Chicago, IL · Est. 79th & Cottage Grove

Michael Raashad
McGuire

One operator, four ways. Twenty-two years building companies, products and systems — then formalizing the engineering underneath what I was already doing. I don't specialize. I get dropped into a thing that isn't working and I come out the other side with it running.

Twenty-two years · Six industries · One job

Every room I've ever been put in was already broken when I got there. That turned out to be the career.

I started my first company at nineteen. Raised the capital, bought the buildings, and lost the entire portfolio in 2008 when the credit markets closed. Most people take a hit like that at fifty. I took mine early enough to still have time to spend it.

What came after was fifteen years of running rooms — restaurants, nightlife, logistics, consumer packaged goods. Not managing them. Running them. Being the person responsible when the system breaks at 2am and there is nobody else to call.

2022: a $1M hospitality business collapsed in thirty days. I found $634,000 sitting unclaimed in its own payroll records, filed for it, and turned it into three brands, a 70,000-unit production run, and a signed LOI on Woodward Avenue. No investor. No dilution. The money was already in the building. Nobody had read the paperwork.

Then I went and got the degree. B.S. Information Technology, WGU, 2026, eight certifications under it. Not for permission — I already knew how to build. I was done being the only person in the room who couldn't prove it on paper.

Now I write Rust and Python and I still run a P&L. Two of those builds went live this year: traphousetraders.com and aitrustid.com.

I don't get hired because the résumé is tidy. I get hired because the thing still works after I leave.

The Professional

MICHAEL

People call me in to scale things. I learn how a business actually works, then rebuild it on infrastructure that holds. Most recently: a HIPAA-regulated services company taken from paper files to a fully digitized AWS operation in under six months, on an engagement I scoped with the owners.

Now

System Administrator — Life and Favor Home Care

Indianapolis, IN · March 2026 — Present

Brought in by ownership to scale the business. I scoped the engagement directly with the owners and shareholders, delivered past the original scope, and was retained as salaried System Administrator over the systems I built. I didn't apply — they called.

Executed the AWS cloud migration end to end — data migration, HIPAA-aligned access controls, encryption, audit logging — with no interruption to service at cutover. Implemented HubSpot CRM and Slack as the core operating systems, then designed and staffed the back-office administration function around them.

How I work

I don't need the feature explained to me. I've been the person who decides what the feature is for — the one signing the vendor contract, carrying the P&L, answering for the number at the end of the month. That's the part most engineers have to be handed.

So I move faster than my title suggests. I read the documentation everybody skips, I find the place the system quietly lies to you, and I build around it before it costs anybody money. When the budget disappears mid-build — and it has — I don't shelve the project. I re-engineer it to survive on less.

I take the job nobody has scoped yet. Then I scope it, build it, document it, and hand somebody else the runbook.

The Ventures

RAASHAD

I'm the friend people come to to launch. Somebody has an idea. I turn it into a brand with a category thesis, a price list, packaging that ships, and a loyalty program. I've run that playbook across restaurants, consumer packaged goods, real estate and fintech since 2004.

$634K
Capital recovered
70,000
Units, first run
6
Brands launched

The rebuild

Roll & Smoke · Killer Coney Island · Shop Hookah Headz

Co-Founder & Co-Owner · Atlanta, GA & Detroit, MI · 2022 — 2024

A $1M hospitality business collapsed in thirty days. I developed a new consumer product, pitched it, and financed the launch with $634,000 in Employee Retention Credits I identified and filed — non-dilutive capital nobody else in the building had noticed was sitting in the payroll records.

The portable hookah line went from concept to sell-out: product design, manufacturer sourcing, packaging dielines, pricing, southern U.S. distribution. First production run of 70,000 units sold out in one summer, peaking at 500 units a day in the French Quarter.

Shop Hookah Headz launched end to end and under budget — brand identity, packaging design, multi-SKU production, live e-commerce, marketing creative. Killer Coney reached a signed letter of intent on 3,600 square feet on Woodward Avenue.

