Entrepreneurship
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.
Entrepreneurship
Entrepreneurship
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
Entrepreneurship
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.
Entrepreneurship
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
BusinessWeb
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
BusinessWeb
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.
Entrepreneurship
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.
Entrepreneurship
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
Entrepreneurship
The End of Chapter 3: Expert Mode
Earlier this month we sold Accelo, a company I co-founded 15 years ago, and last Friday was my last day at the company. With this transition, I wanted to share a few reflections on a massive journey, appreciation for the work of our amazing team and thanks for support of
Entrepreneurship
The SaaS Fundraising Death Zone
TL;DR: the ecosystem of early-stage investors (angels, seed and VC) has a structure and set of incentives that creates ideal (or even necessary) points in a SaaS startups life for raising capital. Unfortunately, changes in the ecosystem have created what I call a "Death Zone" between Seed
General
Stop puffing out your chest
Eric Ries, the author of "The Lean Startup", defines a startup as "a human institution designed to create a new product or service under conditions of extreme uncertainty". Implicitly, a startup entrepreneur is someone who chooses, willingly, to embrace extreme uncertainty. Most people think uncertainty=high
Entrepreneurship
UOW Occasional Address - It's what you do with it that counts
Introduction Today is one of the days you'll remember for the rest of your life. It might be because you feel proud - it is the culmination of thousands of hours work and study. It might be because you feel relieved - no more cramming for exams and