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Yoshi Komada's writings and scavengings. Some responsibility accepted.

Does Authenticity Exist (anymore)?

Came across this great video, which applies not only to our work, but who we are. Today, when so much of our personal and professional lives exist on the foundations of social media and the internet in general, it would do us well to keep de Zengotita’s opinion in mind: Authenticity today consists of “being honest about the process of fabricating who you are.”

"We are who what pretend to be, so we must be careful about what we pretend to be." Vonnegut’s observation 50 years ago rings all the more true today, and this sense of responsibility should be something we all consider.

Twitter in the Dark Ages

Back in the Middle Ages, monks laboriously creating illuminated manuscripts would occasionally scribble notes in the margins. This great piece gives a summary, with the image below. It is so striking how similar these notes are to the twitter and Facebook status updates we see every day, 700 or so years later: “I am very cold,” “Give me a drink.” If the ubiquitous “FML” or “best.x.ever.” were in use back then, surely these would have been written in the margins as well. Like us, these monks knew they were “broadcasting” their status, opinions and complaints to an audience. The need for social broadcasting is, apparently, timeless…


How I finally “got” Twitter

I went to a meetup last week where I met the founders of a startup called Weendy. They pitched it as a “mobile social network for the weather” which I thought was amusing, but they then sold me on the application’s utility as well: most of the current ~1,000 users are surfers. When a surfer gets to the beach, he takes a video of the weather and the waves and uploads it to Weendy so other surfers can see and decide whether to come out that day or not.  It’s easy to see this expanding to skiers, skydivers, rock climbers, etc…not to mention weather channel addicts.

My A-ha moment came when we got around to discussing partnerships and integrations. They are in the process of integrating into twitter so that users can publish to twitter through Weendy. The obvious question from my end was: Why not the reverse? Why not pull data on a location’s weather from twitter and integrate that into the informational feed on the Weendy app? Users would get more complete, recently updated data on the weather. A lengthy discussion over cheap beer ensued.

My key realization was the twitter offers utlity in real-time. Of course, I’d read all about this before, but it was not until this conversation that it really hit home. I constantly hear twitter will be huge, and it is clear why: Imagine all the current and future twitter data that already exists for flights, for traffic, for where taxis are concentrated on Saturday night; imagine a customizable mobile dashboard where all of this info is visualized. I would certainly pay for that.  The possible uses of twitter data are endless, and, importantly, they are very useful. The twitter of tomorrow will not be for celebrity stalking or talking about breakfast.

However, going on this logic, for most future users the greatest value will be provided via applications built on top of twitter data, not twitter itself. Even at this early stage, I exclusively use tweet deck; the amount of information from following only ~250 people is like drinking from a fire hose when using the twitter client (yes, I know twitter owns tweet deck). Thus from a monetization/business model perspective, I don’t see how advertisements can fit into twitter’s big-picture value proposition. This only leaves two choices for twitter itself: get busy building or buying new ways to consume its own own data or end up charging for data/API calls. Is there any other way?

There is nothing honorable about failure, unless…

Entrepreneurs, former and future Entrepreneurs, and regurgitators of silicon valley conventional wisdom, please take note: Failure is not an honor unless you:

1) Truly put in 100% effort at building and growing your company, and
2) Have honestly and openly reflected on your failure and subsequently learned from it.

So many standardized sound bytes have become embedded in SF/SV lingo, that we sometimes forget the substance behind those words. “Oh yeah, I failed.” (“No big deal” is implied). Did you produce the blood, sweat and tears needed to make it work, or just throw something against the wall to see if it stuck? Did you focus on building your company, or was it just a hobby? I think the answer is the latter more often than we like to admit. Have you gone through the 5 whys to see what your personal and commercial deficiencies were? Do you have a plan to improve on those? This painful step is all too easy to skip, and if you don’t go through it, you are guaranteed to fail again. While serious effort is a pre-requisite for just about anything, self-critical reflection is key to squeezing honor- and future success- out of failure.

Enterprise Social and Innovation

One takeaway from my organizational behavior classes in B-school was the importance of informal company networks on both corporate culture and innovation. There are probably hundreds of academic articles on this- googling will turn up papers like this one- and corporations understand the importance of these networks. Many larger multinationals have an innovation process or management in place, including emphasizing inter-divisional and international collaboration. Companies also realize personal relationships formed via global rotational programs and corporate social interest groups are vital for innovation.

Working on PingPigeon and looking into potential partnerships brought me in touch with many companies falling under the “Enterprise 2.0” category. While applications such as Yammer, Jive and salesforce chatter help with collaboration and general communication, they have an important secondary consequence: creating and  fostering informal networks across the company. Through these tools, If I’m in the New York office, I can easily begin a relationship with someone in London or Tokyo simply by asking questions, posting ideas, responding to others’ posts, etc. Likewise, If I’m in marketing and wondering about an aspect of supply chain operations, I can interact with people from that department; over time, we begin to enjoy collaborating more. Innovation never happens in a vacuum and it is oftentimes through diverse groups repeating these spontaneous, informal interactions that ideas and conceived, refined, and ultimately implemented.

