DOSSIER · JOE WILSON · ST. LOUIS

Builds with AI.

I'm Joe. Thirty years in tech — twenty-seven at Microsoft. Laid off twice in twelve months. The second time, I built a working AI tool the same night. Now I teach mid-career people to build something nobody can take from them.

Doors open after episode six. The list hears first.

Bets placed
2
Confirmed
1
Busted
0
Pending
1

Ask Luna.

Live · by voice or by chat
Live line

Luna is the AI I built. Ask her about my work, out loud or in a chat: the Bets, the builds, my résumé, where I've worked, how to reach me. She answers from this site and nothing else.

Checking the line…

Rather type?

For a call, your browser will ask for the microphone; Luna hears you only while the call is open. Calls run up to 3 minutes, 2 a day. Typed chat: up to 40 messages a day. This site keeps no audio and no transcript, and ElevenLabs, the service behind both, is set to keep none either.

The Bets

Claim · Clock · Cost · Verdict
Bet №2

ObeyVision

Placed Nov 2, 2026

PENDING
Claim
Claude reads a working photographer's whole archive like a second shooter and writes it into Lightroom as keywords, for a fifth of a cent a frame.
Clock
One night for the tool (Nov 2, 2026, 3:00 AM start); one weekend for 31,719 cloud photos to come down and get read
Cost
$0.0019 per image, $0.0026 per video in model calls, logged per call; about $60 for the whole library
Verdict
PENDING

Goals

  1. Every frame: session type, framing, pose, expression, lighting pattern, wardrobe, retouch needed
  2. A portfolio score with one blunt sentence of why
  3. Hierarchical keywords, caption and stars written into the file
  4. Lightroom Classic reads them in one click; cloud sync carries them to the Lightroom app
  5. A photographer finds the keeper faster than with a $199 plugin
  6. Under $75 in AI for the whole archive

In progress.

A 38-field read of each photo by Grok vision (framing, pose, expression, eye contact, lighting pattern and key direction, background, wardrobe, hair, props, focus on the eyes, exposure, retouch needed, four 1-10 scores and a portfolio score with a reason), written into the file as hierarchical keywords, caption and star rating. First 157 synced frames tagged; 7,495 keyword rows reached the Lightroom app's catalog within minutes. The incumbent is Excire Search 2026 at $199-229, not yet run head to head; the Bet is whether a written judgment on each frame finds the keeper faster for a real photographer.

Part of Lightroom Classic's Keyword List panel with generated keywords and counts: blonde hair, blue eyes, branding headshot, branding portrait 2, brunette 3, butterfly lighting, with Body as an expandable parent.
Receipt: part of the Keyword List in Lightroom Classic minutes after the first read, Nov 2, 2026.
Bet №1

Who's Hiring, 15 Years

Placed Nov 1, 2026

CONFIRMED
Claim
In one sitting, Claude turns fifteen years of Hacker News hiring threads into a page a laid-off forty-five-year-old can actually use.
Clock
One sitting: 9:12 PM start, page live 9:25, every October post judged by 10:15 (Nov 1, 2026)
Cost
$0.85 in model calls, logged per call, plus a $10.19 domain
Verdict
CONFIRMED

Goals

  1. Every thread since 2011, every post, no sampling
  2. The trends: posts, remote, pay, roles
  3. The companies that hire every single year
  4. Every post this month, read and judged for that reader
  5. Every number one click from its source
  6. Under $5 in AI, finished before bed

All goals met. Verdict by evidence.

184 monthly threads, 93,193 job posts from the public HN API, sifted into one static page: posts per month (a third of the 2021 peak), remote by year (92% in 2022, 76% now), stated pay ($175k median midpoint in 2026), roles over time (AI/ML 5% → 20%, frontend 15% → 5%), the 600 companies that hired in three or more years, and every October post read by Claude for one reader: 206 real roles, 204 open to experience, 15 needing no code.

Bar chart of Hacker News Who's Hiring posts per month, 2011 to 2026, peaking in 2021 and falling to about a third of that peak by 2026.
Receipt: posts per month, every thread since 2011.
Screenshot of the Who's Hiring, 15 Years page: headline, the posts-per-month chart, remote by year, stated pay, and roles over time.
Exhibit: the page as it went live, Nov 1, 2026.

A Bet is a claim that can lose. BUSTED is sacred: evidence decides, never the host.

What should I bet next? →

Also built

Live, and not a Bet
Live

Popcorn

Researched facts that pop up over YouTube while you watch.

Pop-Up Video for anything on YouTube, except the bubbles are researched. Click the popcorn on a video and it reads the transcript, researches the video on the web, and pins each fact to the second its subject comes up: the backstory, who the people are, what happened after, and where the video is wrong. Every card links its source. It runs on the AI you already pay for (Claude Code, Codex or an OpenRouter key), with no Popcorn account or server. What broke: before release, an outside AI review found that a malicious web page could have reached the local server and spent your plan. The server now refuses anything that isn't you. Setup is one message pasted to your coding agent.

