Category Archives: Startups

The difference between a startup and a hobby is paying customers

Waaaaaay back in 2010, I wrote a read “The Lean Startup” by Eric Ries. Roundabout the same time, there was a Southpark episode about underwear gnomes stealing everyone’s drawers for profit. The gist of it is: Phase 1: Steal Underpants Phase 3: Profit. Yeah, but what’s Phase 2? Welp, in the spirit of those twoContinue reading “The difference between a startup and a hobby is paying customers”

Death and Despair in America

I just finished the most boring book that has ever changed my life. Bear with me here: In their 2020 book, “Deaths of Despair and The Future of Capitalism”, Professors Anne Case and Angus Deaton explore the decrease in life expectancy in the U.S. More specifically, in white people without a college degree. And notContinue reading “Death and Despair in America”

What’s in an IPO? My experiences through GrubHub’s offering from start to finish

GrubHub had it’s Initial Public Offering on April 4, 2014.  In many important ways, this was the start line for a new phase of the company.  For me personally, it was the finish line after eleven years of hard work. Now, ten months later, I’m far enough from the events that I’m able to speak about them.  This thenContinue reading “What’s in an IPO? My experiences through GrubHub’s offering from start to finish”

Our cities are running out of Tradespeople

Skilled electricians, carpenters, painters, all-arounders – people who are knowledgeable, handy, and can fix our homes. They’re dying. Literally. This frog got boiled slowly, but the fact is, it’s cooked now.  Taken individually, each of the drivers behind the dwindling numbers of skilled workers make sense.  As the years have slipped by the sum ofContinue reading “Our cities are running out of Tradespeople”

From 1 to 50 employees. The early days at GrubHub

Bootstrapping my business from 1 to 5,000 employees has been a wild ride.  The nature of the business has changed a lot.  As it has, I’ve had to stay on my toes to adapt to the new realities.  There have been shifts in the nature of my work as I’ve needed to raise my ownContinue reading “From 1 to 50 employees. The early days at GrubHub”

After $81 million in investment, some things are the same & some things are different

Well, it’s high time I share some of what I’ve learned over the last year, 81 million million dollars, and 200ish additional employees. And here it is: some things are different; some things are the same.

Opportunity vs Focus is the key struggle of the entrepreneur

Simplicity is necessary for excellent execution. Excellent execution is necessary for bringing a product to market. The flash of insight that starts the ball rolling is the critical big bang, but that same insight adds complexity, which is anathema to excellent execution.