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Brad Garlinghouse

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Brad Garlinghouse was most recently CEO of Hightail (formerly YouSendIt), the file sharing site. Before Hightail, Brad was President of Consumer Applications at AOL for two years, after his role as Senior Vice President at Yahoo! running its Communications business. While at Yahoo!, Brad penned the famous Peanut Butter Manifesto calling for a shake up at the then fledgling Internet company.

Brad also had stints at Silver Lake Partners, @Ventures, @Home Network, SBC Communications and was CEO of Dialpad Communications. He is an active angel investor in hardware company Pure Storage and AI startup Diffbot.

He has a BA in economics from the University of Kansas and an MBA from Harvard Business School.

Companies and Investments

Hightail (CEO)

Lessons Learned

I think any great culture is born out of transparent, authentic communication. You almost can’t overcommunicate. You can try, and you might think, “Oh, do I really have to say this again?” And the answer is yes. One thing I started doing was to send out every Sunday night an e-mail to the whole company. The e-mails aren’t particularly structured, and they might be on all kinds of topics, like what’s really going on with our monthly results.

We also started a free Monday lunch to bring everybody together to share a meal. The first Monday lunch we did, some people got their food and went back to their desk. So I started to talk at these Monday lunches for a few minutes and then just take questions. I set the tone that all questions are fair game. The third thing I did was require everyone to do what we call a “fly along” with our customer support desk for several hours so they could really understand our customers.

We are all products of our experiences, good and bad. Sometimes you learn as much from the negative experiences as you do from the positive. I’ve had the good fortune of working for a number of profound leaders. But I’ve also been in companies where the communication increasingly became noncommunication — where the C.E.O. would do an all-hands meeting, and at the end of it I would be wondering: “What did they just say? I don’t even know what that meant.”

I was most engaged with leaders who made it clear to me what we were trying to do, and where we were trying to go. I became invested in that. With people who didn’t do that, you feel a little bit alienated because you don’t internalize what they’re saying.

We rewrote the company values. So our three values are: be in, be real, and be bold. “Be in” is all about passion. Life is short. There are so many interesting things we can do in our life, and I feel like if someone is just kind of showing up, it’s not worth it for them or for us.

The second value, “be real,” is really about being authentic in our communication. I have seen different cultures in my career that I felt had atrophied and needed revitalization, and they were the ones where you just didn’t feel like people were being real in terms of their communication. You’d sit in a meeting and work through something and think you got somewhere, and then you walk out of the room and someone’s putting the parking brake on and you don’t even know they’re doing that.

And the last one’s about being bold. As some companies grow and develop, that instinct is almost beaten out of the system. To me, if we’re not failing a little bit, we’re not trying hard enough. I think great cultures encourage risk and are tolerant of failure. If you don’t do that, you’re going to end up with a culture that is stagnant and not thinking about the next generation of products and experiences.

Inspiring Quotes

Leaving the house without your phone is the new streaking.

Dave Pell

Nothing makes you shout

John Perry Barlow

Relationships is a long-game. People remember when you treat them well.

Ryan Hoover

The communists have beaten us at capitalism.

Jon Stewart

Its actually pretty easy to become contrarian. Its hard to be contrarian and right.

Reid Hoffman

Brad Garlinghouse's Quotes

My dad told me at a relatively early age about this idea of “take the professor, not the class,” meaning just seek out the best professors, whatever they’re teaching. And the idea of taking the professor, not the class, applies to your professional life, too.

Brad Garlinghouse

Bring on the millennials & their apps. Keeps IT folks on their toes & I feel like Im still apart of the

Brad Garlinghouse

If I ever forget, please remind me to never pass on an angel opportunity that Bill Tai, AKA @KiteVC offers me!

Brad Garlinghouse

Further fueling my obsession with movies…fellow Jayhawk Paul Rudd starts filming @AntMan in SF.

Brad Garlinghouse

Time tracking apps are there to remind, but motivation to get up and actually DO is a completely different story.

Brad Garlinghouse

Influential Books


Irene Au, Michael Walrath, Jason Titus, Tren Griffin, Katie Benner