MR|
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 2024 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 implementation partner. I'm the one building the infrastructure behind it.
In March 2026 I wiped Windows off a gaming laptop, installed Ubuntu, and started building. Within two months I had 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.
Hermes takes over the scheduler layer
Retirement sprint moved 40 legacy matt-agent scheduled jobs into Hermes ma-* twins across read/reporting, content, social, and LinkedIn lanes. Old watcher jobs were consolidated under Atlas exception-supervisor, with rollback paths documented for every wave.
Supplement affiliate content infrastructure added
Supplement content agent + affiliate tracking skill wired into the system. Click-tracking API, affiliate_links and affiliate_clicks tables, and an autonomous content posting agent ready to go. First non-insurance, non-trading revenue infrastructure. Waiting on Amazon affiliate URLs before the cron goes live.
AI trading agent launched (@casualabsurdity)
First financial agent in the system. Paper-trades using the Alpaca API, reads morning newsletters via Gmail, and posts to X as @casualabsurdity. A new revenue vertical separate from WIMPER and Medicare -- and the first time the system is trading, not just marketing.
Build Chronicler agent launched
New agent dedicated to documenting the build-in-public journey. Runs daily at 9am: reads 24h of git commits, agent events, and work logs, then synthesizes a structured build log and drafts a mattragudo.com article. The system now documents itself.
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.
$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.
Read the full story1,040+ commits across three apps
medicare-agent, wimper-ops-agent, matt-agent. One developer. Zero employees. All built with Claude Code and Gemini CLI.
Read the full story22 active WIMPER enrollments
Real clients, real implementations, real payroll tax savings. The ops side has paying customers while the marketing side catches up.
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.
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.
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.
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.
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.
Read the full storyMarketing 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.
Read the full storyWIMPER 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.
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.
Read the full storyLocal LLMs to Claude Code
Tried running models locally on the RTX 3060. Consumer hardware can't handle production reasoning. Moved to the Claude API and Claude Code. That was the turning point.
Wiped Windows. Installed Ubuntu. LaptopLLM.
Took a gaming laptop, wiped Windows, installed Ubuntu, and dedicated it to running infrastructure. Named it LaptopLLM. The AI build starts here.
Read the full storyMet Brandon Attebury. WIMPER begins.
Section 125 and 105 programs that save employers real money on payroll taxes. Brandon is the implementation partner. I start building the infrastructure behind it.
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.
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.
Where the money is (and isn't)
Real numbers. Updated as things change.
WIMPER Operations
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
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
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.
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.
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.
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.
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.
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.
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.orgWIMPER Hawaii
Local landing page for Hawaii employers. FICA savings calculator, Hawaii Advantage angle, ProForma request flow.
wimperhawaii.comMedicare 808
Hawaii-focused Medicare resource. Union retiree benefits directory (EUTF, HGEA, UPW, HSTA), education blog, healthcare news.
medicare808.comUnderstand My Medicare
National Medicare education hub. Learn section, plan comparisons, enrollment guides. Full transparency philosophy.
understandmymedicare.orgWIMPER Partners
CPA, broker, and CFO partner referral site. Partners refer their employer clients into the WIMPER program.
wimperpartners.comThe optimization stack
I apply the same numbers-first thinking to nutrition that I apply to business. These aren't opinions — they're models I've actually built and tested.
I track macros obsessively (IIFYM). I've run every major protein source through a protein-per-dollar and protein-per-calorie model. I've mapped energy drink ingredient profiles against their cost per dose of actual actives. The content lives on X (@mattragudo) — this is the framework behind it.
Protein Efficiency
The model is simple: grams of protein per dollar, grams of protein per calorie, and taste score. Most expensive protein sources fail on at least two of the three. I've ranked the common ones — the winner isn't what the fitness industry wants you to buy.
Energy Stack
I've mapped caffeine, L-theanine, and citicoline content across 30+ energy drinks and pre-workouts. Cost per mg of actual actives varies by 10x. Most premium products are paying for branding and flavoring, not dosing. I track what I use and what it costs per effective dose.
Taste Engineering
High-protein food doesn't have to taste like protein powder. I've built a system for hitting macro targets with food that's actually enjoyable — flavor profiles, sauces, meal structures that work at scale without meal prep becoming a second job.
