If All Else Fails, Cast a Nasty Spell on Google
On agility and learning to fly.
POD 143: Substack as Unicorn
Anonymous Banker joins to unpack Substack's $100 million funding round that values the creator platform at $1.1 billion. The valuation is a classic bet on potential vs reality, as Substack’s execution has been spotty. We unpack the bet on creating an OnlyFans-like network, presumably with less risqué content. Plus: the mini-pivot to livestreams, AI's brand problem with Gen Z, Google Discover gets compressed, the power shift to golf YouTube, and AI coming for Excel jockeys because nothing is sacred. Out Friday AM. Listen.
PVA CONVERSATION
Troy: Wilbur was a high-agency guy.
It was the Wilbur Wright story that stuck with me as a try to pull a thread through the topics we discussed on the podcast this week.
I came across a very clickbaity X post asking for “all-time great articles,” and someone replied with “High Agency in 30 Minutes” by George Mack. Thirty minutes is a little long for my puny attention span but I took the bait. I enjoyed it so much I sent it to my kids who probably won’t read it just like I don’t read things that my mom shares from Facebook.
Maybe the story is true, maybe not. Doesn’t matter. It’s part of a broader lesson: take control of life before it takes control of you.
Back to Wilbur… you know the guy who invented flying. Well as the story goes, Wilbur had a nice childhood and everything was bright and sunny as he prepared to head off to Yale. Then, a cocaine-addled, serial-killing psychopath beat the shit out of Wilbur with a hockey stick and derailed his plans.
Fortunately for all you jet setters, Wilbur was obsessed with birds. So while bedridden, he ordered lots of books about birds and physics and mechanics and things from libraries and boned up on the topic. Around the same time the New York Times, ever the sourpuss, declared “Man won’t fly for a million years.” Wilbur was undeterred. He called up his brother, moved to a more breezy Kitty Hawk, North Carolina and got to work. The locals thought they were dumb asses. But, step by step they built a flying machine. Last year, 6 billion people boarded one.
Turns out, Wilbur was an epically high agency guy.
The world is navigating a period of violent change. Change demands agility. Agility requires agency. This post is a great primer.
Agility is the business strategy
Business is, at its core, the art of managing change. And today’s level of disruption demands more agility than I can remember.
What does it mean to be agile? Like really agile... not committees, consultants or 24 month plans, agile. Like water is filling the boat, we better do something now, agile.
I suppose it is the ability to ruthlessly and courageously focus energy and resource on the next thing while ringfencing and minimizing investment on the old thing that pays the bills. Agility requires the vision of where to go next, but prioritization is even more important as crushing forces put pressure on the now. A good reminder.
OpenAI appears to be very agile company
Former OpenAI employee, Calvin, gives us a view into a company that is navigating crazy scaling pressures with its deeply meritocratic culture, moving resources fearlessly against fast shifting mandates, accepting the chaos as a necessary but manageable consequence. Sensibly, Slack is the communication operating system inside OpenAI. Email is an afterthought.
OpenAI is incredibly bottoms-up, especially in research. When I first showed up, I started asking questions about the roadmap for the next quarter. The answer I got was: "this doesn't exist" (though now it does). Good ideas can come from anywhere, and it's often not really clear which ideas will prove most fruitful ahead of time. Rather than a grand 'master plan', progress is iterative and uncovered as new research bears fruit.
Thanks to this bottoms-up culture, OpenAI is also very meritocratic. Historically, leaders in the company are promoted primarily based upon their ability to have good ideas and then execute upon them. Many leaders who were incredibly competent weren't very good at things like presenting at all-hands or political maneuvering. That matters less at OpenAI then it might at other companies. The best ideas do tend to win.
Brian thinks agility will come from embracing the idiosyncratic
From this weeks post… traditional media brands like consistency and polish. Brian is advocating a messier path:
While much of the focus of the AI-and-media discussion has focused on the important issues of getting paid for training data and driving efficiencies in a more-with-less era, comparatively less has been placed on the essential question of how publishers can win loyalty in a world mediated by AI.
That's led many to lean on idiosyncrasy, both in terms of the brands they create and business models they pursue. In the Traffic Apocalpyse™, nobody knows what their businesses will look like in three years, so you might as well just do things. That will lead to messy brands and messy strategies…
A brand like Emily Sundberg’s Feed Me is a case in point. It’s very idiosyncratic because, as Emily likes to say, it’s a product of her experience in the world. That makes it a difficult brand to pigeonhole. The organizing construct, to me, is around what it’s like to be a striver in New York. The flattening of global culture means that audience is worldwide, not just literally in New York City. Brands like Feed Me cut across categories in ways typical media brands do not.
