virtualization)
5. O/S (e.g., Linux)
6. Systems Management (e.g., tools to manage EC2 instances)
7. Application Middleware (e.g., mysql/apache/etc. running on EC2)
8. Application Code
9. Application APIs / Web Service
10. GUI for Application
11. GUI for Application Development / Customization

Each “cloud” stack operates at a different level of depth. For example:

• “Old school” colos provide level 1 (facilities) and level 2 (network).
• “Old school” hosting provide level 1, 2 and 3 (hardware).
• Amazon EC2 provides levels 1-3 and level 4 (virtualization) and lets you go from there, so you don’t need to think about specific hardware instances.
• Google AppEngine provides level 1-4 (sans virtualization), level 5 (their OS build) and level 6 (their own middleware - BigTable, focus on Python, etc.).
• SalesForce.com provides a full application (levels 1-8 and 10) as well as an application platform (level 9) for others to build on. In totally different context, Facebook provides a similar application platform, though without the hosting of the application itself (so they provide in some sense level 9 but require you to find levels 1-7 yourself through another host like Joyent).
• Startups like Coghead provide all of that plus a UI for application development without having to even write code (level 11).

RackSpace (which has its own cloud initiative called Mosso) has a nice writeup in a similar vein here.

We can now intuit the Cloud Depth Postulate:

The higher up the stack a cloud platform goes, the lower the barrier to entry for building an application. For example, it’s easier for someone with no programming skills to build an application on Coghead than it is to build one on Force or Facebook. And it’s easier for someone with no programming skills to build on one of those platforms than it is to build one on AWS.

As well as the Cloud Depth Corollary:

The lower down the stack a cloud platform is, the higher the flexibility for any type of application to run on it. In this extreme, a colo is more flexible than shared hosting (because you can run your own VAX/VMS server if you want ), while EC2 is more flexible than AppEngine (because you can use mySQL, simpleDB, flat files or anything else for storing data, for example).

So is there money for startups focused on building cloud infrastructure and tools?

Over time, you would imagine that the lower-level parts of the cloud stack will be owned by the largest infrastructure providers (Amazon, Google, Microsoft, Yahoo!, Microsoft/Yahoo!, telcos, large hosting providers, CDNs, etc.) Similarly, application-level platforms (like Facebook Platform and Force) are a whole separate discussion since they’re less about infrastructure and more about the reach and customer acquisition value of the underlying network in which they live. Finally, the application development/customization UIs like Coghead provide direct business value (e.g., a business person could see why you’d use Coghead) so you could imagine companies created there, though with significant competition from Microsoft and other players in the mashup/app dev space.

The hardest question for me (and the one closest to my heart, based upon my background) is whether there is money to be made in systems management and middleware in the cloud computing space. Companies like heroku, RightScale and others are getting traction here, so it’s worth a look.

I worry about a few issues in this segment of the market:

• In the long-term, I think the core cloud players (e.g., Google with AppEngine or Amazon as it adds more functionality to AWS) will continue to move up the stack and encroach on the systems management and middleware layers. You could say “yeah, but that should have been true in the enterprise, where the systems vendors like HP and IBM should have owned the whole stack, yet you had companies like Oracle, CA, BMC, Symantec, BEA and others make billions in systems management and middleware.” I’d argue that the difference is that in the cloud environment, the cloud provider controls their stack operationally while in the enterprise environment, the likes of HP and IBM often just sell the customer the systems and don’t control them operationally.  If you control the operations, it’s much easier and more logical to control the systems management and middleware.
• While a solution like AppEngine does restrict developers significantly (e.g., to not using an RDBMS and to today using Python), I think it also delivers the real promise of cloud computing (auto-scaling) in a more meaningful way than lower-level platforms. As AppEngine adds more languages, it becomes a very compelling option for new applications and new developers. In some ways, the hard problems of scaling applications seem unsolvable in a generic way unless you constrict the environment in some way like AppEngine has. While systems management, adding web servers, configuring load balancers, etc. is a tactical problem, so much of application scalability involves data and database scalability, as per this presentation. Because of this, a restrictive but automated approach like AppEngine becomes attractive.