Supplement Honesty
Most supplements are underdosed, overhyped, or redundant with food. I track what the research actually shows vs. what the labels claim. Creatine works. Most proprietary blends don't. I'll tell you which products I actually use and why — no affiliate-first recommendations.
Follow the data
I post the actual models, rankings, and comparisons on X. If you want to see the protein efficiency breakdown or the energy stack ranking, that's where it lives. I post when I update the model or find something surprising.
You've already decided.
You want life insurance. You want to apply online. You don't want a medical exam, and you're not calling an agent. This is for you — I'm not going to try to change that.
I'm a licensed insurance agent. I know exactly why you're here instead of on the phone with someone like me. Probably one of these:
- You've had your number sold the moment you inquired somewhere else
- You know what you need and don't want to be educated
- You want to apply at midnight, not during business hours
- A previous agent sold you the wrong thing or too much
- You don't want to talk about your health history with a live person
- You're embarrassed about weight, past smoking, an old DUI, or something else
- Talking to an agent feels like a commitment you're not ready to make
- You don't trust that the agent is working for you vs. their commission
- You had a claim denied somewhere and the industry lost you
- You've done the research — you just want to apply
- You know simplified issue costs a bit more than fully underwritten, and that's fine
- You just had a kid, or you're covering a mortgage, and you want it done today
All of those are valid. Here's what I use when I want to get it done online: instabrain.io. No agent call. No exam. Apply now.
But your situation affects what you should expect when you apply. Read your situation below first.
Your situation
What you need to know before you apply, based on where you're coming from.
Type 2 Diabetes and Life Insurance: Can You Still Qualify?
Well-controlled T2D doesn't automatically disqualify you. Here's what simplified issue applications actually ask and what affects your outcome.
2026-06-07Self-Employed? Your Life Insurance Is Not Coming From Work
If you work for yourself, there is no employer group life benefit in the background. Here is how to think about coverage without turning it into a sales call.
2026-06-07Buying a House? How Much Life Insurance Should You Check?
A plain-English way to think about mortgage protection, term length, and whether an online life insurance application makes sense.
2026-06-05Life Insurance Coverage Check
A simple way to decide whether it is worth starting a life insurance application online.
2026-06-02New Baby: How Much Life Insurance Do You Actually Need?
New parent, one income, spouse staying home. Here's how to think about coverage amounts and get it done online tonight.
2026-05-29You're Losing Your Job's Life Insurance. Here's What to Do This Week.
Employer group life coverage disappears on your last day. Here's how to replace it before the gap, without calling an agent.
2026-05-29You Keep Putting This Off. Here's What Waiting Actually Costs You.
Every year you wait, life insurance costs more. Here's the actual math on what procrastination is worth in dollars over a 20-year term.
2026-05-29You Just Quit Smoking. Here's When Your Rates Actually Change.
Smoker rates don't disappear the day you quit. Here's the exact timeline carriers use and when you can apply for non-smoker rates.
I'm a licensed life insurance agent. Rate comparisons on this site reflect quotes I've pulled for myself as a test profile — not personalized advice. Your rates will vary based on age, health, state, and coverage amount. Last updated: June 2026.
The log
Longer thoughts on what I'm building and why.
Week 24: Approved Was Not Published
The agent system found a gap between content approval and live publication, then built a deterministic publisher that verifies the page before calling it shipped.
2026-06-11Week 24: The Old Scheduler Is Finally Quiet
The system retired the last enabled legacy cron jobs, moved control loops into Hermes, and kept outreach paused while content and social still moved.
2026-06-10Week 24: 40 Jobs Moved Out of the Old Machine
The system moved 40 scheduled jobs from the old matt-agent cron layer into Hermes, then paused paid research because the email gate is still closed.
2026-06-09Week 24: Six Days Blind. 329 Emails Still Queued.
The reply-check system has been silently broken since June 3. The send gate holding 329 outreach emails has been protecting against a drought it couldn't actually measure.
2026-06-08Week 24: A Script Was Silently Failing for 64 Hours. The System Found It Itself.
Atlas caught a 64-hour data gap from a host/container network mismatch and patched it without being asked. Meanwhile, 329 emails are still parked.
2026-06-07Week 23: 3 Blog Posts Were Written Weeks Ago. They Just Never Made It to the Site.
A silent path filter was quietly closing content PRs with no error, no alert, and no trace. 9 pieces published today. 3 of them were recoveries.
