Drivetime Consulting: Amr Shady

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

Gaming The System Doesn’t Work, And Everyone Has Worries

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

The Manic Side of Entrepreneurship

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

What Entrepreneurs Should Do Differently To Stay Married

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

I’m a founder, and I’m feeling down. What should I do?

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?

The Value of Investors: Why I Focus On Helping Entrepreneurs

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

You Can’t Avoid Putting In The Time

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

How To Use Portfolio Theory At Your Startup

Famously, VCs take a portfolio approach, betting on numerous startups, while entrepreneurs bet the farm on their single startup.  This fundamental difference helps explain many of the conflicts that arise between entrepreneurs and their VCs, because an entrepreneur is focused on the success of a single startup, while a VC has a fiduciary obligation to … Continue reading How To Use Portfolio Theory At Your Startup

Life as a Startup Barber

One of the popular expressions used by investors is “How much hair is on the deal?” A hairy deal includes messy complications, like a product that hasn’t yet found a market, or inexperienced founders. Some investors shy away from hairy deals. I, on the other hand, have decided to ply my trade as a startup … Continue reading Life as a Startup Barber

Startups Are A Numbers Game, But Use Your Good Sense

One of the expressions I hear a lot in the startup world (and which I even use from time to time) is “it’s a numbers game.” What the speaker means is that in certain activities, such as selling a product, pitching a VC, or asking a woman out, failure is the most likely result, and … Continue reading Startups Are A Numbers Game, But Use Your Good Sense