A few weeks ago, Brian asked Brittany and me:

"do you think it's better to build your career around skills or around ideas?".

Brittany immediately said "skills" and I immediately said "ideas".  We argued about it for a few minutes, and ultimately we both agreed that skills and ideas are both important (duh) and that you can of course build both sides in parallel. But more interestingly was Brian's respnose -- he had previously asked the same question to Albert, who had a more interesting answer, which was:

"you should build your career around momentum"

In other words, you want one thing to flow into the next, accumulating a crescendo of importance, impact and reach, that builds its own center of gravity and energy.  This really struck me, and has been on my mind since then.  Now that I'm writing this, it strikes me as a very natural answer to get from an investor, as momentum is what startups hope to create -- traction, energy, network effects, "the flywheel". Separately, the word momentum has been on my mind a lot lately because of the really awesome and inspiring Momentum chrome extension that replaces your "new tab" screen with an inspirational photo and a simple prompt asking you what your goal for the day is.  Mine looks like this today:

As simple as it is, the Momentum screen has really been great in the week or two I've been using it.  The idea of identifying a single focal point and priority for the day is refreshingly simple and surprisingly calming.  And really nailing your top priority, rather than getting spread thin and scattered across a million other things, is how you build momentum. So, momentum.  Momentum.  mmmmm.

Last night, I had the pleasure of joining Meetup.com GC David Pashman's NYU Law class on Internet and Business Law for Technology Companies as a guest speaker.  Over the course of the past semester, David's students have played the role of internet company General Counsel, working on a variety of legal and public policy issues -- everything from terms of service & privacy policies to considerations around patents, copyrights and regulation of the "peer economy". The students workshopped, for example, how a company like Skillshare might consider entering the realm of accredited, degree-granting universities, and how a company like Instagram might respond to backlash from scaring users with an aggressive privacy policy change. The big question that I posed to the group was about Regulation 2.0.  The idea that, given the huge volume of real-time data produced by modern web services and the potential for radical transparency based on that, there is an opportunity to explore  completely new regulatory approaches.  Approaches that, rather than make up-front decisions about an activity (say, ride-sharing or peer-to-peer apartment renting), as we do in a "1.0" regulatory regime, we can instead be more permissive on the front-end, while at the same time introducing increased accountability through transparency.  If this kind of approach worked, it would theoretically be simpler and cheaper to operate, while at the same time allowing for more new kinds of activities to be explored without fear of regulatory shut-down. That is the big idea -- that our regulatory regime can shift from "1.0" regulation to "2.0" regulation, the same way that online communities of user-generated content and transactions (think back to Ebay's peer rating system) have developed internal systems that generate trust and enhance community safety. A few months ago I drew up the basic idea like this:

Assuming you agree that there's potential to forge a more effective, efficient, scalable regulatory regime based on transparency and accountability, that raises two major practical challenges, which I posed to the NYU students: Protecting User Privacy: A transparency-based regulatory regime necessarily depends on some kind of data sharing agreement between web platforms (think Skillshare, Airbnb, Sidecar, etc) and the public (either the entire public, or maybe certain government entities).  How do you square that with the need to protect the privacy of your users?  How do you communicate the trade that users could be making (i.e., transparency in exchange for the freedom to participate) in a way that makes sense? Protecting the Freedom to Experiment: Many new, web-enabled, network oriented businesses start off by operating in legal gray areas.  This is almost a guarantee in some respects, as these companies explicitly exist to forge a new model, establish new norms, and prove that new ways of doing things are possible and ideally beneficial to all participants.  But that puts them in an extremely tenuous situation: exploring new models while protecting users, avoiding undue regulatory or legal scrutiny (especially during early phases).  An approach built on transparency would seem to need an explicit safe harbor in exchange for that transparency, otherwise it's difficult to imagine that companies would voluntary participate. Both of these considerations are borne out in the recent kerfuffle between Airbnb and the NYS Attorney General's office.  The AG is wants the data to suss out "bad actors" on the platform, and Airbnb wants to protect their users privacy (and likely, to some extent, the details of their business model.  But this case is already years in the making.  Can we imagine what it would have looked like to build a new Airbnb in a "regulation 2.0" era where transparency in exchange for freedom to operate was the norm?  Can we imagine that in other sectors that are emergent now (such as digital health)? It's seems clear to me that 1.0 regulation in the era of web and mobile everything is not going to work.  So we need to forge a new model -- one that's innovation-oriented, scalable, and takes advantage of tools & data that never existed before.  This idea of "regulation 2.0" is a direction I've been thinking about a lot -- I think there is a kernel of truth in it that we should try and build around.

