Silicon Valley puts tremendous focus and attention around products and their interfaces, interactions, and form-factors. And with good reason because it’s really hard to 1.) distill abstract human wants and needs into actionable insights, and then 2.) productize those insights into apps, websites, or devices. Within the last 5-10 years, the technology component in many classes of products have become more and more of a commodity. In conjunction, the target demographics have expanded from just geeky early adopters to virtually everyone in the world. As a result, companies today compete more and more on design and interface. In fact, the very best products have an essence of aesthetics ascribed to them. They’re elegant and beautiful, and even sometimes get put into modern art...

Today is my last day at Groupon. It’s been fun these past 13 months – with all the highs and lows that come with selling a startup to and working for a company re-discovering its legs after falling out of favor with commentators that once hailed it as the fastest growing company in history. But it’s not only my last day with Groupon, it’s also really the close of the Glassmap arc, an adventure I embarked on with a couple friends just over 3 years ago.

I’m truly honored to have had the chance to work alongside and learn from some of the most talented people in the world. The opportunity that Groupon is doggedly pursuing is extremely ambitious. Perhaps it’s not yet understood by the general public. Local brick-and-mortar commerce, the businesses and...

Most popular consumer social internet products sound stupid when they first started. I’d argue that most of them are still stupid. The only difference is that the popular ones gained enough social proof to not look stupid.

So if they’re all stupid, what then separates the products that take off and the ones that don’t? Well, this reminds me of the old ‘hedge funds are all luck’ theory: take 100 hedge funds. They’re run by the same white-shoe, pedigreed types, and they’re all investing according to their own arbitrary ‘investment theses’. 80 of them suck, 10 match the S&P500, 9 beat the market, and 1 looks like Midas. Statistically, someone’s going to luckbox their way to the top. The problem is that you can’t play...

Early-stage technology (especially software) start-ups today are over-priced as an investment class. Over the last decade, technology development techniques have matured, the costs are well-understood, and all infrastructural problems now have commodity solutions. I argue that most technology startups created today are structurally similar to brick-and-mortar small businesses and manufacturing-based ventures, and therefore should be priced at multiples similar to those businesses.

Defenders of current valuations might argue that the technology component opens up vast scaling opportunities and capabilities that brick-and-mortar and manufactured goods companies cannot. I’m not convinced that there’s particularly more real estate for a business to conquer in the technology...