The last time I did a mailbag or Q&A, it was early 2022. Much has changed since then. I can’t give a good reason for why I didn’t do another one, only that time passes far more quickly than I ever realize. If you like these, I’ll make it a recurring feature. For now, the mailbag is open to everyone, but in the future, I will probably restrict the questions to paying subscribers. I’ve got to find ways to turn more of you wonderful non-paying people into wonderful paying people. In the meantime, I tried to get to as many of these as I could. Without further ado…
I’d love to know how you choose what to write about and how you organize your work. As in, do you outline first or shoot from the hip?
I believe outlines are excellent, but I generally do not do outlines, unless I am writing a novel. And even then, the outline is sparse, and I’m bound to deviate from it. With longer projects like that, I use the analogy of following the lighthouse through the fog. I see the light there, I know where I’m going, but I’m on open seas and you never quite know how you’ll end up where you need to be.
When I write something shorter than a book—whether it’s a magazine feature or a piece for this Substack—I always want to get my first paragraph down before I do anything else. The lead (or lede), for me, is crucial. Once I’ve found I know how to start, the rest of a piece can flow. When writing a Substack, I find basic headlines, even if they are placeholders, can jumpstart a piece.
In some sense, I shoot from the hip—structure matters, but I think writers and teachers sometimes overrate structure. I write a fair amount of essays, for example, and I can say that how I learned to write analyses as an undergraduate and graduate student had little bearing on how I write essays today. The reader demands a certain profundity of thought and style. It matters what you are saying and how you say it. The how, though, doesn’t have to be a pared down, reverse pyramid-style efficiency. I am happy to meander from time to time. Reported journalism is different—a magazine or newspaper piece demands structure, and in some sense you are a little engineer with words—and conveying critical information, to the public, is your primary aim.
How do I choose what to write about? For Substack, it really is what strikes my fancy. I follow the news and think about how I can add to the conversation. Sometimes, I get stray thoughts and try to expand them. I believe long walks (or shorter runs) are a great way to get the mind flowing. I keep a notebook, too, and try to jot down ideas. Occasionally, I tweet something and decide this really needs to be expanded into something bigger. I read a good deal, and from my reading, ideas generally flow. I’ve got a natural urge (or itch) to write and I get restless if I’m not doing it for more than a day or two. That’s genetic, I suppose. You can’t teach someone to be that way. Writing brings me great pleasure.
I’ve got a lot more to say on writing words here.
Hi Ross! Do you have any thoughts about the recent layoffs impacting big tech, and how that relates to tech’s ambivalence with society over the last decade?
The tech layoffs can be viewed as a market correction. For more than a decade, we’ve had nonexistent interest rates and nonexistent inflation. Money was easy. And with that easy money, in the world of Big Tech, came the idea that you only have to figure out a business model later on. In the twentieth century, capitalism obeyed certain rules of gravity. If General Motors or U.S. Steel couldn’t turn a profit, they couldn’t dominate. Smaller businesses were the same way. A bank could loan you money and give you some runway, but at some point, soon, you’d have to figure out how to make a profit or it was all over.
The calculus changed with the arrival of the tech giant. Amazon showed you could be a money-loser for a while as long as you achieved market dominance. Eventually, Amazon made money—lots of it—and other ambitious start-ups could point to that model when talking up venture capitalists. Venture capitalists know most start-ups will fail but they only need to hit one homerun to be set for life. One Facebook, one Google—or invest in something that gets acquired by one of those behemoths, like Instagram.
The trouble with all of this is that it creates a deeply unrealistic business environment and slowly divorces business from the public good—what most people require to live better lives. Henry Ford was a raging anti-Semite, but assembly line automobile production did a lot of good for the United States while making him incredibly rich. I don’t think Facebook, TikTok, or addictive smartphone technology are public goods in the same way. I’m going to steal a point from Matt Yglesias and say we live in a disconcerting era when our very smartest engineers and computer scientists are engaged in the relatively useless mission of bolstering social media or figuring out how some app can further suck up a person’s attention span. This kind of talent should be channeled into trying to launch a manned mission to Mars, curing dreaded diseases, combating climate change, or figuring out how to make public infrastructure far more efficient.
