AI Is Coming for the Middlemen: What Investors Should Watch
AI agents could disrupt search, travel, shopping, and lead generation by changing how consumers make decisions. Here’s where investors should be watching.
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AI Is Coming for the Middlemen
Some of the internet’s most profitable businesses sit between buyers and sellers. AI agents could change that.
✍️ Editor's Note
For most of the AI boom, investors have been asking one question:
Who wins?
Which chipmaker wins? Which software company wins? Which cloud provider wins?
But technological revolutions create losers, too.
And one of the most interesting possibilities emerging from artificial intelligence is that AI could threaten an extremely profitable Internet business model:
Being the middleman.
Think about how much of your online life involves intermediaries.
You don't call 30 hotels to compare prices. You visit a travel website.
You don't visit every insurer individually. You use a comparison service.
You don't browse every retailer on the Internet. You search Google or Amazon.
You don't personally evaluate thousands of available financial products, restaurants, contractors, or software applications.
Other businesses help you find, compare, and choose them.
And many make billions of dollars doing it.
But what happens when your AI can do that work for you?
That could become one of the most important - and underappreciated - investment consequences of AI.
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🤖 Meet the AI Shopper
Imagine telling an AI assistant:
“Find me a nonstop flight to Miami next month, departing Friday afternoon and returning Monday evening. I want an aisle seat, don't want to fly Spirit, and the total trip should cost less than $500.”
Today, you would probably open a travel site and start searching.
Tomorrow, your AI agent could potentially search multiple airlines and travel services, compare the results, account for your preferences, and present you with the best three choices.
Eventually, it might complete the transaction.
Now apply that concept to everything else.
“Find me the best homeowners insurance policy.”
“Renew my Internet service at the lowest available rate.”
“Find a four-star hotel within walking distance of this address.”
“Choose the best accounting software for my five-person business.”
“Order another six months of the vitamins I normally buy, but switch brands if there's a better value.”
Suddenly, the AI isn't simply answering questions.
It's becoming the customer.
And that's potentially a huge change.
💰 The Internet's $100 Billion Tollbooths
Some of the world's most successful Internet businesses essentially operate tollbooths.
They aggregate buyers.
Then businesses pay for access to those buyers.
Google is an obvious example.
A plumber might pay Google because someone searches for:
“plumber near me.”
Travel websites earn money by connecting travelers with airlines and hotels.
Marketplaces connect buyers with sellers.
Lead-generation companies connect consumers with mortgage lenders, insurers, contractors, attorneys, and other service providers.
The economics can be fantastic because the middleman doesn't necessarily manufacture the product being sold.
It controls something enormously valuable:
The customer's attention.
AI agents could challenge that arrangement.
If I ask my personal AI to find a plumber instead of searching Google, who controls my attention?
If my AI compares hotel prices for me, do I need to visit an online travel agency?
If an AI negotiates my insurance renewal, how valuable is the comparison website I previously used?
The answer won't necessarily be “not valuable at all.”
But investors should start asking the question.
🔎 Four Businesses That Could Feel the Pressure
✈️ 1. Online Travel
Travel is almost tailor-made for AI agents.
There are enormous numbers of flights, hotels, rental cars, prices, restrictions, loyalty programs, and consumer preferences to evaluate.
That's exactly the kind of complicated comparison problem AI is getting better at solving.
Online travel agencies aren't going to disappear tomorrow.
They have enormous inventories, relationships, brands, payment infrastructure, and customer bases.
But the investment question is different:
If AI becomes the primary interface for planning travel, who owns the customer relationship?
That's worth watching.
🛒 2. Shopping Search and Marketplaces
Online shopping currently requires consumers to do a surprising amount of work.
Search.
Scroll.
Compare reviews.
Check prices.
Investigate specifications.
Decide whether the reviews are trustworthy.
An AI shopping agent could potentially compress that entire process into one request:
“Find the best cordless drill under $150 for occasional homeowner projects.”
The consumer might never see 50 competing products.
The AI may reduce them to three.
That creates an entirely new battleground:
How does a company get its product recommended by an AI?
For decades, companies optimized websites for Google.
The next era may involve optimizing products for machines making recommendations on behalf of humans.
