Sunday Conversation #5: Matt Ocko, Data Collective

Welcome to the fifth “Sunday Conversation,” this week featuring Data Collective’s Matt Ocko. Many folks here will likely not know who “Ocko” is, and until recently, I did not either, though it seems everyone who has been around the Valley and technology investing knows Ocko well. I was at an event earlier this year and saw him on a panel — he was different than everyone else, speaking directly and unafraid to say some direct and potentially controversial things during a time of politically correct investor-speak. I hunted him down to be on this video series (I don’t think he was too eager at the start!) and wanted to profile him and his thought process because I think many founders and investors can learn from his unique, experienced perspective. In the videos below, Ocko shares his depth of enterprise IT and fundamental technology, as well as shares plain-spoken advice that entrepreneurs should hear but often don’t given the current investor-celebs of the day. ♦

Part I, On The Adversarial Relationship Between Some Investors And Entrepreneurs (4:09) — Ocko pushes back against the current meme of founders playing a chess game to obtain funding at the potential cost of long-term relationships. ♦

Part II, What’s The One Thing Founders And Investors Need To Hear (2:34) — Ocko encourages founders to think through the implications of being adversarial in business as business lifetimes are long, and encourages investors to not discount the value of hard value-add work during an environment when social media amplifies the “hot” investors of the day. ♦

Part III, What Is Data Collective (4:59) — Ocko explains what his firm, Data Collective, focuses on. These guys are some of the most innovative early-stage technology investors, that this is worth listening to closely. ♦

Part IV, “Big Data” Dissected By An Expert (4:56) — “Big Data” is one of the biggest buzzwords thrown around web and mobile tech companies. Here’s how one pure expert pulls the signal from the noise. ♦

Part V, Big Long-Term Trends In The Enterprise IT Stack (6:19) — Ocko gives a brief survey of all the big thematic changes in the enterprise IT stack. ♦

Part VI, Advice To First-Time Entrepreneurs Attacking The Enterprise (6:13) — Ocko gives tactical advice to younger entrepreneurs who are looking to build new enterprise-facing companies, the first bit of advice being to move to the Valley. ♦

Audio Recording, Full Conversation via SoundCloud

A special thanks to the team at Scaffold Labs for sponsoring the Sunday Conversation series on Haywire. Scaffold Labs is a boutique technology advisory firm based in Silicon Valley which designs and builds scientific and predictable talent acquisition programs that helps technology startups hire great people. Scaffold Labs has previously partnered with companies such as Cloudera, Appirio, and Nimble Storage, among others. For more information, please visit