However, looking at the websites of the major E2.0/Enterprise Social players doesn’t tell this story in its entirety. Most benefits described include increased communication between employees- across geographic barriers- and time savings through cutting down on email and searching for information (Yammer, to its credit, does list a couple case studies where innovation and informal network building are mentioned).

The benefits mentioned are real,  important and some are one part of the innovation process. That said, perhaps the collaboration story isn’t carried fully to its conclusion to include increased innovation as one of many benefits. Importantly, innovation adds to the top-line while most other benefits described are cost-savers. From a sales/marketing perspective, innovation is often the panacea that many C-level executives yearn for when competition or the macro economy turns tough. Given, this is a vitamin, not a pin-killer; increased productivity is the painkiller and is rightfully given prominence. However, while I’m not familiar with the internal sales tactics of any of these players, if these applications were positioned more as greasing the wheels of innovation, and not as simple tools to cut down on email, more customers might be willing to pay a greater amount for them. Just a thought.


I’ve been spending the past week in New York, catching up with people, getting re-acquainted with the city and doing some thinking. I’m closing up shop in Santiago later this month and will make a decision to move to either New York or San Francisco. For everything I’ve been working on, the obvious choice is SF, but I just love being in NYC so much.

During dinner last night with an old friend and her boyfriend, an (enterprise) tech executive, we talked a bit about the technology scene here. His perspective was very interesting since he spends lots of time in the Bay Area (Mountain View company HQ) and to him, tech in NYC still seemed “flat.”

This is probably true. There are obviously some visible initiatives trying to change that; as a tech entrepreneur himself, Bloomberg knows the potential that innovation brings to a city. One thing that is not talked about is the amount of tech talent already here, and the reason is that all of that talent is tied up in finance. Hedge funds, prop trading groups, exchanges and even some commercial banking functions require immensely talented IT people to build and maintain their systems. These engineers aren’t just “agile RoR hackers who can pivot and iterate” to build the next facebook for dogs or whatever, but are professionals who have been seriously challenged mathematically, algorithmically, and architecturally while building extremely robust enterprise-class applications that need to scale to epic proportions. And this is pure speculation on my part, but with the shrinking of the finance sector- and those of prime entrepreneurial age especially affected- there may soon be a big talent transfer from closed financial innovation to more open entrepreneurial initiatives here in the future. Again, just an opinion, and there surely are more engineers of this caliber in SV/SF, but perhaps NYC does deserve some more credit.

Then there is just that energy and drive that NYC gives you. Everyone sings about it. Everyone feels it. And I’m sure it is great for potential and current start up founders.

Silicon Valley’s Innovator’s Dilemma

I’ve repeatedly told people that I would never have gotten this far working on PingPigeon if I hadn’t started the company in the Bay Area. (Specifically, this involved couch surfing for 2 months, and 3 months of moving between apartments in the Mission and Redwood City.) Staying in London, or hanging out longer in Tokyo would have been non-starters. In SF/SV, I met programmers who worked on the product with me, I got feedback on the idea from potential customers and other entrepreneurs, but I think the most important thing I got was the emotional support from an entire entrepreneurial community built over the course of 60 or so years. Talking to people on the entrepreneurial journey provided inspiration, opportunities for commiseration, and most importantly let me put my vision to words which in my mind helps to make them come true. I’m pretty sure Paul Graham wrote about this in one of his essays but I can’t remember which one.  I also think there are parallels with the Japanese notion of Kotodama. Like I said, much of this made my success to this point possible.

I do believe there is a downside, though, however small. And this does not relate directly to my own experience, so would love to get feedback. I think the word for what the Bay Area offers is “institutionalized entrepreneurship.” This encompasses attitudes encapsulated in all the usual sound bytes like “failure is accepted as a badge of honor” “working for a startup is not unusual” along with an ecosystem of investors, entrepreneurs, partners, advisors, etc. All this happens in person there, but much of the ecosystem is also diffused online in various blogs, essays, etc. We know all about the good this does, but what, if any, are the negative parts?

One case I want to make is that certain parts of the ecosystem in the Bay Area are falling into traps of conventional wisdom or even dogma. There is more and more an attitude of a “formula” for starting, building and selling a successful business. The lean startup movement is the best example I can think of here. While on the whole I think the Eric Reis Steve Blank methodology is great, I really believe that no system or theory is powerful enough to capture something so dynamic as doing a startup. Even after hundreds of years, economics itself can’t be reasonably predicted or explained. The “data-driven” mentality, popularized by Google, is also starting to become dogmatic.

