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On Privilege

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Last week, I published a blog post titled, ‘Decoding the Qualities of a Great VC.’ The spirit behind the piece was to spark a conversation about what makes a good venture investor and whether that can be predicted. It was generally well received until I saw this Tweet from Nathalie Molina Nino, CEO of BRAVA Investments, an investment platform that cares less about creating the next woman billionaire and instead backs businesses that create wealth […]

Decoding the Qualities of a Great VC

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Last Friday, I was talking with Parker Thompson of AngelList and creator of Startup L Jackson about a range of topics from investing in pre-seed companies to building a venture firm from scratch. Towards the end of the call, he asked what I thought are the attributes of a successful VC. Rather than answering on the spot because we were essentially out of time, I told him that I’d give the question more thought and I’d email him my […]

10 Days of Silence for a Lifetime of Wisdom

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10 Days of Silence for a Lifetime of Wisdom Dhamma Dhara, Shelburne Falls, Massachusetts Three weeks ago, I returned from a 10-day Goenka Vipassana meditation retreat at Dhamma Dara in Shelburne Falls, Massachusetts. Goenka (1924–2013) was a Burmese-Indian teacher of Vipassanā meditation. His teaching was notable for emphasizing that the Buddha’s path to liberation was non-sectarian, universal, and scientific in character. He became an influential teacher and established meditation centers, like the one I attended in the Berkshires, all over the world. […]

Hug O’ War

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Last weekend, I was hanging out at my twin brother’s house. It was early in the morning and wanted to kill some time so I decided to browse his vast book collection. I came across one of our most cherished books from childhood, Where The Sidewalk Ends by the legendary artist and writer Shel Silverstein. As I was flipping through the book, I arrived at one of my favorite poems, Hug O’ War:  I immediately Google’d Hug […]

Introducing Huddle: Peer-to-Peer Support Groups for the Masses

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Everyone struggles with something. For me, it was anxiety, addiction and imposter syndrome. For a long time, I was afraid to seek help because I was worried about what others would think of me and how they’d react since I was extremely functional in all facets of my life. I ultimately healed myself and transformed my life over several years through mediation, nurtrition, radical candor, sleep, exercise and positivity. I also turned to a variety […]

Embracing Radical Candor to Overcome Your Worst Habits at Work

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Last month, while I was on a cross country flight, I read Ray Dalio’s seminal document, Principles, for the second time this year. For those of you who don’t know Ray, he is the Founder of Bridgewater Associates, the world’s largest and arguably most successful hedge fund. Ray runs Bridgewater according to principles that he has developed over his 40+ year career. Some would suggest his approach and views of the world are radical but […]

Venture Investments Are Not Bets

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Countless times over the last decade, I’ve heard other venture investors refer to their investments as “bets.” Earlier in my venture career, I was absolutely guilty of this because I wasn’t being mindful and probably lacked some necessary empathy. At the time, I don’t think I truly appreciated what it meant and took to be an active investor and support a company over the long haul. A few years ago after a conversation with my […]