Boomerang Mode: Engaged
I'm heading to Sydney this week to talk at Sunrise about the experience of building a startup in the US. But this is my last trip as a visitor to my homeland because after 15 years away, I'm moving back home.
The Death of Story Points - How AI Finally Makes Agile Work
In the last month I shipped more working software than my team used to ship with five times the developers in six months. Here's why story points are finished, why Agile is finally about to work, and who's on the right side of the bifurcation that's coming.
How I Used AI to Pivot a Company in a Week
The thinking took weeks. AI compressed the execution into days.
The Signal That Made Me Pivot TeamScore Into WorkSights AI
Why I pivoted TeamScore into WorkSights AI - a founder’s lesson about product-market fit, revealed preference, and discovering the real opportunity.
Building with AI: Everything Except the Code
How I’m using AI to design, plan, analyze, and build a tech company - and why the most exciting things aren't happening in engineering.
75 Books in 12 Months
Today is Election Day in the US, and after the “shoot-self-in-the-other-foot” results came out this time last year, I decided the news - which for me was mostly podcasts - didn’t deserve my attention anymore. I’ve always been a news junkie - from being an early user of
The Corrosive Spiral of Poor Performance
In remote teams, poor performance isn’t just bad — it’s contagious. One disengaged person can corrode trust, effort, and culture faster than you think. Here’s what I learned the hard way about stopping the spiral before it spreads.
Fifteen Years of Paying It Forward
Every few months, I’m reminded just how special Startmate is - and Demo Day for the Winter 2025 cohort today is another one of those moments. It’s a celebration not just of another set of ambitious founders, but of the community that has quietly shaped the startup landscape
Chapter 4: Building Ascendius in Public with AI
After two decades building and running technology companies, I wanted to approach Chapter 4 differently - not by forgetting what I’ve learned, but by questioning everything I thought I knew, because I believe with AI, the rules have changed. That’s what Ascendius is about - and this post
The Analytics Trap
Analytics sounds smart and data-driven. But for most people, it’s just homework they’ll never do. Here’s why analytics is a trap for founders who build it - and for the leaders who buy it.
Fixing the Machine: The False Trade-Off Between Health and Success
It took me twenty-five years to realize that sacrificing health for business isn’t ambition - it’s a lose-lose deal.
Kicking off Chapter 4
When I sold Accelo a year and a half ago, I promised myself something I’d never really given before: a break. Truth is, I wasn’t great at it. My family will tell you I failed miserably at "learning how to sit still." But spending more time