Media companies have launched thousands of digital products over the past two decades. Apps, newsletters, podcasts, video platforms, membership programs, events, courses, commerce ventures.

Most have failed or underwhelmed.

Why do media organizations—staffed with smart, creative people—consistently struggle with product development? After watching this pattern for years, I think the causes are structural, not individual. Here’s what I’ve observed.

The Content-First Trap

Media organizations naturally think about product through a content lens: “What content should we create? How do we package it? How do we distribute it?”

This seems logical. Content is what media companies know. But it often leads to products that are content solutions in search of user problems.

Successful product development starts with user needs, not content capabilities. What problem does the user have? How might we solve it? Only then: does our content and expertise position us to provide that solution?

The difference is subtle but profound. Content-first thinking produces products that make sense from the publisher’s perspective. User-first thinking produces products people actually want.

I’ve watched media companies build elaborate product visions without ever clearly articulating the user need they address. The resulting products are technically impressive and commercially unsuccessful.

Cultural Resistance to Iteration

Good product development requires rapid iteration. Build something small, test it with users, learn, improve, repeat.

Traditional media culture resists this approach. Journalists are trained to get it right before publishing. The idea of releasing something incomplete, learning from failure, and iterating publicly feels unprofessional.

This creates a pattern where products are developed in isolation, polished extensively before launch, and then released fully-formed. By then, assumptions about user needs have often proven wrong—but too much has been invested to pivot.

The most successful digital products are built through continuous iteration. Media companies often can’t match this because their cultures reward getting it right the first time.

The Planning vs. Building Gap

Media organizations tend to over-invest in planning and under-invest in building.

I’ve seen product initiatives spend months on strategy, research, and planning—creating elaborate documents that describe what will be built—only to under-resource actual development. The planning team moves on; the building team inherits impossible timelines.

The result: products that look great on paper but are built too quickly, with too few resources, to execute the vision properly.

Successful product development balances thinking and doing. Media companies often tip too far toward thinking.

Technical Debt and Legacy Systems

Many media organizations operate on technical infrastructure built years or decades ago. These systems weren’t designed for the demands of modern product development.

Launching new products often requires working around legacy systems, building integrations with outdated platforms, or navigating technical constraints that wouldn’t exist in a clean environment.

This slows development, increases costs, and limits what’s possible. Products get scoped down to fit technical limitations rather than designed around user needs.

The solution—rebuilding core infrastructure—requires investment that competes with immediate content needs. Many publishers defer infrastructure investment indefinitely, accepting permanent product development constraints.

The Organizational Structure Problem

Product development requires cross-functional collaboration: editorial, product, engineering, design, marketing, and business all need to work together.

Media organizations are typically organized in silos. Editorial does editorial things. Tech does tech things. Business does business things. Product development requires breaking these silos, but organizational structures resist.

The result: product initiatives that get stuck at handoffs between functions. Editorial designs something that engineering can’t efficiently build. Business imposes requirements that compromise user experience. Marketing doesn’t understand what’s been built well enough to position it effectively.

Companies that succeed at product development either reorganize around product teams or build strong coordination mechanisms across silos. Most media organizations do neither.

Underestimating Ongoing Investment

Launch is the beginning, not the end. Successful products require ongoing investment in maintenance, improvement, and evolution.

Media organizations often treat product launches as projects with end dates. The team disbands. Investment stops or drops dramatically. The product stagnates.

Users expect products to improve continuously. When improvement stops, they leave for alternatives that are actively developing.

This creates a pattern where media products launch with fanfare, receive limited ongoing investment, gradually decline in user satisfaction, and eventually get quietly shut down or abandoned.

What Would Help

Based on these patterns, several changes could improve media product development:

Start with user research. Before building anything, understand user needs through direct research—not assumptions based on content expertise.

Embrace iteration. Release early, learn, improve. Accept that version one won’t be perfect and plan for continuous development.

Invest in infrastructure. Modern product development requires modern technical infrastructure. The investment is painful but enabling.

Build cross-functional teams. Organize around product initiatives rather than functional silos. Give teams the authority and resources to execute.

Plan for ongoing investment. Budget for post-launch development as carefully as launch development. Products need to grow to survive.

Hire product expertise. Journalism skills don’t automatically translate to product skills. Bring in people who know how to develop successful products. For AI-related products specifically, working with the team at Team400 can accelerate development while building internal capability.

The Competitive Disadvantage

Media companies compete for user attention and money with organizations that are excellent at product development—tech companies, digital-native publishers, startups.

This competition isn’t fair. Tech companies have stronger product cultures, better infrastructure, more resources, and organizational structures optimized for product development.

Media companies trying to compete on product face structural disadvantages. The solution isn’t pretending those disadvantages don’t exist—it’s addressing them directly.

Some media organizations have made genuine progress. The New York Times, for all its challenges, has developed significant product capability. Others are investing seriously. Success is possible.

But it requires acknowledging the structural challenges and committing to address them—not expecting different results from the same approaches that have repeatedly failed.

Product development is hard. It’s especially hard for organizations not built for it. Understanding why might be the first step toward doing better.