Building in public

Matt Ragudo

Insurance guy from Hawaii, living in Texas, building AI systems that run my businesses. No CS degree. No dev team. Just me and a lot of Claude Code sessions.

The short version

I spent a decade in financial services: Mutual of Omaha, AXA, Ameriprise. I've held a Series 7 and 66. I currently run a solo Medicare supplement practice, licensed in 8 states.

In 2022 I met Brandon Attebury and started working on WIMPER, a Section 125 and 105 program that saves employers real money on payroll taxes. Brandon is the sales guy. I'm the one building the infrastructure behind it.

In 2024 I discovered I could make AI agents do things. Not chatbot things. Business operations things. I taught myself enough code to be dangerous, then built an entire system: 12+ autonomous agents, 5 websites, a command dashboard, event bus, cron scheduling, email outreach, content generation, social media posting, and a full prospect pipeline. All running on a single VPS.

I'm not a developer. I'm a business owner who figured out that AI could do the work of an entire marketing department if you wire it up right. This site is where I show what that looks like, including the parts that aren't working yet.

The timeline

Every milestone, every pivot, every honest number. Newest first.

2024

Discovered AI could do real business operations

Not chatbots. Agents that research prospects, compose emails, generate content. Wiped Windows off the laptop, installed Ubuntu, and named it LaptopLLM.

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2024

Hit the ceiling on local LLMs

Consumer hardware can run models. It can't run production reasoning. Moved to the Claude API and Claude Code. That was the turning point.

2022

Met Brandon Attebury. WIMPER begins.

Section 125 and 105 programs that save employers real money on payroll taxes. Brandon handles the sales. I start building the infrastructure behind it.

2021

Bought a gaming laptop for video editing

Eluktronics RP-17 with an RTX 3060 and 32GB RAM. Needed a mobile office. Had no idea it would end up running my entire business infrastructure.

2013

Financial services career begins

Mutual of Omaha, then AXA, then Ameriprise. Series 7 and 66. A decade of learning how the industry actually works from the inside.

2026-05-10

The journey page goes live

Started documenting every milestone, every pivot, every honest number. Because building in public means the timeline is part of the product.

2026-05

1,040+ commits across three apps

medicare-agent, wimper-ops-agent, matt-agent. One developer. Zero employees. All built with Claude Code and Gemini CLI.

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2026-05

22 active WIMPER enrollments

Real clients, real implementations, real payroll tax savings. The ops side has paying customers while the marketing side catches up.

2026-05

$0 marketing revenue. Still building.

12 agents running daily. Pipeline built and operational. Prospects researched, emails composed, content generated, social posted. No deals closed through it yet. Posting this number because that is the point.

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2026-05

3 lead-gen sites added to the portfolio

businessbrokerhawaii.com, lifesettlementflorida.com, selllifeinsurancepolicyflorida.com. Migrated from legacy CMS to Hugo. Exact-match domain SEO strategy for local service markets.

2026-04-25

Strategic pivot: employers only

Paused the CPA and broker partner channel entirely. All agent effort now targets employers and business owners directly. Focus over spread.

2026-04-22

5 websites built and deployed

wimperinstitute.org, wimperhawaii.com, medicare808.com, understandmymedicare.org, wimperpartners.com. All Hugo static sites on Cloudflare Pages. SEO infrastructure baked in from day one.

2026-04-16

Marketing system goes live

14+ AI agents, event bus, cron scheduling, prospect pipeline, email engine, content generation, social posting. 659 commits in 13 days. The big one.

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2026-04-04

WIMPER Ops Agent: started building

Full servicing platform. 17-milestone implementation pipeline, partner portals, document auto-detection. Replacing three separate systems with one I built myself.

2026-04-01

Medicare Agent: first line of code

AI-powered Medicare analysis tool. RAG over CMS data, plan comparison engine, client CRM, PDF generation. A licensed agent building his own tools because the industry ones kept disappearing.

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2026-04

Internet went out. Everything went down.