Clearly, as the big players try to improve their cloud stacks, many startups (like the ones mentioned above) will end up getting acquired for time-to-market (as is happening in the virtualization space), but I’m wondering where the standalone company opportunity truly is.

If I continue my wild speculation, I’ll throw out three conditions (not existing today) that could foster a big enough opportunity for startups in cloud infrastructure:

1. Enterprises adopt the cloud

From my research, it seems that most cloud usage today comes from two categories: (a) consumer Internet applications being launched primarily by startups who want to be able to experiment cheaply and easily and to scale gracefully and (b) scientific and High Performance Computing (HPC) applications that need massive numbers of system resources for relatively brief periods of time.

The unfortunate reality is that it is nearly impossible to build a business in software infrastructure for Internet startups, since the market is small and is often averse to paying for software (because of the predominance of open source). Furthermore, the customer base is so technical that they often don’t even need the premium support provided by commercial open source vendors (e.g., Facebook is supposedly one of mySQL’s biggest customers yet only pays them thousands of dollars per year). HPC is very similar in a way in that university labs and other large grid users are technical-heavy and budget-light.

But enterprise IT departments are used to (and often demand) paying for technology, support, services and having “one throat to choke.” Furthermore, enterprise IT developers are often not nearly as technical as the developers you find in the average Silicon Valley startup or MIT research lab.

So what enterprise applications really need the features of cloud infrastructure? Financial services companies have large grid-like applications that would be a good start. And similar technology is also used heavily by other industries like energy (oil exploration) and biotech (gene mapping). These still fall into the HPC use case of applications that need huge compute power intermittently.

Are there other, more traditional, enterprise applications that can benefit from the cloud? Unfortunately because of the internal nature of many applications, they don’t often deal with the same “flash crowd” scaling problem that Internet applications face.

So I don’t have the answers, but I’m confident that if there are strong enterprise use cases around cloud computing, there are startup opportunities to take the existing clouds and make them enterprise-ready from developer (e.g., Java support), SLA, support, service and other perspectives.

2. Customers start using multiple clouds

Another history lesson from systems management and middleware is that those technologies were much more successful in environments where you had customers managing multiple hardware technologies. In the closed mainframe world, systems management and middlware came from your hardware vendor. As things opened up with Unix and Windows, many new companies were created. Similarly, will applications start using infrastructure from multiple clouds - either by stitching together different resources (e.g., storage from Amazon S3 and compute from Google AppEngine) or even trading off resources (e.g., price arbitraging storage between Amazon and Microsoft).

You would imagine that some standardization on approaches and conventions in the cloud stacks themselves needs to happen before this is truly possible. But this multi-cloud world of the future seems like it would open gaps for new startup innovation to help customers manage and migrate between them. I’d argue that it will take some time before people start using multiple clouds in a meaningful way, however, since they are still getting their arms around Amazon and Google themselves.

3. New service providers enter cloud business

There are more than three cell phone companies in the world.  There are more than three cable companies.  There are more three Web hosting providers.  So I see no reason why there won’t be many cloud providers over time.

In some way, deeper cloud stacks threaten the traditional colo and hosting businesses, so I’d imagine those companies (as RackSpace is doing with Mosso) will have to enter the space.  Similarly, large telcos with existing Web hosting businesses will view cloud as a growth opportunity.  Now most service providers don’t have the technical talent of a RackSpace, so I see the third business opportunity as creating technology for service providers to offer cloud services themselves, without investing the R&D resources.

Again this will take some time for the xSPs to warm to the idea.  In addition, it is notoriously difficult to make money selling technology to service providers, since they frequently want it customized so much and since margins get collapsed by their thin margins over time.  Businesses like 3tera and QLayer provide this kind of capability today for service providers.  Though I wonder if, in the long term, service providers will want an open source stack backed by a commercial vendor instead of a proprietary stack.  I’ve heard rumors of such projects and it will be interesting to watch this space develop.

Conclusion

So my take is that there is money to be made in cloud infrastructure, though it will take several years for real business opportunity to develop, once enterprises start using clouds, multiple clouds become real and new service providers enter the cloud market.  That’s not to say that several startups won’t get snapped up for $100 mm for strategic value in the interim.

