Interesting articles I’ve read recently.
Oct 2025
- When Agents Attack: How AI Collapses and Rebuilds Marketplace Moats — Casey Winters
- How AI is rewriting the rules of hiring — Craig Johnson
Sep 2025
- The FDE model for AI startups — Y Combinator
- The Gen AI PLG renaissance — Selina Wang
- How to size the market for vertical AI — Felicis Ventures
- Land and expand in the AI era — Guru Chahal
Aug 2025
- 996 in the age of building AI startups is real — Inaki Berenguer
- Voice AI market map — Sierra Ventures
July 2025
- Meta’s bet on Scale AI and the new AI data paradigm — Ashu Garg
- The claims revolution that’s already too late — Annelies Gamble
- Five ways to help traditional industries embrace tech — Adi Bathla
- Voice agents: easy to use, hard to build — Sophia Luo
- The future of voice AI: how companies can thrive in a speech-to-speech world — Chelcie Taylor
- The blitzhire acquisition — Villi Iltchev
- Hypercapitalism and the AI talent wars — John Luttig
- Reflections on working at OpenAI — Calvin French-Owen
- The pricing evolution of AI coding agents — Dan Nguyen-Huu
- Reasoning + RL: a new recipe for AI apps — Ashu Garg
June 2025
- The race to become the system of action — Dave Yuan
- Will AI kill the power law? — Gaurav Jain
- The Great SaaS Consolidation: AI Won’t Destroy SaaS Moats, It Will Make the Biggest Ones Even Bigger — Konstantine Buhler
April 2025
- The creator economy is breathing new life into affiliate marketing — Scott Friend
- 43 things we’ve learned about hiring at Posthog — Charles Cook
- How many businesses-in-a-box are there? — Sam Gerstenzang
- How to do startup sales with no experience — James Hawkins
- AI horseless carriages — Pete Koomen
March 2025
- When brokers become the marketplace — Jared Rosner
- Something is rotten in the state of Cupertino — John Gruber
- Vertical AI: beware what you wrap — Matt Brown
- Insurtech spring has sprung — Teddy Himler
Feb 2025
- Deep research — Tyler Cowen
- How AI changes customer acquisition — Rex Woodbury
- AI or die — Ravi Gupta
- Are bad markets good for AI agents? — Sandya Hegde
Jan 2025
- Things we learned about LLMs in 2024 — Simon Willison
- How to think about stablecoins — Alex Johnson
- How I made AI think like a focus group — Michael Taylor
- The dawn of AI rollups — Vinay Iyengar
- Making markets in time — Abraham Thomas
- Why did Doordash win? — Dan Hockenmaier
- Deepseek FAQ — Ben Thompson
- The short case for Nvidia stock — Jeffrey Emanuel
- AI agents and the future of professional services — Sam Parker
- AI voice agent update — Olivia Moore
Dec 2024
- Our source of truth on marketplaces — Forerunner Ventures
- The leaky bucket theory of network effects — Dan Hockenmaier
Nov 2024
- AI for small vertical SaaS markets — a16z
Oct 2024
- What do you invest in? — Pratyush Buddiga
- The pipeline metrics that matter — David Sacks
- What do we mean when we say AI agent? — Gil Dibner
- Why did Stripe spend $1.1B on a Series A stablecoin startup? — Simon Taylor
- The rise of disruptive pricing models — Kyle Poyar
Sep 2024
- The Agent Economy — Felicis Ventures
- Founder market fit — Charles Moldow
Aug 2024
- Control point patterns in vSaaS — Dave Yuan
July 2024
- AI and education — Bond Capital
- Rumors of the death of software are greatly exaggerated — Christoph Janz
- The right kind of stubborn — Paul Graham
- Make money selling money — Matt Brown
- Finding your killer wedge — Pete Flint
- How AI will reinvent marketing — Andrew Chen
June 2024
- The future of AI is vertical — Euclid Ventures
- Is seat-based pricing dead? — Jamin Ball
- Wells Fargo bet on a flashy card. It’s cost the bank dearly — WSJ
- Why has Padsplit survived? — Atticus LeBlanc
- Gen AI and accounting — a16z
May 2024
- What makes some lending companies more valuable than others? — Ali Hamed
- The art of the pivot — Lenny Rachitsky
- AI unlocks the small businesses legacy SMB tech can’t acquire — Jason Shuman
