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Here’s what you should ask before marrying a VC

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Raising money from VCs is an important step in the company building process. It marks the beginning of a long-term relationship that can last longer than a decade. In my experience investing in and advising countless founders, company building is not rainbows, unicorns and lollipops. Startups are filled with adversity, challenge and struggle. That’s why it’s critical to find the right investors who are going to support you when times are good and have your back when […]

The Dilemma of Sunk Costs in Venture Capital

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Last week, I bumped into a buddy who runs a fairly large venture-backed company. I asked him how things were going. Rather than getting the common response, “everything is great,” he explained that he had spent the last few quarters developing a new product only to discover the customer response has been lukewarm. He said this experience stung because countless hours and hundreds of thousands of dollars were spent building the product. He had also […]

Crowdsourcing the ‘Global Life School’

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Yesterday, I was thinking back to my experience in high school. While I had some amazing teachers and treasure many of the lessons that I learned, I wish I had been taught more fundamental ‘life skills’ during my adolescence. That reflection prompted me to write the following tweet: Less than twenty-four hours later, the tweet has been shared and liked thousands of times. It turns out the idea of teaching “life skills” in schools struck […]

Introducing One Change Club

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Several months ago while I was on my Vipassana meditation retreat, I was captivated by the idea that change is a constant. By unplugging for ten days and increasing my sense of awareness, it became very apparent that objects around us and within us, even at the tiniest levels, are always in a state of flux. Despite the fleeting nature of everything, we as humans tend to cling to objects, people, places, memories, emotional states, […]

Helping Boomers Find Purpose & Meaning in Life

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(My dad this summer in Woodstock, NY) I recently read an excellent essay by Andrew Kortina titled, “They Say the #1 Killer of Old People is Retirement.” In this piece, he discusses the importance of finding purpose and meaning deep into life. Andrew outlines a confluence of factors that are causing mental and financial hardships for baby boomers. Many are struggling emotionally and financially for a variety of reasons including lack of savings, meaningful work […]

My First Think Week: Going Off The Grid for Exploration and Reflection

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My First Think Week: Going Off The Grid for Exploration and Reflection Sundown on one of my many nature walks Earlier this month, my good buddy, Mike Karnjanaprakorn, Founder / CEO of Skillshare, stopped by our place in the Catskills for a few hours. He was just coming off his seventh ‘Think Week.’ Over lunch, Mike explained the inspiration behind this annual ritual and outlined the basic structure he has used over the years. He even […]

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 […]