Dear Food Delivery Startup,

Hello again, old friend — it’s your favorite customer, Alex. I know we missed each other for a few months when I was living nomadically, and you probably thought I had finally said goodbye forever. But fear not! Like most dysfunctional, codependent relationships, a change in life circumstances caused me to long for you once more. As sure as the sun sets and the moon changes phase, I always come back to you.

And thus it was so, that on one dark and stormy Saturday night in San Francisco (except it wasn’t stormy, because this is San Francisco), I felt that urge again. Nay! The need. Having noticed an odd growling sound bellowing from my stomach, I realized it was 9:45pm and I hadn’t eaten dinner. I was working late to get something ready for Monday when the thought hit me: “What if there was a way I could have food brought to me?”

That’s where you came back into my life, dear friend. Yet, like most relationships revisited, the second time around wasn’t as good as the first.

In Boston, we both had clear expectations — GrubHub was the only game in town, or I would have to figure out what restaurant I wanted and call for delivery. Like a luddite. I knew going in that I was going to have limited options, the estimated delivery time would be off by at least 30 minutes in either direction, and I’d have to wade through a website whose design inspiration appears to have been those ransom notes with the cut out letters from magazines pasted haphazardly on sheets of paper.

Am I being extorted?

But I accepted my fate with cheer, because I had no taste of an alternative. (Haha, you see what I did there? I know you missed my sense of humor.)

But now I’m in San Francisco, the 21st century mecca for laziness-empowering, first-world-problem-solving, adulthood-delaying innovation. No longer would I be bound to GrubHub’s monopoly! Here, we have DoorDash, Postmates, Munchery, Sprig, and so many more. You can’t walk down a street in the Bay Area without running into someone wearing one of their tshirts, like worker drones shuffling materials around an ant colony. “This,” I tell myself as I pass by the worker drones, “is how I will be feeding myself.”

Thus, a 2 hour journey through at least 6 different apps and websites and god knows how many restaurants began. You have some fucking explaining to do.

Doe-eyed and eager to begin this new chapter of our relationship, I started with DoorDash — the startup I had heard the most about. Upon entering my address, I am presented with this endless wall of logos and names I don’t recognize. (Besides Denny’s, but what am I, a peasant?)

So. Many. Options.

DoorDash seems to believe that I am an adult who knows what he wants, but it is here that they are mistaken. This is what I’m thinking looking at this page:

Do I want Chinese? Ehhhhh, not really. What about Mediterranean? I guess that would be okay. Thai? I hear there is good Thai food here. But what would I get? Actually, come to think of it Chinese could be good. Oh! What about Mexican? Ehhh, no I had that already today. Will any of these not give me cardiac arrest?

Needing to start somewhere, I search, “best Chinese restaurants in San Francisco.” I find this article with lots of photos:

You’re probably delicious, but you’re not what the body needs right now.

My stomach is intrigued, but it is by no means aroused. It’s holding out for something better.

“What about…pizza?” I wonder.

I return to Google and search “best pizza in San Francisco.” This leads me here.

Oh, hey there beautiful.

My stomach has seen what it wants, and the thunderous growls coming from my abdomen tell me it wants it bad. But I don’t know anything about the different restaurants, so I spend the next 10 minutes looking them up on Yelp, staring at photos of food porn, and resolving that I want Little Star Pizza.

I return to DoorDash with conviction and pride in my decision.

I see that my resolve is being tested, but no matter! This is San Francisco, if DoorDash won’t accept my business, surely there is some other VC-funded, cashflow-negative app that will take my money.

Enter Postmates.

After spending another 15 minutes waffling on whether or not I really wanted Little Star, or whether perhaps Pizza Delfina would be a more appropriate choice, or Capo, or another pizza place listed, I finally entered my order. At $20, it was already more expensive than I was hoping to pay for pizza, but dammit, I had been through an ordeal tonight. Dammit, I deserve this.

And then I saw the delivery fee: $10.

WHAT THE FLYING FUCK?! I’m not paying $10 for someone to deliver my $20 pizza! Apparently, Postmates has surge pricing just like Uber, but I am not giving in.

Feeling angered and betrayed by food delivery startups as a whole, I decide to throw in the towel and just get Sprig. My body simply needs food, and what am I going to do? Go outside? I’m busy! Busy with business things.