- The opportunity for AI voice agents — a16z
April 2024
- What Midjourney, DeepL and HeyGen have in common — Sarah Tavel
- Beyond the SMB: the rise of enterprise grade vertical SaaS — Patrick McGovern
- YCW24 Demo Day: the implications for enterprise tech — Rajeev Chand
- Turning services into AI — Ruth Sheridan
- The death of Deloitte: AI enabled services are opening a whole new market — Jake Saper
- The AI workforce is here — NFX
- The $100+ billion market you're overlooking: Why coliving is more than just a niche — Atticus LeBlanc
March 2024
- AI-first services businesses — Louis Coppey
- When your cap table makes you uninvestable — Haje Kemps
- Business-in-a-box 2.0 — Rex Woodbury
- Financial services are the new wedge — Ryan Isono
- Consumer trend report — Forerunner Ventures
- How LLMs are ushering in a new era of process automation — Foundation Capital
- The Lindy Effect of venture capital — Zain Rizavi
- Turning payments into profitable revenue stream for vertical SaaS — TX Zhuo
Feb 2024
- Startups need dual theories on PMF and distribution — Andrew Chen
- Payfac in 1000 words — Matt Brown
- Interchange in 1000 words — Matt Brown
- Interchange is a burning platform — Matt Brown
- Can anyone win in BaaS? — Alex Johnson
- How to build and identify a great robotics startup — Brad Porter
- Foundation models, internet-scale data and the path to generalized robots — Luke Holoubek
- Demystifying the journey to PMF — Gaurav Jain
- Measuring the moat — Michael Mauboussin
Jan 2024
- Padsplit: helping others is just good business — The Physicality
- No VC wants to fund a startup with So-So growth — Jason Lemkin
- What I learned selling my company — Harry Glaser
December 2023
- Saturn: Building a viral consumer app — Lenny Rachitsky
- Vertical AI — Christine Kim / Greylock
- Legaltech x AI: the Lightspeed view — LSVP
- When and how to build second products — Casey Winters
November 2023
- 3 types of markets — Rebecca Kaden
- B2B marketplaces, inevitable or impossible? — Mass Mutual Ventures
October 2023
- The business of AI agents — Nandu Anilal
- An obituary for Convoy — Freightwaves
- Some musings on the state of innovation in logistics tech — Ajay Agarwal
- The elephant in the room: the myth of exponential hypergrowth — A Smart Bear
- We grew from $0 to $150K in 6 months, then pivoted. Here’s why — Evis Drenova
- Generative AI exists because of the transformer — Financial Times
September 2023
- In the age of AI, build platforms not products — Rick Zullo
- Will AI accelerate vertical SaaS adoption? — Christoph Janz
- Product-led AI — Seth Rosenberg
- Understanding Instacart — Goodwater Capital
- Generative AI’s Act Two — Sequoia Capital
- Early stage partnerships — Jared Hecht
August 2023
- Negative CAC and the next generation of fintech — Adam Nelson
- Vertical SaaS: flipping the playbook — Jeff Bussgang
- Founder-compensated startups are default dead — Sid Sijbrandij
- Sell work, not software — Sarah Tavel
- B2B marketplace interview: Seafair — Bowery Capital
- Lending business equation for your startup — Rohit Mittal
- Klaviyo S-1 breakdown — Meritech Capital
- What’s next for FedNow? — a16z
July 2023
- 44 failed marketplaces — Failory
- Invisible details of interaction design — Rauno Freiberg
- How to blow up a timeline — Eugene Wei
- 10 articles on PMF — Todd Jackson
- Why consumer subscription is so hard and what to do about it — Casey Winters
- Hollywood on strike — Ben Thompson
- The future of TMS — Activant Capital
- Identifying AI opportunities in financial services — Emergence Capital
- Fundraising advice — Tracy Young
- Payroll is big business — Richard Kerby
- The next trillion dollar marketplace will put SKUs on services — Dan Hockenmaier
- Kindred: Trusting strangers in your home — Safi Aziz
- I built a Lenny chatbot using GPT-3 — Dan Shipper
- Why product doesn’t matter in getting to product market fit — Hari Raghavan
June 2023
- What happens when small and large VC firms decouple? — Charles Hudson
