Three Years In: From AI Awakening to AI Reckoning

Three years ago, ChatGPT lit a fuse. Not just under OpenAI, but under the entire tech industry. Like the iPhone in 2007 or the launch of Skype in 2003, it wasn’t just a product drop — it was a moment. In the span of 36 months, the world moved from wondering what this chatbot thing … Read more

GenAI’s Breakneck Adoption: What History Tells Us About the Future

We’ve seen our fair share of tech hype cycles over the past two decades: smartphones, the rise of VoIP, the birth of cloud computing. But generative AI isn’t just another entrant on the innovation leaderboard. It has now earned a title no other technology has: the fastest adopted general-purpose technology in U.S. history. Let that … Read more

Google Earth AI and the Rise of Geospatial Intelligence That Actually Matters

Over the years, I’ve watched tech announcements come and go—most landing with a splash and fading with a whimper. But every so often, something drops that feels less like a shiny new feature and more like a tectonic shift. That’s what’s happening with Google’s latest update to Earth AI, a platform that blends satellite imagery, … Read more

Working Anywhere: A 2025 Perspective

In the old days, we used to say getting “out of the office” to work somewhere else was taking a break. Now, for me, it’s getting out of the house. You have to realize that I’ve been working from home since the dawn of time. Back in the ’70s, it was calling in scores late … Read more

WhatsApp: The Silent Front Door to AI Over the last two decades, we’ve watched communications shift, from desktop dialers and browser-based apps to mobile-first, message-driven interactions. We’ve seen the rise (and often the fall) of platform plays. But now, as AI becomes the next wave, the real story isn’t in new apps. It’s in existing … Read more

Your Inbox Just Got a Personal Assistant (And It’s About Time)

I’ve always had a love-hate relationship with my inbox. It’s simultaneously the central nervous system of my work life and the biggest time vampire in my digital existence. So when I heard about Perplexity’s new Email Assistant, I couldn’t help but feel that familiar mix of tech optimism and “but will it actually work?” skepticism … 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

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

The AI Market Is Splitting Into Two Distinct Paths

After diving into the merged findings from Bessemer’s “State of AI 2025” and Janelle Tang’s Next Big Teng’s analysis, I’m struck by how the AI startup landscape is crystallizing into a fascinating dichotomy. Three years post-ChatGPT, we’re seeing the market mature in ways that tell us a lot about where things are headed. What’s immediately … Read more

Why the HIPAA Conduit Exemption Should Be Dead and Gone

The HIPAA conduit exemption is a narrow carve-out in the HIPAA Privacy and Security Rules. It says that if an entity merely transports protected health information (PHI) from point A to point B without storing it or having routine access to it, they’re not considered a business associate and therefore don’t need a Business Associate … Read more