Navigating Startups: Optimism, Uncertainty, and Strategic Benchmarks

Last week, we recirculated one of my favorite episodes in the entire archive, our May 2022 lunch debate on risk, bias and decision-making with Nobel Prize Winner Danny Kahneman, World Series of Poker champion Annie Duke, legendary investment strategist Michael Maubaussin of Morgan Stanley’s Counterpoint Global, and our own founding managing partner Josh Wolfe. In last week’s episode, the group discussed the value of premortems, the possibility or impossibility of humans changing their minds and dissonance reduction.

Now we turn to the second half of their conversation as they look at the illusions and amplifications of optimism, overconfidence, and whether hot hands exist in real life.