🏠 3. Lead-Generation Businesses
Some industries pay extraordinary amounts for qualified leads.
Mortgages.
Insurance.
Home improvement.
Legal services.
Real estate.
Financial services.
That's because a customer who's actively looking for one of these services can be extremely valuable.
AI could potentially insert itself between the consumer and today's lead generator.
Instead of filling out a form asking five insurers to contact you, your AI might collect quotes and compare policies itself.
That doesn't eliminate the need to connect buyers and sellers.
But it could change who gets paid for making the connection.
🔍 4. Traditional Search
This may be the biggest one.
For more than two decades, we've been trained to search the Internet using keywords.
AI introduces a fundamentally different behavior.
Instead of:
Search → websites → research → comparison → decision
we could increasingly move toward:
Question → AI → decision
Every step AI eliminates potentially affects someone else's business model.
Traditional search is extraordinarily entrenched, and advertising isn't going away simply because AI exists.
But if fewer commercial decisions begin with a conventional search-results page, the economics of online customer acquisition could change dramatically.
📊 What Investors Should Actually Watch
Trying to predict that “Company X will be destroyed by AI” is probably a mistake.
Major companies adapt.
They buy competitors, launch new products, change business models, and sometimes become leaders in technologies that initially threatened them.
Instead, I'd watch several measurable signals.
1. Where are searches beginning?
If consumers increasingly begin commercial searches inside AI assistants rather than traditional search engines or marketplaces, that's significant.
2. Who owns the transaction?
Providing an AI answer is one thing.
Allowing the consumer to actually purchase through the AI is much more important.
3. Who pays for placement?
The moment businesses begin paying meaningful amounts to appear inside AI recommendations, an entirely new advertising market could emerge.
4. Are customer-acquisition costs changing?
If AI sends buyers directly to suppliers, some businesses could spend less on traditional intermediaries.
That money doesn't simply disappear.
It moves somewhere else.
Finding where it moves could reveal the investment opportunity.
⚠️ Don't Declare the Middleman Dead Yet
There's an important counterargument.
AI agents themselves may need the middlemen.
An AI planning a vacation needs reliable information about hotel availability, airfare, reviews, prices, and reservations.
An AI shopping assistant needs product catalogs, inventory information, payment systems, shipping data, and trusted sellers.
Today's marketplaces already possess enormous amounts of that infrastructure.
So rather than being destroyed, some middlemen could evolve into the infrastructure behind AI agents.
There's another possibility.
They could build powerful agents themselves.
Amazon doesn't have to sit back while someone else develops an AI shopping agent.
Google doesn't have to surrender commercial search.
Travel companies don't have to let outside AI companies own travel planning.
That means the real battle may not be:
AI versus the middleman.
It may be:
Who becomes the middleman for AI?
👀 The Vault Watchlist
Over the next several years, I'd keep an eye on three developments.
🤖 Agent Transactions
Watch for AI platforms moving from recommending things to actually purchasing them.
That's the crucial leap from chatbot to economic agent.
💵 AI Advertising
Someone will eventually figure out how businesses compete for visibility when machines - not humans - are choosing what gets recommended.
The economics could be enormous.
🤝 Direct Supplier Relationships
Watch airlines, hotels, retailers, financial companies, and service providers.
If they can connect directly with consumer AI agents, some may have an opportunity to reduce the tolls they currently pay intermediaries.
🔐 One Idea to Take From the Vault
One of the easiest mistakes in investing is looking only for the companies a new technology could help.
Sometimes the bigger opportunity comes from asking:
Whose economics does this technology threaten?
AI agents could eventually do much more than answer our questions.
They could search for us.
Compare for us.
Negotiate for us.
Shop for us.
And eventually transact for us.
If that happens, some extraordinarily profitable businesses sitting between buyers and sellers could discover that the Internet has a new gatekeeper.
At the same time, entirely new gatekeepers could emerge.
Investors don't need to know the winners today.
But it's worth watching who controls three things:
The recommendation. The customer relationship. And the transaction.
Because wherever those three things move, a lot of money could move with them.
Vaulting Your Wealth Forward,
– T. D. Thompson
AI Investing Vault
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