I launched the original “Uphoff on Media” blog back in 2006, and I’d love to tell you it was born from some grand vision about the future of digital publishing. It wasn’t. I was running UBM TechWeb, and I needed to convince a building full of journalists and editors that blogging wasn’t a passing fad — that they should embrace the format and make it part of how they connected with their audiences. The problem was, none of them were going to take blogging advice from a “suit.” So I did what any self-respecting business-side exec would do when trying to earn credibility with a newsroom: I jumped in first and dared them to follow.
Here’s the thing nobody on the editorial side ever wanted to admit — the suits were writing just as much as the journalists were. I wasn’t filing stories, but between the emails, strategy briefs, board narratives, market trend memos, and investor presentations, I was putting out somewhere north of 20,000 words a month. That’s roughly what a busy trade journalist was producing in published copy. The difference was that my audience was a boardroom, not a readership. Blogging just meant pointing the fire hose in a different direction. Nearly two decades later, I’m relaunching Uphoff on Media on Substack, and while the platforms and the stakes have changed dramatically, the impulse is the same — put your thinking out there, make the case, and see who wants to argue about it.
When I launched the original blog in 2006, the digital transformation of media and marketing felt like it had a destination. We were migrating print publications to digital, building websites, figuring out search, experimenting with email newsletters, and learning to sell online advertising. It was complicated, sometimes painful work — but there was an implicit assumption that we’d get to the other side. We’d crack the model, find the right mix of content and commerce and audience, and arrive at something stable and scalable. The transformation had a beginning, a middle, and presumably an end.
That was charmingly naive.
What we didn’t fully appreciate was that digital transformation isn’t a journey with a destination — it’s a permanent condition. The web reshaped distribution. Social media reshaped influence. Mobile reshaped attention. Programmatic reshaped advertising economics. Each wave arrived before the previous one had fully played out, and the “safe, scalable business model” we were all navigating toward kept moving further out on the horizon. Some companies adapted brilliantly. Many didn’t survive.
And now here we are, two decades in, and the transformation isn’t just continuing — it’s accelerating in ways that make the earlier disruptions look like warmup acts. Agentic AI isn’t just another wave. It has the potential to fundamentally restructure how content is created, how buyers research and make decisions, how marketing campaigns are built and optimized, and how entire go-to-market organizations operate. We’re not talking about better tools to do the same work. We’re talking about the work itself changing.
That’s what has me so energized about relaunching Uphoff on Media right now. In 2006, I was writing about a transformation I thought we could see the end of. In 2026, I know better — and that’s actually more exciting. Because the leaders and companies who understand that this is a permanent state of reinvention, not a problem to be solved and moved past, are the ones who will build what comes next. I want to be part of that conversation, and I want this newsletter to be where it happens.
So what exactly will you find here? Uphoff on Media has always lived at the intersection of media, marketing, and technology — not because that’s a convenient Venn diagram, but because that’s where the most consequential decisions are being made and where the most interesting collisions are happening. That hasn’t changed. What has changed is the velocity and the stakes.
I’ll be writing regularly about a handful of themes that I believe will define the next era of B2B marketing. How Agentic AI will dismantle the Marketing playbook that an entire industry has been running for the past decade — and what replaces it. How AI will change marketing organizations. Whether the shift from SEO to AI Engine Optimization is as profound as I think it is, and what it means for companies that built their growth engines on search. What happens to ad agencies, martech platforms, and the sprawling ecosystem of sales and marketing technology when AI can orchestrate what previously required dozens of tools and teams? And the question I keep coming back to: will this wave of disruption favor the incumbents who have the data and distribution, or will it crack open the market for new entrants who build AI-native from the ground up?
If those sound like the questions a CEO would ask rather than a marketing practitioner, that’s intentional. I’ve spent 35+ years running media, marketing and technology companies, not analyzing them from the outside. I’ve sat in the board meetings, led transformations, negotiated the acquisitions, wrestled with the margin models, and made the bets — some brilliant, some humbling. That operating experience is the lens I bring to everything I write here. I’m less interested in what’s theoretically possible with AI and more interested in what it actually means for business models, P&L’s, organizational structures and the competitive landscape. I’ve also learned that the best insights come from pattern recognition across industries, not from going deeper into a single silo. The convergence of media, marketing, and technology isn’t a trend — it’s the operating reality for any growth-oriented business, and most of the conventional wisdom about each of those domains is about to be stress-tested in ways we haven’t seen before.
I’m writing this for a specific audience: the operators running media, marketing, and technology companies, who need to make decisions about where to invest, where to allocate resources and what to build next. The analysts trying to make sense of a landscape that’s shifting beneath their models. And the investors evaluating which companies and categories will emerge stronger from the AI disruption and which are running on borrowed time. If you’re in one of those seats, I think you’ll find the perspective here useful, occasionally provocative, and grounded in the reality of actually having done the work.
One more thing. I want to hear from you. If there’s a topic you think I should be tackling, a trend you’re seeing that nobody’s talking about, or a take of mine that you think is dead wrong, drop it in the comments or reach out directly. The best writing I’ve done over the years has come from conversations, not monologues, and some of the sharpest insights I’ve encountered have come from operators in the trenches who see things the analysts and pundits miss entirely. This newsletter will be better if it’s a two-way street, and I intend to make it one.
My plan is to publish a longer piece here on Substack each week — the deeper analysis, the frameworks, the arguments worth having. In between, I’ll be sharing shorter, sharper takes on LinkedIn where the conversation tends to move faster. Think of Substack as the main course and LinkedIn as the appetizers, though I make no promises about which will be spicier.
And yes, it’s free. I’m not putting a paywall between you and my opinions. Frankly, after 35 years of having to be diplomatic in boardrooms, the opportunity to say what I actually think in public is payment enough. Hit subscribe, and you’ll get each new post delivered straight to your inbox. No spam, no sales pitch, just one veteran operator’s honest read on where media, marketing, and technology are headed, and what to do about it.
Keep going: The Function and the Form and Rage Against the Machines
The views expressed in Uphoff on Media are entirely my own. They don’t represent the opinions of any company I’ve led, any board I’ve sat on, or any investor who’s had the pleasure of debating strategy with me over the years. If something I write here sounds brilliant, I’ll take full credit. If it turns out to be wrong, I was clearly misquoted by myself.
“Uphoff on Media” is published by Tony Uphoff, Founder and Managing Partner of Uphoff Advisory, a strategic advisory practice for founders, CEOs, and investors in B2B information, marketing, and technology. The businesses that drive business.