I think back to 2019, when I wrote extensively on Uber’s dubious business practices. Uber still does not turn a profit. Yet it has saturated the market to such a degree and intimidated politicians enough that it doesn’t really matter. Uber won. How did Uber win, exactly? The company still has not figured out how to make money. And it’s unclear to me if we're all better off for it. Uber has brought convenience to urban life. But couldn’t we have just equipped conventional taxis with smartphone apps, as we’ve done belatedly? The streets are flooded with cars. Uber undercut taxis by keeping their fares low for many years, and they were able to do this because VC cash kept flowing. It was the sort of model that couldn’t exist 30 or 40 years ago. Now Uber fares are rising because they’re a public company and can’t light cash on fire forever. Or can they?
The great correction is here. Interest rates will stay high. Many tech companies, especially those without incumbency advantage, are getting punished.
Any thoughts on the prospects or lack thereof for ending at-will employment at state/federal levels?
I support the concept of strengthening workplace protections and making it, in general, much harder to fire people. You don’t want to swing the pendulum too far the other way where you get a workplace culture like Japan's in the twentieth century—no one gets fired, and therefore companies feel they have a right to controlling your entire life—but the U.S. is nowhere near that reality. I think you’ll continue to see efforts, with rising unionization, to end at-will employment. I’m not sure how successful, ultimately, this will all be, given the transient nature of some workplaces and corporate America’s general commitment to union-busting. I’m hopeful some good will come. Just as important is building the kind of federal safety net where losing a job doesn’t spell financial disaster. Free childcare, free (or very cheap) healthcare, subsidized housing, and better public transportation options can certainly do this.
I’ve been reading Richard Rorty’s more political writings, recently. Rorty considered himself a leftist but pissed off a lot of other leftists, advocating points of view and approaches grounded in his version of pragmatism that seem to anticipate some of yours. Have you read Rorty? If so, do you have any thoughts on his political writings?
I haven’t read much of Rorty, but I read, with great interest, the recent essay in Harper’s about how his ideas have influenced the current political discourse. I do have some concerns about pragmatism and the idea, true in a philosophical sense, that an objective truth cannot be found. Unwittingly, perhaps, Donald Trump has become something of an embodiment of Rortian concepts, of what happens when truth itself does not matter, only outcomes. I see some of these pathologies on the left, as well. The idea is that if the other side lies, we have to lie too, as long as we are combating them and doing it for the worthier cause. I very much wish Rorty were alive today, as I long for the Gore Vidal resurrection, so we wouldn’t have to speak for him. He would be appalled by Trump but I would also want to know how he reckons with a man who lives his very life in a (pathologically selfish) pragmatistic manner, wholly concerned with what his words can achieve for himself and his movement.
“Does Trump know he lost the election? In a way, it’s an absurd question. It’s a mistake to ask what Trump really thinks about X or Y. Confronted with an issue, he aims and fires—or, sometimes, he fires then aims,” Mark Edmundson asks in Harper’s. “Is Trump a racist? Is Trump a sexist? Is Trump a patriot? Is Trump an advocate of freedom? Trump is not anything. He is what will get him what he wants at any given moment. He aligns himself with what he senses will advance his cause—and his cause is himself.”
Have you seen Love & Mercy about Brian Wilson?
Yes! I saw it back in 2015, when it was released widely. Love & Mercy, for those who don’t know, is the biopic about Brian Wilson, the founder and visionary behind the Beach Boys. It’s a great film in its own right and can be enjoyed by anyone, even those who know little about the band or Wilson’s tortured life. Paul Dano, with real brilliance, plays young Wilson during the making of Pet Sounds, and John Cusack portrays him in early middle age as he’s trying to escape the clutches of his predatory psychologist, Eugene Landy, played with wonderful menace by Paul Giamatti. What makes Love & Mercy work, for me at least, is that it’s as accurate a portrayal as you’ll ever get on film of the making of a rock record. Only extensive archival footage, of the like found in The Beatles: Get Back, will bring you any closer to such a genesis. You’re with Brian and the boys as he dreams up one of the greatest albums ever made. You’re with Brian as he achingly auditions “God Only Knows” for his bullying father and is told, dismissively, the song is too “wishy-washy.”
