Blockbuster had every advantage—brand, reach, loyal customers. They saw Netflix coming and had the resources to compete. They waited too long. The window closed.

Kodak invented the digital camera in 1975. They knew film was vulnerable. They protected margins instead of building the future. When they finally moved, others had already won.

BlackBerry watched the iPhone launch and dismissed touchscreens as toys. They waited for validation. The window closed again.

The pattern is clear: in disruption, hesitation is the most expensive decision you can make.

When ROI stops working

In stable markets, ROI analysis works: estimate effort, project impact, prioritize by return. But in fast-moving markets, the numbers turn into guesses. That’s when cost of delay becomes a better lens by measuring what you lose by not acting sooner.

Jeff Bezos used this logic in 1994. The ROI of selling books online was unknowable, so he asked himself which decision he’d regret more at age 80. The answer was obvious: he’d regret not trying.

The AI-era shift

This moment is different. Building is faster and cheaper than ever. What once took months now takes days with AI tools, context engineering, and rapid prototyping.

That makes the choice of what to build more important—and more dangerous to delay. Every month spent “waiting to see” is a month others spend shipping and learning. They’re not better funded; they’re just moving.

Consider Chegg. For years, it dominated online homework help. Then generative AI gave students free answers. Chegg waited to adapt. Subscribers left. The model cracked almost overnight.

When barriers to building fall, the cost of delay compounds. What once felt like prudence becomes paralysis.

From maximizing value to minimizing regret

In stable markets, you ask, “What will maximize value?”
In turbulent markets, ask, “What will we regret not having tried?”

This isn’t about chasing every shiny thing. It’s about recognizing inflection points. Investing in AI, rethinking your platform, rebuilding for the next developer generation, and knowing when traditional ROI thinking slows you down.

Project yourself forward. In 2027, what will you wish you had started in 2025? That’s your signal. The cost of delay isn’t just lost revenue; it’s lost learning, lost compounding advantage, lost momentum.

The real risk

This isn’t a call to panic. It’s a call to move.

You can now build and test faster than ever, run more experiments with fewer resources, and learn from the market in weeks instead of quarters.

Some windows stay open for years. Others close in months. The work of product leadership is knowing which is which and having the courage to act when waiting costs more than being wrong.

The market won’t wait for you to be certain. Neither should you.