- Apple VisionPro: the MVP for AR — Raven Jiang
- How to find PMF: the counterintuitive secrets — Andy Rachleff and Unusual VC
- A very gentle introduction to LLMs without the hype — Mark Riedl
- The new language model stack — Sequoia Capital
- The guide to SaaS cohort analysis — Christoph Janz
- How to build your startup brand — Rex Woodbury
- A guide to programmatic SEO — Nick O’Brien
- How FedNow and faster payments will impact US fintech — Charles Birnbaum
- The new new moats — Jerry Chen
- The concept that explains everything about marketplaces — Dan Hockenmaier
May 2023
- The unbundling fallacy — Dan Hockenmaier
- Comparing physician and AI Chatbot responses to patient questions — John Ayers
- Deposits as natural franchises — Patrick McKenzie
- Think $1m ARR means you’ve achieved PMF? Think again — Kaitlyn Henry
- Putting the tech back in proptech — Lightspeed Venture Partners
- Prompt engineering — Brex
- Second order effects of AI in vertical SaaS — Akash Bawja
- How hybrid carriers will finally unlock economies of scale in trucking — Dan Lewis
- Differentiating Good vs Great in vertical SaaS — Medha Agarwal
- The new problems every marketplace faces after product-market fit — Dan Hockenmaier
- Investing for alpha or beta? — Rick Zullo
Apr 2023
- How to sell your startup — Dan Debow
- A rapidly changing procurement space provides a wealth of opportunity — Pascal Croak
- ChatGPT plugins — automation for everyone — Nandu Anilal
- A new kind of startup is coming — Nathan Baschez
- Early stage investing with Saam Motamedi — Abnormal Security
- The meritocracy of venture capital — Kyle Karrison
Mar 2023
- The unbundling of the pizza franchise (Slice Pizza) — Dave Yuan
- The defining decade of vertical SaaS — Redpoint Ventures
- Unlocking the next wave of lending innovation — Alex Johnson
- What is ChatGPT and why does it work? — Stephen Wolfram
- How one guy’s car blog became a $1 billion marketplace — Ben Cohen
- Banking in very uncertain times — Patrick McKenzie
- As a human I’m excited about generative AI. As an investor, I’m still wrestling with a few questions — Hunter Walk
- The road to ChatGPT - an informal explainer on how it was built — Rama Ramakrishnan
- The give-to-get model for AI startups — David Sacks
Feb 2023
- The opportunity at the intersection of healthcare and fintech — a16z
- How the Gas app made it to the top of the App Store — Chris Woods
- Thoughts on how to disrupt Google Search — Talia Goldberg
- Five unexpected takeaways about vertical SaaS — Anna Khan
- Startups and defensibility — Elad Gil
- Interchange is a burning platform — Matrix Partners
- More vertical fintech, please — Richard Kerby
Jan 2023
- How to sell your company - tweet thread
- How early-stage startup valuations actually work (from the perspective of VCs) — tweet thread
- How do do customer reference calls as an early-stage VC — tweet thread
- Deep dive into structured and dirty term sheets - Janelle Teng
- 5 failure points between $5M and $100M ARR - Tracy Young
- AI and the big five — Ben Thompson
- On the road to recap — Bill Gurley
- Enterprise software is dead, long live enterprise software (overview of opportunities in enterprise software) — Rex Woodbury
- Deep dive on auto lending — Alex Johnson
- Deep dive on trucking — Richard Kong
- Making money from open source — Amanda Robson
- Tiktok may be a Chinese superweapon — Gurwinder
- Ideas for AI in sales software — Sara Du
Dec 2022
- Selling to SMBs - a16z
- Niche is the next big thing - Rick Zullo
- Venture Capital’s reckoning looms closer - Financial Times
- Hard won startup lessons - tweet thread
- Product Led Growth’s failure - Evan Armstrong
- SaaS benchmark calculator (2022) - Openview
- Venture valuation benchmarks by stage (updated with r-t data as at Q4 2022) - Cooley
- An Interview with Daniel Gross and Nat Friedman about ChatGPT and the Near-Term Future of AI - Ben Thompson