An Autopsy of Imagination: Technology didn’t kill Kodak and Blockbuster
By Dean Waye & Alan Gonsenhauser When corporate giants collapse, the story usually gets simplified into a tech morality tale: disrupt or die. Kodak was killed by digital cameras. Blockbuster was steamrolled by Netflix. These stories are neat, satisfying, but dead wrong. Neither company was destroyed by technology. They were destroyed by a failure of […]
The Efficiency Trap: How Obsessing Over CAC and LTV Kills Your Brand
By Dean Waye & Alan Gonsenhauser In today’s boardrooms, two metrics dominate the conversation: Customer Acquisition Cost (CAC) and Lifetime Value (LTV). These numbers are everywhere, in pitch decks, budget forecasts, and quarterly reviews. On the surface, the logic is irresistible: acquire customers for less than they’re worth over time, and you’ve engineered growth. But […]
”The Customer is Always Right” is Dead
By Dean Waye & Alan Gonsenhauser It’s time to kill this phrase. It’s hurting your business. It’s hurting your people. And it’s definitely hurting your profits. “The customer is always right” made sense when customers had no megaphone. Now they have Twitter, TikTok, and review sites. One angry person can hijack your entire strategy. That’s […]
AI is Your Analyst, Not Your Strategist
By Dean Waye & Alan Gonsenhauser Every boardroom wants an “AI strategy.” They’re making a mistake. AI can’t create strategy. It can only repeat what already worked. Here’s why that matters, and what to do instead. The Machine Gives You Yesterday’s Answer AI is trained on the past. It predicts the most probable next thing. […]
From Bug to Feature: How a Founder’s “Flaw” Became a Brand’s Genius
By Dean Waye & Alan Gonsenhauser In today’s polished, performance-optimized business world, leadership is still defined by sameness. Executives are trained to iron out flaws, follow best practices, and emulate textbook competence. The goal is to look “well-rounded.” Safe. Predictable. But sameness is not a strength. It’s a slow death. In a world full of […]
AI Makes Your SWOT Analysis a Strategic Sedative. Here’s What to Do Instead
By Dean Waye & Alan Gonsenhauser In boardrooms and strategy off-sites across the world, the same ritual plays out: someone walks to a whiteboard, draws a grid, and writes four words that have launched a thousand underwhelming PowerPoints: Strengths, Weaknesses, Opportunities, Threats. This is the SWOT analysis. It feels orderly. Logical. Safe. It also dulls […]
The Generative AI Trap: Not Just Average… Predictable
By Dean Waye & Alan Gonsenhauser AI will soon be able to simulate any public company’s next moves. The only thing it can’t decode is a genuinely non-obvious idea. For 3 years, the fear around generative AI has been homogenization. The idea that if every company uses the same models, they’ll end up sounding the […]
How CMOs Can Create Breakthrough Messaging After an Acquisition
Especially when your B2B company is stuck, merged, and sounding like everyone else. And when your competitors control the narrative, it doesn’t just hurt sales—it damages your valuation. Let’s walk through how to fix it. The symptoms of post-acquisition messaging problems Even strong companies fall into these traps: Why this happens (even with smart marketers) […]
The Future of B2B Outreach
An interactive guide to the strategies, technologies, and skills defining modern sales and marketing.
Nobody does what you don’t ask them to
Return to winstonwrites.com | Subscribe to this newsletter Check out my epic failure. This is a 6-email campaign from 18 months ago. Sent to a cold list of 247 CROs. It looks like a huge success. It wasn’t. (Disclosure: I wrote all 6 emails). Check out those open rates: 84 to 101%. Check out those […]