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Investing In AI

A twice monthly digest of ideas and market analysis focused on AI and how it impacts companies, business models, and investors.

Newsletter · By Rob May · Official site

Indexed issues, last 90 days
19
Latest publication
Sep 29, 2026
Audience
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Earliest in this view
Aug 2, 2026

Latest issues

  1. Issue · Sep 29, 2026

    Investing in AI Interviews: Ash Ashutosh, CEO at Pinecone (opens the original)

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    This is our second installment of our CEO interview series. The goal is to ask tech company CEOs key questions on AI that they might not get from analysts. I hope their answers contribute to your understanding of what is happening in a given AI market segment.Today’s interview is with Ash Ashutosh from Pinecone. Pinecone was an early player in the vector DB space, but has moved to a full agentic knowledge platform. Ash discusses why this move was needed, both for the company and for customers, a

  2. Issue · Sep 27, 2026

    Should Investors Be Concerned About The Recent AI Safety Incidents? (opens the original)

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    Happy Sunday and welcome to Investing in AI. The book is now live and you can order it on amazon, and our AI in NYC podcast is now on Instagram if you want to follow along and see all the short clips. Yesterday Madison Mills from Axios wrote that OpenAI and other frontier labs are probing way more security incidents than we were previously aware of. The media is awash in AI doomsday forecasts but, as someone who is a little more optimistic th

  3. Issue · Sep 24, 2026

    The 2028 Handoff: Silicon Motion’s (SIMO) Bear Case and Bull Case Arrive in the Same Year (opens the original)

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    Welcome to the paid version of Investing in AI. Today we look at Silicon Motion (SIMO), which is a play on the memory shortage because they make the controller chips that make memory usable. Remember this is primarily an AI analysis, so please do your own research before investing. Disclosure: We own no position in SIMO.Silicon Motion has had a year that would unsettle any shareholder. The ADS has traded between roughly $80 and $355 over the past 52 weeks and now sits around $250. That is nearly

  4. Issue · Sep 20, 2026

    The Owning Phase of AI Part 3: Companies To Research (opens the original)

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    Happy Sunday and welcome to Investing in AI. Be sure to checkout the AI in NYC podcast, and my new book “Investing in AI” on Amazon. If you are building AI, also check out or new task explorer - type in a task and it recommends the best model for that task. The last two weeks we have been covering this idea of “owning your AI.” As small models and open source models become more viable, it makes sense for companies to build their own systems for more pieces of their AI stack and re

  5. Issue · Sep 17, 2026

    Stress Testing Anthropic’s Revenue Pre-IPO (opens the original)

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    This paid edition of Investing in AI is an independent investment research analysis based on data up until September 7th, 2026. Note that Anthropic is private: no audited financials, no public covenants. This report separates official disclosures, reputable reported estimates, and model assumptions, and says so explicitly wherever a number is not confirmed. The goal is a diligence framework, not a final answer.Executive summaryAnthropic is not, on current evidence, a near-term solvency risk. It

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