Revenue
October 13, 2026
The Next Media Winners May Be the Ones Willing to Shrink First
# B2B Media
# Enterprise Value
# Business growth
# AI
# Data
# Revenue optimization
# CEO Strategy
# Customer Retention
# Events Industry
Why strategic focus, recurring revenue, and AI-driven intelligence may create more enterprise value than growth alone.
Heather Holst-Knudsen
The Next Media Winners May Be the Ones Willing to Shrink First
In a recent episode of The Revenue Room™ with Jon Howland, a provocative question emerged: What if the fastest path to greater enterprise value starts with walking away from revenue?
What if the smartest growth strategy isn't to get bigger—but to get smaller first?
For decades, the growth playbook across media, events, and information services has been relatively straightforward: launch more products, attract more customers, expand the event portfolio, and find new ways to monetize an existing audience.
But there's a problem with that playbook.
More revenue doesn't necessarily mean more enterprise value.
A business can grow while becoming less profitable, more operationally complex, and harder to differentiate. It can add customers who consume disproportionate resources. It can launch events that generate revenue but distract from more valuable recurring-revenue opportunities. And it can accumulate products that no longer deserve the capital or attention they require.
In a recent episode of The Revenue Room™ with Jon Howland, the conversation challenged one of the most deeply held assumptions in business: that bigger is always better.
For CEOs navigating AI disruption, changing customer economics, and pressure to create enterprise value, a different growth philosophy is emerging.
The companies best positioned to win the next decade may be the ones disciplined enough to abandon parts of the last one.
Here are five tensions from the conversation that every media, events, and information services CEO should be thinking about.
1. The Most Valuable Revenue May Be the Revenue You Walk Away From
Growth is easy to celebrate. Strategic subtraction is harder to explain.
Yet one of the most compelling themes was the willingness to challenge revenue that looks attractive on the top line but contributes too little to the long-term economics of the business.
Which customers create more complexity than value? Which products absorb management attention without generating attractive returns? Which events should disappear because they don't support the company's most valuable growth engine?
One example explored how greater customer selectivity coincided with retention improving from roughly 80% to 93%. New-business annual contract value doubled despite acquiring approximately half as many new logos.
The lesson isn't that every company should pursue fewer customers.
It's that customer quality, revenue durability, and economic contribution matter more than customer count.
Another example examined the ambition to move EBITDA margins from approximately 10% toward 20%. That kind of improvement demands more than incremental cost reduction. It requires rethinking which activities belong in the business at all.
For event operators, the question becomes especially pointed: if an event generates revenue but doesn't strengthen subscription annual recurring revenue, deepen a strategic customer relationship, or create a defensible market position, is it really helping?
The provocative question: If you had to rebuild your company today, which 20% of your revenue would you refuse to bring back?
2. AI Is Making Information Cheaper. That Changes What Customers Will Pay For.
AI is forcing an uncomfortable reckoning across the information economy.
If customers can summarize content, synthesize research, and generate plausible answers in seconds, the value of simply possessing or distributing information is under pressure.
That doesn't mean proprietary information businesses are doomed.
It means their competitive advantage has to move beyond content access.
The episode explored how established information assets—including decades of specialized financial-services content—might be transformed into more valuable intelligence products.
The opportunity is not merely to apply AI to existing content and call it innovation.
It's to turn differentiated information into something customers can use to make better decisions, reduce uncertainty, or act faster.
That shift has significant implications for capital allocation.
Should a company build its own AI capabilities? Partner with technology providers? Acquire specialized talent or assets? Reorganize product development around new customer workflows?
There is no universal answer. But waiting for the technology landscape to settle is itself a strategic choice—with a cost.
The real question is not whether your company has an AI strategy. It's whether AI makes your business more essential or more replaceable.
For CEOs, that distinction will increasingly determine pricing power, defensibility, and ultimately valuation.
3. The Events Growth Paradox: Bigger Can Make You Less Valuable
Events businesses face a particularly interesting contradiction.
Scale is usually considered a sign of success. More attendees, more sponsors, more exhibitors, more revenue.
But some of the most valuable events succeed precisely because they are difficult to replicate.
Their power comes from the concentration of decision-makers, the quality of interactions, and the scarcity of access.
The episode examined event businesses experiencing annual growth in the 20–30% range while wrestling with how to preserve the experience that made those events valuable in the first place.
Consider an event with 3,000 attendees where approximately 300 participants drive a disproportionate share of the strategic value.
The challenge is obvious.
How do you expand the business without diluting the experience for the people who matter most?
How do you create year-round digital products, intelligence offerings, and recurring commercial relationships without weakening the flagship event?
And when does another thousand attendees create more congestion than value?
This is where traditional event growth metrics can become misleading.
An event's value isn't simply a function of how many people attend. It's a function of who attends, what happens because they're there, and whether that value can be extended beyond the event itself.
The next generation of successful events companies may look less like traditional organizers and more like high-trust, high-value commercial ecosystems.
But that transformation requires discipline. Not every audience extension deserves to become a product. Not every event deserves to scale.
Sometimes scarcity is the asset.