Mmmm

At USV, we talk a lot about how the landscape is changing, as more entrepreneurs and investors get behind the idea of building networks around problems, communities & verticals.  And that means that we are seeing more competitors in each space we look at, especially compared to what it looked like when USV invested in tumblr, etsy etc. (i.e., the halcyon days of yore) I have a suspicion that -- while this is no doubt true -- that there was more competition around these ideas than we remember, especially because many competitors fell off as the leaders emerged, so we don't remember them anymore. It would make for a neat research project to look at modern-day category leaders across a bunch of categories, and map them back to the competitors around them at various times in their history.  Funding milestones would be an easy way to do this. Does any such thing exist?  Seems like something that could be done relatively easily using the Crunchbase API.

Saying no to things is something I've always been bad at.  I have always been (and to some extent, have prided myself on being) more of a "why not" guy than a "why" guy. This has many of advantages -- I'm open minded and I end up doing tons of interesting things w interesting people.  But it also has some obvious disadvantages -- like feeling overwhelmed, getting behind on things, getting spread too thin, not doing a good enough job on any one thing. I remember reading that one of the cornerstones of Warren Buffet's approach to life is writing up a list of the 10 things you want to do, prioritizing them, then putting the bottom six on a "avoid at all costs" list. And I believe in my heart that the projects / apps / ideas that are tight, focused and well executed are better than the ones that are broadly ambitious and try to boil the ocean. One of my favorite lines, from one of my favorite books is "half, not half-assed". But still, it's hard to say no to things.  Meetings, phone calls, projects, you name it.  It's just hard. But every time I look at my long to do list, or my inbox, or my calendar, and think -- what can I do to be more efficient and effective at doing all of this?  The obvious answer is to just do less.  That's by far the most simple and most impactful approach. How do you save money? Spend less.  How do you save time?  Do less. Easier said than done, but no doubt important.

Andy and I were talking yesterday about how both of us really struggle on email, especially during busy weeks when we're really focused on something (travel, a project, etc).  I can't tell you how many emails I start with: "I apologize for the long delay here..." I described it as being afraid of the inbox.  I live in fear of the inbox, especially when I get behind.  And then, rather than just dive in, face the fear, and get through with things, I end up procrastinating and then of course it only gets worse. One way to think about it is that you have to keep swimming so you don't drown.  Like a shark.  That's how I think about walking through NYC, or driving in a car -- in the midst of chaos, it's better to be assertive and aggressive, make your own path, rather than get swept up by being tentative and timid. But while that really works for me for driving and walking, I still often live in fear of my inbox. I am not an inbox shark.  I am a tiny minnow getting cast about in the sea.  I suspect I'm not alone. And of course, it's not just email.  There is an overwhelming stream of stuff coming at all of us from every angle.  I'm adding to it this very second by writing this blog post on Tumblr :-). It seems to me -- though I haven't mastered this yet -- that the right way to face it is to swim ahead like a shark, stay in the game, not get afraid, and not feel guilty for all the things you're inevitably going to miss, despite all that.  Easier said than done.