The Chief ramblings: Home alone

Back when I was in a real job :), I had to travel a lot.  Many of you are road warriors too so you probably know the feeling.  At Symantec, between company meetings, sales conferences, user groups, sales calls and customer rescue missions (we had a few of those too), I was on the road about 3-4 days per week pretty consistently.  United became my home away from home.

As such, Mrs. Fitful Dreams and The Chief were home without “Daddy” (”Daddy be right back”) far too often.

The past six months have been wonderful in so many ways but one of them is that I’ve been home nearly every night (sans a few work dinners) to put The Chief (who just turned 2) to bed, which involves:

• “Asha eat-it dinner; Asha want dad-dy’s dinner”
• “Asha go bath-time!”
• “Asha potty” (just recently started potty-training )
• “Asha and Daddy dan-cing” (our usual routine is one dance in the study room to some cheesy father-daughter song like “Daddy’s Little Girl” by Al Martino on the iPod)
• “Daddy read-it sto-wy” (Where Is Baby’s Valentine is my favorite)
• [Put The Chief in the crib]
• “Daddy cleam-up” [Instructions for me to clean up the room before I leave ]
• [Various words, songs, bribes to get her to fall asleep]

Tonight, for the first time I can remember, I get to be the one home alone.  Mommy and baby have flown back to Pittsburgh to see “Nana, Nani, Dada and Dadi” [confusingly, the Hindi words for your dad's parents are "dada" and "dadi"] and I don’t meet them there until next Thursday!

At least I can catch up on blogging…

Career ramblings: The options and the option-ed

Quote from my friend Matt this past Saturday night:

“I like reading your blog.  But what’s up with no new posts since February 27th?  Get with the program!  Write something or I’m going to unsubscribe from your feed.”

So apologies to Matt and the others who have mistakenly waited on baited breath for my truly incoherent babble.  One of my New Year’s resolutions was to write more consistently and I’m definitely failing on this one, but here’s my chance to turn it around.   No more bloggers’ block.

On a side note, one thing I’ve realized is that writing is very cathartic for me and that these past six weeks of WordPress-withdrawal have left me somewhat unsettled.  Time to fix that now.

In addition, I recently started sharing an office with Ashu Garg, a fellow EIR here at Trinity Ventures.  Ashu decided to start a blog after joining and has written 4 posts during my funk the last 6 weeks.  So the competitive spirit in me got me off my…

One of the reasons I’ve been preoccupied is that I’ve been stuck in this whole business about figuring what I want to do with my life.  It’s been a bit of an emotional roller coaster the last few weeks as I’ve come close on a few things and ended up not pulling the trigger, but it’s also been a great reflective experience.

Have you ever been in a situation in your life where you are on one side of a situation and then in the next moment, you are on the opposite side?  This happened to me the past few weeks in regard to options I was looking to explore for my next venture.

The concept of options is interesting.  Wise adages or fatherly cliches tell us  to “keep your options open” or “make sure you have multiple options.”  “Get a backup plan.”  “What’s your plan B?”   No one wants to be stuck with one choice that goes away or in which you have no leverage.

In some ways, what I’m doing and the whole startup world in general is all about options:

• I’m looking to find multiple options to run a company and choose the best amongst them.   This includes multiple companies to join, multiple co-founders with whom to work, etc.
• Entrepreneurs (like me if I have my own company) look for multiple options for venture funding to both have backup plans as well as ensure a good market price.
• Venture firms often talk to multiple startups in a market category, trying to identify the best option in the sector.

At a high-level, there are two ways to prosecute options:

• Serially.  Find one, decide go or no-go and if no-go, move on to the next.  This is how most individuals approach dating and finding a spouse, as an example.
• In parallel.  Find a number of options, orchestrate them so they align on a similar timeline and then choose the best amongst them, possibly using the options’ knowledge of the competitive process to increase leverage.  This is how most entrepreneurs approach fundraising, for example, and how some of my guy friends approach dating.

One of the biggest challenges in parallelizing options is aligning timelines.  Some options (jobs, VCs, significant others) move faster than others.  Many people spend time in a fundraising process, for example, trying to speed up some VCs while slowing down others.