When I saw Love & Mercy for the first time, I was not, at all, a devotee of the Beach Boys. I had heard Pet Sounds but little else. It would take another seven years for me to transform into the obsessive I am today. I own, as of this month, about 22 Beach Boys vinyl records and I’ve heard almost all of their very enormous discography. I’ve read five books about the Beach Boys and I wrote more than 8,000 words about the band last year. Naturally, I had to rewatch Love & Mercy, this time with the discerning eye of someone who has spent countless hours listening to and thinking about them. The movie certainly holds up. If I have any criticism, it’s how Bill Pohlad, the director and producer, chose to portray Van Dyke Parks and the Smile period. Naturally, you can only do so much in one movie, and cuts had to be made. But the making of Smile, so pivotal to the Beach Boys legend and also a turning point in Brian’s fragile mental state, is elided more than I would have liked, and Parks himself, a fabulous lyricist and musician, is sidelined almost entirely, portrayed as a strange and mostly inconsequential accomplice to Brian. I would’ve liked some nod, too, to the post-Smile era, when the Beach Boys did some of their best work, increasingly without Brian. You can watch a film like this and have no idea that Wild Honey, 20/20, Sunflower, Surf’s Up, and Holland ever happened. You can have no idea that Dennis Wilson evolved into the band’s second most talented songwriter. I also wonder how much the image of Brian’s second wife, Melinda Ledbetter, is enhanced by the film. Melinda is shown as the sole force who liberated Brian from Landy, when it was family members like Carl, his brother, who also played such a role in real life. There is no 1980s version of Carl in the film and that, for me, is problematic.
What are your thoughts on WBC/World Series debate and what it means to baseball in the US and worldwide?
I wouldn’t pit the two against each other. The World Series is the World Series, and will always be preeminent for American fans. But I love how the WBC has evolved. The 2023 edition, culminating with Team Japan’s Shohei Ohtani striking out Team USA’s Mike Trout, was its greatest yet, and it’s deeply exciting to see how many different nations and territories rally behind their teams. The viewership statistics are stunning. More Japanese tuned into a WBC game than any event of the Tokyo Olympics. In Puerto Rico, more than 60 percent of households watched a pivotal game for Team Puerto Rico. Venezuelan, Dominican, Colombian, and Mexican fans were raucous during games in Miami, packing the ballpark. Some fans will gripe about the players who got hurt in what is technically an exhibition series—for many players, this is their de facto World Series—but you can ruin your season in spring training, as Gavin Lux demonstrated. It’s not like Harrison Bader is lingering on the IL for the Yankees because he went to play for Team USA. The WBC has really grown on me and I’m already excited for the next one. It’s a reminder that baseball, for all the talk of its challenges in the United States, has never been more popular around the world. It is more of a global sport than American football and outstrips basketball in East Asian, the Caribbean, and parts of South America. The Czech Republic is apparently taking to the game, too.
Two thoughts, any sense of what's happening in the city council races? (Feels pretty sleepy but I'm also in Crown Heights where no one is getting challenged in the districts near me.) / Is there a way for Hochul to actually build power during her time in office?? I don't see anything right now to change what feels like her being sidelined by the assembly/senate, when most dems (especially in power: Heastie, Cousins, Gianaris) aren't in danger from a primary or a republican challenge and I doubt would operate any differently with a simple majority vs. supermajority.
The NY City Council isn’t entirely sleepy. In the general election, Justin Brannan should have a competitive race in my neck of the woods, in southern Brooklyn. The redrawn district, taking in Bay Ridge and Coney Island, has become more Democratic, so I expect him to win. Marjorie Velázquez in the eastern Bronx will also need to work hard against a Republican. I expect her to prevail. Watch the City Council race in Harlem, where socialist (but not DSA-endorsed) incumbent Kristin Richardson Jordan is endangered. I don’t know who will win but I increasingly do not think it will be her.
