Gianfranco's Best of May 2025 Reading List

Welcome to the May 2025 edition of my monthly reading list.

This month, I've curated my favorite essays across categories like artificial intelligence, startup strategy, finance, society, and the craft of writing.

If you only have a few minutes, these three posts were my favorite, and are included in the list below:

• Data and Defensibility - Abraham Thomas
  • Most data moats are mirages. Thomas cuts through the mythology: unique data alone confers zero defensibility. The real power emerges from self-reinforcing loops—systems of record that capture workflow, give-to-get exchanges that compound network effects, and implicit knowledge engines that improve with use. He maps the lifecycle of data advantages: when they strengthen (integration depth), when they crumble (AI commoditization), and why founders betting on proprietary datasets without loop dynamics are building on sand. Essential reading for anyone claiming data as their competitive edge.
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• The Agentic Web and Original Sin - Ben Thompson
  • The web's original sin wasn't ads—it was the absence of native payments. Thompson connects the dots: AI agents will destroy search traffic, gutting ad revenue. Microsoft's agent protocols (MCP, NLWeb) need embedded stablecoin micropayments or they're DOA. Without this payment layer, OpenAI and Anthropic will lock up content deals, starve competitors of training data, and kill the open web. The punchline: ads aligned incentives perfectly; their disappearance creates a zero-sum game where creators lose first, then everyone else.
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• The Heart of Innovation: Why Most Startups Fail - Cedric Chin
  • Startups don't fail from bad products. They fail from misreading demand. Chin unpacks Furst's "Deliberate Innovation": real PMF happens when buyers face a situation where they "cannot not" adopt—not pain, not desire, but structural inevitability. The tools: situation diagrams to map context, the "not-not" razor to test authenticity, Documented Primary Interactions to prove gap-closing behavior. Damballa's $69M implosion exemplifies the cost of confusing interest with necessity. This reframes product-market fit from fuzzy sentiment to observable behavior change.
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Artificial Intelligence

• When Will Robots Go Mainstream? – Join Colossus
  • Hardware is solved, but robots still trip over edge cases because no one owns internet-scale “physical intelligence” data. Until founders bankroll Tesla-class flywheels or profit from narrow RaaS loops while tele-ops label reality, warehouses and homes stay demo territory. The essay asks whether your team can endure a decade of corner-case boredom after the launch video goes viral.
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• Unpacking Decentralized Training – Knower
  • Protocols like DiLoCo and DisTrO knit idle GPUs into one trust-minimized swarm and cut capex by orders of magnitude. Token economics align strangers while denying any single lab a monopoly on scale. Knower claims crypto needs this purpose more than AI needs crypto, daring founders to design fair rewards and stomach uncertainty.
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• Data and Defensibility – Abraham Thomas
  • Thomas dismantles the myth that a rare CSV equals a moat. Lasting power comes from loops—systems of record, give-to-get exchanges, implicit feedback—that grow stronger every time a user clicks. He charts when those loops harden, when AI flattens them, and why betting on static exclusivity is building on sand.
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• The Agentic Web and Original Sin – Ben Thompson – Stratechery
  • Thompson argues ads were never the problem; skipping native payments was. AI agents will vaporize search clicks unless open protocols embed micropayments that fund creation. Without that layer, closed labs will lock up content deals and starve the open web.
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• Google I/O, The Search Funnel, Product Possibilities – Ben Thompson – Stratechery
  • Google flaunted Gemini, Imagen, and Veo, yet only Search turns breakthroughs into production software. “AI Mode” is a public funnel where features prove safety, utility, and monetization before graduating to core results. Execution gaps leave startups free to build opinionated apps atop Google APIs while Cloud cashes the checks.
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• AI Arrives in the Middle East: US Strikes a Deal with UAE and KSA – SemiAnalysis
  • The United States traded export licenses for 5 GW of Gulf datacenters and 500,000 Nvidia GPUs a year. Gulf capital monetizes stranded gas while Washington fences Beijing out of high-end compute. SemiAnalysis frames the move as an early scramble to lock AI chokepoints.
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• The Reasoning Revolution in AI: How We Got Here & Why It Matters – Jon Stokes
  • Stokes charts the jump from token prediction to chain-of-thought reasoning. Reinforcement loops where models grade themselves turn extra electricity into permanent IQ gains. In that world, AGI becomes an infrastructure scaling plan, not a research puzzle.
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Startup Strategy

