BRANDS THAT BET ON THE WRONG SIDE OF HISTORY
I'm annoyed at myself for not reminding people to register to vote, so let me say it plainly: if your state lets you show up and vote, GO. This is a hugely consequential election, and I say that as a full-blown history and political junkie.
What makes America work is its constant reinvention. This has always been the place where dreamers come to succeed, the Frank Sinatra promise that if you can make it here, you can make it anywhere. Watching that promise get dismantled is horrifying to me, and I think a lot of people underestimate how much of the country's power lived in it.
Now I'm hearing that brands that cozied up to Trump are fearing the backlash, looking to add prominent left-leaning individuals to their boards. I understand why his message to business was seductive. Tax talk, deregulation talk and the promise of a friendly White House are easy to want. But I (and many others) never believed it was a sustainable position, and anyone who built a brand strategy on it made a short-term bet with long-term money.
I don't have data on how many brands are worried, only what I'm hearing from conversations, so take that as my read of the room and not a survey. My read is that customers, employees and creators have long memories, and they keep receipts.
Here is the takeaway for founders and brand leaders. You can always choose to be on the right side of the long-term swings, and you should audit who you have aligned with, publicly or quietly. If you chose proximity to power over your own customers, don't expect them to forgive it, and don't expect them to forget it either. Also… VOTE.
MAHJ MATTERS: BRANDS, GET YOUR TILES IN A ROW
What do Meghan Markle, Steph Curry, Sarah Jessica Parker, and Mindy Kaling have in common? Love of the Mahj. I can add one more name to that list, mine. I am fully, unapologetically addicted, and now I'm busy rearranging my whole week to squeeze in as many games as possible.
So when I say mahjong is having a moment, I'm speaking from the table. Between September 2024 and August 2025, Yelp searches for "mahjong clubs" rose 4,467% and searches for "mahjong lessons" rose 819%. Read those together. People aren't only curious about the game, they're looking for a seat at a table and someone to teach them how to sit there. That is a demand for belonging.
The money has taken notice. Oh My Mahjong turned a $10,000 investment into $30 million. That's just one company's story, but it tells you the appetite is real and people will pay to be part of the ritual.
A game with roots in China, reshaped by Jewish American communities, and kept alive by Asian American families has now become a shared language across cultures. That is cultural exchange spreading faster than any ad budget can.
Passion always has the possibility to go viral, and brands that join in authentically get to partake in that virality. The ones that only borrow the look of it will watch the crowd move on without them.
EMPTY OFFICES, FULL OF LETTUCE
The most interesting business idea in Chicago right now is growing lettuce in a building that used to hold cubicles. Innovation gets overrated as a buzzword and underrated as a habit, and this is the habit in action.
Walk Michigan Ave or a few blocks off it and you will still see vacant storefronts and half-empty office buildings, years after life supposedly went back to normal. Companies keep pushing people to return to work, and the buildings keep telling a different story.
Then I learned Chicago is home to the first vertical farm repurposed from an office building, and I immediately thought of Matt Damon growing potatoes in The Martian. I am a lifelong sci-fi fan, so seeing it happen in my hometown, inside real estate everyone else had written off, made my week. FarmZero describes its mission as bringing fresh, locally grown produce to the urban environment year-round, and I will let the company's own description stand for its operations.
This is what Chicago does best. We are a start-up city that gets very little love next to the coasts, and we keep producing the next big thing while everyone is looking elsewhere. Office space is hard to turn residential, so someone asked a better question about what the building could be.
My takeaway for founders and marketers is to audit what you have labeled dead weight. An aging product, a stalled channel, or a customer segment you gave up on may be a vacant floor waiting for a different use. Most companies will keep waiting for the old demand to return, and they will lose to the people who stopped waiting, usually from the cities nobody was watching. If your brand cannot name a single thing it has abandoned that someone else could build a business on, you have not looked hard enough, and a competitor probably has.
MOMSOMNIA AND THE MIDNIGHT SHIFT
There is now a name for why so many moms are awake at midnight, and the name is a little too cute for what is actually going on. I found "momsomnia" while mid-slog through my daughter's 4th grade year, where she needs us more and our days have stretched right along with her.
The term gets tied to sleep expert Dr. Shelby Harris, who talks about revenge bedtime procrastination: staying up late on purpose to claim some quiet the day never gave you. She also describes a brain so tuned to listening for your kid and planning tomorrow that it won't power down.
My take is that the sleep angle is real, but the headline is the hidden work. Women still carry most of the unpaid care work, and that includes the mental load of schedules, homework, logistics and emotional weather, none of which shows up on a ledger. When the only time you control is 12:30 a.m., that tells you what the other 18 hours cost.
For marketers, this is a media planning opportunity. A huge buyer is awake and paying attention at the hour most plans ignore, so test late night campaigns and see what she actually responds to. Then make sure what she finds at midnight is worth her time, which means something that measurably makes her life easier, pitched to her like the CEO of a household, because she is one.
Skip the pastel "self-care" bottle. If your product can't give a woman time back, don't brand it as a gift to her, and don't spend her 12:30 a.m. on it.
Brands love to claim they see women, but most only show up when she has nothing left to give. If you want her attention at midnight, earn it by doing the work that put her there in the first place.
WHAT IN THE WNBA?
The WNBA got lucky when the Valkryies lost game six, because a championship cannot be crowned at 12:30pm on a Thursday. I say that as someone who wants this league to win everything, and that is exactly why the scheduling made me wince. The league has spent years building real momentum with fans, sponsors and players, and a title decided while most of the country is at work or in school would have handed critics an easy line about a league that does not know how to showcase its own product. Sponsors buy attention, and they remember where their logos sat when the biggest moment of the season landed in a dead time slot. Players who fought for respect, investment and visibility deserve a stage that matches what they have earned, and one afternoon tip-off can make hard-won progress look like a rounding error. Congrats to the Valkyries on the title, and congrats to the league for escaping the headline it almost wrote itself. My takeaway for anyone building a brand on the rise: growth gets you invited to the big table, but timing, placement and respect for your audience decide whether you get to stay. Momentum is a business asset, and you can burn it with a single careless calendar decision.
MUSK WINS FOR NOW
I think the Streisand effect is the most reliable law in marketing, and the Musk documentary is the newest proof. Try to bury something and people go looking for it, and that instinct is older than any ad platform.
Since I wrote about the ad blackouts last month, Bleecker Street Films has been bought by another eBay billionaire. Sadly, the blackouts did not stop, and the box office suffered for it. But with a pending streaming deal, and the studio already pushing up the PVOD release date due to demand. So we'll see if money can beat the Streisand Effect.
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