Gianfranco's Best of April 2025 Reading List

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

This month, I've curated my favorite essays across a range of topics including artificial intelligence, startups, finance, technology and society, and personal development.

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

• You Are Not Late - Kevin Kelly
  • Kevin Kelly argues that the internet remains in its infancy, brimming with untapped potential even after decades of rapid innovation. He insists that right now is the most opportune moment in history to invent something new, as future generations will marvel at today’s wide-open frontiers.
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• AI Horseless Carriages - Pete Koomen
  • Pete Koomen critiques how most current AI software applications, like Gmail’s Gemini-powered email drafts, fail because they're constrained by old, non-AI design paradigms, producing generic and ineffective results—he calls these “horseless carriages.”
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• A Surprising Route to the Best Life Possible (h/t to Joe Casey for sharing with me) - Brooks
  • Brooks argues that the most rewarding life flows from embracing voluntary hardship: 76-year old Murakami logs daily miles, writers grind through blank pages, and craftsmen endure tedium because a sudden “annunciation” moment once seized their imagination and converted pain into purpose. These ignition points fuel curiosity, stamina, and character—answering why mastery demands suffering, how leaders cultivate relentless conviction, and where true meaning eclipses hedonic ease.
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AI

• Vibe Check: o3 Is Here—And It’s Great - Dan Shipper
  • Dan Shipper reports that OpenAI’s o3 beats Anthropic and Gemini on speed and reasoning, cracking expert Sudoku, reading entire books, and chaining web searches through integrated tools. By embedding memory, reminders, and code execution inside ChatGPT, o3 acts like a personal operating system, shifting the locus of advantage from sheer model size to product-layer orchestration. Leaders should note how this release raises the bar for execution velocity and durable moats in AI-enabled work.
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• On Jagged AGI: o3, Gemini 2.5, and Everything After - Ethan Mollick
  • New AI models like OpenAI's o3 and Google's Gemini 2.5 show remarkable leaps in real-world capabilities, performing complex, multi-step tasks autonomously, prompting debate on whether we've reached "Jagged AGI"—superhuman in certain areas but still prone to errors in simpler ones.
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• Tariff Armageddon? | GPU Loopholes and Supply Chain Shifts ($) - SemiAnalysis
  • Trump's aggressive tariffs disrupt global AI infrastructure trade but spare GPU imports assembled in Mexico due to USMCA loopholes, solidifying Mexico as an assembly hub. While costs for data center equipment and optical modules rise moderately, the major threat is financial uncertainty that may curb critical investments needed for continued U.S. leadership in AI.
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• AI 2027 - AI-2027.com
  • This scenario envisions an accelerating global “arms race” for ever-smarter AI systems, culminating in models that can out-research human teams. Fueled by continuous training, these AIs become both essential and difficult to trust, while geopolitical tensions and fears of misalignment intensify.
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• AI Horseless Carriages - Pete Koomen
  • Pete Koomen critiques how most current AI software applications, like Gmail’s Gemini-powered email drafts, fail because they're constrained by old, non-AI design paradigms, producing generic and ineffective results—he calls these "horseless carriages."
  • Read More

• Historical Analogies for Large Language Models - Dynomight
  • “Dynomight” compares LLMs to everything from tractors and chess computers to photography and Segways, illustrating the many ways technology can reshape an industry—sometimes by outcompeting humans entirely, sometimes by sparking niche demand or new creative frontiers. He highlights the uncertainty around whether AI writing will be cherished or shunned, and whether it will complement human authors or substitute them altogether.
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• Doing Real Work With LLMs: How to Manage Context - Jon Stokes
  • Jon Stokes introduces the idea that effective prompting is an incremental, collaborative search for “grounded” sequences, as opposed to letting the model’s own ungrounded outputs dominate the conversation. He explains that breaking tasks into discrete steps, continually verifying and refining the AI’s responses, and maintaining a shared context (such as a Markdown file) helps align results with real-world goals. By treating each session as a series of “runs” in a roguelike-style exploration, humans can keep the AI tethered to accurate, relevant information rather than drifting off into unproductive tangents.
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Startups

• A Founder's Guide: Essential Sales Advice for Startups - Tomasz Tunguz
  • Tomasz Tunguz highlights the role of a deliberate sales foundation—from pipeline coverage to compensation design—to fuel revenue growth.
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• All That Is Rare and Valuable ($) - Cedric Chin
  • Cedric Chin illustrates how “rare and valuable” applies beyond unique skill sets—whether in family fortunes, charismatic personal brands, or intricate networks of influence—while reminding us that barriers stave off commoditization. He highlights how personal reflections around this scarcity can shape career decisions, touching on the tension between chasing advantages and cultivating hard-won expertise.
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• A Consumer Investing Masterclass ($) - Kirsten Green (The Generalist)
  • Kirsten Green of Forerunner Ventures outlines how enduring consumer startups combine structural business model advantages, inevitable consumer behavior shifts, and self-reinforcing effects, emphasizing that the next wave of consumer hits will deliver "relief" over mere "delight," empowering users to proactively manage complexity rather than passively consuming more options.
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Technology and Society

