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HOUSEKEEPING 📨

I’ve had a long weekend here in Argentina. I used my Thursday and Friday to work on some really important personal projects, such as my ‘Rainbox Workstation.’ I am moving back to Australia in a couple of weeks, and my partner and I have secured a nice place right next to Melbourne’s Albert Park Lake.

I am not sure why but I’ve been totally obsessed with the rain over the last years. When it rains in the evening I will turn off all the lights and open as many windows and doors as possible to just enjoy the downpour—the heavier the better of course. So my plan now when I get back to Australia is to be able to work, in the rain, by the lake.

I will keep you all abreast as this useful monstrosity comes to fruition over the coming weeks and months. Anyway, I LOVED writing today’s post. I hope you love reading it. Enjoy!

STRATEGISM 🔮

Strategism: NY Times, A Games Company

New York Times, the most revered name in news, is now officially, a gaming company. It’s not totally uncommon. Nintendo started with playing cards (and love hotels), Wrigley’s gum cut it’s teeth selling soap, and in the tech world, Twitter was a podcasting platform, while Slack was a video game.

But how did we get here? And even more importantly, why? What on earth would compel a 175 year old brand, and the largest media publisher in the want and / or need to do this?

This is our question for today. We’ll take a look at the early days of the Gray Lady, what the Fourth Estate means to democracy through history, the rise, and fall, and (maybe) rise again of legacy media, and more. We’ll also explore how, when pushed, the New York Times was able to find, launch, and execute on what might be a life saving revenue stream. This is a fun one. And it’s not all as simple as it sounds.

The TL;DR

• The gaming revolution: The New York Times has successfully transformed from a traditional newspaper into a digital subscription powerhouse, with games now driving more user engagement than news content.

• Strategic acquisition: By purchasing Wordle and building a games ecosystem, NYT created habit-forming daily rituals that keep subscribers engaged and reduce churn.

• Ecosystem approach: Rather than just selling news, the Times now offers a complete daily ecosystem (news, games, cooking, sports, audio) that follows users throughout their day.

• Financial success: This transformation has driven serious subscriber growth, with bundle subscriptions up 29% year-over-year while news-only subscriptions decline.

• Industry lesson: Traditional media companies must find new ways to create value and daily habits with audiences rather than simply digitising existing content formats.

The founding of New York Times

The New York Times is an American newspaper, in—you guessed it—New York City, New York, and has come to be read the world over by slightly left-leaning business and tech folk, from the worlds of venture capital and finance to media and tech. As of November 2024, The New York Times boast over 11M active subscribers.

But it wasn’t always this way. Founded in 1851 under the original name, The New-York Daily Times, the legendary broadsheet was originally a conservative leaning read. Founded by New-York Tribune journalists, Henry Jarvis Raymond and George Jones, the paper was circulating well through conservative circle, but it wasn’t until the 1870s that it really started to gain notoriety across the United States for it’s series of articles criticising Tammany Hall political boss William M. Tweed (yes, the character from Gangs of New York).

In 1871, The New-York Times published Tammany Hall's accounting books; which led the Tweed being busted for embezzlement and corruption of between $25M and $45M (~$200M today). Thanks in part to the Times reporting, Tweed was tried in 1873 and sentenced to twelve years in prison.

Through the late 19th and early 20th centuries, The Times solidified its reputation for high-quality journalism, adopting the motto “All the News That’s Fit to Print” in 1896. Under publisher Adolph Ochs, the paper transitioned away from sensationalist news—think ‘if it bleeds it leads’ on steroids—to the rigorous reporting and editorial standards we see today. The daily rag became a beacon of objective journalism during a time when partisan papers were all the rage.

By the mid-20th century, The New York Times had established itself as America’s newspaper of record, covering huge global events from World Wars and the Great Depression, to civil rights movements and presidential elections. Its commitment to investigative reporting was famously demonstrated in the 1971 Pentagon Papers exposé, when the Times published classified documents revealing government deception about the Vietnam War, further showing its critical role as a pillar of the Fourth Estate.

The history page of the the New York Times website cites that; “The Times has long deployed journalists to every corner of the world to witness history unfold, sometimes at personal risk.” Something we should all be incredibly appreciative of today.

The import of the 4th Estate

“Were it left to me to decide whether we should have a government without newspapers or newspapers without a government,” Thomas Jefferson would say, “I should not hesitate a moment to prefer the latter.” But what is the Fourth Estate? If you ask Google, it will tell you it is ‘the press; the profession of journalism.’