However, the biggest struggle I’ve had with this process of parallelizing options is the inherent emotions that are involved:

• Having multiple options feels good.  It means you’re in-demand and you have safety, leverage and choice.
• Being one of one multiple options for someone else feels bad when you’re not the one chosen.
• So inherently, having multiple options to choose from means you will feed good but  you are going to make some (n-1, where n is the number of options you have) other people feel bad.

Of course, most would say some cliche like “that’s life.”  Which is true.  But what I’ve been interested in is how you strike the right balance of having the right number of options for you to maximize you’re own interests and protect yourself while minimizing harm in the process.

In the past few weeks, I have been on both sides of this situation.  I had a few parallelized options that I had setup from which I was to choose.  In parallel, one of the options I was looking at involved someone who himself had multiple options, me being one of them.

Long story short, I’m still exploring “options” because the one option I was excited about decided I wasn’t the right option for him, while the other two that required me to decide weren’t perfect for me.

While this process has been draining, I found it to be net positive because it made me appreciate the emotion involved in this process. How many options should you keep open?  How do you communicate to your options (when they ask) where they stack rank?  How do you close out the options that you choose not to choose in as respectful a way as possible?

There is no clear answer to these questions, but the observation I took away from this process is to handle the process of choosing with care because there are other people on the other end of every one of the paths being explored.

For entrepreneurs, I see this every day as they pitch VCs:

• Pitch enough investors in parallel to build competition but don’t pitch so many such that they feel like the deal is being shopped around that they have no “preference” to win it.  Make the list small (my advice is to parallelize 5-7 at a time) and make each investor feel special that you have selected them for a reason (personal affinity, sector focus, network in the domain, etc.)  “I’m really interested in VC firm [x] because you seem to believe in the online video advertising space based upon your other investments A, B and C.”  “I believe it’s more about the partner than the firm so my personal relationship with you, VC partner X, is key.”  “I think this investment is going to take some fortitude and you have demonstrated that in investments A, B and C.”
• When a particular investor asks where they stand in the process, make sure to answer as honestly as possible so the final news isn’t too much of a shock.  “I am talking to several investors and we’ve fortunately garnered a lot of interest.  This will be a tough decision.  The factors that I’m going to use are X, Y and Z.”
• When delivering the bad news (the good news is easy) to the n-1 options that don’t make the cut, try to do it in a way that maintains the relationship, explains your thought process and respects their time.  Don’t forget that you’ll need them for the Series B or future companies. :)  Beyond that, it’s just the right thing to do.

Obvious stuff but still important.

Steelers ramblings: Yoi, what a life

It’s been way too long since my last post and I should be writing about the VMware Europe conference that I’m attending right now (I’ll do that shortly).   But today there is much more important news to comment on.

Today, Pittsburgh Steelers broadcaster Myron Cope, of Terrible Towel, Immaculate Reception and Yoi fame, died at the ripe-old-yet-still-young age of 79.

To non-Steelers-fans, I’m sure you’re wondering why the heck I’m writing about this.  But for those of us that bleed Black and Gold, this is a sad and profound day.  Myron’s voice and diction defined our Steeler Nation, even after his retirement in 2004.  When I think of a “Stiller” game, there is one shrill set of vocal chords that comes to mind, and that’s Cope.

Andy Russell said it best: “”It is a very sad day, but Myron lived every day to make people happy, to use his great sense of humor to dissect the various issues of the sporting world.”  I can only hope to aspire to create 1/100th the joy Myron has for people in my life.  He will be missed dearly.

Steelers (err Giants) ramblings: Reflecting on Giant happiness

Quote from Mrs. Fitful Dreams on the way back from my brother-in-law (he-who-owns the 60″ HD TV)’s house Sunday night: “I don’t know why, but I feel - it’s not the same but - almost as good as if the Steelers had won.”

So the question to you (outside of the 508/617/781/603 area codes): why are you so happy?  Seriously.  Outside of my Pats friends (and I have many), everyone I know - everyone - was rooting for, though not predicting a win for, the Giants.  “Someone’s got to beat them.”  “Anybody but the Pats.”  You could see it in the TV commentators reluctantly picking the Pats to win.  You could hear it in the radio announcers talking this past week about how “you’ve got to at least give credit to Bellicheck for knowing how to win” (the equivalent of describing a girl to your friend as having a “good personality”).

