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.

Elon Musk’s Genius: Understanding the Cost of a Screw and the Value of a Photo

Last night, Elon Musk inspired the audience at D. It is hard to overstate the scope and breadth of his ambitions or the impact of his start ups PayPal, Tesla, and SpaceX on payments, automobiles and space.

Behind the desire to listen to great men like Musk speak about their perspectives is a hope to receive some insight, some pearl of wisdom. Last night, I came away with two of those both about startups.

First, when the inevitable question came along along asking Musk to compare his ...

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Block and Tackle Product Marketing

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At the D conference yesterday, Tim Cook said many things without saying much. But one story did strike me. Cook described the product management and strategy process at Apple.

Walt Mossberg asked Cook why the iPhone has only one flavor when the iPod had so many including the shuffle, the nano, the mini, and the classic. Even though both products originally launched as a single model, the iPod flourished into a family of products while the iPhone has remained a single SKU.

Cook responded by telling ...

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Startup Pricing: How to Manage Channel Conflict

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You have just launched your new software start up. The last webpage to go up on the website is the pricing page. Like many other SaaS startups, you decide to employ some version the three pane pricing plan: first the free version, second a paid upgrade costing between $5-$40 per month, and third an enterprise tier with a “Call for Quote” in place of the price.

A few days after you launch, an enterprise customer contacts you asking for a quote. You respond with an offer ...

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A Startup’s Guide to Maximizing Last Mover Advantage

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About a year ago, Peter Thiel spoke at a PandoDaily event where he extolled the last mover advantage:

“First mover isn’t what’s important — it’s the last mover. Like Microsoft was the last operating system, and Google was the last search engine.”

I hear this refrain more and more in pitches. The thinking goes the last entrant to the market benefit from mistakes made by earlier entrants.

But being the last mover isn’t always advantageous. The reality is more nuanced.

When Last ...

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Antagonism is the Heart of the Consumerization of IT Movement

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At today’s Under the Radar Consumerization of IT (CoIT), the predominant theme will be antagonism. Friction, dislike, resentment within organizations marks opportunity for consumerization of IT startups.

Taking advantage of this sentiment, Expensify employs a very deliberate marketing tactic: “Expense reports that don’t suck.” Talk to anyone who uses antiquated expense report systems and they are bound to sigh and complain, frustrated by the experience but resigned to the fact they can’t do much about it. Expensify provides those people with a better alternative and, most ...

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Investing in the Consumer Web is Dead

Reading through the tech press since the Facebook IPO, you might get the impression venture capitalists are still reeling from that apocalyptic offering, believe no further successes can be had in the consumer web, and so are fleeing the consumer web in droves to pursue enterprise investments.

That’s because in the past year or so most major tech publications have swung from focusing on consumer products to enterprise companies. GigaOm made this transition first, now TechCrunch and PandoDaily are following suit.

But the problem with sounding the alarm for the ...

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You Shouldn’t Start an Ad Tech Company, But If You Do…

I started working in ad tech in 2005 and during the past eight years, the ad tech ecosystem has progressively become more sophisticated, competitive and oligopolistic. It’s hard to innovate in ad tech. But if you’re looking to start a company in the sector, you’ll need to amass proprietary data or develop a market place with unassailable liquidity to vie successfully in the market.

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A Mental Model for the Ad Ecosystem

The structure of the ad ecosystem, greatly simplified, ...

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The Future of Human Data Interaction

On the day of Tableau’s IPO, a company known for innovating in data visualization, I thought I would share the most impressive HCI concept I’ve seen in a long time.

In my view, Bret Victor is on the forefront of human computer interaction design. In the first two or three minutes of this video at Stanford, he demonstrates his home-built software that combines data analysis with visualization. It’s magnificent and really hard to describe because it’s so novel.

Drawing Dynamic Visualizations ...

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Coding and Cooking: The Connection between Jacques Pepin and Database Migrations

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When I was a little boy, I watched a cooking show on Sundays called “Jacques Pépin.” Over the course of 30 minutes, Jacques would orchestrate a symphony of raw ingredients into a dish that I yearned to smell and taste. That chicken paillard looked sumptuous.

Over the past few weeks, I’ve been coding in Rails 3 quite a bit, building a collection of tools to be more effective as a VC. And oddly enough, I think back to Jacques Pepin quite often.

The Jacques Pepin ...

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Social Network Alchemy: The Five Ways of Turning Users Into Gold

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Derek Powazek questions the intrinsic economic viability social networks in his post “What If Social Networks Just Aren’t Profitable?”. It’s a logical question to pose in the aftermath of the Digg sale and the wobbly Facebook IPO.

There is one clear lesson from Digg’s sale: the technology that powered a once-massive social network is worth about $500,000.

The Big Digg Lesson

The Atlantic summed up the essence of social networks' business models brilliantly. It’s not the technology that’s intrinisically valuable, but the activity ...

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