Ankur’s Substack

I am a dabbler. A hyper-generalist - better than most people at most things. Pretty much never in the top percentile in anything!

By Ankur Gupta

· Launched 3 years ago

On Risk

It's about the trade-offs. It's a triangle - like most life principles. Move one of the three vertices and you need to adjust and adapt one or both of…

Jun 21•Ankur Gupta

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Cognitive obesity

Not something that we will choose. But, not something that will not happen.

Apr 24•Ankur Gupta

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Measure What Matters: In the era of AI monetization

2026 is the year of AI's true adoption, scaling and monetization. Getting it right requires measuring what actually matters.

Mar 25•Ankur Gupta

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Intellectual growth in the age of Machine Intelligence

As Machine Intelligence democratizes, our opportunity lies in our intellectual growth. Lean hard on staying "curious", exercising "agency" and…

May 21, 2025•Ankur Gupta

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The Global Expansion Imperative

GTM Strategies for AI-First Enterprise Software companies in a Shifting global Landscape

Apr 21, 2025•Ankur Gupta

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Unlocking the Trillion-Dollar Opportunity

The Next Trillion-Dollar Software shift: Building and Selling for the Agentic Age-SaaS (2.0) & transitioning from traditional SaaS (1.0) to tap the big…

Mar 26, 2025•Ankur Gupta

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From Internet Rails to AI Agents: The Story of TelCos to LLMs

Internetification to the Agenticfication of the world. The Internet Era's Playbook and Anticipating AI's Evolution Through History's Lens.

Feb 3, 2025•Ankur Gupta

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