Can Kathy Hochul build power? Yes! She’s the governor of New York for the next four years. Don’t underestimate the clout of that office. The legislature, undoubtedly, enjoys a great deal of leverage, but it did under Andrew Cuomo as well once Democrats took control of the State Senate. In 2019, I’d argue the Democrats in both chambers very much sidelined Cuomo. I am very curious to see how this budget develops. My sense is Hochul is already getting her way with further changes to the state’s bail laws.
Longtime fan of your reporting. As someone who grew up in new york city and is now planning on moving back in September, one of the biggest concerns on my mind is housing prices - I've had friends who grew up in my neighborhood (the upper west side) leave for cheaper cities (like Nashville), or if they don't work in very high paying industries (like tech, finance, law), have to move to places in manhattan or brooklyn that are quite far from where they grow up due to high rents.
My question is - what is your understanding of the current dynamics of Hochul's housing plan among the legislature? The recent legislative budgets removed the state over-ride provision, rendering the targets effectively meaningless. Will Hochul prioritize this over other policy goals the legislature disagrees with (like the charter school cap, or bail reform changes)? And how willing do you see the democratic caucus being to go along with such changes?
These are very good questions, and should be answered soon. I’m on the record arguing that overriding local zoning in the suburbs to build more housing is a fine idea, and it’s the only way you’ll get the housing you need to counter decades of stagnation. Will it happen? We will find out soon. I would guess that the state legislature, worried about a suburban backlash, will try to neuter the plan as much as they can.
The reality is that even if Hochul gets what she wants and progressives win on Good Cause eviction, limiting rent increases and evictions, housing will still be far too expensive in New York. Creating supply will help, but it’s not as if that’s a short-term answer—it will take many years, realistically, for a supply-driven approach to pay dividends, and this is something YIMBYs must acknowledge. The real answer is that government, both state and federal, gets back in the business of building housing, encourages the creation of social housing, and tries to subsidize as many affordable units as possible. We need more public housing (repeal the Faircloth Amendment) and a revival of the Mitchell-Lama-style developments. We need an SRO revival. Cheap, dignified single-room housing will go a long way toward solving this perpetual homelessness crisis.
Hi, I appreciate your work and am a big fan!
Why is Eric Adams decreasing library funding? The library is a cultural resource for everyone and offers resume and Internet services for people in temporary housing. I don't understand why this has become a hot button issue here.
What do you make of the new We Heart NY campaign, riffing on the Milton Glaser classic?
School support staff in LA are striking over low pay. I know NYC DOE paraprofessionals are paid very low salaries. Is there a comparison to be made between LA and NYC public schools? How do the salaries of paras and teachers compare to people working for other NYC departments?
Eric Adams reminds me of Michael Bloomberg, in some ways. Bloomberg seemed to revel in the “budget dance,” forever threatening social service cuts that the City Council would have to reverse in budget negotiations. Cutting library funding seems morally wrong but also politically silly; it really doesn’t cost all that much to have a world-class library system. Neighborhood libraries should be open seven days a week, from dawn to dusk. The city budget is large enough to accommodate this. It’s about priorities. Adams is not a bleeding heart liberal, and the fate of libraries may not be all that meaningful to him.
The We Heart NY campaign has a whiff of desperation to it. I’d try to be more creative. The logo, at the minimum, is ugly.
I can’t speak as much to the New York-Los Angeles comparisons, other than to say teachers, once they’re in the system long enough, are fairly well-compensated in New York. I think starting salaries should be raised to attract more young talent. The backend of it—if you last long enough—is pretty good, with a strong pension and paid time off. I don’t know para salaries offhand but I imagine they make much less. In general, the salary situation is less dire in New York so you aren’t seeing labor unrest. Housing certainly is very expensive but there’s a greater supply of somewhat affordable apartments in New York near public transit than there are in Los Angeles.
You can snap your fingers and get any one (1) New York politician, at any level, to change their position on one (1) issue. The change can be as drastic or nuanced as you want. Which politician and issue do you pick for maximum impact?
What's the maximum number of ducks you think you could take in a fight? The ducks are normal but they absolutely will not give up.
These questions! Not many ducks. I am little afraid of them. I went to a high school with a duck pond and the geese were a bit menacing. The ducks, less so, but I imagine I’d successfully kick a few ducks before the rest would swarm.
