I’m too fired up right now to do the topic justice, but I just read this pair of tweets from Alex Payne (someone I don’t know personally but have huge respect for by reputation) and the article / blog post he links out to, I and just couldn’t fit my reply into 140 characters. I continue…

I love Y Combinator founder Paul Graham’s “Request for Startup” meme. In that spirit, here’s an idea I’ve been kicking around with a few folks and would love to see happen. The traditional enterprise software business is crumbling. Once-dominant vendors like HP, SAP and Oracle aren’t going away anytime soon, but their iron grip on continue…

Note: this post is one of several drill-downs on the topic of why angel investing and early-stage venture investing are not just different in scale, but different in type. The most exciting thing to happen in software investing over the past 10 years isn’t Facebook, or Twitter, or even Instagram. It’s the total collapse in the continue…

Note: this post is one of several drill-downs on the topic of why angel investing and early-stage venture investing are not just different in scale, but different in type. Venture investors who seek to maximize returns face a difficult problem: unlike publicly-traded securities, private company investments are highly illiquid — no returns, no exchanges. In addition, continue…

Note: this post is one of several drill-downs on the topic of why angel investing and early-stage venture investing are not just different in scale, but different in type. Most angel investors I know don’t consider their early-stage investments to be integral components of their personal investment strategy. Instead, they’re more often viewed as “off continue…

Note: this is part of a series of posts unpacking what I’ve learned over the past four years as a professional investor. Looking back, it seems so obvious. But the #1 lesson learned from my past four years as a “professional” venture investor has nothing to do with how I evaluate people, companies or ideas. Instead, continue…

Four years ago I began a new journey. After a 15-year career as a participant in and co-founder of various businesses, I “switched sides” and became a full-time investor in early-stage software companies. At the time, I published a series of posts that described how I was thinking about my work, and laid out in continue…

Tom Friedman’s op-ed today was a riff on Why Nations Fail, a new book from MIT economist Daron Acemoglu and Harvard political scientist James Robinson. Per Friedman, the core thesis of the book is the long-term instability of “extractive” as opposed to “inclusive” political and economic systems: “Inclusive economic institutions that enforce property rights, create continue…

I had an emotionally intense conversation with a startup CEO today about the benefits and costs of regular, transparent communication with company investors and close advisors. My point of view — which I articulated forcefully if not very effectively — was that transparency within this limited set of insiders was incredibly valuable and created far continue…

I found myself ranting again in a meeting today, a sure sign that another blog post was brewing… The topic of the conversation was startup accelerators and the do’s and don’ts for starting one. Setting aside for a minute the broader question of whether the world needs yet another accelerator, here is a short but continue…