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Summer of Love 2017: Counterculture Remixed

January 14, 1967. Counterculture icon, Timothy Leary, stands before a free-loving gathering of some 30,000 hippies. They’ve come to San Francisco to attend the legendary Human Be-In, on a quest to explore a different approach to, well, everything. A few month’s later, some 100,000 will reconvene in Haight-Ashbury for what will become known as the […]

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The Unfortunate Middle

When it comes to the way we earn a living, whether entrepreneurs or employees, we tend to get stuck in the unfortunate middle…   We are taught, from a young age, to exist in the middle. Everything in moderation. Don’t be a tall poppy, nor a shrinking violet. Good enough is good enough. The middle […]

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What’s Your Unfair Advantage?

What makes one business succeed, while others around it fail? There is no one thing. But a simple question asked by famed investor, Chris Sacca, to then new founder, Alex Blumberg, in an early episode of the Startup podcast reveals a critical, yet often overlooked trait. I want to invest in companies that have an […]

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The Vision Fallacy: Are You Chasing the Wrong Thing?

Everything great starts with a clear vision…   That’s what we’re told from a young age. Define your endpoint. Make a concrete goal. Know where you’re going before you begin. See it, taste it, smell it, feel it, hear it. This is your vision. Without it, you end up going nowhere. You are doomed to […]

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The 5 Saboteurs of an Entrepreneur

Entrepreneurship, starting anything from nothing, is brutally hard.     “Conscious” entrepreneurship–building a business that doesn’t just serve a consumer need and generate profit, but also makes a bigger difference–is even harder. Because it’s not just about money, it’s about unleashing expression, connection and potential, and making meaning. Helping others rise. I’ve worked with hundreds […]

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The Tyranny of Always

I always get nauseous before speaking I always get headaches when I fly I always end up getting screwed I always freeze at exam time I always come in last place I always get there late I always get rejected I always lose I always… Ahhhhh, the tyranny of always. The minute we attach always […]

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Happiness. It’s Complicated.

What if the quest to be perpetually happy was actually making us miserable?   Summer 2012. Two thousands miles west of New York City, nearly 9,000 feet above sea-level. Deep into the Colorado Rockies, I’m sitting in the wood-clad home of soon-to-be friend, venture-capitalist, entrepreneur and deeply-wise and truthful explorer of life, Brad Feld. We’re […]

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Us and Them.

I’ve been asked of late why I’ve been relatively silent on many of the major issues of the day. It’s something I’ve been thinking on a lot over the last year. What is the best/right way for me to bring my own intention, voice and lens to the world of social justice. It’s not that […]

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Unbusy: A Manifesto

Busyness. It’s a problem. But, what if there was something deeper happening? An epic battle between intention and surrender that is both a source of profound pain, and an unlock key for life unbounded? And, along with that, an undiagnosed condition—Reactive Life Syndrome—that so many of us are living with, without even knowing it, or […]

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Grateful Yearning

“You learn more and more that everything exists at once with its opposite, so the contradictions of life are never-ending and somehow the mediation between these opposites is the game of life.” – Milton Glaser To be around acclaimed psychologist, behavioral economist, researcher and legendary Duke University professor, Dan Ariely, is to be in the […]

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