Gary Flake - CEO of Clipboard Inc.

[quote style=”boxed”]Focus on the product as much as possible.  I outsource as much of the business operations as I can.[/quote]

Dr. Gary William Flake is the CEO of Clipboard Inc., a seed stage Internet startup that allows users to save, organize and share their favorite parts of the web. Prior to founding Clipboard, Gary held executive positions at Microsoft, Yahoo!, and Overture, where he managed applied research teams, corporate-wide innovation efforts, and helped guide corporate strategy.  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. Gary 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 and has served on numerous academic committees and university advisory boards. Gary wrote the award-winning book, The Computational Beauty of Nature, which is used in college courses worldwide.  Gary 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.

What are you working on right now?

I’ve been mostly focusing on my startup, Clipboard (a.k.a. clipboard.com) for the past year.  I also keep a couple of pet problems in the background that range over math, CS, physics, and even a little bit of philosophy, but these are admittedly more fun than serious work.

Where did the idea for Clipboard come from?

It was born out of my own frustration with trying to save and share parts of the Web.  For a long time, I wanted to be able to save just a part of a Web page but have the saved part retain the look and functionality of the original.  I was really quite surprised that no one had solved this particular problem very well.

What does your typical day look like?

I unofficially divide my workday into three parts.  In the morning, from home, I tend to be in an “input mode” where I’ll consume anything that educates and informs.  This could include news, social media, technical details, ideas, designs, or anything else that may inspire me.  By mid morning, I’ll be at my desk with my team.  During this time, and for most of the day, I’ll be in “execution mode”.  I’ll ignore email, try to refrain from looking at blogs, and mostly attempt to do what needs to be done.  What I do on any particular day could range from design, business, or grunt work, but is more often than not product and engineering focused.  I still code quite a bit and on a really good day I may ship a feature or three.  The end of the day is my “output mode” where I am typically responding to the emails that are the most time sensitive.

How do you bring ideas to life?

I am a big believer in distilling ideas down to their core components and rapidly prototyping them.  I’ve always been a prolific coder, but it wasn’t until I fully embraced the entire Web stack that I was able to make this approach especially effective.  The combination of HTML, CSS, and Javascript has its annoyances, but in the grand scheme of things it is quite possibly the most efficient way to bring new ideas to life.

What’s one trend that really excites you?

As the Web matures, we are seeing ever more information intermediaries evolve or die.  In some cases, such as in the recording industry, there are strong arguments that the intermediaries are causing more harm than good because they siphon off value and add little back.  In other cases, the decline of an intermediary brings about a crisis of sorts, as we’ve seen now in mainstream print media and the societal role of quality journalism.

I find this pattern both exciting and terrifying.  I can’t wait to see the major academic publishers die off (they are parasites, as far as I am concerned).  But I am also worried about how truly expert and quality content will be found, especially when a producer lacks the self-promotion gene seemingly required to succeed in this new world.

What was the worst job you ever had and what did you learn from it?

As a kid, I worked in my family’s sheet metal shop and I did everything from sweeping the floor, to running all of the heavy machines, to welding.  My parents were always very keen on making sure that their kids were never spoiled, so I often got the shittiest jobs.  One summer, when I was about sixteen, my job was to crawl inside of some large steal vats and to paint the insides with grease so that they wouldn’t rust.  The vats were outside and this was in Miami when it was over 90 degrees and close to 100% humidity.  I did this for a day or two, and I after each session I would be soaked with a mixture of sweat, grease, and dirt.  I am also kind of retroactively surprised that I didn’t suffer from a heat stroke.

Anyhow, having had such a shitty job is like being inoculated against every possible employment disease.  No matter what happens, I can always say to myself “well, at least it’s not the grease tanks again,” and that’s priceless.  (Thanks mom and dad!)

If you were to start again, what would you do differently?

This is going to sound lame, but I am not really sure.  Failing is never fun in the moment, but some of the most important things that I’ve learned have come from my mistakes, so I am note sure that I would even want to redo those either.  I often think back to the 1990s, when the Internet was experiencing its first boom, and I wonder how things could have been had I not spent most of that time in research labs.  Perhaps my career on the Internet could have started earlier, but I also know that I would have missed out on writing my book.  So I really don’t know.  I guess it’s kind of nice to not have any obvious regrets, so I won’t complain.

