Product leader at Webflow, previously Slack — known for building influence without authority and the art of persuasion in product orgs.
Head of Design at Anthropic — went back to IC to truly understand how AI is changing design before managing again.
Runs all product for Cisco — says there's zero chance he could have done this job without AI. Former Sizzler waiter who broke his stutter by entertaining customers.
Says the simplest way to get value is to point Cowork at a real Slack thread and let it act like a teammate.
HubSpot co-founder who stopped wasting time after a near-death snowmobile accident and got radically intentional about what he does next.
OpenAI engineering leader who devoured Antimemetics, got worldview jolts from US–China books, is an anime fan, went all-in on Ubiquiti, and repeats ‘never feel sorry for…
Clinical psychologist and founder of Good Inside — known for translating parenting insight into ultra-practical scripts and tools.
Two-time founder who re-watches ER with his teenage daughter, loves dictation, and thinks most A/B testing is false-positive theater.
PM who tells a Failure Corner story about being a 10X learner, recommends Mindset, watched The Pitt + Severance, loves the open-source Loom alternative Cap, and repeats ‘…
Investor who recommends history books as high ‘intellectual return,’ watches Landman, pitches June date, keeps a ‘Carthage Must Burn’ poster, and built an AI cartoon news…
Leads Codex at OpenAI — believes the bottleneck to AGI is human review speed, not model capability.
Married couple both building AI products at OpenAI — she teaches and simplifies, he thinks deeply and stays calm. They run a popular enterprise AI course together.
SaaStr’s loudest voice who loves freemium, uses Opus Clip to manufacture shorts, and keeps a simple motto: ‘Be kind.’
CEO who runs a ‘Conscious Business’ reading club, owns three Fellow coffee makers, and keeps a dark dad-motto ready for bad days.
Elena Verna 4.0 — fourth appearance; lightning round is explicitly a custom one-question version (no standard five questions).
Founder of Surge AI; deep sci-fi taste and a lifelong fascination with decoding alien communication (in books, films, and LLMs).
LinkedIn CPO who recommends Mindset, Thinking Fast and Slow, and High Output Management, loves Bluey as layered ‘family product design’, plays with Spark Amp + Ultimate G…
Sales leader whose mom’s sayings still power her through ‘off-pace’ quarters.
Coach who loves Loom for human scaling, quotes Joseph Campbell, and uses Granola + ChatGPT to support clients (and is building an in-between-sessions AI).
CEO of Gamma; pairs founder memoirs with strategy frameworks and a worldview motto about seeing beyond your ‘well’.
Canva founder whose daily Calm habit supports an imagination-first worldview: you can’t will anything into existence unless you can picture it.
Block CTO who reads classics and poetry (not work books), loves Alien’s aesthetic, and champions open hardware you can truly customize.
AI engineering author and researcher at Nvidia — wrote the definitive 'AI Engineering' book. Previously built ML platforms at Netflix and taught at Stanford.
DORA/SPACE researcher who re-watches Suits, loves Eight Sleep, and buys COSRX face masks 10 for $15.
