Blog

You can build anything with AI now, so everyone is. I've been testing what they ship, and the same gaps keep showing up, no way to delete your account, privacy policies that never mention what the vendors do with your data, and welcome emails that break mid-sentence on a phone. Here is what finishing a product properly still takes.

• AI Slop
• Product Quality
• Data Rights

At a time when it seems harder than ever to get a job in software, I quit mine. A month of no formal work, a four-month-old who does not sleep, getting back to the gym, and the first steps toward building something of my own.

• Life
• Family
• Career
• Entrepreneurship

I joined Constant Contact to lead a team building a brand-new email editor. It never found customers, so we repurposed it into Rise, the platform that now powers the whole product for over 150 developers shipping code twice a day.

• Constant Contact
• Platform
• Leadership

I don't think leaders are made by an org chart. They're made by a mindset, showing up to own a problem whether or not it's yours to own. Here are four moments, at every stage of my career, that drove it home.

• Leadership
• Ownership
• Mentorship

A dementia-care app was spiking on the idea trackers, and it hit close to home, so I downloaded it. The developer's own email was hardcoded into the login, the settings were placeholders, and the data policy was a 404. Here is what that taught me about shipping AI slop, and why it left me strangely hopeful.

• AI Slop
• Product Quality
• Customer Empathy

I spent a whole career sharpening my craft, and then AI came along and made a big chunk of it stop mattering. This is my honest account of the identity crisis that followed, the token-budget hangover that grounded me, and trying to find my balance in an industry that moved on.

• AI-Assisted Development
• Software Craftsmanship
• Career

The first entry in a new Life Log series. Less about leadership, more about life: our dog Sasha losing a tooth the hard way, our daughter Shea forgetting how to sleep, and a smoke-filled week spent indoors.

• Life
• Family

In 2014 I bought a red Mazda 3 that turned out to be a rebuild write-off. Coming to terms with that bad decision, then learning to fix the car myself, taught me a resilience I leaned on the day I crashed Constant Contact.

• Resilience
• Growth
• Engineering Leadership

For the first year, every line that shipped had my fingerprints on it. Then the team grew and the job quietly changed underneath me: it stopped being what I could build and became what four other people could ship without me in the room. Staying close to the code is what made that possible, and it's the same instinct that carried me to VP.

• Technical Leadership
• Staying Hands-On
• Distributed Systems

I spent two months building something in a silo, sure I understood the vision. The demo died in under a minute. What I actually got wrong was not the code. It was the customer.

• Customer Empathy
• Feedback Loops
• Learning from Failure

At eighteen I was handed a zero-to-one iPad app in a language I'd never touched, wired to a SOAP service that did not forgive typos. The real lesson wasn't Objective-C. It was how much you can figure out when there's no one left to hand the problem to.

• First Software Job
• Imposter Syndrome
• Shipping Your First App

AI is very good at making sure you never hit a wall, which sounds like a win until you notice what you didn't learn on the way around it. I'm one of the engineers letting their judgement atrophy, and here's my plan to stay sharp.

• AI-Assisted Development
• Software Craftsmanship
• Technical Debt

There is a version of me who took art class. I picked software instead, because it looked like an easier grade, and I have built a career on worse reasoning since.

• Software Career
• Career Reflection
• Learning to Code