I'm a partner at Redpoint. I write daily, data-driven blog posts about key questions facing startups. I co-authored the book, Winning with Data. Join more than 20,000 others receiving these blog posts by email.

Subscriber Cannibalization and Other Mysteries in Content Marketing

As I've described in a previous post, this blog's goal is to create and sustain relationships with readers across the startup landscape. Tuning the engine is proving much harder than I expected and I suspect content marketers are facing similar issues.

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My Surreal UberX Experience

Last week, I had a surreal experience with Uber. It was mid-morning on Friday and I pushed a button to request an UberX as I walked out of Sightglass, the coffee shop deep in the South of Market district. When the car arrived a few minutes later, I got in. Without saying a word, the driver passed me his iPhone. Confused, I looked up from my emails and he mouthed to me, "I am deaf."

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Reflections on YCombinator Demo Day: How the Seed Market Has Changed

Earlier this week, I attended the Spring YCombinator Demo Day. I've been attending for six years now. Each time, I'm impressed by the intelligence, ambition and the polish of the founders presenting companies only a few weeks or months old. As I listened to the pitches, I wondered if the types of startups founders decide to build at YC has changed over time and whether those trends are lagging or leading indicators of the market as a whole. At each Demo Day, the YC team provides investors a list of all the companies pitching and I've kept a few. To get a sense of the broader trends in YC companies, I've compared the Winter 2012 class and the Spring 2014 class by sector (consumer v. enterprise), segment (ecommerce, education, social, gaming, delivery) and by revenue model (subscription, ads, transactional).

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Benchmarking Box's S-1 - How 7 Key SaaS Metrics Stack Up

Yesterday, Box filed for its IPO and released its S-1. I enjoy going through S-1s because the S-1 discloses some very important details about the business operations. Over the past several months, I've analyzed the basket of the roughly 40 public SaaS companies many different ways. With the Box S-1 in hand, I can now benchmark Box's business against other publics, and in particular, SaaS companies nine years after founding. Box is also nine years old. Below are six key comparisons between Box and the average public SaaS business.

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Startup Best Practices 6 - Avoiding the Bike Rack Effect

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The Hardest Round to Raise for Startups

Over the past few years, I've debated the existence of a Series A crunch and found in that analysis that the volume of Series As was increasing. This trend hasn't abated. The number of Series As has grown by 31% annually for the past 5 years, reaching more than 831 Series As in 2013, up from 284 in 2009. In short, no founder should be concerned about the Series A market. Rather, the Series B market is worrisome.

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The Machinery of Blogging

I've been getting a few questions about the tools I use to publish this blog, so I figured I'd write about it and reveal the machinery behind the curtain. I use four main tools Jekyll, Github Mou, and RStudio. Jekyll is the blogging engine; Github is the hosting provider; Mou is the app I use to write these posts; and RStudio is the place I analyze data and make charts.

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Are VC Mega-Rounds the New Normal?

Each morning's news seems to bring another fund-raising announcement of ever larger scale. Just a few months ago, Pure Storage raised $150M in the largest ever venture investment in a storage company. These record financings certainly generate significant press interest. But how representative of the fund raising environment are these mega-rounds?

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How Fast Must a SaaS Startup Grow to Raise a Series A?

Last week, Sean Ellis made an interesting comment in response to this post on public SaaS companies' growth rates. "Everyone seems to throw out the 15% - 20% month over month MRR growth as the target. But seems like it's just a random target." I'm guilty of giving the same advice to startup founders without providing a transparent rationale. This post is my explanation of why the 15-20% MRR growth number is a reasonably good target for post-Seed/pre-Series A SaaS startups to aim for.

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How Quickly Does a SaaS Startup Have to Grow to Go Public?

At the time of the IPO, the median Software-as-a-Service (SaaS) company generates $100M in revenue, creates $2.6M in profit and holds $85M in cash on the balance sheet. A company in this position typically raises $107M in its IPO and trades at 11x revenue, for a $1.1B market cap.

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