Design Systems, Not Just Firefighting, for Lasting Growth
When you're building a company, fires will always come. Your job isn’t racing between them, it’s mapping the territory, building firebreaks, and designing the whole system so one spark doesn’t burn everything down. "Your team kills today’s flames. You shape the forest that survives them." @dickc
Compensate AI‑enhanced Workers at Higher than Market Rates
Pay above range. Because the job is bigger now. If AI makes already great people 3x, 10x, even 100x more productive, they should be compensated accordingly.
AI Lets CEOs Choose Focus or Breadth—Which Wins?
With AI tools today, CEOs can either be laser focused, and say no to almost everything (like Jobs) or they can use the tools to do even more, and get involved in everything (like Bezos). Which is better? @dickc talks about...
CEOs Deploy 20+ AI Agents, Younger Founders Hold Back
For the last few months I’ve been interviewing CEOs about their personal AI stacks 🤖. What helps them run the company better / faster / smarter/ The most AI-pilled ones are running 20+ agents that basically run their entire day....
Limit Approvals to Direct Managers to Unleash Ideas
Most companies don't kill ideas by saying No. They kill them by making you ask 14 people for permission. @dickc fixed this at Twitter when he was CEO with one rule: only your direct manager can block you. "Experiments started flying...
Dick Costolo’s Raw Lessons From Twitter IPO for AI Founders
🚨NEW PODCAST EPISODE🚨 Dick Costolo: the man who IPO'ed Twitter. I’ve heard every Twitter war story….but never from the CEO who actually had to take the "drama queen of hypergrowth companies" to IPO. This episode with @dickc is simply perfect. ...
From Manager to Founder: The Next Startup Mode
.@jack started it, @brian_armstrong built on it, most 2025 vintage startups are running it. What is it called? Manager Mode -> Founder Mode -> _____ Mode
CEOs Tighten Ops While Tech and Marketing Thrive
Native Mode CEOs tech teams and marketing seem to be on point. They are having to push hard on ops: HR - Wider pay bands, narrower promotion criteria. CFO - Bigger token budget, smaller planning cycle IT - More legible, less budget
HubSpot’s Early Culture Code Inspires AI‑native Playbooks
One thing that really worked for HubSpot in the early days was that we published our "culture code" which, at the time, was quite unique. I'm waiting for someone to create a version of that for a truly ai native company....
10 Red Flags You’re Stuck in Manager Mode
Manager Mode -> Founder Mode -> Native Mode 10 Signs you're not in Native Mode: 1. Your cfo isn’t freaking out about the token bill 2. Budget allocation still roughly equals headcount allocation 3. You haven't changed how you draw your org chart 4. You...
HubSpot Agents Charge per Result, Aligning Incentives
HubSpot’s agent pricing Prospecting agent - $1 per qualified lead. Customer support agent - $.50 per resolved conversation. Both agents work well and now have aligned incentives. If using HubSpot, give them a go!
AI Enables Real‑Time Alignment,
It turns out @RayDalio was right all along. The top AI-pilled CEOs I work with use the recorded meetings that we're now used to (Granola, Otter, Fireflies etc) to get to ground truth. Every insight is surfaced in a daily...
Uniform AI Strategies Erase Competitive Edge, Humans Needed
"If every CEO uses the same LLM models to generate strategy and determine product roadmap, no one has alpha. Yes, get context and have AI do all the low leverage things. But for high leverage decisions, I want as much...
Founder Scales 300‑person Team Overnight Using AI
What's the smartest, fastest way you've seen a company force-multiply their people with AI? Just saw the most clever way a founder is AI-pilling their entire 300-person team. Writing it up to share, but I wonder if it can be...
2026 Marks AI App Layer Boom with RogoAI
2026 is the year the ai app layer really starts to crank. @RogoAI is central casting for it. @GabeStengel = 5 tool CEO.