There are a lot of great insights in Benedict Evans' most recent report. It's worth a read. One that stood out to me is this one:

Because a lot of our social network lives at the phone OS layer (contacts), and because mobile social may be "sticky like nightclubs, not like banks", perhaps the switching costs among mobile social networks are low. At USV, we've been talking about this a lot in terms of how a network's policies (e.g., user privacy, share of economics) relate to its ultimate ability to retain users.  And the idea that perhaps the most sticky networks are NOT the ones that are the most heavy handed in terms of attempting to lock in their users (e.g., by making data export/import hard). This would suggest that in many cases (at least in mobile / social), data lock in is less of a "lock" than you might think, and in fact, there may be something cathartic and cleansing about walking away from your data, i.e., "detoxing".

I've been a remote or semi-remote worker for a long time now.  Which has a boatload of pros (flexibility) as well as cons (distance from "the watercooler"). Over time, I've tried lots of things to help forge a stronger connection among my distributed or semi-distributed teams.  As you would expect, it's always a lot harder in the semi-distributed context, where some people are face to face and some people aren't.  In those cases, it's always hard to get the f2f people to adopt technology for casual chatting. My new favorite tool for this is Sqwiggle.   Sqwiggle is a chat / video service for distributed teams.  My favorite feature is that, rather than seeing each person in always-on real-time video, you see black & white snapshots in 10-second intervals.  This removes a lot of awkwardness.  My second favorite feature is the ability to initiate a video conversation unilaterally -- in other words, if I want to video with Zander, I just click on his face and start talking.  No need for "ring him".  The folks at Sqwiggle like to note that this results in much more frequent, but a lot shorter, conversations (like what you get when you're in an office together). At USV, we've set up a "Sqwiggle Bot" in the office -- it's an old iMac, sitting on my desk, which is hooked up to a wide-angle camera and is persistently logged into Sqwiggle.  Anyone who is working remotely (as lots of us always are), can just dial into the bot, and "poof" we're sitting in the office.  It looks like this:

From my home office, it looks like this:

You can see Zander on the right, and Fred's and Albert's offices in the background. So, that's been great, and we're using it more and more. The thing that is more vexing is actually a much simpler problem:  Group chat. Back when I was at OpenPlans, we were heavy IRC users.  The whole team (folks spread across multiple cities, but concentrated in NYC) was always in the #openplans IRC channel, and it was the social hub of the office.  And not just for remote folks -- when it was time for lunch, people would ping the IRC channel.  There was tons of chatting back and forth, via IRC, among people sitting next to each other.  It was, and is, great. There are a few features that make group chat in IRC awesome: 1) regular chat is unobtrusive.  Meaning, you can be in a room, but not get a notification of every single message. 2) username notifications.  when someone wants to get your attention, they just mention your handle, and your client bounces a notification to get your attention. 1 and 2 together mean that you can stay logged in to the channel all day long, not be overwhelmed by it, but still be directly reachable when people want to get your attention. 3) it's hackable. Since it's an open system, you can write all kinds of hacks.  Our SVN repo was tied into IRC, so every time someone committed code, it posted to the channel.  We had a bot that would reply to certain kinds of questions with silly answers.  You can build whatever kinds of things on it you want. In sum, it was (and is) a fantastic tool for staying connected with a large group. If you were to add in persistent history and video-chat, you'd have the perfect tool. it's worth noting that you can do similar things with other tools.  Campfire, by 37signals, does a lot of this. So does Skype. Those are good tools, but what I've been looking for recently, but haven't been able to find, is a way to get a similar experience out of Google Hangouts.  The reason being that the entire USV team is in Gmail all day long, and does a fair amount of one-to-one chatting in gChat (now Hangouts).  So, rather than doing the (likely impossible) work of getting everyone to use a new tool, I really really want a way to accomplish this in Hangouts, which we all already use. What's extra frustrating is that, until recently, you could accomplish something similar in Google Talk using Partychat, since Google talk was built on the open XMPP protocol.  But with the switch from Google Talk to Google Hangouts, Google dropped support for this:

We realise Google's migration to Hangouts breaks @partychat due to removal of XMPP federation support. We are considering workarounds...

