Zillow Surfing Is the Escape We Need [Content Made Simple]

Issue #199: Will Fleets work? Thoughts on paid newsletters. Happy Turkey Day!

Have a wonderful Thanksgiving, everyone! And Happy Christmas season! Thank you for subscribing to this newsletter. I am grateful for all of you and I hope this is helpful for you.



Scrolling through real estate listings in far-flung destinations is a way to visualize an alternate life, whether you’re trying to move or not.



Millions of people have spent far more time at home than they expected to this year. It’s made many of them daydream about what it might be like to live somewhere else, often while scrolling through listings on Zillow.

“I go into neighborhoods that obviously I can’t afford as a college student and look at my ideal house and fantasize about when this is all over,” said Crystal Silva, 20, who lives in North Carolina. She spends hours at a time surfing the app, touring homes she’ll never buy.

She’s likely not alone in that. Zillow usage has climbed since March, with online visitors to for-sale listings up more than 50 percent year-over-year in the early months of the pandemic.


I laughed really hard when I saw this story from Taylor Lorenz in the NYT because I have found myself mindlessly scrolling Zillow more than usual since March. We have no plans to move. We just had our master shower re-done into a larger tiled space. But Taylor is on to something here—there is a therapeutic element to scrolling Zillow without any intent to move or buy a new house.


Episode #028: Fleets and Thanksgiving Faves

This week on the podcast, we talk about our thoughts on Twitter’s new Fleets feature as well as our favorite Thanksgiving foods.


Link #1: Will Twitter’s Fleets Work?

I share my thoughts on whether or not Fleets will work.

Twitter has always struggled with monetization. Its lackluster advertising features and effectiveness have always been a thorn in the side of Twitter’s shareholders. As a social media consultant and former manager I can tell you that “running Twitter ads” is almost always a waste of money and generally not a good idea.

But with Fleets, Twitter has a whole new way to easily deliver advertisements that have every reason to perform better than tweets in a timeline. Instagram has indicated that their stories ads are very successful, and it is honestly just a more natural place to see an ad for lots of folks than in the main Twitter timeline.

Link #2: Apple Fights With Facebook Over Ad Tracking Dispute

I often praise Apple for their consistency in caring for user privacy. I often bash Facebook for the opposite—the concern for monetizing user data. Here, we see the two titans of tech clashing on the topic.

An Apple executive slammed Facebook for having a “disregard for user privacy” after the social media firm criticized ad targeting restrictions coming to the iPhone.

In an open letter to the Electronic Frontier Foundation and other privacy watchdog groups, Apple’s senior director of global privacy, Jane Horvath, said Apple was making it harder for advertisers to track people across iPhone apps because “we simply think tracking should be transparent and under user control.” The coming changes, which Apple delayed in September after Facebook and others pushed back, will require an app to gain consent before using data about a user to inform ad targeting elsewhere.

Link #3: The Multi-SKU Creator and Newsletters

This is a super insightful commentary on the indie-zation of the writing/creator industry. I’m bookmarking this to refer back to in the future.

A number of reporters and columnists these days are “going indie,” detaching from their previous employer and signing up with a site like Substack, Patreon or Medium to get paid for their writing by their readers. The motivations are usually blends of seeking freedom (to write at their own cadence and on whatever they want to cover) and the accelerating austerity at media companies from ad supported business models collapsing. Friends of mine like tech journalist Casey Newton have recently made this transition (he left Vox to launch Platformer) so I’ve gotten a bit of insider perspectives on the ambitions and economics of these launches.

Much of the discussion around the sustainability of this movement is focused on the math of converting readers (or followers) to paying subscribers. “If she can get just 10% of her 500,000 Twitter followers to pay $100/year…” is the type of simple analysis that accompanies both the glass half-full and glass half-empty outlooks, benchmarked against either their previous salary or some notion of what economic success looks like. And while this framing isn’t wrong, it’s very incomplete. It’s my belief that very few “Substack writers” will make 100% of their income from their newsletter and this won’t be a failure of the platforms but instead related to the nature of creation itself. Enter, the Multi-SKU Creator.


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