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I believe machine learning will drive the next big wave of innovation in consumer web services. The very same technologies that power Google’s search and Netflix video recommendation engine will become far more common and useful, perhaps even predominant in the consumer web.

Every great consumer product has a little bit of magic. Apple employs static software and hardware design to anticipate user needs - to create that magic.

Compared to user experience design and forethought, intelligence, when it works, is far more compelling and impressive. Most of the time though, it’s easy to be disappointed. If you’re anything like me, the first time you played with Siri, you tried to find places where it failed. We expect and to a degree have been trained to expect the technology to fail. Like Dorothy, we all look behind the curtain to find the little man making the magic, the Mechanical Turk.

Among my friends in college, a frequent response to the question, “How’s it going?” was “Strikes and gutters.” In other words, really well and really poorly - at the same time.

Five years into the venture business, I think that expression is much better suited to the day-to-day swings a startup experiences than the life of a college student.

It’s hard to imagine these two diametric feelings at the same time, but for entrepreneurs it’s a daily occurrence. Launch a new great product feature but lose a big customer. Grow really fast but struggle with fund raising. Get a lot of great press but fire an under-performer.

I often wonder about how to measure the success of this blog. While there are many tools to measure page views and visitors, the absolute number of readers is probably the worst measure because it’s a false idol. Feedburner subscribers, retweets, time on site aren’t much better because they don’t measure the true performance of a blog - what fraction of an audience the blog reaches.

In order for content marketing and blogs to be effective, the writing must have a target audience in mind. By focusing on that audience, bloggers build a brand in a scalable and cost-effective way. So engaging the very highest fractions of that audience possible is the best metric of success.

The three tier feature based pricing model is so common it’s almost a cliché. For some businesses it works well. But as Kenny van Zant explained to me, feature based pricing can slow growth in freemium businesses in two ways: first, feature based pricing creates incentives within a company to offer a subpar product and consequently creates unnecessary friction in the adoption process slowing growth. Both of these challenges arise when the pricing model is applied to end users, instead of the right target, the manager.

It’s been a little while since I traded code with anyone. But a few weeks ago, one of our entrepreneurs-in-residence, Javier, who joined Redpoint from VMWare, told me about a Ruby gem called Mechanize that makes it really easy to crawl websites, particularly those with username/password logins.

In about 30 minutes I had a working LinkedIn crawler built, pulling the names of new followers, new LinkedIn connections and LinkedIn status updates. All of that information is useful for me. But I just can’t seem to pull it from LinkedIn any other way. Crawling is the fastest, easiest and best solution.

For over two years, Larry and Sergey met CEO candidates before deciding to hire Eric Schmidt. Hiring a CEO was a condition investors imposed as part of the Series A terms. After the investment closed, the founders wanted to renege on that part of the agreement, but the board asked the duo to meet some of the valley’s top CEOs. At which point, Larry and Sergey only wanted to hire Steve Jobs. Eventually, they found and hired Eric.

Writing on the web is undergoing a renaissance. What started in the late 90s as mass-market adoption of blogging has given way to high production quality, curated magazines. Despite all the innovation in blogging, there’s one part of the magazine that hasn’t been reinvented: the Letter to the Editor.

If you’ve ever read the Economist, you might have breezed past this section. Two pages long and full of small quips and challenges, the Letter to the Editor section has its own culture. Each letter starts with “SIR –”, a relic of the magazine’s roots that I adore. Every major publication has such a section. But the blogging magazines like Svbtle, Medium, LinkedIn and the Magazine lack it.

Tracing the arc of Facebook’s user sharing model is to identify the biggest case of frog boiling in history. Contrast Facebook’s origins as a dating site limited to students attending a particular college to an exhibitionist’s dream syndicating every detail of a life across of 1000+ friend networks and potentially many more followers.

The question for users is: what is the quid pro quo? What value am I gaining in exchange for my data. Is it a fair swap or a bait and switch? What do you think? Message me on twitter with your thoughts

Amazon operates its businesses at very close to break-even, zero net margin, to win the greatest share and prevent competition from undercutting them. This is as true for their books business as their infrastructure business, AWS. Bezos has explicitly stated this strategy and it’s the one that has led to Amazon’s massive success in many different lines of business.

Over sushi, a friend explained to me that this strategy might also extend to the way the company views acquisitions. If Amazon’s strategy is to run most of their businesses at break-even including acquisitions, then the value of a profitable and fast-growing startup to Amazon is decidedly less than to a another acquirer who will run a business at greater margin if for no other reason than the startup will spin-off less cash under Amazon’s low-margin strategy.

“Blades square,” the coach yelled from the Boston Whaler as he increased the speed on his outboard motor, pursuing the eight man boat as we gained speed. I sat in four-seat, right in the middle of the engine room, the place for the taller, heavier rowers. The eight man team reluctantly complied with the coach’s order and rowed across the Long Island Sound, NYAC jerseys on our backs and the muggy, humid early summer morning sun reflecting in the water, practicing for national championships.