The history of the Fourth Estate, though, goes back centuries. Depending on which scholarly SEO optimised Google search you do, it can be dated back to around 1787 England, when Edmund Burke MP used the phrase “the Fourth Estate” to describe reporters being admitted to the House of Commons.

Around the same time, the French Revolution of 1789 was afoot. And in France, they had their own version of the idea, except with the first three estates differed somewhat from today’s version.

First, there was the Clergy: official offers of the church, Bishops and the like. Next was the second estate: Nobility. Kings, Queens, rusted on nobles, and those ‘new money’ folks who had risen through the ranks. Next down the rung was: Common people. Typical townspeople, landowners, merchants etc. And then came the Fourth Estate: The Press, or ‘quatrième pouvoir’ as the croissant wielding Français would have it.

The United States would differ slightly from the French and the English. With the U.S. Constitution being settled in 1789—a busy year, the same year as French Revolution—and with neither King, state church, or nobles to speak of, the four estates as the U.S. sees things today are as follows.

In its ideal form, the Fourth Estate offers citizens the accurate information they need to participate meaningfully in democracy, creates a platform for diverse voices and perspectives, and holds the powerful accountable through tough reporting and fact-checking.

This combination of roles explains why Jefferson and other democratic theorists have long believed a free press to be indispensable to a strong, self-governing democracy.

Where did it all go wrong?

There is a famous story from the life of George Best, the man a lot of people would call football’s first superstar. Blessed with rugged good looks, and a mop of hair that led him to gain the moniker of the Fifth Beatle (or the ‘o Quinto Beatle’ in Portuguese as it was the Portuguese who gave him the nickname), Best would go on to a storied career in football, albeit marred with alcohol and drug use.

The possible apocryphal, but fun story goes that one night in 1973, a waiter was called upon to deliver the morning paper, a serving of caviar, and a fresh bottle of champagne to Best’s hotel room. After opening the door, the waiter was stunned to see gambling winnings strewn all over the room, and a half naked Miss World laying on the bed with Best. The waiter looked down at the scene, understanding George’s wasted potential, looked him straight in the eyes and uttered the famous words; “So George, where did it all go wrong?”

This leads us back to the Fourth Estate. An institution that—should you anthropomorphise it—you could look squarely in the eyes and ask the very same question.

Today, in 2025, at least half of the political aisle does not trust the Fourth Estate. While Democratic voters trust in traditional outlets slightly more than they did a decade ago, Independents and Republicans are losing trust, and fast. The latter to a cataclysmic degree. The question is—why?

In 1949, largely to combat and protect against the political one-sidedness seen in the Nazi propaganda machine, the Federal Communications Commission (FCC) passed the Fairness Doctrine, requiring broadcast licensees to present controversial issues of public importance in an honest, equitable, and balanced manner.

This.
Sounds.
Awesome.

Unfortunately for all of us, the Fairness Doctrine had a similar lifespan as the average person in the 1800s—that is to say it was dead before the age of 40—after Reagan administration abolished the policy on grounds that it restricted journalistic freedom and inhibited debate. So it was really Ronald Reagan we can blame for Fox News, MSNC, and the general (Tucker) Carlson-ification of media we see today.

People are sick of it. They are fed up with hyper-polarising, biased media takes left, right and centre today. So they are moving away in droves, prioritising podcasts, social media snippets, and conspiracy laden Reddit threads and YouTube channels to get their news. And the entire legacy media landscape is being forced to accept that they need to adapt or die.

While most publishers doubled down on the same news content that was driving readers away, the New York Times found salvation in an unexpected direction. Their solution to declining relevance wasn't more journalism—it was games.

WTF is a Wordle anyway?

Some companies have been able to transition to digital, but others have fallen victim to what the scholarly amongst us call ‘The Innovator's Dilemma’—clinging to outdated business models while disruptive technologies reshape their industry.

Like Blockbuster dismissing Netflix, or Kodak clinging to film, many legacy media outlets failed to recognise how fundamentally the internet would transform information consumption. But around the same time that the New York Times was looking for ways to digitise, a fun little mobile game was taking over the internet. That game was Wordle.

Created by Welsh software engineer Josh Wardle (obviously born to found this company) as a gift for his partner in 2021, this simple word-guessing game became a viral sensation almost overnight. The Times, recognising both its popularity and strategic fit with their existing games portfolio, acquired Wordle in early 2022 for a reported seven-figure sum.