4. Calling Yourself a Data Business Won't Earn You a Data-Business Valuation
Across media and information services, the aspiration to build higher-value recurring-revenue businesses is hardly new.
Everyone wants more subscriptions. More proprietary data. More predictable revenue. Higher valuation multiples.
But there's an important distinction between adopting the language of a better business model and actually building one.
Recurring revenue is valuable when it is durable.
Data is valuable when it is differentiated, difficult to replicate, and embedded in customer decisions.
Subscriptions are valuable when customers have compelling reasons to renew—and when the economics support attractive growth.
Simply relabeling content as intelligence or bundling products into annual contracts does not create those characteristics.
Nor does adding a data product automatically transform the economics of an events or media business.
The real work is harder.
It means developing proprietary assets, building products around consequential customer problems, improving retention, and creating commercial models that compound over time.
Enterprise value isn't created by the category you claim to occupy. It's created by the quality of the economics you can prove.
That raises a question every CEO should be able to answer:
If a sophisticated buyer examined your business tomorrow, what evidence would convince them that your future revenue is more predictable, profitable, and defensible than your historical revenue?
If the answer depends mostly on a strategic narrative, there is more work to do.
5. The Biggest Barrier to Growth May Be the Business You Already Built
Perhaps the most revealing theme is that CEOs often know what needs to change.
They understand the appeal of recurring revenue. They recognize the potential of proprietary data. They see the disruption AI is creating.
The obstacle is execution.
Legacy sales compensation may reward the wrong revenue. Customer data may be fragmented across products and platforms. Technology infrastructure may make cross-selling harder than it should be. Teams may be organized around historical business lines rather than future customer needs.
And leaders may be reluctant to disrupt profitable products before the replacement economics are proven.
These are not minor implementation details.
They are strategic constraints.
A company cannot credibly pursue a recurring-revenue strategy while rewarding its commercial organization primarily for one-time transactions.
It cannot deliver integrated customer intelligence if its data remains trapped in disconnected systems.
And it cannot build a focused portfolio if every legacy product has an internal constituency defending its existence.
The hardest part of transformation isn't identifying the future business model. It's dismantling the habits and incentives that protect the old one.
This is where CEO leadership becomes decisive.
Not through another strategy presentation, but through resource allocation, organizational design, commercial incentives, and the willingness to make unpopular choices.
The New Growth Question: What Deserves to Get Bigger?
The central takeaway from this episode of The Revenue Room™ with Jon Howland isn't that growth is bad.
Quite the opposite.
The opportunity to build valuable businesses across media, events, and information services remains substantial. AI creates new product possibilities. Proprietary information can become more commercially powerful. Events can anchor deeper, year-round customer relationships.
But growth is becoming more selective.
The winning question is shifting from How do we grow everything? to Which parts of this business deserve to compound?
That means being willing to:
- Walk away from low-quality revenue.
- Protect the scarcity that makes an event valuable.
- Invest in intelligence customers cannot easily replicate.
- Prove the economics behind recurring-revenue ambitions.
- Rebuild operating models around the business you want to become.
None of these choices is easy. Most involve near-term tradeoffs. Some may make the business smaller before they make it more valuable.
But that's precisely why they matter.
The next winners in media, events, and information services may not be the companies that add the most revenue, products, or customers.
They may be the companies with the courage to decide what no longer belongs—and the discipline to invest disproportionately in what does.
Because the ultimate measure of growth isn't how much bigger your company becomes.
It's how much more valuable.
The Decisions That Create Enterprise Value Shouldn't Be Made in Isolation
Knowing what needs to change is one thing. Making the hard decisions—and executing them—is another.
That's why Revenue Room™ CXO exists.
Built for CEOs and CXOs leading media, events, data, information services, marketplace, and professional network businesses, Revenue Room™ CXO brings together a carefully curated group of operators confronting the same high-stakes questions:
Where should we invest? What should we stop doing? How do we turn AI and proprietary data into competitive advantage? And how do we build a business that's not just bigger—but fundamentally more valuable?
This isn't another networking group.
It's an executive growth environment combining trusted CEO peers with a structured framework for confronting strategic choices, challenging assumptions, and translating insight into action.
Because the decisions that shape enterprise value are too consequential for superficial conversations.
If you're rethinking what growth should look like for your business, you belong in a room where other CEOs are doing the same.
Want to explore the ideas behind this article? Listen to the full episode of The Revenue Room™ with Jon Howland.
Where to Take This Next
The Revenue Room™ CXO Growth Room is where this exact question, who owns the decision once AI sits inside the workflow, is being worked through in real time by CEOs, CROs, and RevOps leaders building the next revenue operating model together. The Revenue Room™ Growth Readiness Diagnostic's AI Value Creation Scorecard is a practical starting point for mapping where decision rights are currently missing inside your own commercial workflows.
About The Revenue Room™
The Revenue Room™ CXO is an invite-only executive peer network and year-round decision system for profitable growth, serving CEOs, Presidents, and C-suite operating leaders across media, events, data, information services, marketplaces, subscriptions, and professional communities. Explore Revenue Room™ CXO membership or start with the Growth Readiness Diagnostic.
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