2026-06-07Week 2: The Trade That Lasted Three Seconds
The Mancini Protocol got its first fill, hit its first target, then exposed a structural flaw in its own order logic. Here is what building automated systems looks like when reality does not match the model.
2026-06-06Week 23: 12 Commits Shipped. I Wrote Zero of Them.
The agents built without me today. A monitoring bug self-detected, 20 issues auto-remediated, and 329 email drafts sit approved and waiting for a send gate to open.
2026-06-04568 Sends. 0 Replies. I Put My Outbound on Hold.
100 commits from agents, none from me. And a decision to halt all email outbound until I know why nobody is responding.
2026-06-03Week 23: The System Built 50 Emails. Then Got Stuck Waiting for Me.
88 of 91 commits came from agents. 50 outreach drafts generated. 0 emails sent. The bottleneck is the parts only a human can unlock.
2026-06-02The Same Agent Failed for the Second Day in a Row. My System Filed a Report.
85 commits from agents, 0 from me. 46 drafts composed. And a content-review job that hit the same missing API endpoint two days running without once sending me a Telegram.
2026-06-01One of My Agents Went Silent 41 Days Ago. Nobody Noticed Until Today.
94 commits, 89 drafts composed, zero emails sent. A critical agent had been running dark for six weeks without a single alert.
2026-05-31Week 1: Right About Direction, Zero Trades
The Mancini Protocol called the market direction correctly on both trading days in Week 1 and made zero trades. Here is why both statements are true and what it reveals about building automated systems.
2026-05-3176 Commits on a Sunday. None of Them Were Mine.
100% autonomous weekend: agents ran 76 jobs, added 9 prospects, published 2 posts. But a trading bot alert silently failed to reach me, and 11 days of email silence needs a human decision.
2026-05-30I Made One Commit Today. Agents Made 70. And the Data Bridge Is Still Down.
41 agent jobs ran, 51 WIMPER prospects staged for outreach, and a P&C app idea emerged from my own memory files. The data bridge has been unreachable two days running.
2026-05-29The Queries Were Running Fine. They Were Just Returning the Wrong Rows.
A silent SQLite parameter bug returned unfiltered data without a single error. 76 agent commits ran today, zero outreach emails went out -- and that was the right call.
2026-05-2830 Days of Corrupt Data, Averted. One Missing Table Still Has Two Agents Down.
Fixed a silent API schema mismatch before it could ruin a 30-day trading experiment, shipped the diagnosis framework, and watched a missing database table knock out two agents for hours.
2026-05-27The System Fixed Itself at 6am. Hugo Has Been Broken Since Thursday.
Pipeline-health auto-healed two issues while I slept. The Hugo deploy has failed six consecutive times. And after five days of lockout, outreach restarted.
2026-05-26A Trading Agent Shipped This Morning. Four Fixes Before It Worked. That's Normal.
I launched a new AI trading account and 75 outreach drafts in one day — while a critical tracking bug sat open all day that no agent could self-fix.
2026-05-25134 Hours. 46 Drafts. Zero Emails Sent.
A P0 bug halted every outreach email for over five days. Here's what the system did instead — and why it still built a full pipeline while locked down.
2026-05-10$0 Revenue from the Marketing System. Here's Why I'm Still Building.
12 agents running daily, hundreds of prospects in the pipeline, and zero dollars to show for it. This is what building in public actually looks like.
2026-05-051,040 Commits in 30 Days. One Developer. Zero Employees.
Three production applications built from scratch with AI coding tools. What solo velocity actually looks like when you stop pretending you need a team.
2026-04-20The Internet Went Out and I Lost Everything
A home internet outage took the whole operation offline overnight. The fix was obvious in hindsight.
2026-04-16659 Commits in 13 Days: Building an Entire Marketing Department
How 14 AI agents, an event bus, 5 websites, an email engine, and a social media engine came together in under two weeks.
2026-04-01Why I Built My Own Medicare Analysis Tool
Carriers kept pulling their tools. Commissions kept shrinking. So I built an AI-powered research assistant biased toward official CMS data.
2026-03-15I Wiped Windows Off a Gaming Laptop and Built an AI Department
How a licensed insurance agent with zero engineering background ended up running 14 autonomous AI agents on a gaming laptop named LaptopLLM.
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, that's the place.