• Steam Networks - Jamie Rumbelow
  • Jamie Rumbelow recounts how Manhattan’s centuries-old steam system—once a daring solution to space and pollution constraints—still warms, sterilizes, and humidifies iconic buildings and businesses throughout the city. He shows how this network emerged from 19th-century fire-protection experiments and ultimately replaced thousands of individual coal boilers, thereby shaping New York’s vertical growth. While steam has since given way to more efficient hot-water systems in new projects worldwide, its enduring presence in Manhattan highlights the lasting impact of historical infrastructure and the trade-offs behind modern district heating.
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• The Right Amount of Fraud in Seed Stages Startups is Greater than 0% But It Shouldn’t Be Pardoned - Hunter Walk
  • Hunter Walk argues that early-stage startup ecosystems require a baseline of trust and speed, inevitably allowing a minimal, nonzero occurrence of fraud; overly aggressive diligence would disproportionately penalize honest founders. Yet he insists fraud must diminish progressively at later stages. Critically, Walk warns against pardoning high-profile financial fraudsters, emphasizing it undermines the deterrent effect necessary for preserving trust and fairness.
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• You Are Not Late - Kevin Kelly
  • Kevin Kelly argues that the internet remains in its infancy, brimming with untapped potential even after decades of rapid innovation. He insists that right now is the most opportune moment in history to invent something new, as future generations will marvel at today’s wide-open frontiers.
  • Read More

Finance and Economics

• Nobody Knows (Yet Again) - Howard Marks
  • Howard Marks reflects on historical crises, from the 2008 Global Financial Crisis to the current economic uncertainty triggered by Trump’s tariffs, underscoring the perpetual unpredictability of markets and the futility of forecasting in unprecedented times. Despite immense uncertainty, Marks argues investors must act logically rather than freeze in indecision.
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• Cash is King ($) - Marc Rubinstein
  • Yale’s decision to sell $6 billion of private equity assets at a potential 10% discount demonstrates a shift in market conditions, reflecting the rising cost of illiquidity as volatility returns. Firms facilitating trades and those holding large cash reserves, like Berkshire Hathaway, are poised to benefit, while institutions heavily reliant on illiquid investments face reassessment of liquidity premiums and strategic flexibility.
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• Buy the Dip: The Draw and Dangers of Contrarian Investing! - Aswath Damodaran
  • Aswath Damodaran explores four approaches to contrarian investing—knee-jerk, technical, constrained, and opportunistic—highlighting the mixed empirical evidence and psychological challenges of each. He emphasizes that successful contrarian investing requires not only rigorous analysis but also the right temperament, a willingness to withstand extended downturns, and the emotional resilience to act against prevailing market sentiment. What is simple is rarely easy.
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• Praise Our Lord for Secondary Markets Because Selling Shares is Now an Essential Part of Seed Venture Capital - Hunter Walk
  • Hunter Walk argues that secondary share sales—once stigmatized as signaling weakness—are now vital for the health of seed-stage investing, providing crucial liquidity for investors and founders, and enabling greater alignment, flexibility, and resilience during extended periods of market volatility.
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• Trade Deficits Do Not Make a Country Poorer ($) - Noah Smith
  • Noah Smith explains that importing goods and paying with IOUs—akin to using a credit card—doesn’t automatically reduce a nation’s prosperity or GDP. He emphasizes that while certain trade deficits contribute to deindustrialization, forcibly eliminating them misunderstands how trade works and jeopardizes American manufacturing even more.
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• The Punitive Cost of High-Skill Hiring - Byrne Hobart
  • Byrne Hobart discusses how the complexities of identifying, interviewing, and retaining top-tier talent carry opportunity costs, particularly in roles requiring near-O-ring precision. He notes that rigid screening processes, coupled with the risk of “bad hires” in high-stakes positions, drive companies to offer increasingly exponential compensation to secure the very best.
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Personal Development

• A Surprising Route to the Best Life Possible (h/t to Joe Casey for sharing with me) - David Brooks
  • Brooks argues that the most rewarding life flows from embracing voluntary hardship: Murakami logs daily miles, writers grind through blank pages, and craftsmen endure tedium because a sudden “annunciation” moment once seized their imagination and converted pain into purpose. These ignition points fuel curiosity, stamina, and character—answering why mastery demands suffering, how leaders cultivate relentless conviction, and where true meaning eclipses hedonic ease.
  • Read More

• Career Networking and Power - Cedric Chin
  • Cedric Chin contrasts “schmoozers” who simply name-drop with “power brokers” whose relationships directly shape outcomes, offering a yardstick of influence: the ability to harm or help. He argues that career power grows from delivering real value to a network and leveraging that credibility, rather than knowing many people. This perspective invites founders and leaders to consider how real authority emerges from consistent results and cultivated trust.
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