Runs on
Claude Code · Codex · OpenRouter
First facts
~1 min
Python dependencies
0 (standard library only)
Setup
one message to your agent
Live

SwordFinder

Finds the ugliest strikeout swings in baseball, every day.

A live MLB product that ranks swords, the two-strike swings where a fooled hitter's bat dies out front. It reads every pitch from Statcast, scores each strikeout swing, and gives each one a share page, a place on the leaderboards and a clip wherever MLB still serves one. What broke: the first version ran across five services, and when the API disappeared and the database paused, the site went dark while a failing health check went unread. I rebuilt it with no database and no server. A daily job writes plain data files, so a quiet off-season can't take it down.

Pitches read (to Sep 27)
716,792
Swords ranked (to Sep 27)
2,399
Servers
0
Live

We Read Them

True-crime reels built from the record, not the retelling. Published as a Claude Code skill.

We read the FBI file, the depositions and the bodycam so you don't have to, and show what they say against what everyone thinks they know. First case: Gabby Petito, a 3:44 film and eleven vertical reels made in one day. The whole process is published as a skill anyone can install: three research agents, a facts gate where every quote is checked against the page image, FBI Vault files through the Wayback Machine, news clips cut on Whisper word timings, one-take ElevenLabs narration with a second voice that reads the record, and picture rendered in code. It's updated in the open as it improves.

Version
1.3.1
Reels, first case
11
Full film
3:44
Install
/plugin marketplace add joewilsonai/skills
Live

Open Feedback Factory

Feedback from inside your app becomes guarded pull requests, and each user is told what happened.

Users ask for things in a small widget inside the app. Each ask is scrubbed of emails, keys and tokens, grouped with similar requests, and either queued, held until enough people ask, sent back with a question, or blocked; requests that touch auth, billing or privacy go to a person. A worker hands the sanitized summary to a coding agent on its own branch, a pull request and CI follow, and nothing merges until a recorded reviewer approval and every policy gate pass. The user who asked sees the outcome in the same widget. The public repository is an early alpha; newer work isn't released yet.

SDK on npm
@open-feedback-factory/sdk 0.1.0
Public code
early alpha
Live

CanvaKilla

The banner maker that knows where every platform actually crops.

AI banners and profile pictures for X and LinkedIn. Every prompt carries the platform's crop rules, so the face, logo and tagline stay out of the avatar circle, the mobile buttons and the strips the platform trims off. A live desktop and mobile preview shows where they land, and the proof export draws the crop guides on the image. Built because Canva kept hiding banner text behind avatars, mobile follow buttons and the strips X clips off the top and bottom.

X banner
1500×500
LinkedIn banner
1584×396
Profile picture
1024×1024

The tank

Months, never dollars.
Runway reportReport №1 lands December 1, 2026.
Pending

No report yet. The gauge fills when the first one lands.

The file

DeclassifiedThirty years, five entries, latest first
Entry 05 / 05

Obey LLC · AI Builders Club

March 2025 — Present
O'Fallon, MO (St. Louis) · Remote

Independent AI Architect

  • Always-on personal agent, built and run since 2024: Claude Code agents, a custom MCP memory server with vector search (RAG), a session briefing that rebuilds context at every start, and a daemon that runs scheduled work around the clock across two machines.
  • Published Future Pruning (working paper, Zenodo DOI 10.5281/zenodo.23637938): an agent plants decision points in its own future and, when each comes due, reopens the current record and does it, changes it, or lets it go. First evidence: a 28-moment field sample (acted on 9, changed 6, let 13 go) and a 346-chain simulation across 16 language models.
  • One agent, many channels: chat, Telegram, a browser call page, ElevenLabs voice notes and a live phone line all route into the same memory-carrying session, with least-privilege tools, human approval for every outward-facing action, audit trails and kill switches.
  • Shipped Open Feedback Factory (agent-based feedback-to-feature platform with a published npm SDK) and production AI apps for clients, including an AI compliance tool for Missouri lobbying disclosures and a teacher-inquiry platform.
  • Created AI Builders Club (aibuildersclub.ai): 25 weekly live Build Nights and a 14-day build sprint course teaching non-technical professionals to build AI workflows.
  • Named inventor on U.S. provisional patent application No. 63/793,621 for a privacy-first AI personalization engine.
Entry 04 / 05

Rapsodo

May 2025 — April 2026
St. Louis · Remote
MLM2Pro (golf) · Diamond Sports (baseball)

Director of Customer Success

  • Developed and deployed agents for ticket triage, Gong-style coaching for sales, support and CX teams, and customer success workflows.
  • Deployed a root-cause agent that reviewed every support issue and routed true bugs, UI problems and documentation gaps to the right team; in a 6-component pilot it cut Product fix times from months to weeks and surfaced an 86% mislabel rate in "alignment" tickets.
  • Led AI adoption across Rapsodo North America: trained 50 of roughly 180 employees across sales, support, customer success, marketing and product over 25 hands-on sessions.
  • Built a gradient-boosting churn-risk model across 2,000+ accounts; the tiered plan it produced became a CEO-backed Q1 priority.
Read the case file →
Entry 03 / 05

