Hi, I'm a partner at Redpoint. I invest in Series A and B SaaS companies. I write daily, data-driven blog posts about key questions facing startups. I co-authored the book, Winning with Data. Join more than 16,000 others receiving these blog posts by email. Subscribe.

Social Proof: The Most Formidable Force Driving Content

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In a world of socially curated news, there is no place for RSS. I wrote last year:

Social streams solve the problem most RSS readers faced: the inbox with 1000+ items to read and no way to sift through them.

Socially curated news syndicated through social networks (Facebook, Twitter) and content networks (LinkedIn, Quibb, HackerNews) solves the relevance problem that RSS never could address.

Brian Shih, former Google Reader PM, wrote an excellent, passionate post-mortem on the product on ...

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Why Branding Is the Next Essential Startup Competency

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How much is the most valuable brand in the world, Coca-Cola worth? $77.8B. That’s 45% of the company’s market cap.

Often times, winners create advantages in a market through brands. These brands evoke emotions within consumers: feelings of trust (Visa), of aspiration (Nike), of adventure (RedBull). And if the brand is strong enough, it replaces the generic term: tissues/Kleenex, internet search/Google, glass cleaner/Windex.

In Silicon Valley, we tend to believe that better products win markets. It’s atypical to overhear a conversation at Blue ...

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Machine Learning in Consumer Products

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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 ...

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Strikes and Gutters

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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 ...

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How To Measure the Success of a Blog

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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 ...

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Crafting a Pricing Plan to Maximize Freemium Growth

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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 ...

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Crawling - The Most Underrated Hack

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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 ...

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Searching for Eric Schmidt

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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.

From Netflix to Facebook, Twitter to ...

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A Letter to the Editor

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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 ...

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Boiling a Billion Frogs

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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 ...

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