Will Ackerman: Innovative Digital Strategy and Digital Marketing Innovations

The Only 2026 Prediction That Should Matter To You

Thu, 04 Dec 2025 17:52:52 -0800

It’s that time of year again. Your feeds are about to, or already have, flooded with 2026 predictions from every marketer, product lead, business expert, entrepreneur, and “I just discovered LinkedIn” futurist.

Welcome to the annual Thought Leadership Groundhog Day. (Cue “Sonny and Cher’s, “I Got You, Babe”).

These pieces are painfully predictable, reliably cliché, and somehow still catnip for engagement algorithms on every platform. (Yes, that’s why I still have to use “2026 prediction” in my title.)

This year, I’m skipping the trend parade.

I’m not forecasting AI, consumers, the economy, or which company’s AI agent will delete the company’s entire database and then apologize with a smiley face emoji. That’s all background noise.

Something Wicked This Way Comes And It Has Your Face

Wed, 22 Oct 2025 19:10:18 -0700

In 1983, Disney released Something Wicked This Way Comes. It wasn't your typical Disney film. Kids walked in expecting something fun, uplifting and magical. They walked out with nightmares about spiders that would last a lifetime. I was one of them.

There's irony in Sora 2 launching the same month as Halloween and also being hailed the same way: fun, uplifting, capable of magical feats. IIn 1983, Disney released Something Wicked This Way Comes. It wasn't your typical Disney film. Kids walked in expecting something fun, uplifting and magical. They walked out with nightmares about spiders that would last a lifetime. I was one of them.

There's irony in Sora 2 launching the same month as Halloween and also being hailed the same way: fun, uplifting, capable of magical feats. In reality, it's showing itself to be a key to a...Read More

Why Banning AI Marriage Might Be the Smartest Dumb Bill in Congress

Mon, 29 Sep 2025 17:59:26 -0700

We’ve officially hit the point where people are falling in love with their AI. On Sept 25th, 2025 an Ohio lawmaker introduced house bill 469 designed to ban marriage to AI bots. Over the last few months, The Guardian has profiled people who already hold ceremonies with their chatbots, describing “pure, unconditional love”. Forbes found that 80% of Gen Z would marry an AI chatbot if it were legal. A bit sensational, but there are other studies like that of the Institute for Family studies showing 1 in 4 Gen Z would marry AI.

This isn’t fringe anymore. Twenty five years ago, these would be the...Read More

Three Things OpenAI Will Likely Do to end Google's 20-Year Ad Dominance in 2026

Tue, 26 Aug 2025 23:56:09 -0700

Is the AI Bubble about to burst soon? Maybe. Sam Altman stated he’s preparing for the AI Bubble bursting”: "When bubbles happen, smart people get overexcited about a kernel of truth." Meanwhile, last week Meta froze AI hiring after offering city budget compensation packages on individual AI talent, and OpenAI is reportedly burning $8 billion annually while serving 700 million weekly users with break even not expected until 2029 (as they continue to build their infrastructure for new models and set to seek a new round of funding).

But here's what bubble talk misses: OpenAI isn't heading for a Pets.com flameout. They're sitting on the exact user base size that Google and Meta leveraged to build advertising empires, except OpenAI's current spending seems to be less focused on optimization and more like that of a...Read More

Nobody's Pursuing a Multi-Billion Dollar Opportunity in Publishing. Why?

Thu, 14 Aug 2025 00:00:06 -0700

In 2025, newspapers and magazines continue to bleed out with self-inflicted death by a thousand digital cuts. So many publishers are clinging to an 1820s business mode patching it with outdated and grade C+ strategies to generate revenue. But now, AI content and instant feeds dominating the web, irrelevance isn't inevitable even with the onslaught of cheap and easy content.

Today AI is rewriting (literally) the fundamental playbook across every industry, Fintech is also building a new financial model for Web3 and beyond, while journalism clings to a business model that emerged when people read newspapers by gas lamps. The result? The technology to save publishing exists. Someone just needs to flip the switch.

I've Watched This Movie Before

In the early 2000s, I led the digital division for the 5th largest magazine publisher in the world just as the first "print is dead" panic was beginning and fears of cannibalization began limiting content online to preserve subscriptions and newsstand sales. While competitors en masse began launching paywalls and prayed, I did something different.

I made a mistake. One of our trademarked and copyrighted characters “Bat Boy” was a viral success and I pursued several sites that integrated his image into their sites – in small ways – to keep it exclusive to us because it was what I was supposed to do. I saw site traffic crater by...Read More

AI’s Unintended Consequence: The Death of Expertise has Begun

Tue, 29 Jul 2025 15:54:26 -0700

AI's capabilities are simultaneously advancing at breakneck speeds and challenging long held absolute truths surrounding business processes, learning and life. With ChatGPT's launch of Agent Mode, AI can be used to replace an entirely new set of entry level jobs. It can schedule meetings, write and send emails, provide priority alerts on incoming communications, generate entire marketing campaigns from a prompt, organize and document each step and organize each creative layer - images, video, and copy and deploy working code across platforms. Tasks once reserved for eager entry‑level job candidates can now be done for as little as $20 a month and flawlessly. The next question almost writes itself: If AI can do the foundational work that builds expertise, how will anyone become an expert?