Roll & Smoke — the 70,000-unit run

Roll and Smoke retail box held at the warehouse
Production · the run, at the warehouse
Boxed inventory stacked at the warehouse
Freight · pallets in
Roll and Smoke carton instruction panel
Carton back · how to roll and smoke
Roll and Smoke pop-up flyer, Jackson
Pop-up · Jackson, event creative
Roll and Smoke pop-up flyer, alternate direction
Pop-up · second direction
Roll and Smoke pop-up story creative
Pop-up · story format, new hours
Portable hookah unit, four colourways
The unit · four-colourway range
Portable hookah unit, five colourways
The unit · full colour range
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Concept, product design, manufacturer sourcing, dielines, pricing, southern U.S. distribution. First run of 70,000 units sold out in one summer.

Killer Coney Island

Killer Coney brand book cover
Brand book · cover — "To Die For"
Killer Coney positioning page
The thesis · "We Got Next" — why this, here
Killer Coney wings and marketing plan pages
Brand book · wings, and the marketing plan
Killer Coney no-tipping model page
No tipping · the model, with the data
Killer Coney menu pages
Menu · sandwiches, brunch, the bar
Killer Coney market sizing page
Market sizing · "Numbers don't lie"
Killer Coney hot dog menu page
The dawgs · six builds, named
Killer Coney burger menu page
Burgers · "Pay Like You Weigh"
Killer-Aid cup render
Killer-Aid · the drink mark
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The brand book end to end: category thesis, market sizing, full menu architecture, packaging system, marketing plan — and a no-tipping model argued from the data (72% of American customers are uncomfortable with tip suggestions; servers paid above the legal rate with a service charge instead). Signed LOI on 3,600 SF, Woodward Avenue.

The build-out — 14131 Woodward Avenue

This is what the landlord handed me to work zoning against. The existing stamped set for the Highland Park space — site plan and scope, plumbing supply, kitchen exhaust and hood ventilation with the full BTU and CFM schedule, equipment schedule, ADA requirements. Drawn by LSA Inc. for the prior tenant.

My job was to read it and price the deal against it: what the existing hood and gas service would carry, what the bar addition did to the plumbing, how the seating count landed against occupancy, what had to be redrawn before anything could be permitted. A letter of intent on 3,600 SF is a number on paper until somebody reads the mechanical plan.

Title sheet and site plan, 14131 Woodward Avenue
Title sheet · site plan and scope
Plumbing supply plan with the new bar addition
Plumbing · supply plan, bar addition
Kitchen exhaust system plan and hood sections
Kitchen exhaust · hood sections, CFM
Equipment schedule and fixture elevations
Equipment · schedule and elevations
1 / 4 Tap to read

Four sheets, Highland Park, Michigan. The landlord's existing set, drawn by LSA Inc. — read, priced and negotiated against.

The run, on video

The carton · retail packaging, in hand
Product · campaign cut
Social reel · the campaign library in motion
1 / 3 Press play

Three clips, same stack. Shot and cut in house.

Shop Hookah Headz

Shop Hookah Headz full pack lineup render
The line · six SKUs, resealable pouches
Shop Hookah Headz printed pack in hand
In hand · printed pack, Kama Sutra
Shop Hookah Headz pack front, peach
Pack front · peach SKU, resealable pouch
Shop Hookah Headz pack front, ice
Pack front · ice SKU, resealable pouch
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Brand identity, packaging with compliant warning panels, multi-SKU production, a live storefront and the full campaign library. End to end, under budget.

For me to continue, I need equity, profit, design rights, ownership. The terms, 2022 — IP valued at parity with the cash investment

Before

True Life Management

Founder · 2004 — 2010

Structured as a REIT. Raised capital, deployed it into residential real estate across Michigan and Ohio, and lost the portfolio when the credit markets closed in 2008. Twenty-two years later I'm still raising capital — different instruments, same instinct for finding the money a situation actually has available to it.

