Holding the room
Facilitation, feedback, and what actually happens between the agenda items. A teacher’s turning point, Feedback for you and for me, Act like you want to be there; next, How I open a room in the first five minutes.
Willie Jackson
I help people change how they work together.
I started as a technologist, building enterprise software at Accenture and the learning platform behind Seth Godin’s altMBA. Then I spent fifteen years on a harder problem: how do you get people to actually change? I ran a magazine, helped grow a consultancy from three people, and now advise leaders who are managing people and AI agents side by side. These are the stories behind that work.
Over the years, I’ve…
- Sold mistletoe door to door in the fifth grade (and learned what happens when you run out of product) 5th grade
- Deployed enterprise software across the country for Accenture, then walked away from the cubicle in 2010 with no plan 2010
- Was CTO of The Domino Project, Seth’s publishing experiment powered by Amazon [YEAR]
- Built the tech behind Seth Godin’s altMBA, now 7,000+ alumni in 100+ countries 2015
- Ran a magazine for Black men out of Harlem and published 400+ stories in four years 2015
- Sat across from a new client who started telling racial jokes at our kickoff meeting c. 2015
- Gave a talk in Berkeley, got recruited as hire #3 at ReadySet, and stayed six years 2017
- Led ReadySet trainings from Portland to Portugal for 200+ organizations 2017–24
- Went house hunting on HGTV [YEAR]
- Started managing AI agents like direct reports (and taught one to run the servers in my closet) 2026
What I write about
Managing humans and agents
Direction, trust, and context, whether your report is a person or a model. Agentic Management, Trust and ego in management, Unnecessary heroics; next, AI upskilling is a management problem, not a training problem.
The Seth Godin years
Building the altMBA and The Domino Project, and what shipping weekly does to you. Coming first: Building the altMBA: learning infrastructure for 7,000 people.
Media and identity
Abernathy, Black leadership, and who gets to tell the story. A love letter to Oak Bluffs, The Fierce Urgency of Compassion; next, Four years of publishing a magazine for Black men.
Culture work
Six years and 200+ organizations of inclusion work, and what actually stuck. Six & Change, From Day One, A message for the moment; next, What inclusion work actually changed.
The portfolio career
Accruing assets, starting before you’re ready, and pivots nobody planned. Accruing Assets, What’s in a Power Circle?, The problem with waiting; next, From IT consultant to facilitator.
Tinkering
Vibe coding, home servers, and doing an impression of a software developer. The vibes are right; next, I let an AI run the servers in my closet.
People and places
Weak ties, mutual introductions, and the places that made me. Strengthening weak ties, Mutual introductions, You just had to be there; next, Jacksonville made me.