A perfect—yet altogether quite unconventional—example of how traditional media can adapt to our ever changing consumer preferences.

Sidepiece: Gaming is much bigger than you think

Just quickly before we continue the story of the New York Times, I’d like to stop to show you just how insane the world of gaming is. For me, when I think of culture, I think television and film first and foremost. Star Wars pops to mind, its emotional successor, the Lord of The Rings. I think then of the 90s and the 7pm back-to-back duo of Seinfeld and Friends. Chewbacca, the Wookiees (yes it has two e’s), Newman, Kramer, and ‘where Rachel and Ross actually on a break?’

After film and TV, my mind goes to music. My childhood was filled with the sounds of Pink Floyd, Bob Marley, and Cat Stevens, a man that absolutely positively loves his dog as much as he loves you. Then I think to the Chilli Peppers, Eminem, the artist formally knows as Kanye.

_{*Fun fact: When I was 16-22 or so I saw Kanye play live on three separate occasions. The first, was when College Dropout had just been released and no one knew who he was. It was a great show. The second, was him headlining a popular festival. He sung ‘Hey Mama’ for the first time since his mother had passed away. Incredibly powerful stuff.}

_{The third though was the best. In the wake of his first somewhat unsuccessful album, 808s & Heartbreak, instead of playing his hits, Kayne proceeded to play the backing track to the song Love Lockdown for 25 minutes while he walked up and down the stage abusing the crowd for not understanding his music. Abusing his own fans. It was insane. We were at a Kanye West concert, we’d all paid good money to be at and he was abusing us all. And in turn we were all booing him. The most Kanye West experience ever.}

But the truth is, for decades—music, TV, streaming, even the NFL—roll them all into one and you still don’t reach the size of the video game industry. It really is Mario’s world, and we are just living in it.

And if video games are eating the world, mobile gaming is eating video games.

The rise of gaming as a dominant cultural and economic force shows exactly the kind of digital transition that trad-media needs to navigate. While the New York Times wasn't racing to create the next Fortnite or Minecraft, they knew that engaging, habit-forming digital experiences—such as my tradition with my partner to hit Wordle every night before we go to bed—were key to building lasting relationships with subscribers.

With their bear-hug-ish level of embrace towards interactive experiences, alongside traditional journalism, the Times found a way to remain relevant while staying true to its core mission of delivering quality content—proving that even the grayest of old ladies can learn new tricks in the digital age.

Making the transition from news publisher, to habitual ecosystem

Technically speaking, the New York Times has been a games company—or at least a company that did games—since the the crossword hit their pages in 1942. The initial idea was that during the throws of WW2, readers would have something to take their mind off the terrible news they were reading.

It wasn’t until decades later that we saw the digital version hit the Times’ first website in 1996, and subsequently the Crossword app in 2009. Still though, games were an afterthought.

This would start to change in the 2010s, with the Times taking it’s first steps towards serious gaming. First in 2014, they would (re)release the Mini Crossword by removing the paywall, and lowering the difficulty level for ‘solvers.’

_{*I am not sure when they started this but the New York Times refer to their users as solvers.}

Next, after seeing continued success of the Mini Crossword, came the release of the digital Spelling Bee in 2018, eventually proving there was an appetite for a suite of branded games. And the pièce de résistance, their acquisitive magnum opus—the addition of Wordle in January of 2022.

The acquisition works because it was one piece of the Times’ ultimate habit stacking bundle. Check out the family of New York Times owned apps listed in the app store.

So, while the readership + revenue of other legacy media brands continues to dwindle over time, the Gray Lady sets you up to live your day inside of their nifty little ecosystem.

1/ Start the day, open the New York Times app, get the weather and some news.

2/ At lunch time, check The Athletic to see if your team got spanked the night prior.

3/ Open the audio app during your afternoon dog walk to the sweet sounds of The Daily.

4/ Then open up the NYT Cooking to prepare dinner.

5/ And wind down before bed to some Wordley goodness.

The Times’ also acquired popular gadget recommendation site, The Wirecutter in 2016. Although, it doesn’t have a stand alone app, you can throw some shopping in throughout your day too.

The New York Times is not trying to be your source of news anymore. It’s your full-time sidekick, helping you to get through the daily grind, guiding you every step of the way. And it seems like it’s working.

