The Restaurant Reservation Trap

Picture this: You’re sitting in gridlock traffic, watching the minutes tick by as your 7:30 PM reservation slips further out of reach. Your Uber driver is apologetically explaining why the GPS routed you through what appears to be the world’s longest construction zone. You do what any reasonable person would do—you grab your phone and … Read more

Why Guidance, Info-Seeking, and Writing Apps Are Features, Not Companies OpenAI released a report on how people are using ChatGPT. Here’s my take: Investors chasing the current wave of AI apps that give you practical guidance, fetch information, or write your emails are buying into a familiar illusion: short-term traction equals long-term value. It doesn’t. … Read more

AI Today vs. Dot-Com Then

The AI sector right now mirrors the late 1990s internet boom almost to the letter. Back then, startups raised absurd amounts of capital on little more than a domain name and a pitch deck. Companies with no revenue—and in some cases no real product—were suddenly valued in the billions. The bubble burst hard in 2000–2001, … Read more

From Cellar to Summit – Lessons in Building World-Class Teams

Over the years, I’ve worked alongside teams that went from barely surviving to thriving in ways no one expected. Whether it was a startup emerging from stealth or a Fortune 100 undergoing reinvention, the pattern is always the same—transformation begins with belief, but is sustained by systems. That’s why McKinsey’s latest article, “Worst to First: … Read more

Poke-onomics: How Poke Turns iMessage, SMS and WhatsApp into Your Digital Wingman

So here’s the deets on Poke. It’s an embedded AI assistant that’s woven into iMessage, SMS and WhatsApp, surfacing tasks from email, calendar, and more as actionable chat nudges. Backed with $15 million in seed funding and built with strong privacy protocols, it’s already gaining traction among Silicon Valley insiders—making frictionless AI genuinely useful. Since … Read more

Six Hats, One Future: How Superlist, Todoist, and Supernotes Are Reimagining Productivity with AI

If you’ve been around productivity apps for a while, you know the story: lists, notes, tasks, rinse, repeat. Useful, but not game-changing. Fast-forward to 2025, and suddenly AI isn’t just a bolt-on—it’s becoming the co-pilot in how these apps think with us. Superlist, Todoist, and Supernotes have all turned on their AI engines, each taking … Read more

Why I Say “Press 1” Is Dead

Since the early days of VoIP, we’ve been talking about the demise of legacy telephony structures. “Press 1 for sales” was always a symptom of old-school thinking. Now, with OpenAI’s real-time SIP integration, that era is finally over. For years, I’ve advocated for smarter systems. In 2018, when Dialpad acquired TalkIQ, I wrote how AI … Read more

Press 1 Is Dead

For decades, the first words you heard when calling a company were, “Press 1 for sales, 2 for support, 3 to hear these options again.” That relic of the past is about to vanish. With OpenAI’s new Realtime SIP integration, artificial intelligence is no longer bolted awkwardly onto the phone system. It’s wired directly in. … Read more