Jason Agostoni | Projects
A selection of products, experiments, and tools I’ve built over the years — some shipped, some archived, some still evolving.
Featured work
DumbQuestion.ai
A satirical AI Q&A product built to answer dumb questions with just enough attitude to be useful. It started as a fun side project and became a live experiment in product, personality, and low-cost LLM delivery.
- Role: Creator
- Status: Active
- Launched: March 2026
- Focus: AI product, LLM evaluation, content and product iteration
- Links: dumbquestion.ai, Origin series
- Notes: Best known for the roast-y persona and cost-conscious architecture.
Ship-Bench
An agentic software-delivery benchmark that tests whether AI systems can actually ship realistic work instead of just generating isolated code snippets. It evaluates planning, architecture, implementation, testing, and release across a full workflow.
- Role: Creator
- Status: Active
- Focus: AI evaluation, agentic SDLC, benchmark design
- Links: GitHub repo, Post series
- Notes: Built to measure practical delivery across real software tasks.
DevLoop
An autonomous developer loop that uses GitHub Issues as a task queue and state machine for specialized AI subagents. It is designed to reduce context bloat by splitting work into planning, coding, testing, reviewing, and release stages.
- Role: Creator
- Status: Experimental
- Focus: Agentic workflows, developer tooling, orchestration
- Stack: Gemini CLI, GitHub Issues, GitHub CLI, Node.js
- Notes: Private for now, with plans to publish more broadly.
Copilot Env Manager
A cross-platform Go CLI/TUI that helps users configure GitHub Copilot CLI for BYOK providers and OpenAI-compatible endpoints. It walks through provider selection, live model discovery, and shell-aware environment output generation.
- Role: Creator
- Status: Public
- Focus: Developer tooling, CLI ergonomics, model/provider switching
- Stack: Go
- Links: GitHub repo
- Notes: Built to make Copilot CLI easier to use for benchmark runs and repeatable setup.
Past products
Tagalong Tour
A crowd-sourced walking-tour startup I co-founded and helped build, with a strong focus on the Android and iOS apps. We launched the product live, operated it as a Pennsylvania LLC, and eventually decommissioned it after the run ended.
- Role: Co-founder, primary mobile developer
- Status: Archived / decommissioned
- Years: Formed in 2017
- Focus: Mobile apps, backend, local discovery, startup execution
- Notes: Won Startup Weekend Pittsburgh with the original idea.
In The Money
A cross-platform React Native app built for an options-trading-focused client. It helped users simulate price movement, understand when a trade becomes profitable, and estimate max gain and loss exposure.
- Role: Product vision, UX/UI, development, deployment, support
- Status: Archived / no longer maintained
- Years: Launched in early 2020
- Focus: Finance, simulation, decision support
- Stack: React Native, no backend
- Notes: Built for a friend-of-a-friend who was deeply into finance.
Sports Schedules App
A mobile app that kept fans up to date on all of their teams’ schedules in one place and sent notifications when games were coming up. I built and owned the product end-to-end through AppFinch LLC.
- Role: Sole developer, owner
- Status: Archived / delisted
- Years: Active April 2019 to December 2019
- Focus: Mobile app, sports data, schedule aggregation
- Stack: iOS, Android, PostgreSQL, offline integration scripts, static XML publishing
- Notes: Had a loyal user base, but event data costs eventually exceeded the hobby business model.
Older contributions
A small set of legacy OSS contributions that show older technical depth across integration, encryption, UI behaviors, and build automation.
- BizTalk null adapter modernization.
- sqlite-net field-level encryption support.
- Masked Text Box behavior for Windows Store apps.
- XCode build automation with TFS 2010.
Professional work
This page intentionally focuses on products, experiments, and utilities. Professional client and consulting work lives on a separate page.