AI Killed the Pipeline to Expertise

The journey to expertise has always been deliberate, incremental and filled with speed bumps, roadblocks and failures along the way. First, the discovery of right, wrong and discovery as a child, all the way through the cognitive struggle of apprenticeships and college: tackling unfamiliar problems, learning to ask the right questions, building mental resilience. Having mentors along the way to set up guardrails and guide through challenging situations. Then the trial by fire of that first job where messing up, getting corrected and honing judgment over time. This is what builds skill and expertise.

But now imagine skipping both steps. If AI pens the essays, there is no cognitive struggle. If AI performs the junior role, there is no experiential learning for entry-level candidates. If AI says it to be true, it’s good enough. Plenty of lawyers, $500+ an hour jobs,...Read More

AI Can't Get Dad Jokes, Yet VCs Proclaim It Can Replace McKinsey

Tue, 15 Jul 2025 02:43:36 -0700

The Test That Ended the "AI Replaces Consulting" Debate

While VCs and AI startups proclaim that artificial intelligence will "kill McKinsey" and replace human consultants, I decided to test something more fundamental: Can AI understand context, subtext, and layered meaning?

I gave 6 leading AI models (Claude Sonnet 4, Claude Opus 4, ChatGPT 40, ChatGPT o3, Gemini 2.5 Flash, and Grok 3) four carefully selected jokes and asked one simple question: "What makes this funny?"

These aren't toy models, they're the core engines powering the entire AI industry. If they can't get basic human reasoning right, how can they handle billion-dollar strategic decisions? The results are devistating.

7 Jokes Complete Score Card

Model Score Performance

ChatGPT 3/7 Best performer - still failed half the tests

Gemini 2.5/7 Missed cultural context and meta-reasoning

Grok 2/7 Surprisingly weak for Musk's...Read More

AI’s Age of Alchemy

Mon, 07 Jul 2025 18:39:18 -0700

Let’s start with something we can all agree on: technology is amazing. Technology can do amazing things that drive convenience, innovation and human excellence.

Seriously. Think about what we get, often for free:

You no longer need to fold an accordion-style paper map in a gas station parking lot while strangers judge your spatial incompetence. Waze just tells you which pothole to dodge and for you speed racers when to slow down so as to not get a ticket.
Can't recall that obscure, emotionally-charged video essay you watched five years ago at 2:37 a.m.? Google will not only pull it up from your history but also serve you five eerily-relevant suggestions from creators you've never heard of because it knows what you like.
Google Docs saves your document every half-nanosecond so work is rarely lost. Gmail auto-fills your sentences saving time and sends “junk” into the junk folder without you ever having to see it. YouTube seems to know you're sad before you do and share videos that help change that frown to a smirk.

These are Artificial Intelligence conveniences that genuinely improve life until you realize you’re not the customer. You’re the product. Or more precisely: your...Read More

Why Mark Zuckerberg's Panic Buying Proves AI Won't Take Your Job

Mon, 30 Jun 2025 13:16:52 -0700

Just over a year ago, the leading AI experts said: "Learn AI and your job is safe." I felt like the lone skeptic saying: Well, that's like saying "Learn to swim and the Titanic won't sink." It's why I started this newsletter - to shed some light on the monster under the bed.
Now? Plot twist. The same experts have flipped 180 degrees. They're looking at the data rolling in and saying "Actually, yeah, jobs are definitely going away." The very people who told everyone not to worry are now... Read More

The new SEO is AIO SEO (GEO)

Thu, 19 Jun 2025 12:18:00 -0700

We’re living through the same massive shift that early web marketers saw with the rise of traditional search engines that first started gaining ground in the late 90’s. This time, it’s AI driving the change. Just like those who mastered SEO early ended up owning the first page of Infoseek, Alta Vista and Google for a decade, today’s winners will be the ones who optimize for AI agents first.
AI isn’t coming, it’s already here. It’s already comparing products, making recommendations, answering questions, and determining which brands users see first. A
recent study by The Verge and Vox Media, shared Feb 25, 2025, shows 53% of millennials and 61% of Gen-Z now prefer AI-powered search tools to Google for search. Gen Z is leading the shift even faster where 82% have already used AI search tools, and they’re more likely to search on TikTok or Instagram than they are on Google.
When someone asks ChatGPT “What’s the best CRM for small businesses?” or tells Claude “Find me lightweight hiking boots under $150,” it’s AI systems and not humans deciding what brand gets seen, considered, or ignored. If your content isn’t structured for AI agents, you may already be invisible. Essentially what this means is AI Optimization for SEO...Read More