If you take a look from their Q4 2024 earning report you see something any investor in the Times would like. Growth in bundle and multi-product, and also in digital subscribers. And receding revenues in news only, and overall print subscribers. Sure, metrics moving backwards is never good, but this is a digital transformation story overall.

And if that’s not all, an SEC report from March of 2024 showed that the overall time spent on New York Times apps had shifted so much that games—that’s right Wordle nerdles, GAMES—was now the leader in customer (/solver) time spent.

If the news was the caterpillar, then gaming is now the Times’ beautifully addictive butterfly.

Thanks to the strength of their games product—80% of related Google searches are for games—the New York Times is able to add ~100,000 paying subscribers a month. Not only that, the Times found that a user who has multiple ‘habit points’ is the stickiest. In other words, the least likely to churn.

It’s clear that the brand that used to be known for news is definitely something, and they have big plans. “Our vision is to be the premier subscription destination for digital puzzles,” Jonathan Knight, NYT’s Head of Games has said. They are well on their way.

New media, Trump, and the future of news

The success of the New York Times’ transition may prove important in years to come. Today, we are in the strange place, with most legacy media outlets clinging to relevance in the age of short form content, podcasts and fake news. They are constantly on attack from the right of the political aisle. A lot of pundits actually think the best place to find the truth today is depths of the cesspool that is Twitter. The battle for control of the information landscape is well and truly on.

In 2025, we just went through what they are calling the first ever ‘podcast election,’ with Donald Trump joining Joe Rogan, Andrew Shultz and crew, even Theo Von to talk life, politics and whether cocaine will turn you into a damn owl homie (see below if you miss the reference).

I am somewhat torn here. I’ve listened to podcasts every day since the Ricky Gervais Show was the biggest show in the world. I think it’s the best form of media in the world. You just can’t hide in long form conversations. I have also listened to Theo Von since well before anyone knew his name. But if this is how we are going to grade our politicians moving forward, I think we need to be better. I am not sure how, but we need to be better.

_{*For fun below, I have put the statistics of how many times Trump tweeted since joining the platform. He tweeted 25,000 times during his first term as president. On his most prolific day, June 5, 2020, he tweeted 200 times alone.}

In sum

For verging on two centuries, we have called upon the Fourth Estate—The New York Times, The Wall Street Journal, The Guardian and other journalistic institutions—to provide us with well-researched, deeply fact-checked news. They've given us what we need to know, precisely when we need to know it.

And now the digital age demands evolution for our media, not extinction. The New York Times' gaming strategy shows that traditional journalism can find new vessels while preserving its original mission. For me, it would be a huge gut punch to throw the democratic baby out with the bathwater. Legacy media is dead, long live legacy media.

Playbook / how you can apply this

The playbook the Times rolled out is not applicable to too many businesses, but for those that it is, this is the rules to follow in order to swipe their strategy.

• Identify habit-forming opportunities: Look for daily touch-points where your product can become part of users' routines. The Times recognised that games like Wordle create consistent engagement patterns that news alone couldn't match.

• Bundle complementary experiences: Instead of treating different products as separate revenue streams, create ecosystem bundles that increase overall value. The Times successfully combined news, games, cooking, sports and audio into a unified subscription.

• Focus on retention, not just acquisition: The Times' strategy shows that preventing churn is as important as gaining new users. Games keep people engaged even when they're tired of news content.

• Turn passive consumption into community participation: Transform one-way information delivery into interactive experiences. Games invite engagement while still leveraging the company's core intellectual assets.

• Embrace acquisitions over building (when applicable): The Times saw Wordle's potential and moved quickly rather than building a competing product. Look for existing products that already have audience traction and snap them up.

Fun facts

• The key is a good start: The ten most popular Wordle starting words are; adieu, audio, raise, crane, stare, crate, train, slate, heart, and arise.

• “A new Whig paper” launch ad: The Whigs rose in the 1830s in opposition to president Andrew Jackson, pulling former members of the National Republican Party, the Anti-Masonic Party, and disaffected Democrats.

• Gangs of New York: During the New York City draft riots of July 1863, owner Henry Jarvis Raymond, installed Gatling guns on its roof and windows to deter rioters.

Extra reading / learning

• The New York Times is a games company with a newspaper side hustle - August, 2024

• The NYT’s winning Connection - November, 2024

• Strategism: Unwrapping Spotify Wrapped - January, 2025

BRAIN FOOD 🧠 

TWEETS OF THE WEEK 🐣 

TOOLS WE USE 🛠️

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