The Best Non-Obvious Books of 2025, How to Break AI and the Wrong Way to Measure Innovation
Dear Fellow Non-Obvious Thinker,
I’m in Indonesia this week for an event and sorting through more stories than usual, given the gift guide from last week and plenty of travel time on my 30-hour journey over here. The big news this week that many of you probably already saw was the announcement of our Longlist Selections for the Non-Obvious Book Awards. Those were the Top 100 Non-Fiction books of the year selected from well over 1200 entries that our team received in the past months.
I’m the crazy traveler who took about a dozen books in his carry-on bag this week (yes, I have heard of the Kindle – but I prefer the physical books still!) and I’ve made it through more than half of them already. The Shortlist selections are coming December 16th so there’s more judging to do! Aside from books, you’ll find a full range of stories this week on everything from intentionally breaking AI to the innovation lesson Apple hopefully learned from the slow sales of the iPhone Air.
Enjoy and stay curious!
This Week’s New Videos …
How the Breakers Might Make Everything Better … Just After They Destroy It
Back in the year 2000, I remember driving to a client meeting on the streets of Sydney and sitting in the car outside their office building trying to hack their network. We were selling network security, and this was our cyber equivalent of pulling a rabbit out of a hat. In the boardroom an hour later, we’d walk in and show them how easy it was to break into their system from a car sitting outside. And then they would hire us to fix it.
I didn’t have the language for it at the time, but we were breakers without evil intent. The memory came back to me this week as I read about how Google is experimenting with replacing news headlines with AI clickbait nonsense and a writer tired of AI stealing his content has started feeding it “poison pill” stories to mislead the algorithm on purpose. There are entire hackathons united in their desire to break AI chatbots. This is a breaker movement, and I suspect it’s only going to get stronger. On the surface, anger and frustration with these new tools and their ubiquity is driving a lot of this behavior. The result, though, may ultimately be the same as it was 25 years ago with our street hacking scheme.
Eventually, the systems got better as teams like ours came in and figured out how to fix them. It’s almost unimaginable that anyone could hack into a system from a car parked outside a corporate headquarters today. The breakers create change, no matter what they break or how they break it. I’m not sure if that’s a conclusion that should give us hope or the opposite.
Apple Finds the Wrong Way to Measure Innovation
The iPhone Air is a sales disaster with some media outlets reporting “virtually no demand.” The latest Samsung S25 is also facing disappointing sales results. Both phones have doubled down on a feature that was supposed to matter more than any other: thinness. In the quest to make a thinner phone, these latest versions compromise on camera quality, feature less powerful batteries and generally leave out features that their predecessor versions all offered. The result is a common miscalculation that could have been avoided.
Consider the point that Ogilvy legendary ad man Rory Sutherland often makes about “the power of ideas that don’t make sense.” It’s a classic case of optimizing for the wrong thing. When every phone maker optimizes getting the handset to be as thin as possible, they miss out on the other aspects that might be even more appealing for people – such as a battery that lasts the entire day without needing a mid-afternoon recharge.
The example offers a good reminder that even the world’s most innovative companies can get caught in the trap of chasing the wrong metric. Unfortunately, the worst way to learn this lesson is by having too much product sitting on warehouse shelves. Samsung is going the opposite direction with a tri-fold phone that may be popular because it’s so different to anything else in the market. Which sort of proves the point that it’s better to be completely unique than to chase the same expired metric.
The AI Data War in Retail Is Just Getting Started. Lessons from Black Friday …
Last week was the biggest sales week for many online retailers as the Black Friday and Cyber Monday deals all took over. I did my own takeover of the newsletter as I usually do to share a holiday gift list. Now that I’m back sharing stories this week, there have been plenty of reports about what happened on Black Friday and who were the winners and losers from a numbers perspective. Online sales were strong and reportedly up 4% (though these gains may be canceled out by inflation), while store sales were mixed.
The interesting thing about this sales week and the growing role of AI in pricing is that it’s increasingly creating scenarios where pricing is dynamically adjusted based on a number of factors. One story this week mentioned that the price of eggs from one Target store to the next may vary based on real-time market data. On the flip side of this dynamic pricing are the growing capabilities for AI tools to aid consumers in the buying process. ChatGPT launched their shopping research mode and AI has gotten exceedingly good at common consumer tasks such as searching for otherwise hidden discount or promo codes.
All things point to a dual sided war powered by AI data analytics on the retail side allowing extremely granular real-time dynamic pricing … and AI shopping tools on the consumer side allowing online shoppers to always find the lowest prices and most money-saving discount codes.
The Non-Obvious Media Recommendation of the Week
Armchair Expert
Imagine celebrities hanging out on a couch talking about their lives, and Hollywood insider stuff and just random conversations. That’s pretty much the Armchair Expert podcast hosted by actor Dax Shepard (with frequent cameos from his wife Kristin Bell) and the episodes are just easy listening for the background in just about any situation. This isn’t a serious show; it’s more like ambient conversation. But amidst the random topics and easygoing chatting, there are gems of wisdom and insights about things you might never otherwise consider. For that reason, it’s a bit of an unusual recommendation for me as my media choice of the week (and maybe I’m influenced by having a bit too much time on planes listening to podcasts lately), but I’d say give this one a try and see what you think.
The Non-Obvious Book of the Week
The Non-Obvious Book Awards Longlist Announcement …
After months of deliberation, entries and reading – our team has selected the Top 100 Non-Fiction books of 2025. You can see the full list on the awards website and there are some fantastic (and unusual) reads on there. On December 16th, I’ll be posting my live announcement of the Shortlist and the five overall winners for the Best Non-Fiction Books of the Year – so make sure to bookmark that if you love books. In the meantime, see the full list of books and buy from Bookshop.org to support independent bookstores!
Even More Non-Obvious Stories …
Every week I always curate more stories than I’m able to explore in detail. Instead of skipping those stories, I started to share them in this section so you can skim the headlines and click on any that spark your interest:
- The Christmas Tree That’s Lit by Sh*t … Literally
- The Long Awaited Spaceballs 2 Says They Have Been Filming at Ludicrous Speed, Naturally
- 3D Solar Towers May Be Common in the Future
- John Popper on ‘Run-Around’ at 30 — And Nearly Dying This Year
- The Maldives’ Next Chapter
How are these stories curated?
Every week I spend hours going through hundreds of stories in order to curate this email. Looking for a speaker to inspire your team to become non-obvious thinkers through a keynote or workshop?
Watch my new 2025 speaking reel on YouTube >>
