Field Notes
Things I’ve learned, half-learned, and am still arguing with myself about.
2026
- Silicon Valley Taught Me to Ignore Strategy. That Was a Mistake.I’ve spent two decades building startups. Some were fairly successful, a few were acquired, but none became the kind of home run you dream about when you first move to Silicon Valley.
- When Software Goes to Zero: How Private Equity Should Rethink Value CreationI’ve been thinking about how AI is changing the economics of software companies, and I believe this shift has significant implications for how private equity firms create value across their portfolios.
- Starting in Software EngineeringIf you’re starting in software engineering this year, you’re walking into a different job than the one I trained for.
- When You Step Away, What Breaks?What chaos engineering taught me about leadership, control, and my habit of saving everything.
- My team paid for every decision I left openMonths after a strategy offsite, we still could not decide who to invite to an event.
- Hindsight: Giving Claude Code a Memory of Its MistakesHuman hindsight comes with a flaw: knowing the outcome changes how we remember the uncertainty that came before it.
- AI Makes Building Cheap. Attention Still Costs.Crown & Cleats, the app my son and I built together, is officially published on the App Store.
- Are You a Burden or a Blessing?An employee said something to me that bothered me more than it should have.
- Most Teams Don’t Do Strategy. They Do Theatre.Most people treat strategy like a verdict. A choice gets made, someone says “this is the direction,” and then the machinery starts turning.
- AI Brought Me Back to BuildingI started coding again. When I look back at my GitHub profile, I can see sporadic green dots where I showed up for a week, then disappeared again.
- We had the wrong people for the strategic choices we madeI used to think execution problems were mostly about discipline and reviewing dashboards.
- The Strategy Assumes Capabilities That Don’t ExistI used to write strategies that sounded confident as hell. Decisive. Aspirational.
- Your Code Isn’t Special Anymore. Now What?With LLM-powered code generation tools, you can sit down, describe a product in plain English, and watch working code appear.
- We Didn’t Fail the Strategy. We Passed the System Test.Belief feels human. Incentives feel mechanical. For a long time, I wanted to believe belief would be enough — that if people genuinely bought in, they’d naturally align and figure the rest out.
- Execution Fails Because They Never Truly Believed in the Strategy.When execution fails, the easiest question is, “What did they do wrong?”
- I Blamed Execution. The Truth is Much Harder.I often tell people that strategy is the what and execution is the how. And while that distinction is useful, if I’m honest, I’ve inadvertently used it as a shield more than a framework.
2025
- The Paradox of Alignment: Why Great Leaders Stop Steering AloneIt started with a question I didn’t see coming. A colleague asked me what I thought made a great leader.
- Why Prompting Is Really About Understanding OurselvesNot long ago, people thought “prompt engineer” would be a niche role — like getting a degree in MySpace page design: looked promising until the world moved on.
- You Can’t Run From PoliticsPolitics isn’t just in government buildings or campaign ads. It’s in your staff meeting.
- Prompted by Purpose: How an LLM Helped Me Find My “Why”When most people think about GenAI, they think about speed. Write faster. Code cleaner.
- Meta-prompt To Improve Your Prompt Engineering Practices.Many times I construct a prompt. It’s sloppy. Littered with grammatical errors. The desired output is unclear.
- Optimizing for Promotion Isn’t Gaming the System. It Is the System.When you’re early in your career, every problem feels important. You find a broken thing, and you fix it.
- Roadmaps Without Outcomes Are Just To-Do ListsMost teams don’t realize they’ve become a feature factory until it’s too late.
- Moving On QuicklyA few years ago, I had a direct report who looked great on paper. But every 1-on-1 felt like a hostage situation.
- The Hidden Path to Better Outcomes: Why Actions Aren’t EnoughWe’ve all been there: a project falls apart, team collaboration breaks down, or we miss revenue goals.
- Testing LLMs: You’re Probably Doing It WrongWhen most folks start testing LLMs, they reach for the familiar: regex, hard-coded assertions, or golden outputs.
- Don’t Sell GenAI — Sell the OutcomeWhen GenAI founders come to me for advice — especially those navigating enterprise sales — I always start with a straightforward question.
- Letting Go of Control: Testing, Certainty, and the Future of SoftwareWhat keeps me curious about generative AI isn’t just the models or the capabilities — it’s the mindset shift it demands from us.
- The Hidden Cost of Saying Yes: A Corporate Survival GuideLast week during our team’s status meeting, I had an epiphany that I wish I’d had years ago.
- Generative AI and Programming Productivity: Beyond the 10x MythIn the ever-evolving landscape of technology, generative AI (GenAI) has emerged as a transformative force, particularly in the realm of software development.
- Why Shielding Hurts Your Team and YouFor the sake of this post, let’s call shielding what it is: “blocking any bullshit and chaos, whether behind the scenes or out in the open.”
2024
2020
- Announcing Spinnaker’s Vision & MissionThrough a joint effort between the Steering Committee and the Technical Oversight Committee we have crafted and aligned on a vision and mission statement for the Spinnaker project.
- The Pandemic is Driving The Low-Code/No-Code Movement But It Won’t Benefit Everybody EquallyIt happens every six years. Like Haley’s comet, Michael MacGrath has come to expect this behavior from his leadership at Piguet Manufacturing.
- The Pandemic Is Speeding Up Cloud Migrations. Yours Can Too.“Awww, damn!” I said to myself. I had just realized we were going to close the office due to the global pandemic.
- The Real Cause Of Your Workplace HeadachesI am going to take a wild guess that you recently had an argument or heated debate with a colleague.
- The Hidden Cost of Reducing RiskAt a previous company, the CTO said there needs to be a healthy tension between the developers and operations teams.