What if Jay Gould Ran a Media Company in 2025?
A Robber Baron’s Guide to AI-Era Media
Editor’s Note: A career spent in traditional media has left Eric with a vivid imagination for an internet that actually supports and nurtures a thriving media ecosystem. This post represents one of his fever-dream scenarios that we used to host a vibrant Group Chat.
What if a ruthless operator like Jay Gould was running a media company whose content was stolen by AI? (Pick your fave Robber Baron from the 1860s looking to maximize leverage against content. Maybe you're a Vanderbilt fan.)
If you were Gould, what might you do? Here are my answers:
Eric Gillin
Media Executive
1. Collude and Sue
Get every premium publisher together and form a content cabal that would set prices, unify around a single shared user identity -- critical in an age of AI bots pretending to be humans anyway -- pool data and analytics and negotiate as a bloc. Then set up industry-wide monitoring to sue for every single instance content gets stolen. (Not legal, or possible, but whatever. We're pretending it's the 1860s. This is a thought experiment.)
2. Block AI and Search
Take Cloudflare CEO Matthew Prince up on his offer and block all web crawling for AI and social, while we're here. Starve the models of any information after 2024 and build a moat around all new fact-based content. (Have fun with those gift guide ideas from 2023!)
3. Use Social Like a DTC Brand
Only post content to drive real business outcomes. Figure out LTV and CAC models that work, use paid spend to acquire subscribers, upsell superfans and use your handles to generate direct ad revenue. (Call me if you want to discuss that last point -- this can happen right now.)
4. Make Your Website Awesome
Now that you're invisible to search and AI and using social as a marketing channel, your website can be what users want it to be and your new business model requires -- not what Google algorithmically demanded it be. Make it a single screen web-based app. Get rid of that right rail. Make the ad experience immersive. Use AI to personalize the hell out of it. Go back to whatever you wanted the web to be in 1996. There are no more rules.
5. Reinvent Measurement
Now that you have a monopolistic content cabal sharing identity and first-party information, partner with credit card companies and use AI to track conversion. Invent a new mid-funnel metric around intent. Map identity back to credit card conversion data to prove performance out of the mid-funnel. Negative sell against last-click attribution, framing it as a land of dark patterns and fat thumbs.
6. Acquire Talent, Share Readers
To rebuild the top of the funnel, sign influential creators to exclusive publisher-only deals. Continue to use social like a DTC brand. Force your cabal of publishers into using AI to cross-promote each other's content, optimizing against clicks, LTV, etc.
Is any of this possible? No. Would Gould even do this? Probably no.
In his day, Gould was not on the content side. He was a pipes guy and bought railroads and telegraph lines. But I think he'd also recognize that in an AI era, content has become a pipe.
My point: great, high-quality journalism and new facts are super valuable to the AI powered future.
Unlocking that scarcity could take some ruthless behavior.
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