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 […]

From 1 to 700 employees

Bootstrapping my business from 1 to 50 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 own game and continue to be the right person to move the business forward.

A strong business partner decreases startup risk

A good partner increases the likelihood of a positive exit for a company. This increased chance of an exit more than offsets the 50% dilution. Getting paid a million bucks is sweet for the founder. Getting paid two million is even bette

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.

Founder Equity Compensation

I’ve been asked recently about how to compensate non founder employees at the beginning of a venture. Most folks agree there is an upper limit on the ideal number of founders. So taking that for granted, how do you motivate non founder employees with equity before you have cash?

GrubHub closes an $11 million round, and we learned something

GrubHub recently closed an $11 million funding round. During the course of talking to investors a few themes came up for companies in the startup and growth stage emerging from a tough recession

Lean Startup Economics

Here are four steps for building a unit economics model in parallel with starting the business. This makes the model a living document rather than a dusty academic exercise.

A Practical Guide to Writing Your First Business Plan

So you want to start a business. You’ve heard that you should have a business plan. You’ve got a vague idea that you should get started on that sometime. That vague idea has been sitting in the corner getting grumpy as you’ve neglected it. And now the idea is a mean looking little monster with big pointy teeth. The best way to get that sucker is to take a step by step approach that breaks down this big “MAKE A BUSINESS PLAN” task into a bunch of smaller pieces.

Hard work is the unspeakable defensible position

My co-founder at GrubHub and I have engaged about 30 venture capitalist firms over the last 2 years.  As a result of that process we’ve learned quite a bit about things you absolutely never say. These are trigger words that get you mentally thrown out the door before the meeting is physically over. Here’s a […]


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