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Analyst Blog
August 30, 2026

A New Way to Look at Enterprise Technology in 2027+

Board Strategy
It may seem early to revisit the enterprise technology framework for 2026 in August, but considering the dramatic compression of cycles, and the fact that the first eight months provide enough evidence to test the assumptions we carried into this year, its time to update the framework used to discuss and plan....
Esteban Kolsky
Analyst Blog
August 26, 2026

Meta Settles Lawsuit to the Tune of $17 Billion: What it Could Mean for Advertisers

Marketing Transformation
Now that Meta has settled what many are calling a quot;landmark lawsuitquot; brought by multiple US states attorneys general, what happens next and how could it impact marketer's plans to engage with younger audiences? From how this could hit the Meta bottom line to how Meta actually maneuvered to protects its revenue ...
Liz Miller
Analyst Blog
August 22, 2026

The Unsung Heroes of the AI Paradigm Shift: CISOs

Board Strategy
I have been arguing for some time that cybersecurity would become one of the largest areas of enterprise technology investment. AI temporarily absorbed much of that budget and atte...
Esteban Kolsky
Analyst Blog
August 12, 2026

Beyond Public Models: The Return of Enterprise Control

The discussion about open-source AI has inherited too much baggage from the software industry. Most executives, technologists, and advisers understand open source through Linux, da...
Esteban Kolsky
Analyst Blog
August 9, 2026

Beyond RAG: Where Enterprise AI Value Will Come From

Data to Decisions
Retrieval-augmented generation (RAG) solved an important early problem for enterprise AI. Large language models could produce useful responses, but they lacked access to current, p...
Michael Ni
Esteban Kolsky
Analyst Blog
August 9, 2026

The Charlatans at the Inflection Point

Board Strategy
Artificial intelligence has crossed enough adoption, investment, and executive attention thresholds to become mainstream, but it has not yet crossed the threshold into predictable ...
Esteban Kolsky
Analyst Blog
August 3, 2026

The CEO AI Dashboard Series: All the Posts

Board Strategy
Did you miss any of the posts over the two months they published? Cannot get enough of it and want a place where you can find them all together so you can share easily? Here you...
Esteban Kolsky
Analyst Blog
July 29, 2026

The Return to Simple Times Is Near

The transformer architecture was introduced in 2017, and by 2019 several companies, including OpenAI, were already demonstrating language models built on probabilistic token select...
Esteban Kolsky
Analyst Blog
July 28, 2026

The CEO’s AI Dashboard, Part 7: Talent

Board Strategy
In this final installment of the CEO’s AI Dashboard series, I want to focus on the constraint that will determine how far AI can scale after the pilots, infrastructure, data, econo...
Esteban Kolsky