Episode #45: Hire the experimenters, Lessons from "failed" enterprise AI pilots, Valuations soar past the 2021 bubble

We kick off the episode by discussing Rebecca Kaden’s essay, “Hire the Experimenters”, which argues that speed, adaptability, and creative risk-taking are more valuable than traditional credentials in today’s AI-driven startup world. We explore how this mindset shift is reshaping what “great hiring” looks like for early teams — and whether that flexibility can translate into long-term defensibility. Then we break down the MIT report on generative AI deployment across enterprise — and the not-so-great news that 95% of pilots are failing. Charles shares his opinion that these "failures" are signs of future success. Finally, we look at Peter Walker’s data-packed breakdown of bubble-era valuations reappearing at Seed and Series A. With median valuations at the 99th percentile soaring past $160M for Seed and $700M+ for Series A, we ask: what does this mean for startups trying to raise now, and how do you tell signal from noise?