Now the same talking heads (while disavowing their predictions) are unloading on the Pats and how this victory showed that the Pats were “posers” and “choke-artists.”  They “break it down” by pointing to Tom Brady flying his hairdresser in and the Spygate redux this past week as signs of the ship sinking.  They talk about how the Pats were outcoached and “out-physicaled” (if that’s a word).  They reduce the still-amazing-to-me 18-game winning streak to be meaningless now.

Don’t get me wrong - I’m as guilty as any.  I was a self-described “Hatriot.”  They ripped our (Steelers) heart out in the 2001 and 2005 AFC Championship games - along with countless times during the regular season.  And I was as happy Sunday night as I’d felt, football-wise, since February 2006 when we won our own Super Bowl.

But I find it fascinating how I - and the rest of us bandwagon David Tyree fans - can be so ecstatic about a team that truly isn’t our own.  We’re all posers, no?

The standard analysis would be that we’re “all jealous / bitter / envious” of the Pats’ success.  I’m sure there is some truth in that.  If we could go back and measure the Patriots Q-score after the 2001 Super Bowl and again after the ones that followed, I’m confident it has steadily declined, with a rapid drop this year.  Indeed, this is always my visceral / irrational argument in response to anyone saying anything bad about our country.  “They just want what we have.”

A psychologist would next opine that we are simply rooting for the underdog.  As one of the greatest upsets ever, that certainly could be the case here.  David versus Goliath, the comeback and the unbelievable 4:1 money line - all things of beauty.  But it feels like the American sentiment was even stronger than could be explained by the Vegas spread.

I think the only way you can make sense of it is that for some reason, Bill Bellicheck rubbed people the wrong way.  Every action of his (spygate, shoving the cameraman after a game last year, not shaking Tony Dungy’s hand, walking off the field) can be explained away, but the overall number of people who know him in different contexts and struggle with him personally is just staggering.  The most telling for me is to hear other coaches talk about Bellicheck.  I find that the best way to learn about people is to ask really nice, intelligent colleagues about them and see what they don’t say.  If you hear other coaches talk about Bellicheck, they always jump to emphasize respect for his effort and his winning but rarely talk about liking him as a person.

Put another way, I think in an alternate universe where Tony Dungy’s Colts would have been going for their fourth Super Bowl in seven years off of an undefeated season, many of us (perhaps even me) would have been pulling for him and them.  I know it’s impossible to say for sure, but that’s my hypothesis.  This whole experience made me realize how powerful and important our relationships with people are when we no longer have the crutch of winning or perceived success to lean on.

Upon further review though, while I am very happy and thrilled for the Giants and their fans, I also cringe at the joy some folks are taking in piling onto the Pats’ misfortunes.  This “build-people-up-and-tear-them-down-thing” is one of the least attractive qualities of our species.  I know how much it sucks to care for a team with your heart and soul and see them lose, so I actually empathize (though I’m committing Hatriot heresy) with our New England friends this week.  And as much as Bay Area fans despise Randy Moss for his previous transgressions with the Raiders, I couldn’t imagine what it must feel like to go 15-1 (with the Vikings) and 16-0 this year and have no championships to show for it.  It must be devastating.  Even Bellicheck, with all of his personality flaws, must be feeling a pain this week that would be impossible for many of us to handle.

And to think, we make these snap judgments and wrap things up based upon such small actions or non-actions (a ball being caught versus trapped, Asante Samuel holding onto the would-be-game-sealing-INT on the right sideline) that truly could have gone either way.  It’s interesting to think about the stories we’d be writing and talking about this week and the conclusions we’d draw if Tyree hadn’t held onto the ball.  We believe we should write history by pressing hard with a permanent marker, but perhaps we should be lightly scribing with a pencil, always holding the eraser close just in case.

So congrats to the Giants on a truly amazing achievement.  I’m genuinely happy for them, for their supporters and for underdogs everywhere.  As a Steelers fan, it’s good to know that anyone - whether you are a Giant or not - can defeat the incumbent king of the hill.  But I have a hard time taking any joy in the fall itself.

Now the long countdown to next fall begins…

Career ramblings: Ladders in the sky

I had lunch with my good friend Dave last week and we were talking about an idea/metaphor that I’ve been brainstorming for some time.

