Dream Big, Iterate Small: Turn Mistakes Into Magic
My mantra across my 30+ year career: Dream big, iterate small. That has served me very well and has stood the test of time. Adjacent to this idea is something else I believe in, but haven't written about in quite this way: It's fine if you don't get it right as long as you work to make it right. Relentless iteration can turn early mistakes into eventual magic.
Design Agentic UX, Not Just APIs, for B2B Success
Every B2B software company is (or should be) building an agentic version of their product. One that can be used programmatically by agents, not just interactively by humans. But, you can't just wrap your existing APIs into an MCP server...
AI‑Powered Free Tool Simplifies Daily JSON Workflows
NEW: jsondata .com -- The AI-powered JSON data tool. tl;dr: I built a free online tool to look at, work with and manipulate JSON data -- with the power of AI (of course). --- One of the things that I...
Empower Employees to Share Authentically, No Quotas Needed
It's much easier to do influencer marketing when you have influencers on your marketing team. HubSpot has done well in this regard with more than our share of people across the org that have a following. How did we do...
Need Per‑Prompt ‘YOLO’ Mode for Claude Code
I wish Claude Code had a /yolo option for an individual prompt. Or maybe it already exists and I just don't know about it. I don't want to turn on "dangerously-skip-permissions" as a default behavior, but there are times when...
Snapshot Projects to Counter AI Non‑Determinism
The best way I learn is to to just DO THE THING and interact directly with customers. I love being able to own an early project and go into "Full Stack Founder" mode where I do everything from marketing, development...
Leverage AI Ecosystem, Not Just Core Models
The HubSpot team was at an offsite this week. Best 2 days of my year so far. So much to talk about and discuss and I'm biased, but the team is amazingly clueful. On the AI front, here's something that...
Navigating Anthropic API Outage While Maintaining Momentum
Current Status: Dealing with the emotional roller coaster that is the Anthropic API right now (they're having an owie). On the one hand, I'm in a state of flow and trying to finish up some work for a demo video...
Simple AI Agents Now Automate Tasks Software Couldn't Handle
Makes me happy to see teams of easy-to-use AI agents being launched on Agent.ai . AI agents don't have to be complicated. Think of them as smart software that can complete tasks that software really couldn't do before.
AI Empowers Solo Entrepreneurs to Build End‑to‑End Businesses
We are seeing the rise of the full stack entrepreneur. AI is expanding the scope of what an individual entrepreneur can do. She can have the idea. She can test it using a virtual customer panel constructed with LLMs. She...
Build Your Own AI Sales Team Today
The future is about hybrid teams of humans and AI agents. But even today, you can start building your own personal team of simple, easy-to-use agents. If you work in sales or need to sell (because you're a founder/entrepreneur), you...
AI Drives Emergent, Context‑Driven User Interfaces
The history of software is really the history of how humans interact with computers. A (partial) history of user interfaces: TUI: (Terminal User Interface): Type & Read GUI (Graphical User Interface): Point & Click MUI (Mobile User Interface): Touch &...
Context Graphs: Hype Meets Reality Check
A concept is making the rounds in AI circles right now that has many people very excited: context graphs . Foundation Capital published a piece calling it "AI's trillion-dollar opportunity." Engineers and founders are writing technical breakdowns of how it...
Share, Don’t Perform: Build Genuine LinkedIn Impact
Here's a quick tip on how to build an effective presence on LinkedIn. Too many people on LinkedIn are "performing" for their current (and future) followers. Instead of self-centered performing, focus on generous *sharing*. We all have something to share...
Ensuring AI Coding Gains Outpace Technical Debt Costs
I'm a massive fan (and daily user) of agentic coding tools like Claude Code and Codex CLI. One of the questions we'll need to ponder in 2026: How do you make sure that the compounding value you are getting from...