Unformatted by Greg Docter
Rough drafts on startups, tech, and leading teams. If you want pixel perfect, this ain't it.
Saturday, August 16, 2025
Michael Mauboussin on Common Behavioral Biases in Investing and AI-Aided Countermeasures
Behavioral Bias | Description | Impact on Investment Decision-Making | Mauboussin's AI-Aided Countermeasures |
---|---|---|---|
Overconfidence | Overestimating one's knowledge or ability to predict outcomes. | Leads to excessive risk-taking, concentrated bets, ignoring contradictory evidence. | Consciously seek disconfirming evidence; consider a wider range of outcomes; temper optimism with base rates. Use AI tools to surface counterarguments and less obvious risks, generate scenario analysis beyond your initial views, and aggregate probabilistic forecasts from diverse sources to calibrate your confidence. |
Anchoring / Tunnel Vision | Fixating on an initial piece of information or a narrow set of inputs. | Prevents objective reassessment of investments; leads to missing alternatives or holding underperforming assets. | Explicitly consider a full range of alternatives; seek dissent and opposing arguments; "red team" your own ideas. Leverage AI to generate alternative scenarios and viewpoints, identify overlooked opportunities or risks, and simulate decision processes from the perspectives of other investors or market participants. |
Hindsight Bias | Believing, after an event, that one had predicted or known the outcome all along. | Impedes accurate learning from past decisions; fosters false confidence. | Keep a decision journal, documenting rationale, information, and expectations before decisions are made. Employ AI to timestamp, catalog, and later analyze the original logic and context of decisions, ensuring post-outcome reflections are anchored to what was actually known and believed at the time. |
Emotional Extremes | Making decisions under heightened emotional states (greed, fear, euphoria, stress). | Rapid erosion of decision-making skills; leads to irrational choices. | Postpone important decisions when emotionally charged; seek emotional poise. Use AI sentiment tracking to identify periods of heightened emotional language or erratic behavior in your records; set up automated reminders or restrictions to prevent trading or major decisions during high-stress periods. |
Misunderstanding Incentives | Failing to recognize how incentives (financial/non-financial) shape behavior. | Leads to misjudging motivations of market participants or management. | Carefully consider all existing incentives and the behaviors they might motivate, including subconscious effects. Utilize AI to map and analyze incentive structures for all stakeholders, uncovering potential misalignments or hidden motivations that might influence outcomes in ways not readily apparent. |
Overreliance on Intuition | Depending on "gut feelings" in complex, unpredictable environments. | Can lead to disastrous decisions in non-linear systems; fosters false sense of expertise. | Recognize when intuition is appropriate vs. when analytical rigor (System 2 thinking) is needed. |
Base-Rate Neglect | Ignoring statistical averages in favor of specific, vivid information. | Leads to overly optimistic or pessimistic predictions; misinterpreting probabilities. | Always refer to base rates (reference classes) for more realistic probability estimates. Use AI to access, aggregate, and analyze large datasets to establish accurate base rates and reference classes, ensuring decisions are grounded in objective historical probabilities rather than anecdote or vivid detail. |
Monday, August 11, 2025
What's the point of invoking the ghost of Steve Jobs?
"Steve Jobs would have never shipped this."
"No way would this happen if Steve Jobs were still alive and running Apple."
Oh yeah? Which Steve Jobs are you referring to?
- The one who got pushed out of Apple?
- The one who ran NeXT into the ground?
- The one who thought search engines were useless?
- The one who oversaw the launch of a litany of miserable products like the Newton, Apple Lisa, the hockey puck mouse, MobileMe, Ping, or butterfly MacBook keyboard?
The Bitter Lesson
We have to learn the bitter lesson that building in how we think we think does not work in the long run. The bitter lesson is based on the historical observations that
- AI researchers have often tried to build knowledge into their agents
- this always helps in the short term, and is personally satisfying to the researcher, but
- in the long run it plateaus and even inhibits further progress, and
- breakthrough progress eventually arrives by an opposing approach based on scaling computation by search and learning.
The eventual success is tinged with bitterness, and often incompletely digested, because it is success over a favored, human-centric approach.
I think about this a lot right now re: Waymo v. Tesla.
Sunday, August 10, 2025
A running list of tar pit ideas
What is a “tarpit idea”?
These are the startup ideas that seem good — almost too good to be true! — but have been tried by many founders before with little to no success.
Tarpit ideas are often not hard in obvious ways. They might seem so easy and good that it’s unbelievable that no one has done it — but when you look a bit deeper, you realize that they have been tried. Over, and over again.
Via: Tarpit ideas - what are tarpit ideas & how to avoid them
- People do not actually care about taking a sword from one game to another, or whatever.
- Games are self-contained ecosystems. Objects are valuable only within their specific contexts.
- no one wants to treat their life like work
- the tech has been there for 10+ years to make this happen, alas
- economics don't make sense (transaction costs!)
- friction doesn't make sense
- making money > making money "ethically"
- See: Nuclear Weapons Investors Tap ESG Billions [Bloomberg, August 25, 2025]
- generalized tools do the trick
- it's a niche audience
- Harder to use
- Smaller/niche user-base
- Not even 2x better than web2 social, let alone 10x needed to get folks to truly switch
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