For some context, Dave and I have held career counseling / idea brainstorming lunches and dinners every few months for the past ten years since we both graduated from college and moved out here. For some reason, we always end up at a creatively-named Mexican restaurant like El Torrito, El Cerrito, El Burrito or the like. But that’s beside the point.

Dave and I were discussing the fact that the decade of your 30s feels like the period in your career when you go from meandering around as a generalist to becoming a laser-focused specialist, either by intent or accident. Somehow we enter as i-bankers, consultants and startup people and exit as distressed debt divas, media merger mavens and storage subsystem sharks. How does it happen?

Specialization in your 30s is not strictly true, as some folks find their specific calling in their early 20s (e.g., Mark Zuckerberg) while others never feel the need to “declare” their sub-major in life. But we agreed (which seems logical) that it appears much more difficult to make an impact on the world as a jack-of-all-trades, so specialization is par for the course. Every profession has layers upon layers of knowledge and competition, which means you generally need to get deep to do anything substantial.

I was thinking about how far this is from the view we had as children and perhaps even how removed this is from the view we’ll have in our older days.

Most of us remember the first times we were asked “what do you want to be when you grow up?” Admittedly, it now seems an absurd question to ask a 8-year-old, yet alone a 80-year-old. Yet, I can picture popping that question to The Chief in a few years, if just for laughs to see how she’ll respond and how directly Doggy will be involved in her vocation. For me, my parents tell me that I answered that I wanted to be either a garbage-man or a lawyer (insert joke here).

As I think about it, I kind of feel like our journey through our career(s) is, much like the stereotypical climbing to get ahead, about ascending a rope ladder into the sky:

• As kids, we look up and are asked “what do you want to be?” We see a daunting number (perhaps 100s) of rope ladders all diverging from the same spot in the ground. We look up to the sky and see where the ladders disappear into the clouds. It’s not obvious where they all go, but they all seem to go in slightly different directions.
• We pick a ladder - labeled generically as “doctor” or “businessman” or (to scare the parents) “artist.”
• We furiously start climbing, because we know that many of us don’t even make it past the first few rungs.
• In college, we disappear into the first set of clouds. The ladders are still close together, so we might jump from one (engineering) to the other (East Asian studies). No bother. Heck, we might even slip and without knowing it or because we drank too much the night before, end up on a different ladder.
• As we exit college and enter our 20s, a new clear sky appears and a new set of secondary clouds far above the first loom. The ladders now diverge more significantly.
• The business people climb hard, scraping through 100-hour weeks, MBAs and day trading to get ahead. Lawyers chase the 2000-hour per year goal, sweating away through missed promises and friends’ weddings. Doctors sleepwalk 48 hours at a time through residencies.
• And around the time of our 30s, we enter the next set of clouds. Each ladder splits even further, by business area (are you going to be a consultant or an “operating guy”?), medical specialty (laproscopy or lasik?) or the like. At this point, the original ladders have so far diverged that those of us on the business track can no longer see the ladders of our artist brethren.
• Occasionally, people get tired or question where their ladder is going. But the other ladders are so far away that leaping to them (per gravity), necessarily involves falling down a few rungs. A career transformation is required to go from a mechanical engineer to a civil one, let alone from a doctor to a businessman. Some brave souls do it. Most do not try.
• Our sub-specialty often becomes the whole world our 40s and 50s. More clouds and diverging ladders shield us from everything else, so we just focus on those above and below us. Climb away.  The opaqueness to the other ladders and single-minded focus on “up” in some ways is settling.
• Finally, as we reach the end of our careers (or so I hypothesize), we end up high in the fourth level of clouds, on one ladder, with no others in sight. Jumping to another involves blind faith and a likely-painful, possibly-fatal fall. There may be more ladder to climb above us, but, in all likelihood, we are pretty exhausted. We look down and can’t see the ground from our 8-year-old memories or remember whether this is where we thought we’d be.
• My friend Gus tells me that the real end to this analogy is when we get enlightened enough to understand that there is no ladder, while my little brother Samir says that we reach nirvana when we realize that there is a ladder, but we’re not on it.
• I hope I’m as smart and wise as them some day. Until then, I take the infrastructure operating-guy CEO rungs, two-at-a-time.