— Partychat (@partychat)

May 16, 2013

If you listen closely enough, you can hear the eerie mantra "embrace, extend, extinguish" emanating from the Googleplex... So, I've been trying to figure this out.  And it's been frustrating.  If there is a solution out there, I'm dying to know it.

It's fascinating to watch the process of business models exploding. What apple did yesterday in announcing free OSX and free iWork apps is a great example of that.  MS has traded on license fees for Windows and Office forever, and for a long time, Apple has followed suit, charging reasonably high (although continuously declining) prices for each. Now, with outrageous revenues from hardware and the app store, they don't need to do that anymore.  In fact, free distribution of OSX and iWork will just expand the ecosystem and grow those revenues. In most cases, it takes some kind of end-run and a lot of scale to make this kind of thing possible.  Apple can do it now because they created a brand new channel & model with the app store, and built a monster hardware business.  If they had tried, before doing that, to "reinvent" the OS business, they wouldn't have had the leverage.  It's interesting to look at other sectors where this is happening: * Music: Soundcloud is letting artists distribute direct-to-fans, end-running the labels and the traditional pricing and distribution model.  At some point, they will reach a tipping point that will force the old model to change. * Education: textbook publishing and open source.  I don't have examples on the tip of my tongue but I can't wait for this one to happen. * Law: lexis nexis & westlaw vs new platforms like Casetext. Now that I look at these examples, they're all cases where distribution has been expensive, and intermediaries monetized the IP directly.  What we're seeing more and more of are models where distribution is cheap/free and IP is monetized indirectly.

Last week, I traveled to SF, and ended up on a flight with no internet (aaaaaaagh!). And, of course, I forgot to bring the book I'm currently reading. So, I went old school and bought a book at the airport bookstore.  I honestly can't remember the last time I did that.   Actually, I bought two books: Gladwell's new David and Goliath, and the Steve Jobs biography, which I still haven't read. Side note: ever since  I saw this Louis CK clip about people not being able to be away from their phone for 30 seconds, I think about it all the time.   Every time I get on a plane and find myself fidgeting and making phantom phone grabs whie trying to get through that awful time between "the cabin door is closed" and "you may now use your portable electronic devices" I think about it. Anyway, so I was on this flight, with no internet, and I started reading David and Goliath.  Which, in typical Gladwell fashion, draws a bunch of seemingly counterintuitive connections around the idea of "advantages as disadvantages" and "disadvantages as advantages".  Showing us the limits of power, and in particular, the strength of creativity in face of power. I must admit, I am kind of a sucker for pop social science (think: Freakanomics, Antifragile, Where Good Ideas Come From).  I am always more on the "wow, that's so right!" side of things, as opposed to the "OMG, that's so obvious" side of things. Being in the startup business (now), and coming from the open source software business (then) and the advocacy business (then), and as a disciple of Jane Jacobs and Holly White, you'd think I'd have a basic handle on this idea, as you could argue that it's the single strand that runs through everything I've worked on for the past 15 years. But still, I find it to be a really useful frame.  I can't tell you how many times in the past week the idea of "competing on a vector they can't compete on" has come up.  That is all about David and Goliath.  If your competition is a super well-financed startup player, or an industry giant like Google, you can't expect to take them head on, play them at their game, and win.   You have to think about what you can do, that they can't (or won't) and press on that angle. And, from more of a personal perspective: it's easy to get hung up on present-day challenges (financial, family, social, safety, etc.).  For instance, I've written before about growing up scared in NYC, and how that defined an era for me and left a big scar, but ultimately (I think) helped shape my perspective in a positive way.  And there are plenty of other things I can think of that have been, and continue to be, hard. So overall, I find the "disadvantages as advantages" frame to be super useful (critical, possibly), and will no doubt keep it in the back of my head for some time.