Home internet outage took the whole operation offline. Single point of failure, exposed overnight. Migrated production to a VPS the next day. The laptop that started it all is now a black box on the floor.

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2026-04

Dashboard built from scratch

10+ app dashboards. Pipeline management, outreach review queues, content workflow, agent health monitoring, work logs, Systems Map, and a Virtual Office where agents show up as RPG characters.

Where the money is (and isn't)

Real numbers. Updated as things change.

WIMPER Operations

22 Active enrollments
Pending Aflac book of business import (hundreds of clients for Hawaii team)

Built a standalone servicing database and dashboard for tracking enrollments, partner portals, and a 17-milestone implementation pipeline. This side has real clients doing real things.

WIMPER Marketing

$0 Revenue from marketing tools

12 AI agents running daily: prospect research, email outreach, content generation, social posting, performance analysis. Pipeline is built and running. No deals closed through it yet. That's the honest truth.

Medicare Practice

8 States licensed

Solo Medicare supplement and Part D practice. This pays the bills while the bigger bets play out. Building an AI-powered Medicare analysis tool for fee-for-service consulting.

What I built

One person. One VPS. Everything below is live and running.

The Agent System

12+ autonomous AI agents running on cron schedules. They research prospects, compose outreach emails, generate blog content, post to social media, compile daily briefings, audit system health, and fix their own problems. All coordinated through an event bus so they don't step on each other.

  • Claude Code
  • Docker
  • Cron scheduling
  • Event bus
  • SQLite

The Dashboard

A command center I built from scratch. Pipeline management, outreach review queues, content editorial workflow, agent health monitoring, work logs, and a Systems Map that visualizes every connection. Even a "Virtual Office" where agents show up as RPG characters at desks.

  • Node.js
  • Express
  • SQLite
  • D3.js
  • Chart.js

5 Hugo Websites

All content sites are static Hugo builds deployed to Cloudflare Pages. SEO infrastructure (structured data, OG tags, sitemaps, topic clusters) baked in from the start. Content agents generate drafts, I review, agents deploy.

  • Hugo
  • Cloudflare Pages
  • JSON-LD
  • Automated deploys

Email Engine

Multi-touch outreach sequences, warm-up scheduling (ramping from 5/day to 50/day), reply detection, bounce handling, and a full approval gate where nothing sends without human review. Newsletter drip system for opted-in subscribers.

  • Zoho SMTP
  • Postmark
  • Approval workflows
  • NEPQ methodology

Social Media Engine

Autonomous posting to X and LinkedIn. 3-4 posts per day in my voice, plus weekly long-form articles. Monitors engagement metrics, learns what performs, and adjusts. Promotes new blog content automatically when sites deploy. Fully autonomous, no review queue.

  • X API v2
  • LinkedIn API
  • OAuth
  • Engagement tracking

WIMPER Ops Database

A separate Next.js application for Hawaii operations. Tracks enrollments through a 17-milestone pipeline, manages partner portals, and will handle the Aflac book of business migration. This is the production side where real business happens.

  • Next.js
  • Separate repo
  • 17-stage pipeline
  • Partner portals

The properties

Everything I've put on the internet.

WIMPER Institute

Educational authority site for the WIMPER program. Blog, compliance guides, savings calculator. The content engine feeds this.

wimperinstitute.org

WIMPER Hawaii

Local landing page for Hawaii employers. FICA savings calculator, Hawaii Advantage angle, ProForma request flow.

wimperhawaii.com

Medicare 808

Hawaii-focused Medicare resource. Union retiree benefits directory (EUTF, HGEA, UPW, HSTA), education blog, healthcare news.

medicare808.com

Understand My Medicare

National Medicare education hub. Learn section, plan comparisons, enrollment guides. Full transparency philosophy.

understandmymedicare.org

WIMPER Partners

CPA and broker partner conversion site. Currently paused while we focus on the direct-to-employer channel.

wimperpartners.com

Follow along

I post daily on X about what I'm building, what's breaking, and what I'm learning. If you're a solo founder trying to figure out how to use AI for real business operations (not just chatbots), that's the place.