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Investing in AI

A twice monthly digest of ideas and market analysis focused on AI. Written by Rob May. This page collects 190 posts published between August 2020 and October 2026. Recent coverage focuses on AI (Horizontal), AI Infrastructure and Venture Capital & Startups. Investing in AI publishes roughly 9 posts a month; the best of them appear in the SandHill weekly digest.

190 posts indexed9 in the last 30 daysAI (Horizontal) · AI Infrastructure · Venture Capital & Startups · Enterprise SoftwareVisit site ↗

Thursday, 8 October 2026

1 piece
AvePoint: The $15 Feature That Could Eat a $3B Company↗
Enterprise Software · AI (Horizontal)

Sunday, 4 October 2026

1 piece
In AI, Fast Means Fragile: How Wall Street Short-Termism Impacts AI Deployments↗
AI (Horizontal) · Venture Capital & Startups

Tuesday, 29 September 2026

1 piece
Investing in AI Interviews: Ash Ashutosh, CEO at Pinecone↗
AI Infrastructure

Sunday, 27 September 2026

1 piece
Should Investors Be Concerned About The Recent AI Safety Incidents?↗
AI (Horizontal) · Venture Capital & Startups

Thursday, 24 September 2026

1 piece
The 2028 Handoff: Silicon Motion’s (SIMO) Bear Case and Bull Case Arrive in the Same Year↗
Semiconductors · AI Infrastructure

Sunday, 20 September 2026

1 piece
The Owning Phase of AI Part 3: Companies To Research↗
AI (Horizontal) · Venture Capital & Startups

Thursday, 17 September 2026

1 piece
Stress Testing Anthropic’s Revenue Pre-IPO↗
AI (Horizontal) · AI Infrastructure · Venture Capital & Startups

Tuesday, 15 September 2026

1 piece
Investing in AI The Book, Is Live. Here Is Your Free Copy↗
Venture Capital & Startups

Sunday, 13 September 2026

1 piece
The Owning Phase of AI Part 2: When Do The Economics Make Sense↗
AI (Horizontal) · Enterprise Software · Fintech

Thursday, 10 September 2026

1 piece
Nebius: A Software Company With A Data Center Attached↗
AI (Horizontal) · AI Infrastructure

Wednesday, 9 September 2026

1 piece
Reader Submission: A Deeper Dive on Dell↗
AI (Horizontal) · Manufacturing & Industrials

Sunday, 6 September 2026

1 piece
The “Owning” Phase of AI Part 1: What Investors Should Look For In Companies Making Their Own Models.↗
AI (Horizontal) · Enterprise Software · Venture Capital & Startups

Thursday, 3 September 2026

1 piece
The AI Boom And Dell: Can The Company Capture More AI Value?↗
AI (Horizontal) · Semiconductors

Sunday, 30 August 2026

1 piece
How To Think About The Negative ROI on AI Investment↗
AI (Horizontal) · AI Infrastructure

Wednesday, 26 August 2026

1 piece
Flex Ltd: Will Power Be The New Silicon?↗
AI (Horizontal) · Semiconductors · Manufacturing & Industrials

Sunday, 23 August 2026

1 piece
The Speed of Thought: What If Intelligence Has a Universal Limit?↗
AI (Horizontal)

Wednesday, 19 August 2026

1 piece
My Brief Interview With Paddy Srinivasan, CEO of DigitalOcean, On Their AI Growth↗
AI (Horizontal) · AI Infrastructure · Developer Tools

Sunday, 16 August 2026

1 piece
Is There An Inference Glut Coming?↗
AI (Horizontal)

Tuesday, 11 August 2026

1 piece
Constellation Energy (CEG): The Contract Layer of The AI Buildout.↗
Energy & Climate · AI (Horizontal)

Sunday, 9 August 2026

1 piece
World Models And The Companies That May Win This New Space↗
AI (Horizontal) · AI Infrastructure · Robotics

Sunday, 2 August 2026

1 piece
A Strategic Analysis: Neoclouds vs Hyperscalers And The Future of Inference↗
AI (Horizontal) · AI Infrastructure · Fintech

Sunday, 26 July 2026

1 piece
Guest Post: The Trillion Dollar Trade Wall Street Is Ignoring

Friday, 24 July 2026

1 piece
Coherent: The Optical Plumber Of The AI Buildout

Sunday, 19 July 2026

1 piece
Chapter 5 of My Investing in AI Book: Expect Market Dislocations

Wednesday, 15 July 2026

1 piece
Memory Is The Real Bottleneck and Micron Seems To Own It For Now

Sunday, 12 July 2026

1 piece
The CEO's Field Guide To Strategy In An Era of AI Tokenomics

Friday, 10 July 2026

1 piece
Recursion Pharmeceuticals (RXRX): Can AI Turn Biology Into An Operating System?

Sunday, 5 July 2026

1 piece
The New Whitespace in AI

Sunday, 28 June 2026

1 piece
An AI Tokenomics Framework For Investors To Use To Evaluate AI Efficiency At A Company

Wednesday, 24 June 2026

1 piece
TSMC: The Hidden Toll Booth of the AI Boom

Sunday, 21 June 2026

1 piece
Chapter 3 of My Investing In AI Book: The First Mental Model You Need

Sunday, 14 June 2026

1 piece
Everything A Tech Executive Should Know About Harness Engineering

Thursday, 11 June 2026

1 piece
How Much AI is in C3.ai?

Sunday, 7 June 2026

1 piece
Should The Government Take Stakes In Frontier Labs? The Best and Worst Idea in AI

Thursday, 4 June 2026

1 piece
Cerebras Systems and the Speed Bet on AI's Future

Sunday, 31 May 2026

1 piece
Has AI Made VCs Forget Basic Competitive Strategy?

Saturday, 30 May 2026

1 piece
CloudFlare: The Invisible Infrastructure of The Agentic Web

Sunday, 24 May 2026

1 piece
Why America Must Re-Globalize To Win The AI Race

Friday, 22 May 2026

1 piece
AudioEye and the Accessibility Layer of the Agentic Web

Sunday, 17 May 2026

1 piece
The Secret Benefits of Small Language Models
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