March 26

Gary Flake Pt. 2 – Founding Clipboard, Getting Acquired by Salesforce (#43)

Academia, Author, Consultant, Founder, Search, Software Engineering, Startup



Gary was previously the CTO of Search and Data Science at where he managed salesforce’s entire search business unit. Prior to that, Gary was CEO of Clipboard Inc., which was acquired by in May of 2013. Before founding Clipboard, Gary was a Technical Fellow at Microsoft (2005-2010), where he was responsible for bridging Microsoft Research and MSN, and for helping set the technology vision and future direction of the MSN portal, web search, desktop search and commercial search efforts. In this capacity, he founded and directed Live Labs, Microsoft’s greatest investment in applied research focused on the Internet, which was responsible for groundbreaking technologies such as Seadragon, Photosynth, Deepfish, Listas, Volta, and Pivot.

Dr. Gary William Flake is an independent scientist, author, and inventor, that currently advises over a dozen startups, public companies, universities, and non-profits.

Prior to joining Microsoft, Gary founded Yahoo! Research Labs, ran Yahoo!s corporate R&D activities and company-wide innovation effort, and was Overture’s Chief Science Officer. Before joining Overture, Gary was a research scientist at NEC Research Institute and the leader of its Web data-mining program.

Gary has filed over 150 patents and has numerous publications spanning over 20 years which have focused on machine learning, data mining, and complex systems. He has also appeared in leading national publications including The New York Times, The Washington Post, Time Magazine, Forbes Magazine, Nature Science, CNET News, Computer World, Fast Company, TechCrunch and Mashable, and has presented at leadership events such as the TED Conference.

Gary earned his Ph.D. in computer science from the University of Maryland, has served on numerous academic committees and university advisory boards, and wrote the award-winning book, The Computational Beauty of Nature, which is used in college courses worldwide. He was also the 2010 winner of the World Technology Award in the category of individual achievement in software, and was named one of the “Creativity 50” in 2009.

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Episode Summary

“The type of work I do is all over the map. I mentor a lot of CTOs. I work with other companies on their core strategies. I often serve as a sort of domain expert for certain things around machine learning and data science. So i get into the technical weeds for some of them. That’s a way of keeping me relevant and making sure I don’t lose track of whats going on in the rest of the world.”

—Gary Flake

In this episode we’ll cover:

  1. What was it like selling Clipboard to Salesforce?
  2. How was Gary able to get all of his startup fundraising done in two weeks?
  3. What is Gary’s new book about?
  4. The secrets of building amazing teams

Key Milestones

[2:15] – Flake walks us through leaving a high ranking position at Microsoft for the uncertainty of becoming a founder. He explains why the changing culture at Microsoft was also an important reason for pushing him out.
[5:07] – What was it like coming up with an MVP for what would become Clipboard? How was Gary able to get all of his fundraising done in two weeks?
[6:01] – What was it like selling Clipboard to Salesforce? How was it possible that when everything was integrated, Salesforce decided not to go through with it?
[8:05] – Clipboard, Gary’s startup, was essentially a combination of Pinterest and Evernote. Here is Gary’s keynote speech about Clipboard at a conference.
[13:00] – Clipboard was built, created and sold to Salesforce within 18 months. In that short time, they grew to around 150k users and had millions of clips with remarkable user engagement.
[15:59] – Gary talks about building successful teams: The secret to building teams is getting people who are as different as possible but who also have viable communication paths between each other. Similar, but diverse at the same time.
[19:15] – The most important character traits Gary looks for when hiring: emotional maturity, integrity, systems thinking, and willingness to learn new skills!
[27:30] – Flake now splits his time between advising, independent research, writing, and coding. He finds this current blend extremely fulfilling.
[29:20] – Gary advises numerous companies, some with billion-dollar valuations, while others just startups. This includes everything from investing, mentoring CTOs, strategizing, machine learning, programming.
[31:10] – What is Gary’s new book about? Its meant to be a successor to his first book, Computational Beauty of Nature.
[32:07] – Gary is also working on creating his own programming language, called XtoC.
[36:18] – What is Gary’s career advice for others. He mentions learning how to learn, being intentional with what it is that you want to learn, and having the endurance to push past the finish line when things get challenging.
[40:22] – Gary feels like he is good as an individual contributor and also as an executive. But he feels like he’s not naturally a good manager and finds that others can often manage better than him.

Additional Resources

Selected Links from the episode:
Read more about Gary Flake on Wikipedia
Gary’s Book: Computational Beauty of Nature 
Watch Gary’s Ted Talk
Gary’s keynote speech about his startup, Clipboard
9 Mind-Bending Epiphanies That Turned My World Upside-Down – Raptitude Blog





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