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It was 2007 and my wife decided not to return to her corporate job after the birth of our first son. It was a decision I fully supported and has paid dividends since. But our budget was…. screwed.
Between school loans, dumb credit card debt, and now just one paycheck for three people, we weren’t in a good spot at all. We took a financial literacy class, and the speaker kept saying “Look, if you need cash right now, get a job doing something like delivering pizza.”
So I took the advice literally and secretly started delivering pizzas on the weekends.
And I was freaking amazing at it. I memorized the stoplight patterns. I would spend my free time learning cul de sac street names. I converted the backseat of my car to maximize pizza warming and safety. And I reached the point where I could deliver to multiple houses and get back to the shop before most drivers had made it to their first destination.
I could make $25-90/night in tips, depending on how well folks tipped. So it amounted to an average of $150+cash-in-pocket each weekend – dollars that carried my family in that season of life. You could also make and cook yourself a free pizza on each shift, so I would bring home lopsided small pizzas each night. I ate a lot of pizza.
I also learned a lot of life lessons. More on that in a minute.
@PIZZAPIZZA
Of course I set up a Twitter account called @pizzapizza to start to document my weekend adventures as a pizza delivery person!
The iPhone had yet to be introduced, and I was a full-time Blackberry guy. Twitter was a few months old, and I was still using the SMS text-based version of Twitter where you tweeted by text and received tweets via text. Yes, that was how Twitter worked back then.
I used the @pizzapizza account to document tips, misadventures, and nightly $ totals. And overall, I used it to keep myself sane and distracted in an extremely stressful season of life: I was a sleep-deprived new dad. I was delivering pizzas all weekend long. And I didn’t want any of my day job coworkers to know what I was doing.
Even in those early social media days, the account developed a bit of a reputation around town. City Pages, our local alternative newspaper, wrote about it as a reason you should always treat delivery people well – and tip them! And in hindsight, I really shouldn’t have been posting people’s full first and last names when they stiffed me. Even if they were shitty tippers, in hindsight I sincerely regret that move (and yes, I’ve since deleted all those tweets).
But combing back through the account has been a blast from the past. And some common themes started emerging.
Here are some gems from that season of life…
TIP YOUR PIZZA DELIVERY PERSON
animals and pizza don’t mix
PEOPLE ARE… WEIRD
LABEL YOUR DAMN HOUSE. turn on your lights. answer your phone.
PIZZA DELIVERY IS COMPETITIVE
PIZZA PHILOSOPHY
WHY DID YOU STOP DELIVERING THE 🍕?
Well, our budget turned around! We were fortunate to start making one paycheck work for our family, and I quit! And turned in my branded polo shirt and hat for the deposit. And I kind of forgot about the account. People continued to cite @pizzapizza as a reason to tip well, but otherwise life went on.
And then…. dun dun dunnnnn! Three years later — in 2010 — I got an email that Little Caesar’s had finally discovered Twitter and was taking my account from me based on a trademark infringement claim.
What’s hilarious about this is I was actively helping other big brands grab their trademarked accounts from brand-jackers at my day job. I was adept at working with reps to use that trademark ID # to grab those accounts. So it was startling to find myself on the other end of that experience, for once.
Unfortunately, Little Caesar’s took the @pizzapizza handle, branded it, tweeted for less than 6 months and then abandoned the account. In fact, they haven’t tweeted at all 10 years. It’s a travesty, really. And yes, I just emailed Twitter to ask for it back. I won’t get it back, but it’s the principle of it all.
But for now, the the spirit of @pizzapizza lives on as @pizzapizza_ (underscore), which is the handle Twitter assigned me after the trademark infringement.
SHOULD I TIP MY PIZZA DELIVERY DRIVER A MINIMUM OF $5? YES.
Here’s the deal: Always tip everyone at least 20% and minimum $5.
If you are asking another human being to pick up food, drive it to your home, and bring it to you using their own vehicle, gasoline, and time, you should always tip at least 20% and always a minimum of $5.00. Don’t assume a delivery charge, if there is one, goes to your driver. They usually don’t.
If you are asking another human being to pick up food, drive it to your home, and bring it to you using their own vehicle, gasoline, and time, you should always tip at least 20% and always a minimum of $5.00.
When you are working in a service industry where your primary compensation is tips from white collar folks who are better off than you, you realize a lot about the world. Many of them don’t make eye contact. Some treat you like crap. Some of them barely notice your existence in their self-important world.
So when you constantly have to work your butt off to please unpleasable people who hold all the power, you can get pretty jaded. And angry. And feel trapped. This observation won’t come as a surprise to the huge amount of folks who find themselves in this situation daily or weren’t born into privilege as I was. But it was a necessary lesson for me. I’m grateful for it.
And in today’s COVID-19 lifestyle, the U.S. has largely pivoted into a delivery culture. So I think it’s more important than ever to pay attention to how we treat the hard working souls who bring us packages, food, and mail.
After all… You never know when your pizza delivery driver may be tweeting about you and your tip from an anonymous Twitter account.
GREG SWAN 
This is fair. It has been a little while since we ordered pizza for delivery but our usual tip was $3 (or $1 per box if we had more boxes) and it’s time for a change.