These are the posts that, over the years, have gotten the most attention, as well as a couple that are just near and dear to me.
Most summaries written by AI.
Strategy, moats & innovation
- A Taxonomy of Moats (2019) — Sorts moats into four sources (state grants, special know-how, scale, and system rigidity) and argues young startups are protected mainly by uncertainty, not moats.
- Disruption is not a strategy (2016) — Christensen’s disruption describes how incumbents fall; it isn’t a plan, and founders still need ways to deter or delay competitors.
- Schumpeter on Strategy (2019) — Competition erodes profit; only innovation earns temporary “entrepreneurial profit,” which separates innovative startups from job-replacement businesses.
- Who profits from innovation? Startups or incumbents? (2014) — A “neo-Teece” framework: who captures the value depends on how hard the innovation is to copy and who owns the complementary assets.
- iTunes Case: Technological Innovation (2018) — Course material that uses the MP3 player market to show technology succeeds through a social and economic process, not engineering merit alone.
- iTunes and the Basis of Competition in the MP3 Player Market (2018) — Apple won not with a better format but with end-to-end control of hardware, software, and store, which let it bring the record labels on board.
Uncertainty
- Addressing Uncertainty, an overview (2022) — An overview on my project to create a strategy framework that works under Knightian uncertainty.
- Startups and Uncertainty (2019) — Knightian uncertainty deters incumbents, giving startups a window to build real moats; “uncertainty becomes their moat.”
- Productive Uncertainty (2020) — Separates novelty uncertainty from complexity uncertainty, and argues new-market startups make better venture bets than new-technology ones.
- One Process (2020) — Incremental versus radical innovation is a false split; innovation follows a power law, and the big breakthroughs sit near the roots of the technology tree.
- Ruling out rather than ruling in (2017) — Since picking winners means predicting the future, investors should use constraints to rule out what clearly won’t work.
Venture capital
- Heat Death: Venture Capital in the 1980s (2015) — The 1980s VC slump came from avoiding market risk; returns come from betting on markets that don’t yet exist.
- Power Laws in Venture (2015) — Derives power-law venture returns from a simple growth-and-exit model, explaining why observed tail exponents sit near 2.
- Power Laws in Venture Portfolio Construction (2017) — Sample-based simulations misstate fat-tailed returns; bigger portfolios cut the odds of losing money but barely raise the odds of a 5x fund.
- Betting on the Ponies: non-Unicorn Investing (2014) — Angels can’t pick unicorns, so they should specialize in one sector, keep bet sizes constant, and reserve for follow-ons.
- Why do VCs insist on only investing in high-risk, high-return companies? (2019) — Risk-adjusting power-law outcomes shows medium-risk investing rarely pays; the appeal of the middle is “perhaps an illusion.”
- Discount rates in venture backed startups (2023) — Startups should discount internal decisions at about 40%, matching the hurdle rate their venture investors need.
- On being special in the venture business (2017) — Venture success is skill, and the skill lies in consistently telling good pitches from bad in ambiguous cases.
- Your Board of Directors is Probably Going to Fire You (2021) — Boards exist to monitor investors’ money, so founders should manage them deliberately: one-on-ones, no surprises, no problem-solving in the room.
- Prepping for a meeting with someone who wants to become a VC (2010) — Debunks the myths that draw people to venture; VCs allocate capital and react to entrepreneurs rather than drive them.
Technology, history & AI
- The Deployment Age (2015) — Using Carlota Perez’s framework, argues the information-technology revolution has moved from speculative installation to deployment, with major consequences for venture capital.
- The Illusion of Acceleration (2024) — Technology adoption isn’t speeding up indefinitely; it cycles with technology waves, and fast adoption doesn’t help startups.
- AI and the Structure of Reasoning (2023) — AI built on induction can’t scale past its own limits; reaching human-level intelligence would require abduction (“invention”) and self-directed intent.
Other
- Advertising, the Fallacy of Perfectibility, and the Best Minds of My Generation (2011) — Why (and when) advertising is beneficial to the economy.
Personal
- Resignation letter (2024) — Why I stopped making new venture investments.
- Musing on luck & Thank You (January 2010) — An uncharacteristically earnest post about learning humility, back when I still had it.
- On Failure (2011) – The post I go back and re-read, painful as it is, when I start to forget where I came from, how I got here, and why I do this.