• Product/Market Fit (PMF): Experience & Data – Jason Cohen
  • Cohen says real PMF feels like drowning, not coasting. Data from WP Engine, HubSpot, Slack, and Airbnb show linear demand surges when churn drops below 3 % B2B or 5 % B2C. Anything else means you are still guessing, so stop hiring and start fixing.
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• The Heart of Innovation: Why Most Startups Fail – Cedric Chin
  • Startups die from misreading necessity, not from bad code. Use situation diagrams and the “not-not” razor to prove buyers literally cannot avoid adopting your product. Ignore indifference and you risk a Damballa-sized crater in your resume.
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• The Jobs to be Done Framework as a Method to Understand Demand – Cedric Chin
  • JTBD is diagnostic surgery, not a slogan. Timelines, four forces, and trigger mapping revealed condo buyers were “pre-grieving,” leading to obituary ads that tripled sales. Detaching from your product long enough to stare at your customer’s struggle is the real unlock.
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Finance and Economics

• Why VC and Software Have PE Envy – Matt Brown
  • SaaS saturation pushes VCs toward PE playbooks—roll-ups, crown-jewel buys, and embedded fintech. AI magnifies operational leverage while pure software commoditizes. Brown says the game is shifting from funding tools to running the whole factory.
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• The Bank Inside SoftBank – Marc Rubinstein – Net Interest
  • SoftBank is a levered bank in a telecom hoodie. Retail bonds and quasi-equity fund Son’s latest AI moonshots, pushing loan-to-value toward 22 %. If the bets misfire, the rubber band snaps; if they hit, the leverage compounds spectacularly.
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• Endowments Need Cash, but VC Firms Have None to Offer – The Information
  • University LPs became forced sellers as venture exits froze. With cash flows drying up and Washington eyeing their tax breaks, Harvard and Yale are dumping stakes at discounts. The Swensen model meets its liquidity reckoning.
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• The New Money Market – Marc Rubinstein – Net Interest
  • Stablecoins are morphing into 24/7 money-market funds backed by T-bills. The GENIUS Act would lock reserves, ban consumer interest, and open a trillion-dollar bid for short debt. Payments margins collapse while tokenized funds harvest the yield.
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Technology and Society

• Airbnb's New App, Experiences and Services, Chesky's Founder Mode – Ben Thompson – Stratechery
  • Airbnb thrives on rare, high-trust transactions, while local services require constant repeat business. Chesky’s design obsession cannot change that economic mismatch. Beautiful interfaces will not repair misaligned incentives.
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• Apple Held in Contempt, The Crux of the Case, The Takings Clause – Ben Thompson – Stratechery
  • Judge Rogers found Apple in contempt for its 27 % link-tax workaround and sent the matter toward criminal review. The ruling feels righteous but tees up a Fifth Amendment fight over confiscating App Store economics. Moral clarity does not guarantee appellate victory.
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Writing

• Good Writing – Paul Graham
  • Graham discovered that tweaking rhythm tightens thought—shake the box and parts pack tighter. When prose flows naturally, it is because the ideas themselves snapped into place. Aesthetic excellence and intellectual rigor turn out to be the same edit pass.
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Web3

• Crypto Venture Capital Fundraising Springs Back to Life – The Information
  • Crypto VC is thawing under regulatory sunshine, yet investors can now get liquid exposure via ETFs and tokens. Funds like Haun and Pantera must explain why ten-year lockups beat one-click trades. The comeback is real but smaller, reflecting a market that grew up.
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