Pattern Recognition, by Ian Sigalow

Pattern Recognition, by Ian Sigalow

Pattern Recognition is a journal of thoughts and strategies on venture capital investments.


What is native advertising?

Posted on May 14th, 2014.

In the past year we have looked at over 100 companies claiming to do native advertising.  If you haven’t heard of native advertising you will soon, because it is the hottest trend in online advertising right now. I figured it would help to clarify what native advertising actually means.  I wouldn’t normally do this, but […]


High Frequency Media Buying

Posted on April 30th, 2014.

Archaeologists debate when the first stock exchange was formed – most say it was around 400 BC in ancient Rome. By that account the hand-to-hand trading of securities existed for over two millennia before the US Congress and SEC authorized the first electronic exchange in 1998.  Within a few years the physical stock exchange was replaced […]


Rockets, Data, and DMPs

Posted on February 23rd, 2014.

I am amazed at the recent ascent of RocketFuel, which has grown faster than any ad network I have ever seen. Budgets in the display media business are guarded by large agency holding companies, and agencies typically discourage clients from scaling this fast with a specific vendor. It looks like Rocketfuel has found a way […]


A New State Of The Union

Posted on January 31st, 2014.

Welcome to my first political-themed blog post (with a mix of social science): Every election cycle, research firms contact voters and ask questions like “How important is reforming Medicare and Social Security?” or “How important is reducing greenhouse gas emissions by 80% over the next 20 years?” I get these forms in the mail too, […]


Just A Little Bit of History Repeating

Posted on December 18th, 2013.

As we approach the end of 2013 I am feeling a little anxious.  If you are a gambler you might know the feeling, it is the same sense you get during a good run.  The dice are hot and the numbers keep coming.  Like a good sport you keep pressing.  But at some point you […]


Hello Walled Garden

Posted on November 25th, 2013.

When Twitter upgraded their mobile application this year, to a version called “New, New Twitter”, there was one significant change.  When I clicked on a link, rather than open my Chrome browser to load the web page, Twitter loaded a built-in browser.  This made a seamless transition between Twitter and the web, without ever leaving […]


The VC And The Art World

Posted on November 15th, 2013.

In 2010, while the financial crisis was still unwinding, I traveled down to Tampa with my wife to visit her family.  On a back road not far from our hotel was a recently built housing complex.  These were beautiful, low-rise brick buildings, with landscaped lawns and tile roofs that reminded me of Florence. The sign […]


The Unicorn Effect

Posted on November 3rd, 2013.

[Title borrowed from Aileen Lee’s essay “Welcome to the Unicorn Club.” It is worth a read.] [Editors Note:  I don’t know the guy in this photo.] This past February we flew the entire Greycroft team to Utah for a ski weekend, which doubled as our firm-wide offsite.  In addition to the usual stuff, every partner had […]


Winner Take All

Posted on October 17th, 2013.

I recently realized that I have given a lot of entrepreneurs bad advice when it comes to software sales.  Unfortunately I have been doing it for many years as an investor. I used to think that the goal of a Series A software investor was to build a great team, build a great product, and […]


The Second Generation of Social Media Marketing

Posted on September 20th, 2013.

Five years ago, in a three floor walk-up above an Indian restaurant, the team at Buddy Media unveiled the first social media management system.  I remember the board meeting like it was yesterday.  For the first time, someone could create a Facebook page without using Facebook’s obscure, in-house programming language.  This would be a huge […]