Career ramblings: Networking - the anti-diet

I’ll write up more about what I’m doing as an “Entrepreneur-In-Residence.” Suffice it to say, however, that much of being an EIR involves meeting people - whether it’s other investors to tell them about my background, potential technical co-founders with whom to work on ideas or other industry contacts.  This has been the best part because there is little that I love more (besides my family and the Steelers) than meeting new people.

But for some strange reason, we’ve trained ourselves (especially guys) as a species to be unable to meet without consuming some food, beverage or both.  As such, being an EIR truly involves stressing your appetite control.

Because I’m crazy like that and for fun, I decided to do a tally on the meetings I’ve had since I started the EIR program on October 8, 2007.  Note a few things:

• This only includes in-person meetings
• I primarily counted meetings of people for the first time (e.g., not internal meetings at Trinity Ventures)
• I wasn’t even in the office for about 4 weeks during the period (between Thanksgiving, Christmas, New Year’s, etc.)

So I wanted to study how my career transition has benefited local food and beverage merchants and necessitated and increased focus on going to the gym.  Here’s the tally over 3+ months by location:

• 165 meetings in non-descript locations (e.g., our office, other VC offices, company offices) where food and/or beverages may have been served, but the cuisine wasn’t notable.
• 30 breakfasts and lunches at the Sundeck Restaurant right at the heart of VC land (3000 Sand Hill Road) and 1 minute walking from my office.  You can almost hear the din of startups being built up and participating preferred and liquidation preferences being laid down as Luis serves me my egg-white omelette for breakfast or perfectly-cooked sea bass at noon.
• 17 visits to St. Stephens’ Green, an Irish bar on Castro Street in Mountain View.  I like the fact that the #3 entry for my so-called “job” is a bar. :)  Also note that that 17 includes 2 separate sets of back-to-back-to-back “meetings” in the pub.
• 12 trips to Clocktower Coffee in mid-Mountain View, where I sit right now.  Though the Starbucks-knockoff is shameless in its imitation of design and menu, it’s 0.4 miles from my house.
• 8 stints at University Coffee Cafe in downtown Palo Alto (I got tired of hyper-linking).  This place is particularly big for networking.  Wednesday I bumped into 2 other EIRs there.  Keep in mind that there are like 50 EIRs at any given point TOTAL.
• 8 rounds of beers (again including some back-to-backs) at The Old Pro sports bar in downtown Palo Alto.
• 7 scrambles at Hobees, my favorite breakfast place, where they always ask about The Chief.
• 6 breakfasts at Bucks’.  Surprisingly-low for the VC standby but it’s north of my house and office, though I love the charm of Woodside.
• Only 6 coffees at Starbucks.  I guess it’s another sign of the anti-chain mentality of us Californians.  Or my laziness because the nearest Starbucks is 0.8 miles away instead of 0.4.
• 3 stops at Zibbibo (love that place).
• 2 visits to Citizen Cake (over-rated).
• 2 cozy drinks in the soft chairs at Stanford Park Hotel.
• 2 awesome lunches at Junoon, the best Indian fusion around (okay, there’s not that much Indian fusion but still).
• And 1 a-piece at 4 Seasons Palo Alto, Il Fornaio (only one?), Thirsty Bear SF, Michael Minna (now I wish I had more times there!), Bay Cafe, Garibaldi’s, Dutch Goose, Westin SF, Los Altos Pancake House, Peet’s Coffee, Crowne Plaza Palo Alto, Fibber Magees, Courtyard Marriott SF, Straits Cafe (rocks), Residence Inn Sunnyvale (does not), Tamarine (best in Palo Alto still), Palo Alto Sol (decent Mexican) and Cafe Milano (Berkeley).

Now that’s good eating (and drinking)!  On to the gym…

Career ramblings: Infrastructure is cool (enough)

When I left Symantec in October, I told friends who asked that my goal was to “run my own company.” I had this visceral/irrational/psychotic desire to create and lead a great organization. I was and am confident that that’s what I need to do next.

