What Went Wrong: A first-time editor in chief reflects on a startup that didn’t work
Jul 23, 2026 · 57m
Topics discussed
Introduction and the decision to conduct a post-mortem
Olivia's career path and the origin of The Barbed Wire
The nonprofit hybrid business model and its challenges
Recruiting challenges and defining the editorial vision
Differentiating from competitors and content strategy
Revenue struggles and the failure of the initial business model
Audience growth, team dynamics, and social media strategy
Failed verticals and the difficulty of selling niche content
Balancing dark investigative reporting with reader accessibility
The final months: missed funding and the closing announcement
Lessons learned and future plans for Olivia Messer
Listen ad-free on Castria