
Facebook, Part Deux
Nearly two years ago, I asked the question, “Did Peter Thiel Make The Single Best Investment In History?” Today, now that Thiel has sold most of his remaining stake in Facebook, it’s a good time to re-examine the math surrounding his investment. Two years ago, I wrote: In 2005, Peter Thiel paid $500,000 for a […]

How Do You Know A VC Is Interested?
“He told us he was going to fund us,” shouts the happy entrepreneur into my ear. I’m sure he dialed me as soon as he got into the car. “He’s not going to fund you,” I say calmly, “The VCs always say that. It doesn’t mean anything.” A lot of entrepreneurs have a hard time […]

Don’t Confuse Signifiers and Substance
When it comes to startups, its easy to confuse signifiers and substance. The truth is hard to know, especially with early stage companies. If you don’t have a product or customers, it’s hard to have substance. Yet whether you’re a startup or investor, you’d be wise to focus on substance rather than signifiers. Not because […]

Talk With Everyone
Reading Mark Suster‘s excellent post, “Why You Need To Take 50 Coffee Meetings” brought to mind one of my personal corollaries: Talk with everyone. I’m a relatively small-time investor. It’s a documented fact, and I don’t try to hide it. But that means that I need to deliver value beyond money if I’m going to […]

Permanent Portfolio Investing
I learned about Harry Browne‘s “permanent portfolio” from Josh “Personal MBA” Kaufman’s blog. If Harry’s name sounds familiar, you might remember him as the Libertarian Party’s presidential candidate in 1996 and 2000. Browne wrote extensively about investment topics, starting with his first book, 1970’s “How You Can Profit From The Coming Devaluation”. In his 2001 […]

The Power of Love (And Investors)
In this post, I’ll argue that the power of love comes mostly from stuff that doesn’t happen, and for bonus points, explain how my theory of love impacts how a startup should choose its investors. My life is filled with love. I have family, friends, and last but not least (okay, maybe least) you, my […]

Nothing Matters But Traction
Nothing matters but traction. It makes everything easy, but it is the hardest to accomplish.Too many entrepreneurs focus on working around a lack of traction when they would be better off using that energy to get traction.A common occurrence is that an…

Can We Ever Have Too Many Startups?
My recent post on the diatom bloom in the startup ecosystem prompted calls for me to dig deeper and provide more data. Far be it from me to disappoint!Chris Tacy asked, are we seeing too many startups? It’s a loaded question, but a good one.My instin…

How Many Investors are Too Many?
This post originally ran on TechCrunch. Lately I have seen a number of deals announced on TechCrunch in which 5 or more different VCs were participating in the deal. This always makes me chuckle because in my first company we had 5 investors in our first round and we picked up 5 more before we […]

It Can’t All Be Game-Changing
Humans have a weakness (it’s actually physiological, I think): a predilection toward narcissism. As such, we always see whatever time we’re living in as THE crucial time in the span of human history (at every point in history, every one has thought that surely THIS is the critical moment). I mean, with global flattening and […]