Microsoft

August 2021 — April 2025
Greater St. Louis · Remote

Customer Success Manager and AI Architect

  • Designed and delivered Copilot adoption programs: use cases, communications, champion programs, training and Copilot Analytics reviews. Copilot adoption rose 35% across key accounts.
  • Helped customers define, architect and build agent-based systems with Copilot Studio: connectors and actions, authentication, Microsoft Graph connectors, Power Platform environments, Teams publishing and Power Automate flows.
  • Built a Proactive Customer Satisfaction Copilot (Power Automate, Azure OpenAI, Teams); in one quarter across 5 customers, CSAT rose 22%, "very satisfied" rose from 51% to 89%, and escalation response time fell 40%.
  • Led MCEM Copilot, a RAG assistant that coached sellers through Microsoft's sales methodology; Microsoft Global Hackathon 2023 Executive Challenge Honorable Mention, top 1% among 16,000 projects.
  • Prepared customer tenants for Copilot (Entra ID access reviews, oversharing cleanup, Purview sensitivity labels and DLP). Customer Hero Award, January 2025.
Entry 02 / 05

Amazon Web Services (AWS)

July 2020 — August 2021
Greater St. Louis · Remote

Principal, Data Platforms

  • Led customer-facing architecture strategy sessions, providing executive-ready roadmaps for cloud adoption, data modernization, and infrastructure optimization.
  • Bridged Microsoft ecosystem fluency with AWS expertise to guide clients through high-risk migrations — ensuring performance, continuity, and long-term alignment with AWS capabilities.
  • Mentored internal AWS field teams and partner stakeholders on enterprise transformation best practices, co-creating repeatable GTM patterns across industries.
  • Identified friction in customer journeys and proactively restructured solution frameworks, improving retention and increasing expansion potential across cloud engagements.
Entry 01 / 05

Microsoft

1998 — 2020
Greater St. Louis Area · Greater Seattle Area

22 years of progressive seniority across enterprise sales, technical advisory, and field leadership

  • Senior Technology Strategist | Enterprise Cloud & SaaS Transformation (2013–2020). Virtual CIO and Solution Architect for Microsoft's most complex, regulated, high-value accounts. Cloud transformation across finance, healthcare, manufacturing. Forged high-trust relationships with CEOs, CTOs, CDOs, CIOs. Quota overperformance + revenue expansion across core accounts.
  • Enterprise Enablement & Competitive Strategy Lead (2010–2013). Designed Microsoft's national "Compete Clinic" program three consecutive years. 35% win-rate improvement on competitive escalations. 100% CSAT on executive briefings. Launched a field intelligence network that cut time-to-insight by 50%.
  • Enterprise Cloud Transformation Lead | Early SaaS Strategy (2006–2010). Led the launch of one of Microsoft's first commercial cloud customers — pioneering the path to Office 365. Recognized as one of the Top 3 Area Technology Specialists in the U.S.; awarded Central Region Technology Specialist of the Year.
  • Senior Technical Product Manager | Windows Server Launch & Enablement (2002–2004). Created the official Windows Server launch demo presented by Microsoft's CFO to thousands of investors. Reduced support escalations 60% through positioning alignment with real-world value.
  • Pre-Sales Solution Strategist | Collaboration & Mobility GTM (1999–2002). Led Microsoft's largest U.S. product launches for Office and Windows — 10,000+ attendees per event, 93% lead conversion. 240% YoY revenue growth. Quota over-attainment of 115% and 177%.
  • Enterprise Customer Success Manager | Premier Support (1998–1999). Frontline customer advocate. Transformed four key accounts from "somewhat satisfied" to "very satisfied" within 90 days. 300% revenue YoY on dedicated support agreements.
  • Honors: Technology Specialist of the Year, Top Contributor (East and Central Regions), Peer Leadership Award, Goldstar Award.

Certifications

None on file yet.

Speaking

None on file yet.

Résumé

For the hiring manager in the room
Summary

Thirty years in tech, twenty-seven at Microsoft: Microsoft → AWS → Rapsodo → Obey. The operator who turns ambiguous customer problems into systems that ship. At Rapsodo I ran customer success as a one-person function — CS, ops, data engineering, support — by pairing enterprise judgment with Claude Code as the engineering partner. Now I build with AI in public on Joe Wilson Builds and teach mid-career people to build something nobody can take from them through AI Builders Club.

March 2025 — Present
Obey LLC · AI Builders Club — Independent AI Architect
May 2025 — April 2026
Rapsodo — Director of Customer Success
August 2021 — April 2025
Microsoft — Customer Success Manager and AI Architect
July 2020 — August 2021
Amazon Web Services (AWS) — Principal, Data Platforms
1998 — 2020
Microsoft — 22 years of progressive seniority across enterprise sales, technical advisory, and field leadership
© 2026 Joe Wilson · Joe Wilson BuildsRésumé · Rapsodo case file · llms.txt · resume.json