List of websites that have hours of operation: food delivery startups, Massachusetts Department of Unemployment Insurance

Thwarted. Well, I have been meaning to try Munchery

In the throes of hunger-fueled depression, a moment of inspiration strikes. What if…I just called Little Star? Emboldened by my ingenuity, I look up their number on Yelp and call the restaurant.


“Hi, I would like one Pesto Chicken pizza for delivery please.”

“Great! Where do you live?”

“<address in Duboce Triangle>”

“I’m sorry, but we don’t deliver to that area.”

By this point in the evening, I am becoming so distraught that you’ll see I can only express my true feelings through animated gifs and memes.

Then I try another, I believe it was Pizza Delfina.

“Hi! Do you deliver to Duboce Triangle?”

“We sure do!”

For reasons unknown to science, I briefly turned into Ron Paul and my room turned into a fireworks display.

“Oh thank god! You have no idea the kind of ordeal I’ve been through tonight. Can I pay by credit card now?”

“Oh, I’m sorry sir, we don’t accept credit cards.”

“We do accept personal checks.”

“I…I think I might just have one.”

“But it has to be from the State of California.”

“Well, you could go to an ATM nearby.”

Clearly, she did not understand that this is San Francisco, and the fact that I’ve already done anything more than hit a button in an app and had my pizza magically appear is doing her a favor.

Then I try another — closed. And another — outside of their delivery zone. Finally, I go back to GrubHub, the mistress of my past life, and try to order pizza there. Surely my return to her will embraced!

GrubHub’s embrace was not as warm as anticipated.

Set back yet again, I descended deeper into my existential angst.

Not only had technology failed me, but apparently you can’t even order food by phone in this city. By now, it’s past 11pm and I can’t even go pick up pizza because most restaurants are closed. I may even have to — gasp — order Domino’s. Like common folk.

“But this is San Francisco,” I repeat to myself. There must be a better way. A way that I can obtain my pizza without setting foot outside. A way that I can continue to bask in my domestic incompetence. A way that I can have my pizza, and eat it too.

And then, the answer came to me. Having validated that Postmates will indeed procure me pizza at an exorbitant price, I hatched a plan.

I can tell you I don’t have money. But what I do have are a very particular set of skills, skills I have acquired over a very long career. Skills that make me a nightmare for companies like you.

It turns out, Postmates offers free delivery for your first order, and since this was my first order I was able to waive my delivery fee. This brought my order down from “YOU’VE GOT TO BE KIDDING ME” to “ugh…fine, just put this pizza in my belly.” I sent in my order, and…

I think I may have actually cried a little.

This about sums up my reaction.

I got up. I paced. I took three deep breaths, and resigned that if I hit refresh and it didn’t go through, the six pack of IPAs in my fridge would have to do. Refresh.

We’re going to ignore the fact that it turns out there was a Little Star location 5 minutes from my house…I had just moved and didn’t even consider googling to see if it was in walking distance.

HAZZAH! My faith in the pizza gods restored, I waited patiently for John to bring me my Pesto Chicken thin crust. Given that I was obviously his most important delivery of the evening, I imagine his journey was something like this.

If you squint really hard, I think you can actually see John’s car in the background delivering my pizza.

Meanwhile, back at home…

I mean…I was working on those very important pitch deck slides. You know, about the business things.

Finally, around midnight, my knight in shining armor appeared with the goods. When I got upstairs and opened the box, I nearly cried.

About as close to love at first sight as I think I’ll ever experience.

It was every bit as delicious as it looked and more. Thanks, Little Star.

But let’s not lose sight of the fact that this ordeal took two hours and involved not one, not two, but seven different technology companies (Google, Yelp, GrubHub, DoorDash, Sprig, Munchery, and Postmates). Eight if you count Apple making the iPhone I used for my three failed attempts at calling in an order.

What happened to technology making life easier? What happened to the “uberification of everything” and the “on-demand economy?” Don’t you companies understand? I expect better from you.

After all, this is San Francisco.

Your disgruntled fan,


Product @Square. Prior: built Canvas @occipital, co-founder @Fetchnotes, VP @Benzinga, and chief opinionator @michigandaily.

Product @Square. Prior: built Canvas @occipital, co-founder @Fetchnotes, VP @Benzinga, and chief opinionator @michigandaily.