The Future Public Transit Explosion

I was debating with a friend of mine earlier this week about the future of mass transit and public infrastructure. Naturally, the conversation moved toward autonomous cars and Uber/Lyft. The basic argument, which you can read in stories like Spencer Woodman's tale from Altamonte Springs, is that Uber and self-driving cars are just going to outright replace public transit.

I think that is completely wrong for several reasons.

First, few large cities can transfer everyone to private vehicles and still maintain any flow of traffic. New York City, for example, has some of the slowest car transit in the nation, at just 8.51 MPH in Manhattan. It's hard to believe that everyone who takes a subway today (1.76 billion rides in 2015

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Leaderless Rounds and the Problem of

One of the quote-unquote negative characteristics of the New York City tech ecosystem that I talked about a few weeks ago is the lack of VCs who will take the lead role in a fundraise. From my count, there is somewhere between 200-300 active VC firms in New York (yes, there is something of that size in the city today — crazy really), only maybe 6-12 are fully comfortable taking the lead in a fundraise.

Why is this? The answer is actually a mix of resources and weird incentives that are not unique to NYC, but that seem to have hit so many firms simultaneously here that it has become the de facto norm.

To illustrate this, let's take a hypothetical $20 million seed fund which

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Observations on NYC Tech

When I chose to move to NYC from Boston three months ago, it was with serious trepidation. I had spent six years living, working, and learning in Silicon Valley, and despite the growing evidence of New York's success as a tech hub, SV still remains the king of innovation by any statistic. To be frank, I'm ambitious like many of the people in tech I work with, and I want to run the kingdom, not some outlying New Amsterdam duchy.

Since summer is of course the best time in both NYC and venture capital to analyze an ecosystem in action, I figured I would give some early indications of what I have observed.

These observations are of course drafts — three months is quite limited to

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Housing Rant (Part Infinity) and the Economics of Hookups

I am on an on-going rant about housing prices (take me out to lunch and I will rant gratis). Today again, we have an article in the New York Times talking about a housing "glut" in Brooklyn, due to the construction of thousands of new units in Flatbush.

Glut is a political word. It means that there is too much of a resource, and implies that the price of the good will eventually be priced below the suppliers cost. A glut in the oil market means prices are "artificially" low — even though such prices are clearly good for nearly every consumer in the country.

Maybe that language makes sense in the oil markets where oil companies, particularly those who frack in the Dakotas, are legitimately

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Housing Prices Should Go Down - Duh!

Reuters wrote a piece this week on the rising "risk" of a housing glut in South Korea. Korea is one of the few places worldwide where housing prices have only seen moderate growth over the last decade.

This is a good thing.

Yet, reading Reuters, you would be surprised to learn just how terrible it is that housing prices haven't jumped like they do in Manhattan.

And unlike markets such as Hong Kong, Singapore and Sydney, South Korea has low immigration and few foreign buyers to stimulate sales and prices. (emphasis mine).

But why do prices need to be stimulated? To avoid a bubble. How can there be a bubble if prices are going lower? Because people are taking out large mortgages for these apartments,

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The Desperate Docker Disaster

Last month, I wrote about the desperate waves of venture capital, the concept that VCs are investing far too early into new trends in a race for returns. With the mobile, cloud, and social transformations slowing way down, VCs constantly have to search for other nascent movements — artificial intelligent, machine learning, virtual reality — in the hopes of touching greatness.

So yesterday's article about Docker caught my eye. Called "A Docker Fork: Talk of a Split Is Now on the Table", the story gives a brief overview of the acrimonious debate in the Docker community over its support for enterprise, its speed of backwards incompatible changes, and the ecosystem's roadmap for the future.

Talks of forks are hardly new in open source projects, and Docker is

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What I Have Been Reading (Summer 2016)

I read a lot. And despite my best intentions to try to read less this year, I have continued my article and book bingeing habits. This past summer has been no exception. Here are some recommendations.

The Articles

I have read a couple of great articles this summer that I think are worth spending time with:

  1. “A Honeypot For Assholes”: Inside Twitter’s 10-Year Failure To Stop Harassment. Trolling on Twitter and other social networks continues to endanger these communities. Why? Charlie Warzel does a great job of peeling back the challenges facing Twitter as it tries to tame its unruly users. The challenge ultimately is where to draw the line between free speech and censorship. Clearly, we have a long way to go.
  2. Intellectuals
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The Desperate Waves of Venture Capital

VCs are widely perceived to be groupthink aficionados. (What do we invest in? Whatever they are investing in next door!) There is some truth to this notion — clearly, many investments are thesis driven, and intelligent investors are going to recognize the same trends in the marketplace and reach similar conclusions.

One aspect of that groupthink that is lesser noticed is the groupthink among founders. Hundreds of startups don't just materialize out of thin air — founders have to conceive and build their products. They see the same trends in the marketplace as investors, so as an ecosystem, everyone ends up on the same wavelength pretty quickly.

Nowhere is this more obvious than in the the Great Bots Startup Explosion of the past twelve months. There doesn't

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A Plan For New York

As I mentioned in my blog post yesterday about Boston, I just moved to New York City to launch (or perhaps more accurately, relaunch) CRV's presence in the city.

New York City has been written about extensively by investors who have lived here for decades. I just got here — so unlike my piece on Boston — I hardly have the depth of understanding of the local startup scene to write any meaningful analysis.

Instead, I want to talk a little about what I hope to contribute to this growing ecosystem, as well as the reasons why CRV is making a foray into the city (besides access to jianbing).

Head of the Charles

First, I want to talk very briefly about CRV, which acronymized our name officially

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Some Final Thoughts On Boston

For those of you who don't follow me on Facebook, or have somehow managed to convince the LinkedIn gods (i.e. Satya Nadella) to not send you update emails, I have moved to New York City.

I'm super pumped about the move, but as always when I move to new cities, there is a feeling of wistfulness of the places I have been, and the places I might still be. It's also a moment to consider all of the changes that have happened with startups, technology, politics, and society these past few years. While these decisions are individual, the wider strains of society's trends always seem to mark their influence.

In short, it is time to take account of these personal experiences. I have lived

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Graph Associations for Language Learning

I have had quite a few reactions to my post yesterday describing my experience studying Korean using Anki flash cards. The public ones can be read on the Korean subreddit, where the handful of comments tend to be quite critical. Some of that criticism is valid: I probably should use more images in my cards to reduce the need to translate from English, among other suggestions.

Perhaps the largest criticism was that my approach to Anki failed to fully use associations to make it easier for my brain to retain words. Word associations help our memories place words in different contexts, building up a "web" of our vocabulary. Connecting our words with sights, scenes, and sounds allows us to more natively recall vocabulary than simple

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I Quit: 2+ Years of Anki and the (Near) Impossibility of Learning Languages

Language learning sucks. It sort of sucks for kids, but it certainly sucks for adults. This is my journey trying to learn Korean, and slowly coming to the realization that our current learning tools are simply not adequate for the job.

I don't have answers, although I certainly have ideas.


For the past five years or so, I have been studying the Korean language. I began in 2010 as I was preparing to be a Fulbright Researcher in South Korea. (technically, I started studying months before hearing back from the U.S. government that I was actually going — call it youthful confidence).

Since then, I have spent hundreds of hours studying Anki flash cards, reading books and articles, taking classes, getting tutored, watching movies,

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