Hookah by Cece

Project Manager, Business Restructuring · Atlanta, GA · 2020 — 2022

Restructured a 90-plus employee hospitality operation and scaled it to roughly $100,000 in monthly revenue inside a year — through peak COVID, as one of the few operators still trading in an open market.

Hookah by Cece portable unit in hand
Hookah 2 Go · the unit, branded
Hookah by Cece LED portable hookah retail box
Hookah 2 Go · LED retail carton
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Restructuring, brand system and the guest experience program for a 90-plus employee operation.

Trap Burger

Acquired & launched · Detroit, MI

Acquired an independent restaurant concept and secured the location. Operated it single-handed and chose not to continue without a partner.

Breaking Bread

Breaking Bread, plate 18
Breaking Bread · plate 18
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Identity, menu architecture and campaign creative.

Soap & Bubbles

Soap & Bubbles, plate 1
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Pet grooming brand — identity and illustration system.

Trap Burger

Acquired, rebranded, relaunched

Detroit, MI · concept acquisition · live site

Bought an independent burger concept, secured the location, and rebuilt the brand from the mark down. The OG Trappers line-up is eleven named builds — The 517 at five dollars for locals, The Motor City on a half pound of corned beef, The Philly, The Brooklyn, The ATL, The Westside — each one a city, each one a recipe, priced to be ordered by name.

Identity, product photography direction, menu architecture, the board, and the live site. The customer prompt on the menu is the part I'd keep: "Got an OG Trap Burger suggestion? Email us the burger and the toppings. If selected, free burgers for you all month."

Trap Burger logo
The mark · identity
OG Trappers menu board
OG Trappers · the board
Trap Burger live website
Live site · shipped
The 517 burger
The 517 · always $5 for locals
The Jack burger
The Jack · made to order
The Ganson burger
The Ganson · chopped, mozzarella
The Ceal burger
The Ceal · caramelized onion
The Mike burger
The Mike · jalapeño, bacon
The Land burger
The Land · fried mozzarella, A1
The ATL chicken sandwich
The ATL · hot honey
The Philly cheesesteak
The Philly · sirloin and ribeye
The Brooklyn chopped cheese
The Brooklyn · chopped cheese
The Motor City corned beef
The Motor City · half pound of corned beef
The Westside pita wrap
The Westside · pita
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Eleven named builds, one board, one live storefront. Every city on the menu is a city I've worked in.

Nimble

Nimble — an Airtel

Short-stay hospitality · brand and positioning

A category word as the product. An Airtel: hotel-standard accommodation at a short-let address. The thesis is that home-sharing won on supply and lost on consistency — so Nimble sells the thing nobody else guarantees: 24-hour professional staff, full-time property management, one design standard, every stay.

Identity, positioning and the pitch built together, because the name only works if the sentence under it does.

Nimble wordmark and fox mark
The mark · an Airtel
Nimble positioning page, a fresh way to short stay
Positioning · the argument
Nimble x Airtel brand architecture page
Nimble × Airtel · the category
Nimble brand system layout
System · layout and ground
1 / 4

The short-stay thesis that AirMaid was later built to service.

Ho'Cast

Ho'Cast Hustle or Starve cover, motel direction
Final cover · Hustle or Starve
Ho'Cast cover direction, red lip
Direction · third pass
Ho'Cast cover direction, crop variant
Direction · second pass
Ho'Cast cover direction, neon
Direction · first pass
1 / 4

Podcast brand, four cover directions to the one that shipped. By Nic and KNWVMBRR, a Bandz production.

Last Ones Laughing

Last Ones Laughing logo mark
The mark · Worn by Winners
Last Ones Laughing, plate 1
Last Ones Laughing · plate 01
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Apparel mark and campaign assets. Worn by winners.

