
Alasdair Cumming
6K posts

Alasdair Cumming
@Al_Cumming
beach bum. software designer. infrequent luke warm takes. head of design @opensolar


Imagine handing over a design for dev to build and telling them every single icon has unique spacing



Brian on why pure people managers won't survive AI: "I don't think people that only manage people will have any value in the future. Everyone's going to have to be a hybrid people manager or manager IC. In other words, even the managers need to code. You can't just be these managers where you're people's therapists and you're just doing meetings, just one-on-ones. People who have lots of recurring one-on-ones are not going to survive. That kind of leadership style is not gonna work. You need to have context. I hear about heads of design, they don't actually manage the design. Johnny Ive manages the design. He designs and he leads people. A design leader who only manages the people that's crazy to me. The way Frank Lloyd managed his design team is through the work. You don't manage the people, you manage the work. I think a lot of people will survive this age of AI. The two types of people that will not survive are pure people managers, and people that are rigid and don't want to change and evolve."

My guest today is Brian Chesky (@bchesky), founder and CEO of Airbnb and one of the great consumer founders of the last 20 years. Paul Graham coined "founder mode" based on Brian's experience running Airbnb. This conversation is about what comes after it, what he calls AI founder mode, and how it will force founders to focus even more on the details. We talk about his eleven-star exercise for finding product market fit, why your first hire should be a recruiter, and why Airbnb's $100B IPO became one of the saddest days of his life. Brian still comes across like the 17 year-old at the Rhode Island School of Design (RISD) who picked to study industrial design. His heroes are all artists. Da Vinci, Van Gogh, Walt Disney, and Steve Jobs, all of whom were working the week they died because they loved what they did. Rick Rubin taught him that an artist is only an artist when they make things for themselves. Now Brian believes AI is the opportunity for all of us to do the same. Enjoy! Timestamps: 1:00 Studying Industrial Design 11:33 AI Founder Mode 17:02 Lack of Consumer AI Companies 22:10 Small Teams and Focused Problems 30:52 The Evolution from Founder to CEO 38:13 The 11-Star Experience 41:07 AI as a Canvas for Creativity 48:17 Detaching from Success 53:12 Founder-Led Moats 58:34 The Next Chapter of Airbnb 1:03:08 What Endures in the Age of AI 1:06:43 Lessons from Bodybuilding 1:10:20 The CEO's No. 1 Job 1:17:01 Activating Talent 1:20:39 The Kindest Thing


so... I audited Garry's website after he bragged about 37K LOC/day and a 72-day shipping streak. here's what 78,400 lines of AI slop code actually looks like in production. a single homepage load of garryslist.org downloads 6.42 MB across 169 requests. for a newsletter-blog-thingy. 1/9🧵


I’ll say the thing no one is saying: design culture is broken in lots of companies. Often design teams & designers are the most resistant to change org in the EPD triad, with highly vocal AI opponents, and little skill or interest in the art of campaigning for influence or resources. Won’t hold a number like a PM, not yelled at about timelines like engineering. While I have brought design topics to the board convo, not a single board has pressed me our design talent, strategy, or velocity. Most teams treat design like a tax they don’t want to pay, and those that *do* take a deep interest and want to invest in design get back big “get out of my figma” energy. And if you’re too precious about craft to dirty your hands with the dark art of corporate politics, good luck getting more headcount. If a PM or engineer can get 85% there with tailwind and a dream, you better come to the table with more than “I represent the user.” Great designers are worth more than almost anyone on the team, and I’ve worked with lots of gems, but this is 0% surprising to me.

4/ Design roles have plateaued Unlike PM and engineering, open design jobs have been relatively flat since early 2023, and there are also fewer of these roles than PMs and engineers in absolute terms (about 5,700 globally).

AI coding agents can now deliver one-shot custom apps straight to your phone. It’s the beginning of the end for the iPhone’s dominance.



You don’t just wake up a world-class designer. It takes reps, mentors, and environments that raise your bar. Those opportunities have been disappearing — so we’re bringing them back. Introducing DAP: Shopify’s new Design Apprenticeship Program. Apply Oct 20 – 27 → link in reply 🎩 @katarinabatina









