Harry Stebbings

Harry Stebbings sent a personal thank-you to every follower who followed him before 50,000.

He typed each note himself. Every night from 1 till 2.30 a.m. he sent 50 to 100 messages. One note said he saw the person was from Sweden, that he loved the Grand Hotel, and that they should let him know when they were in London.

He treated the messages as a customer acquisition flywheel. The next day a recipient would walk into the office, mention that Harry Stebbings had written, and tell coworkers the show was pretty good and worth a listen.

David Tisch says the venture market now has nothing to do with 2021. It is a standalone condition, funky and interesting and maybe frothy or insane, that investors have to read on its own terms.

He has done early stage investing for 17 years. People keep forcing the present onto an older cycle, and he rejects the 2021 comparison because 2021 had its own macro and micro drivers. Going back through 18, 15, and 2010, each moment was different. He can argue the job has totally changed and, equally, that the job is still whatever the current market presents: see and meet great founders, decide whether to invest, and beg them to take the money.

Harry Stebbings calls 2021 bubble-like, a good time

Satya Nadella says most AI token use becomes a commodity that may be open weights or cheap closed models, while a market for frontier models remains.

Harry Stebbings asked what percent of traffic goes through open versus closed models in 24 months, looking at both traffic and dollars. Satya Nadella says it depends on what the frontier looks like. Most things get saturated, and then open weights or cheaper models of closed weights work. If a company can train on its own traces, it does not need the latest model for a problem that has not changed. If an eval keeps moving forward, the company may still pay for a frontier model. He says there will always be a market for frontier models, because

Satya Nadella says Microsoft Agent 365, with perception, is the trust system Microsoft built for AI agents. It gives every agent an identity, logs activity, tool calls, model calls, and chain of thought, keeps the logs tamper-proof so an agent cannot edit them, sets policy, and checks behavior against the policy.

He says models are becoming more capable and scaling laws are working, but an assumption that alignment would just fall out of scaling does not seem to hold, and mechanistic understanding is elusive. The posture he wants is an engineered zero trust environment that contains any malfunctioning agent before it does harm. Agents that are more capable and less aligned need a trust syst

Harry Stebbings introduces Joey Zwillinger on The Twenty Minute VC as co-founder of Allbirds, the wool-shoe company Stebbings calls the maker of the world's most comfortable shoes. He says Larry Page, Mary Meeker, Ben Horowitz, and Dick Costolo are fans, and that Allbirds has funding from Maveron, Lerer Hippeau, and Slow Ventures. Before the shoe company, Zwillinger worked in investment banking at Goldman Sachs, in venture capital at Industry Ventures, and at TerraVia, a food and nutrition company. He tells Stebbings he was an engineer in biotech when the idea for Allbirds took shape.