Unfortunately, it was the next query that initially stumped me: “What space do you want to focus on?” It’s a natural question - I’m sure I myself ask it to others that are going through career changes. Sometimes there was an undercurrent of “are you going to stick around in that boring, maturing enterprise IT space or go work on something cool?,” although usually it was an honest inquiry.

The challenge for me was that I’m not a sector guy. I like running/starting things simply for the thrill of building a team (see my football passion). The unique energy that comes from a group of people singularly focused on a shared goal is what gets me going. Whether the goal is photo sharing, pet food, photovolatics or parallel file systems isn’t the first thing I worry about. Heck - I worked in investment banking, consulting, golf e-commerce, a file sharing system turned into a storage system, storage/backup, email and legal discovery over my brief career. Each time, I came in as the new guy knowing nothing about the area.

But I did think about the fact that I needed some kind of focus both to help others help me find opportunities / people as well as to help me filter down the things I find. One of the best piece of advice I got was from Kevin, a friend and partner at a venture capital firm, who told me (now-obvious but not as obvious then) that I’ll be jumping into a new role (first-time CEO) so I should do everything I can to stack the deck in my favor.

As such, since I’d worked in infrastructure (enterprise data center “stuff”) broadly the past seven years, I thought long and hard about focusing on what I know.  I really like infrastructure products in one sense because there is a pretty big challenge in bridging these complex technologies into customer value propositions and go-to-markets that make sense and that’s exactly what I love to do.

In this spirit, I’ve spent the last several months looking at many of the new innovations in storage, virtualization, data centers, etc. And you know what? There is a lot going on! Some of the changes happening in the consumer and general application worlds are filtering down to new requirements for infrastructure.  Some of the vision that we were pitching at VERITAS around “Utility Computing” back in 2003 is actually becoming a reality now.  Whether you look at virtualization, cloud computing architecture, infrastructure services like Amazon EC2 or S3, the world of the data center is evolving rapidly.

In addition, I reflected back on my experiences in the changing “conventional wisdom” during past cycles… (paraphrased advice I got from various folks over the years)

1998: This “Internet” thing is risky but looks interesting.  But why would you ever turn down an i-banking job to go into it?
1999: Would you like to cash out your stock in $1,000,000 bills or  $100,000s?
2000: The consumer Internet is dead.  You guys were a bunch of idiots to think it could ever turn into anything.  In fact, you should feel bad for what you did.  Subpoenas are coming shortly.  It’s all about the enterprise.  B-to-B baby.
2002: Enterprise applications and that whole “B-to-B” thing is pretty consolidated now but selling the picks and shovels (infrastructure) is where it’s at.  But don’t go to VMware - Microsoft is going to eat their lunch very soon.
2005: Enterprise what?  Wait - what kinds of CPMs are you getting for your “storage software?”  Or is it CPC?  Why would you want to deal with business customers anyways?
2007: Yeah we kind of over-corrected on the whole consumer versus enterprise thing.  And honestly this consumer world is a total bubble, except for my investments.

So you can’t always listen to what people say.

In any case, I find these deep foundational technologies to be fun.  I believe they demand great work on the sales and marketing side to bring them to the industry.  And I am seeing a number of interesting unmet market needs out there.

Who knows where I’ll end up, but it’s been fun so far.

The Chief ramblings: Doggy discipline

Asha is such a little mom, it’s not even funny.  She has a little stuffed animal that looks like a dog (mysteriously named “Doggy” ).  It’s one of these toys that parents approach like radioactive material after bedtime, since touching nearly every part of it starts an annoying, loud and unstoppable song.

In any case, for some time, Asha has taken to increasing levels of mothering, smothering and now bossing around of Doggy and the other stuffed animals in the house:

• Before she is able to get into the high chair, she takes Doggy to the high chair next to her’s and says “Doggy sit” and then “Doggy bib” and “Doggy milk”
• While on an airplane back from Hawaii, and separated from the window by Doggy, sh shoved Doggy to the side and said “No doggy, Asha’s turn.”
• After holding Doggy up to the mirror and banging his head against it: “Gentle, Doggy.”
• After taking an imaginary bowl of oatmeal that she “cooked” (an empty plastic bowl) to Doggy sitting at the table: “Doggy spill oatmeal; Asha have to clean up Doggy’s mess.”