On the whole things like data-driven-lean-customer-development etc. do work well; they are not easy to execute but they do work. However with this rinse and repeat feeling of security comes complacency. “Have an idea, succeed/fail fast with a local team” is taken as the only way to do things and many will call you crazy if you are taking another path; there is an example [] of a previous successful startup by another Startup Chile entrepreneur that breaks all those rules (a globally distributed team that has only met in person once, and worked together for a year before runaway success).

All of this reminds me of Clay Christensen’s Innovator’s Dilemma. The comparison is not perfect, but the Bay Area can be seen as THE established global center of innovation/entrepreneurship and it has developed a clear set of “value networks”, practices and standards it uses to replicate past success. However, there are other models of entrepreneurial ecosystems out there; the dilemma for Silicon Valley is that the success from these other models is so small compared to their own that they don’t merit attention. The ecosystems of China, India, and even what Chile is doing are different in very specific ways from the Bay Area model. In time, these models may grow more effective and eventually take over the Silicon Valley model. There are plenty in the old and new guard of Silicon Valley who think the ecosystem is getting complacent and innovation there is becoming stale.

This is likely not even a problem. But the biggest surprises always spring from the least likely places. Perhaps its time to open a VC firm in Chile?

Running a Global Startup

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One of the great things about working in the Startup Chile acclerator is being surrounded by entrepreneurs from all over the world. We’ve got people from India, the UK, Brasil and elsewhere. All of us are going after different markets and are focusing on different niches; some have all local teams and some have distributed teams. In fact, its like being in business school, but everyone is building a business instead of studying business.

I was talking to a Chilean contact the other day and during the course of our conversation, we kept coming back to the challenge of building a company in Chile primarily for English-speaking markets. Yes, it is hard- but as all of my startups/entreprenurial companies I’ve worked for have been international to some degree, I’m not sure if it is significantly more difficult than a local venture. I can offer a few observations, though.

I solidified the plans for PingPigeon in Tokyo, I started building the company in San Francisco and moved from a proof-of-concept prototype to a beta version with customers down in Santiago. Along the way, I was working with engineers in the UK, Serbia, and Chile + designers in Macedonia and Serbia along with a business intern who went between Vermont and Santiago. What helped me along in this journey?

1) Over-communicate. This is, by far, the most important rule for smoothly working across borders, time zones and cultures. This means being clear-even redundantly/annoyingly clear- in everything that is written and said but also to be consistent in the delivery of the communication. This means no slang, American business-sports metaphors, and no cutting corners in laying out specifications. We were agile about building PingPigeon, but before development started I still wrote a 40 page document explaining the wireframes + the high-level application architecture. Of course things changed and came up during development, but because we had all started off on the same page, things went smoothly.

The consistency of communication was helped by religiously using productivity/communication tools throughout the process. For development we use Pivotal Tracker which is really just about the best tool I’ve come across for dynamic, highly-collaborative project management. Tracker is obviously at its best when it is used for “building things” but I would be curious try it in other contexts- executing M&A deals for example. For other communication and minor projects I used Wedoist, an application being built by another Startup Chile participant. Most importantly, we’ve been disciplined about keeping most of our communication on these tools (not email), which makes the process highly collaborative & deliberately transparent, helping along the communication.

Other communication tidbits: After two mis-understood/unclear messages, always have a quick Skype chat. Always assume it is your fault; if something is not progressing smoothly  go back and see how the original communication was conducted and see what can be improved- there will always be something, and this exercise will almost always help the project as a whole, if not the specific off-track task.

2) Be Flexible. There is a tendency among the business press to assume that everyone working globally never sleeps and has a Blackberry glued to their hand. In my experience, the only time this happens if the project degenerates into constantly fighting fires. The more important aspect is to establish a disciplined schedule, creating a flow everyone can get used to. Stand-up calls, daily status postings (WeDoist is great for that) that happen no matter what make life predictable for everyone. BUT, inevitably the need to “be flexible” will come up. Be ready for that.

On a startup level, being flexible involves many other small things like buying one way instead of round-trip air tickets (your dates will change), taking a short-term let instead of signing a lease, and keeping your team as lean as possible to maintain that flexibility.

3) Still talk to your customers. This has probably been the most challenging aspect of doing a global startup. As my main customer is English speaking, getting feedback while in Chile vs SF has been hard. Basically, this means I need to work harder to talk to customers while in the states. Also, talking to anyone through Skype has been surprisingly good at getting qualitative insights. Usability testing has mostly been through my peers here in Chile. Still, this hasn’t been detrimental, but it has taken a good deal of effort.

Startup Chile has great parties as well (again, just like B-school), and as always, I have trouble answering the question “where are you from.” At this point, the fact that I’m not “from” anywhere is almost set in stone, and I’m sure this has helped me work on PingPigeon from different parts of the globe. There is so much opportunity everywhere, and all it takes is a bit more effort to run a global startup.