From Geek Squad to Venture Capital with Diana Kimball Berlin of Matrix

Finding the pulse of what’s now and what’s next is a vital part of any VC’s life. You need to see what is both practical as a business, but also what is coming up that might be worth investing time and energy to help grow. Our guest today Diana Kimball Berlin, Partner at Matrix, has only been an investor for a short stint, but she has a long track record of both product management as well as creating and curating internet culture. She founded ROFLCon, an early conference devoted to internet culture and has held product positions at some incredible companies like Microsoft, Soundcloud, and Quip.

This was a great conversation where we discussed Diana’s career, Matrix’s mission and ethos as an early-stage investment fund, how they navigate the ever-evolving boundaries between sectors in the startup world, and her strategy for portfolio construction and how she navigates re-investment decisions.

About Diana Kimball Berlin:Diana Berlin is an early-stage investor at Matrix with a focus on optimizing work tools, innovative apps, and scaling emotional labour. She was also a host on the "Should We" podcast.

Before investing, Diana had roles at Microsoft, SoundCloud, and Quip (acquired by Salesforce). And while studying at Harvard, Diana co-founded ROFLCon one of the first internet culture conferences.

She received a BA and MBA from Harvard.

In this episode we discuss:

(01:34) Diana’s path into tech and investing(04:35) How her degree in history helped shape her career(06:33) Lessons from Soundcloud and Quip(08:10) Differences in the Berlin Startup Scene and San Francisco’s(11:08) Diana experience co-hosting the Should We Podcast(13:52) Why she chose to transition to investing at Matrix(19:35) How deal attribution is structured at Matrix(22:07) Breaking down the factors of why she chose to invest in Accord, a Toronto/SF startup(24:46) How Diana’s product background has informed her investing career(27:16) Areas she is actively investing in(32:51) How Diana stays up on trends(33:59) On not being able to see every deal in the marketplace(37:06) Using metrics to help define success as an introverted investor(40:54) Advice she is giving to her founders to survive this tough market(43:13) How she works with first-time founders(45:15) Decision making around reinvestment(47:36) Diana’s passion for Lego

Fast Favorites

* 🎙- Favorite Podcast: Deep Questions with Cal Newport

* 📰- Favorite Newsletter/Blog: Hello Metaverse with Annie Zhang and Elena Mosse

* 📲- Favorite Tech Gadget: Anker 737 Power Bank

* 📈- Favorite New Trend: Retro apps, especially Retro itself

* 📚- Favorite Book: The Age of Em

* 🤔 - Favorite Life Lesson: Optimize for outlier outcomes

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