Paperboy chronicles

Learning about publishing from the bottom rung

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Gen X kids worked during the summer, other than the lucky ones who went to summer camps. For the rest of us, there were no enrichment classes or internships on offer. We worked as lawn mowers, painters, dishwashers, store attendants, prep cooks and ghosts at boardwalk haunted houses. I believe the idea was to instill a work ethic – not to mention get us out of the house — and maybe even teach us lessons about “the real world.”

Whatever the impulse, this led to my first job in publishing at 13, in the Shore town of Avalon, NJ. My mom signed me up for a paper route delivering the Philadelphia Inquirer for the summer – and, since that wasn’t enough, a spot in front of Orlando’s Bakery to sell more papers. In retrospect, it was odd that a company would rely on random kids to provide essential delivery and customer service. Talk about supply-chain risk. I’d deliver newspapers for an hour or so, then spend four hours in front of the bakery. I don’t remember asking to do this or particularly wanting to do this, but in those days parenting wasn’t as much of a collaborative project. In my imagination, I’d ride my bike around, wing papers perfectly onto doorsteps and then just hang out in front of a bakery for a few hours while getting money to spend on Donkey Kong at the boardwalk arcade or a cone at the Freeze.

My experience was different. Turned out doing the job was harder than I thought. I would often be off target, with newspapers ending up bushes or even breaking windows, as I tried to land it on the doorstep. On a ladies Schwinn three-speed bicycle, jerry-rigged with three baskets of newspapers, your balance is out of whack with the throwing motion. It can be hard to adapt, but if you end up falling to the ground under the weight of 100 newspapers and a ladies Schwinn, you get the message. I found, despite my desire to have the perfect placement in front of the door, my customers hated not knowing if the newspaper would be on their welcome mat or would be somewhere in their petunias. They just wanted it in the same place each day, at the same time. I pivoted to dropping it on the end of the walkway where it meets the sidewalk. Turns out there was no need to show off with the perfect paperboy toss.

What was interesting about the paperboy business is you were working for yourself. The way the Inquirer worked the system is they’d sell me the papers for 25 cents, and I’d resell them for 35 cents. For Sunday papers, the margins were better and the circulation bigger. But like any solo business, you hit a wall. At the beginning, I would get up at 6am, haul in the stacks of paper to fold in three and rubberband. (I still remember the smell of newsprint, and not in a good way; it was nauseating.) Pretty soon, I couldn’t keep up. And Sundays were impossible. The papers came in multiple sections and needed to be assembled and put into plastic bags because they were too big for any rubberband. Luckily, this entire thing was my mom’s idea so she’d rubberband papers with her coffee and on Sundays drive around a wood-paneled Country Squire station wagon filled with newspapers in plastic bags. Thanks, Mom.

Getting a paper route meant being seeded with a customer list. The town was divided up into quadrants, and each kid got subscribers in their area. Many kids were content to just deliver the papers to those houses and hit the beach. I wasn’t enthusiastic about the idea of getting up at 6am, much less doing it every day. Might as well make it worth it. I realized you needed to build your list rather than wait for new subscribers to come your way. What’s more, you got bonuses for signing up new subscribers. That trumped shyness. I put on a nice shirt  – a Polo – and went door-to-door to ask if they wanted to get the paper. Some kids dropped subscription envelopes in mailboxes – this is pretty much the threads approach to newsletter growth – but I found the best way was to ring the doorbell, introduce yourself and shoot your shot. It turns out people liked the human approach.

Yeah, it doesn’t scale. But you always have competition that has better resources and bigger distribution. In the Avalon newspaper game, it was Rainbow, an adult with a van who could deliver far more papers, far more quickly than kids on bikes. He had an entire system, with a massive list, efficient billing and a branded van. Not a great idea to compete head on with that. His multi-person system was based on efficiency. I figured it was better to go higher end and wring more revenue per customer vs trying to deliver more and more papers. So, each week I’d show up to collect my bill, like Johnny after his $2 in “Better Off Dead,” only less adversarial. I timed my collections to 5pm on Thursday and 5pm on Friday.  I found this the perfect time for a 13-year-old in a Polo shirt to come collect for newspaper delivery. The dad would be into cocktail hour and be just delighted there was a paperboy like it was the 1950s. The $3.50 bill usually got a $5 – keep the change, kid – and my margins greatly expanded. Showing up matters.

I applied the same logic to the bakery. As the second-best bakery in town – Kohler’s had far better crullers – Orlando’s got good foot traffic, and the family running it would give me free doughnuts. Other kids had better spots, in particular the waffle house that always had a line around the block. There’s always someone with built-in advantages. The kid at the waffle house just waited for people to ask for a paper, probably because he had the best spot. Sometimes he just left the papers and let people leave the money on top of the stack. Without the volume, I had to sell at a higher rate. So I asked every person who left  the bakery if they wanted an Inquirer – it’s dumb to ask them on their way in because doughnut people are laser-focused on doughnuts – even more if I added “sir” and “ma’am.” Turns out people respond better to more personal approaches.

With the third-party cookie on the way out, publishers are scrambling to understand more about their audiences. That focus on first-party data, while important, is only one piece of the puzzle, since most publishers count 70% or more of their audience as unknown. Enter Bombora, which works across over 5,000 business-to-business websites to identify high value prospects and understand what they’re in the market for buying. The Bombora data co-op allows publishers to tap into this valuable intent data, in a privacy-safe way, as part of a comprehensive data transformation strategy. Learn more about how Bombora partners with publishers to use intent data to improve monetization.


The solo publishing world will likely shrink. Substack is going through a reality check, Medium’s founder is “giving up” and a looming economic downturn will put pressure on subscriptions models. Nathan Baschez at Every’s Divination, a former Substack employee, has a measured but tilting toward optimistic take. One particular challenge is many people have jumped into newsletters around their professional expertise. More will follow the path of Lillian Li, who for the past two years has written the excellent newsletter Chinese characteristics. She’s decided to go back to being an investor. Her sobering view  on the “lonely, nerve-wracking” creator life: “The strain of the balancing act between writing, admin and keeping the vision added up.” My own view is that an independent path not only isn’t for everyone, it isn’t for most. But we’ll see entities that strike a middle ground emerge, whether Every, Workweek, Puck and maybe even Semafor.

Check out my podcast with Joe Marchese if you have a chance. It was a great conversation about why bundles will persist, the limits of performance advertising and how most media is a front end for other (better) businesses.

Efficiency and scale usually come at the expense of quality. Podcast ads are a great example. Podcasting has so many things going against it as an ad medium: terrible measurement, easy ability to skip, and no way to immediately interact with a placement. But the podcast ad market has steadily grown, in large part because it’s mostly still ads read by humans. Naturally programmatic is coming, promising targeting and efficiency and scale. The result: dynamically-inserted ads piss people off.

The church-and-state divide is theoretically about managing conflicts, but it ends up often being used as a power play. The “editorial side” historically was told to stay ignorant of how the business works – and don’t mind that the people making the most money at the company aren’t the ones actually creating the product. My hope is that in the rebundling the same hustle doesn’t repeat itself.

Thanks for reading. I recorded a great conversation earlier today with Workweek’s Adam Ryan, so be sure to subscribe to The Rebooting Show on Apple or Spotify. Also, if you’re not already subscribed to the newsletter, please do.