As an entrepreneur, what is the one thing you do over and over and recommend everyone else do?

Focus on the product as much as possible.  I outsource as much of the business operations as I can.  This includes most accounting related activities, such as payroll, expenses, bookkeeping, etc.  I also have some really good attorneys that are pricey but are worth it because when the stuff that I am weak at is still solid, I have the confidence to take risks elsewhere.

What is one business idea that you’re willing to give away to our readers?

Well, I can’t “give away” this idea because Yahoo! owns the patents for it, but I think it’s the best idea I ever had but also one of the most difficult to fully realize.   In a nutshell, the idea is to make an options and future market on the performance metrics of paid search.  With such a marketplace, you could structure any number of financial instruments that could be used to mitigate all sorts of marketing risks.  Moreover, these instruments could be used to bridge transactional marketing systems (like paid search) to long-term marketing expenses (like display ads and traditional mainstream media ads).  Someday, someone will build this, and it will be worth hundred’s of billions of dollars.

If you could change one thing in the world – what would it be – and how would you go about it?

I would want every person to have access to a quality education, from K to Ph.D., if appropriate.  I know this seems like a pipedream at the moment, but I think within my lifetime this will be possible with a mixture of scale economics, AI, better online curriculums, and the heroic efforts of folks like the Gate’s Foundation and Khan Academy.  Every other problem that we have, be it health, technological, social, or humanitarian, is almost always better pursued — and sometimes outright resolved – when people have the context of a broader education.

Tell us a secret.

I love reading celebrity gossip and I’ve had subscriptions to trash rags for years.

What are your three favorite online tools and what do you love about them?

First, seriously, your readers should try out our service, Clipboard.  The included link has an invite code embedded that will allow you to get in the private beta now.  It really is the best place to save and share your favorites parts of the Web.

Second, wolframalpha.com is simply an amazing source of anything that’s at the intersection between data and analytics.

Third, it’s cliché to site Wikipedia.org, but it’s amazing nonetheless.

What is the one book that you recommend our community should read and why?

I believe that “Open Society” by George Soros is one of the most thought provoking books I’ve ever read.  It looks like a treatise on societal issues disguised as an exploration of financial markets, but it’s also an insightful work on how to think.

I also put in a plug for my own book, “The Computational Beauty of Nature,” for members of your community that like to explore things at the intersection of math, science, and philosophy.

What’s on your playlist?

I am currently listening to Tool, TV on the Radio, Radio Head, The Black Keys, Kings of Leon, and Mumford & Sons.

Three people we should follow on Twitter and why?

I am actually a really bad twitter user.  It’s too much data for me, so I’ve only followed a couple of novelty accounts.  But that doesn’t stop me from ranting on it as @flakenstein.

When was the last time you laughed out loud? What caused it?

I am a sucker for animal videos.  I recently saw a video of a dog standing up to play the piano and howling as it pawed the keys.  It really may have been the greatest video ever made.  But, alas, the video owner took it down from Youtube.

Who is your hero?

Intellectually, I am always amazed at the breadth and depth of John von Neumann.  He played a seminal role in physics, computer science, and economics.  He also had some personal failings that are hard to overlook when you think of someone as a hero.  In terms of having an amazing combination of intellectual, societal, and ethical impact on the world, I think that Jonas Salk is on the top of my list.

What are some of the most interesting trends in Web development?

I am a big fan of the asynchronous programming model that is being used in Node.js, which is what we use in Clipboard.  I think it promotes the design of cleaner web applications because it encourages you to think of APIs first and foremost.  I think the full story of NoSQL is still unfolding, but that in time we will see the data tier for typical web applications become vastly simpler and easier to scale than they are now.  Finally, I think canvas and WebGL are still emerging, but when they do they will make people forget the difference between a service and an application.

What do you hope to be doing ten years from now?

In that time frame I would really like to shift my focus more to my family and leave whatever time surplus remains to learning something entirely new, and possibly more fun than utilitarian.

Connect:

My coordinates include:

Gary Flake on Facebook – https://www.facebook.com/gary.flake
Gary Flake on Clipboard – http://www.clipboard.com/gary
Gary Flake on Twitter – https://twitter.com/#!/flakenstein