I’d pick the governor, I suppose, and get her to make an FDR/LaGuardia-style commitment to the mass construction of affordable housing in New York. I’d love to see New York marshal its enormous resources—we have the money of a small nation sloshing through here—towards the cause of getting us the kinds of housing developments we saw regularly built at midcentury.
I’ll cheat an add a second: to get Hochul to care about building transportation infrastructure efficiently. New York wastes absurd amounts of money. Andrew Cuomo didn’t care at all about this and Hochul, so far, hasn’t made a move toward reforming an awful contracting process or cleaning out the consultant waste when it comes to building a few miles of railroad track. For the love of God, import some global transit experts and give us what they have in Paris, Rome, London, Tokyo, or any other modern global city. Expand the subway system in a serious way. Build out a map that has been, in essence, frozen in time since the late 1920s. (No, the Upper East Side Q expansion doesn’t impress me, nor does the 7 train to Hudson Yards.) What if we got the Utica Avenue line? Subway lines running out to Nassau County and down the Van Wyck? The R to Staten Island?
Avid reader ever since I listened to you on the Bad Faith podcast!
I really would like to ask about the role of worker cooperatives in the “progressive” capital that is NYC. Is there presence growing in the city? Does it have any political backing, any pending laws that would impact them, etc.
Thank you for all that you do!
It’s a good question. I’d like to do more research before I give you a thorough reply. What I’ll say is, generally, there aren’t many of them. In New York media, though, I can think of one good example: the worker-owned local news organization, Hell Gate. With media start-ups, the cooperatives definitely hold appeal. Too many bad bosses and stupid corporate owners out there. I expect to see more of them in the future.
I was going to ask you if Jay Jacobs should resign or be fired because of the loss we suffered in the 2022 Congressional elections but I have another one.
Peter Beinart today announced that, next week, he has Bill DeBlasio on his weekly Zoom show. Is DeBlasio laying the groundwork for a primary run for NY CD#10. What is your opinion on that?
I am not in a position to say whether anyone should be fired. It’s obvious, at the very minimum, the New York Democratic Party is not a functioning political organization. This is a problem that goes beyond Jacobs. There are reasonable arguments for dumping him, but then there would need to be a plan in place to create a statewide party that can recruit candidates, fund them, and play a significant role in getting out the vote. New York is a long way away from that. It will be up to Kathy Hochul, the titular head of the Democratic Party, to make it happen. But the many House Democrats in New York who have been MIA will have to step up, too. Where’s Hakeem Jeffries in all of this? Or, for that matter, where is Kirsten Gillibrand or Chuck Schumer? Neither senator has taken any interest in this project.
I would be shocked if Bill de Blasio ran against Dan Goldman. I don’t expect him to hold elected office again.
What do you know about the current status of the DOHMH? Would you consider doing an article about them in extensive detail?
Not as much as I should! Depending on what I heard—or what I found—I could be open to reporting on what is happening on the agency in the future. City agencies have been bleeding headcount under Eric Adams. Municipal government is not functioning as it should.
Maybe you have commented elsewhere - but of course your take on the potential indictment, both legal and political analysis, would be great to read.
Since this was sent, Donald Trump has been indicted. I expect he’ll be indicted again in Georgia. The Manhattan DA’s case is built around charges that are, within the context of Trump’s transgressions, somewhat marginal. It may be a winnable case, but jail time strikes me as unlikely. In the meantime, Trump can play the martyr. We’ll see what happens. He’s the clear favorite to win the 2024 GOP nomination. I’ve felt this for a while.
And that’s all for this mailbag! Thank you for the great questions. I’m off to Japan for the week. See you all very soon.
Pretty sure Handsome Dan could be beaten handily by anyone who chose to point out that he's a physical avatar of the Vampire Squid - why is it that no one seems to know his name is Dan Sachs Goldman?
Why bribe/fund a flunky when you can put your relations in charge?
"But couldn’t we have just equipped conventional taxis with smartphone apps, as we’ve done belatedly?"
Actually, no we couldn't have, because the taxi industry was very fat and happy to stay stuck in the 20th century, customers be damned. Not unlike the restaurant industry. That had to be forced by the market to catch up to the 21st century.