Checkout a preview of my soon to be released Memoir about Founding GrubHub.

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My memoir, Hangry is about this whole “Create a billion dollar startup, and then punt it to go for a bike ride” thing. Sign up here to get a preorder link and get monthly updates on my publishing journey.

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Prologue

I quit.

The thought is freeing. And a bit sad. I say it out loud: “I’m actually done.” I’d planned this for a solid five years. And even though it took a couple tries to make it stick, here I am, sitting gingerly on the covers of a too-small bed, in America’s shittiest motel room.

I’m wrong about this. It’s not the shittiest. I’m simply ignorant about just how shitty motel rooms can be. But this room does have one outstandingly shitty feature: The front door doesn’t go all the way down. Lights from the parking lot shine through a four-inch gap between it and the floor. Every few seconds, a car passes by on the busy road just past the parking lot, the headlights sweeping in and all over the walls of the room.

Actually, given the gap, is this a room, or just a partially obstructed continuation of “outside”? These are the kind of things you think when you have time; and boy, do I have time. Technically, even though I’m in a motel in Nowhere, I’m still employed by GrubHub until midnight. This is significant, because by finishing out the quarter, I will vest 5,000 stock options. Which, given that GrubHub is riding high at $44 bucks a share … well, you do the math. I could have afforded a better “room” to be honest.

But, that would be missing the point of this ill-begun adventure.

The three cockroaches visible from my perch on the bed suggest that I’m not really indoors. Should I put up my tent–I mean, on top of the actual bed–and get in it? The thin layer of nylon might lend me protection from the fitful sleep of the crawled upon.

And what to do about food? I may need to figure out a plan B. It’s been two hours since I ordered a pizza, and honestly, the chances don’t look all that great of anything turning up. Which, given what I created GrubHub, is pretty funny. Or, would be, if I wasn’t getting hangry-er by the second.

Have I made a mistake?

 I think of my wife, Christine, back at home, likely reading a book in our infinitely more comfortable bed, in a house where the doors go all the way down. Where there is food in the refrigerator. I need to eat, and now.

A knock on the “door” shifts my thoughts from Maslow’s hierarchy of needs to Pavlov and his pooch. I’m salivating at the thought of pizza.

Most people think a Chicago-style pizza is a monstrous, two-inch-thick wheel of cheese, embedded in a thick cornmeal crust, more akin to a birthday cake than a pizza. Each of the two hunks of cheese in the middle should be the equivalent of a frisbee worth of mozzarella. Between them, there should be a substantial border of pepperoni or sausage, usually. (What the hell, throw in some ‘shrooms, make a party of it.)

But most people are wrong. A Chicago pizza has nothing to do with the thickness of the cheese. Any true Chicagoan knows that giardiniera is the key to a great pie. It’s an unassuming ingredient: pickled peppers or vegetables in oil. Spicy or mild, as you like it. It can be found on the bottom shelf in the grocery store, behind the cardboard display of big brand nacho cheese. It’s the giardiniera that makes a pizza into a Chicago pizza.

The pizza that has arrived is sadly devoid of spicy pickled peppers. I have added bell peppers and garlic in an attempt to recreate the effect, and actually, it’s pretty good. Great actually. The peppers are fresh; the crust is hand tossed; the cheese is . . . cheese. And it’s a pie, not square cut (Chicagoans commitment to square cut pizza is lamentable but you can’t have everything.)

I eat.

And eat.

And eat some more.

As I eat, I’m interrupted by an incoming text. “Your pizza is about to leave the restaurant,” it reads.

I presume they’re referring to the mostly eaten pizza sitting here on my crappy motel bed. Clearly, the system we patented at GrubHub almost four years ago, the one that was supposed to increase the accuracy of these texts, still hasn’t been implemented correctly. A decade of habit has me opening up my email to write to the product team about it . . . and then I remember.

I quit today. It’s over. It’s not my problem anymore.

The seventh of piece of pizza represents a Rubicon, of sorts–demolish this, and I may as well finish the whole damn pie. But if I do finish it, I’ll need to get breakfast in the morning–if I resist the temptation, though, there’s one less thing to do before I start rolling. The one thing I’m not worried about is the calories. I’m going to need the calories.

After all, I’m about to ride my bicycle over four thousand miles, right across the United States, Atlantic Ocean to Pacific. The point of the ride is to try to decompress from twelve years of insane work while meeting the people of this great country. It’s an attempt to stay grounded after becoming filthy rich.

As I work through the final piece of delicious garlic and pepper pizza, I stuff a towel into the gap between the door and the floor and perform a final reconnaissance for creepy crawlies before laying down to get some shut eye. I’m still a little creeped out, so I get inside my sleeping bag on top of the bed, letting the food coma drag me into slumber.

Eventually, I sleep. And when I wake up, I will leave my old life behind and ride West.