The Operator

McGUIRE

The hands. Before the cloud certifications there were floors, routes, crews and openings. Everything I know about systems I learned from running operations where the system failing meant somebody's night went wrong at 2am.

Operations

Veho — Logistics Operations Lead

Detroit, MI · 2023 — 2026

Directed daily distribution of 6,000 to 10,000 packages: route troubleshooting, fulfillment execution, driver workflows and shrink analysis in a live, time-critical operation.

Toast on Lenox — Project Manager / Operations Lead

Atlanta, GA · 2022 — 2024

Led a restaurant launch from concept through opening: SOP development, systems setup, vendor coordination, staffing, marketing execution and event coordination, reporting to ownership.

Harold's Chicken Ice Bar — Hospitality

Edgewood · Atlanta, GA · 2019 — 2023

High-volume nightlife, bar and hookah operations, guest recovery, staff training. Harold's was a Chicago staple growing up. Working one in Atlanta was never only a job.

A system is only as good as whoever is running it at 2am.

Builder & Artist

KNWVMBRR

The handle is the signature. It's painted on the canvases and it's on the repositories. Same hand, two materials — one works in acrylic, the other in Rust.

I'm self-taught the way people were before there were courses for it: by needing the thing to exist and refusing to wait for somebody to build it. No team, no seed round, no permission. Fourteen broker integrations, a production stack, and a protocol spec — one pair of hands.

Shipped & live

AITrust-ID

aitrustid.com · Open protocol · Live

An open protocol for labeling AI output with evidence-backed authenticity tags, checked entirely on the reader's own machine. Nine labels, each carrying the signals that produced it and the spans they fired on. When confidence falls below a published floor the system returns UNK instead of guessing.

No paid APIs and no network egress at inference — structurally, not by policy. Content never leaves the machine; assertions carry a hash and character offsets, never text. Inverts the category: every competitor sells detection to institutions so they can accuse people. This one issues receipts to authors so they can answer the accusation. The specification, reference implementation and calibration ledger are free permanently.

aitrustid.com
AI Trust ID person view with fourteen evidence tags
Person view · the tag set
AI Trust ID enterprise view
Enterprise view · the gated half
Fleet tag detail showing a not independently validated notice
Honest state · "not independently validated"
Teamwork governance panel
Governance · who owns which outcome
1 / 4 Tap to read

Every tag is a card you can open. A capability that isn't ready says so on its own face — "Not independently validated. This capability is not available yet." Most products hide that. This one ships it as a state.

Trap House Traders

traphousetraders.com · Independent venture · 2024 — Present · Live

A Rust-first autonomous trading and financial intelligence platform: real-time market data ingestion, multi-broker execution, risk controls, AI reasoning services. Fourteen-plus broker and market data integrations with failover logic and execution safety boundaries. Full production stack run solo.

I exhausted the initial AI compute budget mid-build. Rather than shelve it, I re-engineered the pipeline to survive on less — replaced paid third-party dependencies with internally built services, added cost-aware orchestration and verification gates, and rebuilt the execution path.

traphousetraders.com
Trap House Traders sign-in screen
THT v5.4 · autonomous trading command center
1 / 1 Tap to view

Version 5.4. Separate admin path, separate trader path, and an execution layer that will not place an order without three environment acknowledgements.

In the workshop

SharpShooterBoard

v0.8.8 · Local-first sports intelligence terminal

Probabilistic research platform for NBA, NFL and MLB. Ingests timestamped sports and sportsbook data, engineers as-of features, trains calibrated models, simulates multiple futures, grades market edges, analyzes tickets with OCR, and tracks CLV and bankroll state across FastAPI, Streamlit and Telegram.

Treats operator memory as a hard requirement: the changelog, the inventory and the lessons-learned file must be updated after every meaningful pass, or the pass isn't finished.

