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.

Jason Bot

A self-built AI career agent that lets recruiters explore 28 years of experience conversationally. Go + Gin + HTMX on Cloud Run, Gemini via OpenRouter with 85 to 90% prompt-cache hit rates, and zero logging or telemetry by design.

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 focuses on personal products, experiments, and utilities, but the same engineering approach runs through my client work. I started my career at PPG Industries, spending seven years on technical design for a multi-million-dollar process-management and supply-chain suite and building the .NET platform that became the foundation for all new PPG applications. Since 2005 I've been with Computer Enterprises, Inc. (CEI) in Pittsburgh, first as Principal Architect and now as Director of Enterprise Architecture, leading engagements as architect, mentor, and trusted advisor across web, mobile, integration, cloud, and AI.

My recent work centers on production AI systems and legacy modernization at enterprise scale: multi-agent workflows that turn legacy codebases into backlogs and grounded estimates, agentic coding rollouts inside client organizations, and architecture guidance for GenAI platforms growing from pilot to enterprise. Along the way that's meant directing the rewrite of an 18-year-old platform for a U.S. federal legislative body, leading a 329-application estate consolidation for a regional logistics provider, advising a children's hospital system on scaling its GenAI concierge toward 10,000 users, unifying point-of-sale for a roughly 2,600-store retailer, and stewarding integration platforms moving more than 5 million transactions a day.

Find me on LinkedIn as the best place to reach me.