"CEO of the Year Award: Jensen Huang, Satya Nadella, or Zuck?" @bhalligan + @HarryStebbings + @rodriscoll + me "Jensen is rethinking the entire playbook and role of CEO" - Brian "Satya wins. He has the hardest job, because he's not a founder" - Jason

I chose a ‘prosumer’ vibe coding platform Replit v. Lovable v. Bolt vs some other in about 10 minutes based on 1 criterion: 🌎 I wanted a true 100% solution. I didn’t want to hook up a database, or go somewhere else for hosting, or have to copy stuff into Claude Code, or anything. Notwithstanding bumps, in the end it is super handy to be able to be “all-in one” once you are in production. … Now, if I had to pick over again, security would be my #1 criterion. Actually, #1, #2 and #3. But all-in-one would be #4 still. For me. (Mobile would be #5, but that’s still work-in-progress everywhere) … The space is also super dynamic and every competitive advantage one vendor has likely the rest will catch up very quickly.

Devs: GPT-5 crushes math tournament!! With less token outputs!! New SOTA on GPQA!! Business Peeps: DOES IT STILL HALLUCINATE

A mis-hire at CRO / VPS is a triple-death spiral: - Great folks leave - Momentum slows - Hiring the right one now is much, much harder And then you're in a really tough spot. It was hard enough to hire growing say 70%. Now, 12-18 months later after a mis-hire, you're growing 40%. Now finding the right person is so much harder. And you've lost all that time. And many of the top reps ... left.

.@maggie_hott head of GTM at openai was the first sales hire at Slack Day 4: "We've been hacked. It could cripple the company." "March 2015. Slack was the Silicon Valley darling. ~50 people in one room. I'm ready to start selling, then my boss pulls me aside with the news." That afternoon, Stuart Butterfield stood on a desk and addressed the whole company: "This is going to be challenging and tough, but we will make it through. It's going to take hard work from every single one of you." The trust employees had in Stuart was palpable. First time I'd seen true culture of accountability. 4 days later, we went public with the breach. They put me on the phones for every hacked customer. Trial by fire at its finest. The lesson that stuck: Alignment isn't tested in good times—it's revealed in hard ones. "How the team responded mattered more than the crisis itself. Most people don't even remember that breach today. But I learned 3 things that shaped how I think about culture: → Authentic leadership matters (people follow leaders they trust) → Culture is your strongest defense in crisis → Alignment drives outcomes when teams rally around shared values" The breach didn't define Slack. How we handled it did.

How do founders that have never done it before scale to $10m, $100m, $1B in ARR? They hire people better than them This is the mistake most Stretch VPs make. They don’t hire folks better & later more experienced than them as their managers And they hit a wall at the next stage

New!! "AI for SMBs: Who Will Do The Training?" with @bhalligan + @rodriscoll + @HarryStebbings - Prosumer AI on fire - Vibecoding on fire - Enterprise on fire "But in-between? You need training, and there's no one to do it. For now."

Covfefe, def. 614: When you get an investor update from a start-up you literally have never heard of from before

How @maggie_hott + team built ChatGPT Enterprise from 0 to fastest-growing enterprise app in history: Early 2023: OpenAI had <10 sales people. No SDRs, no Salesforce, no processes. Just 6 API-focused AEs. "Instead of training existing team on both products, we made a bold bet: build a dedicated ChatGPT Enterprise team from scratch." Why? Speed > efficiency in hypergrowth. The playbook: → Months 1-3: 3 enterprise AEs with vertical expertise → Months 4-9: Added SDRs, sales ops, proper systems → Months 10-18: Scaled to full enterprise motion → Months 19-24: Unified 500 people into one GTM org The integration was brutal. Everyone got new roles, new managers, had to learn the opposite product. API sellers learned ChatGPT, ChatGPT sellers learned API. But it worked. Better customer experience, faster execution, less duplication. Key lesson: In AI, old playbooks don't apply. Design around your products and customers, not legacy org structures. Sometimes the "messy" approach beats the "clean" one.

I appreciate the very careful ordering of partners here (You gotta get this stuff right)