Author, Investor, Speaker, Mentor
Alex Schiff is a great guy and the creator of one of my favorite products, Fetchnotes. I met him when he was raising money for Fetchnotes (in the end, I decided not to invest because while I loved the simplicity of the product, I concluded that there weren’t enough self-organizing people like me to represent … Continue reading The Only 4 Reasons Investors Say “Yes”
One of the big dangers that entrepreneurs (and everyone else) face in Silicon Valley is the temptation to conflate money and self-worth. I was reminded of this by an entrepreneur that I’m coaching, who has been dealing with the whipsaw effect of fluctuating net worth and income. Making money and/or getting a big payday through … Continue reading The Dangerous Conflation of Money and Self-Worth
As a happily married man, I can confirm what the latest research indicates: The secret to a happy marriage is kindness and generosity. When I was a kid, I was mystified by altruism; I couldn’t understand why my parents would always let me have the best share. At the time, I just figured that they … Continue reading What Entrepreneurs and Leaders Can Learn From Happy Marriages
I just completed my first Drivetime Consulting engagement yesterday. Amr Shady reached out to me via email yesterday afternoon, and we set up a call for my drive home last night. The call was exactly what I was hoping for; Amr is a successful entrepreneur and all-around interesting guy, and he wanted my feedback on … Continue reading Drivetime Consulting: Amr Shady
One of the exciting things about Paul Graham handing over the reins of Y Combinator to Sam Altman is the fact that it gives Paul more time to write. Paul has long been one of my writing inspirations, and his concise yet conversational style has always struck me a near-perfect fit for his topics. I’m … Continue reading Gaming The System Doesn’t Work, And Everyone Has Worries
One of my long-term projects is to write a book about the psychology of entrepreneurship. One of the issues I want to write about is what I call the manic side of entrepreneurship. Entrepreneurs are innately optimistic; otherwise, they wouldn’t jump into a field of endeavor that has a 90%+ failure rate. I can assure … Continue reading The Manic Side of Entrepreneurship
I recently dove into Jay Goltz’s New York Times post, How To Be An Entrepreneur, and Stay Married. I thought it was an insightful piece, but to me, it was missing the most important part: What entrepreneurs should do differently to stay married. Having recently celebrated my 16th anniversary (and the 18th consecutive year in … Continue reading What Entrepreneurs Should Do Differently To Stay Married
As a founder, your own emotional health is another key metric you need to manage, and you need to treat it as such. I rely on three simple interventions: 1) Get a good night’s rest. Failing that, take a nap. On days when I haven’t had enough sleep, every problem seems like a mountain, and … Continue reading I’m a founder, and I’m feeling down. What should I do?
From Peter Thiel’s recent Reddit AMA: “As an investor, I think one must always maintain a certain amount of humility. There is only so much we can do to help the companies in which we invest. And because of this, the act of making the investment (rather than the ability to fix things later) remains … Continue reading The Value of Investors: Why I Focus On Helping Entrepreneurs
I have a lot of admiration for people who are willing to say unpopular things. Experience has taught me that popularity is only weakly correlated with correctness, and that a willingness to say unpopular things may often be the only way to say true things. Penelope Trunk is one of several friends who have made … Continue reading You Can’t Avoid Putting In The Time