As predicted, Google Discover won’t save you
Google is about to choke off more of your distribution by highjacking Discover links with AI summaries. I remember when Google actually cared what publishers thought.
Anyway, Discover is useful traffic but not the beautiful high-intent stuff that’s connected to people looking to buy stuff. Regardless… the future is less of it and you will absolutely need to be more agile.
If that fails, you can cast mean spells on Google buy buying them from witches on Etsy. I didn’t know you could do this. The WSJ breaks it down for you here: Etsy Witches Charge for Jobs, Sunshine and Knicks Wins. Business Is Booming. Selling spells online shows massive agility.
Witchcraft and spellwork have become an online cottage industry. Faced with economic uncertainty and vapid dating apps, some people are putting their beliefs—and disposable income—into love spells, career charms and spirit cleansers.
Old interfaces need new agility
And in even more news that threaten things that seem to never change. A new release from OpenAI promises to allow you to create spreadsheets and decks without using tools from Microsoft. Apparently, Microsoft doesn’t love the idea. AI ravages all information interfaces. From the Information, OpenAI Preps ChatGPT Agents in Challenge to Microsoft Excel and PowerPoint:
In the latest example, OpenAI has developed features that let ChatGPT customers quickly create and edit presentations and spreadsheets that are compatible with PowerPoint and Excel directly in the chatbot without using the Microsoft apps themselves, according to a person who has used the new features.
First it happens slowly
Finally… from the annals of how things change slowly then fast. Imagine this… The sleepy ole game of golf. The PGA, a powerful monopoly who fiercely protects its IP. A well-funded rival in LIV that hasn’t done much to change the status quo. Then, guess what really threatens PGA dominance while juicing the popularity of the game. YouTube Influencers that’s who.
This week YouTube heavyweight Grant Horvat bowed out of a PGA tournament when they banned his camera crew.
“The reason I will not be playing in a PGA Tour event is due to the rules and regulations around media rights and filming during tournament play of a PGA Tour event," Horvat said in a video on his YouTube page. "Basically, that means I was not going to be allowed to film my round during tournament play.
For me personally, doing YouTube for a living and wanting to document everything I do — this is the reason we got the invite in the first place was because of YouTube and because of the amazing experiences I get to share because of you guys."
All to say that a new generation of golfers having more fun on YouTube is the most important challenge to PGA dominance we have seen to date and this says a lot about media rights now. And that’s why we need to be supremely agile.
Fun pod this week. Look forward to your reactions.
ANONYMOUS BANKER
The First Big Substack Deal - Will It Happen?
While Bari Weiss’s publication may not look like it’s on Substack (they’ve done a good job customizing their template), it is, and it may be the most valuable thing created on the platform thus far.
How did we get here… over the past week, since the NYT reported on a potential transaction that sprang from the annual Allen & Co. conference, there’s been fervent speculation; will she sell, and why would this make sense?
Let’s take stock of The Free Press: a lean digital newsroom with ~1 million subscribers, ~136k of them paying, and an estimated $10 million run-rate revenue. It’s staffed by just 25 journalists and producers and has built a distinct, independent, and intentionally unaffiliated brand with Trump, which, in today’s media landscape, is as much positioning as it is editorial strategy.
So why would Skydance be interested?
There’s no real way to “combine” the Free Press with another newsroom; this would be a new lane entirely. But that might be the point. As traditional media companies chase bundling strategies and linear TV continues to decay, the opportunity to build a differentiated, direct-to-consumer news brand with a clear voice, a loyal audience, and actual unit economics looks increasingly attractive.
Skydance, especially with the support of the CBS ad sales team, could likely double revenue by layering in sponsorship and newsletter-based advertising. Subscription and ad revenue could hit parity, particularly on platforms like email, where the audience is already highly engaged.
And maybe most importantly: this gives Skydance a real shot at leading in newsletters, where most legacy players (Disney, Comcast, etc.) still don’t know what they’re doing. Dow Jones gets it. CNN’s trying. But The Free Press is already one of the largest newsletter-native brands and one that can keep scaling.
There’s also platform leverage. The Free Press has figured out how to win on Substack. That knowledge of how to build, grow, and monetize in this ecosystem is a real asset that could be applied to the rest of the Skydance portfolio. It's not easy to execute, but it's valuable if done right.
From a valuation standpoint, the rumored $100mm valuation would equate to a ~10x revenue multiple. That’s steep, but with advertising synergies, the effective multiple might land closer to 5x. For a fast-growing media asset, that’s not crazy. Others have paid more for less.
This could be a solid deal for Substack, a smart bet for Skydance, and a signal that independent media, built for email, not algorithms, is just getting started.