Working on Wicked Problems
Summary
Noah discusses his transition from serial entrepreneur to founder of Keep, a platform reducing administrative burdens for unhoused individuals. He explains how a failed open-source data locker project revealed systemic flaws in public interest technology, leading him to build a case management tool for nonprofits. The conversation explores "wicked problems" in social services, the political consensus on administrative burden, and the importance of user-centered design in helping vulnerable populations navigate complex bureaucratic systems.
Topics discussed
Intro: Bathroom break banter and family updates
Recapping Oxcon and the MTS Live appearance
Discussing doomerism and AI safety perspectives
Noah's career shift and the Baltimore open-source project
The 18-month journey to permanent supportive housing
Wicked problems and the concept of administrative burden
Reading Sidney Dekker and the Cynefin framework
Deep dive into Safety Anarchist and Drift Into Failure
Defining problems and the painkiller vs vitamin approach
The complexity of counting the homeless population
How administrative burden scales with socioeconomic status
Political consensus on administrative burden and program silos
Finding the lane: User experience and open source software
Partnership with HopX and the power of one person's story
Case study: Using phone photos to verify identity
The disconnect between administrators and actual users
Lessons learned and targeting specific populations
Dynamics of re-entry, foster care, and veteran homelessness
Social referral networks and digital identity platforms
Why enterprise tools like Salesforce fail nonprofits
Keeping infrastructure simple and avoiding complexity
The role of LLMs and the legend of the 'nice guy'
Security, simplicity, and the burden of load-bearing systems
Advice for young technologists tackling wicked problems
Antifragility and the inevitability of new homelessness
Resources for getting involved: Robin Hood and FindHelp
The difficulty of the work and the need for resilience
Personal gratification from making progress on hard problems
Closing thoughts on generational warfare and advice
Impact investing and finding relevant companies to work for
Public Benefit Corporations and dual mandates
Final reflections on team culture and mission
Sign-off and personal anecdotes
Listen ad-free on Castria