Six First Dates

AI matchmaking platform · React, Expo, FastAPI, private LLM/RAG core

A guided six-date process with an AI coach, a structured playbook and human matchmaking underneath. React web, Expo mobile, FastAPI backend, a private LLM/RAG core on Google Cloud Run, consent controls, RBAC and audit logging. Load-tested to 25,000 simulated users.

The deck below is the part worth showing: my own design review, in red, over a running build. Flip the input and output so the answer lands at the bottom. Delete that button entirely and centre the sentence. These two don't work. Make the hero bigger — "make it like we mean it." Then the version that shipped.

Six First Dates running on a local server
Running · localhost, mid-build
Six First Dates running locally
Running · local build
Hero section with red design review notes
Review · the hero, marked up
Hero section after the revisions
Shipped · the same hero, fixed
Ask the Coach module with review notes
Review · flip input and output
Singles profiles section with review notes
Review · cut a button, centre the rest
Singles preview modal, three free profiles
Preview modal · 3 free, then sign in
1 / 7 Tap to read

Build, review in red, ship. The red pen is mine.

Also in the workshop

Agent Michael — a safety-gated trading core where live execution requires three separate environment acknowledgements before it will place an order. CEAL — peer-to-peer lending with an AI assistant on both the borrow and lend side. A county distress-lead workbench with 0–100 scoring and live underwriting math.

Product design

AirMaid / McMaid — short-let turnover marketplace

Product definition · two-sided marketplace · iOS

Defined from zero on paper: which cities carry the most listings, what a checkout clean costs today, what it costs to clean one unit in thirty minutes and six units in a day. Staffing, training, bonding and insurance. How the cleaner gets paid — same day or next.

Then the product. A job board on a live map, every job priced per room, per bed and per square foot. A cleaner side and a client side with separate navigation bars. Supply logistics, a ready / not-ready state per unit, service notes, and a rating loop where the customer approves, denies or complains. The personas came before the screens — Sara, 29, eight units, single mom, works full time. "Just get it done" is her personality.

AirMaid job board wireframe with live map and job cards
Job board · map, job box, income bar
AirMaid personas and profile card flow
Personas · profile and review loop
AirMaid client home with ready and not-ready unit states
Client home · ready / not ready
AirMaid cost calculator and navigation bar study
Cost calc · per room, bed, sq ft
AirMaid market sizing and operations notes
Market & ops · the money questions
AirMaid standard operating procedure for a turnover clean
The SOP · what a clean actually is
1 / 6 Tap to read

Six sheets. The market question, the unit economics, the SOP, then the screens — in that order.

Trap Burger — ordering app

Product design · four pages of flow, one component set

A tappable logo menu that stays put on scroll. A greeting that rotates by name or guest. Then the order path as modals: a draggable burger carousel, sauce and veggie modals you tap and untap, a combo question that only asks when it needs to.

Three menus running off one component set — The Brick and Double Up, Stick-Up Chicken ("how many birds you need?" — 1, 3, 5), and Plug Taco. The sauce modal is specified once and reused. The note I left myself on page two was "reduce words."

Trap Burger landing page wireframe
Landing · sign in, or just shop
Trap Burger order page with burger carousel and modals
Order · carousel, sauce, veggie
Stick-Up Chicken page wireframe
Stick-Up Chicken · reused modals
Plug Taco build-your-meal wireframe
Plug Taco · build your meal
Trap Burger menu page wireframe with signed-in state
Menu page · signed-in and signed-out states
Trap Burger modal specification notes
Modal notes · add / unadd, shell rotation
1 / 6 Tap to read

Four pages. One component set, three menus, and a running argument with myself about word count.

Agent Michael — trading dashboard

Information design · the screen before the code

A trading desk drawn in five pen colours before a single component was built. Total balance, withdrawable cash, stocks and crypto split out, the agent's own P&L beside the account's, open positions and plays on an infinite horizontal scroll, headlines and markets below. Colour is doing the work: each colour is a data class, not a decoration.

The settings rail is marked invisible until called. The widget box is sketched in the corner because the layout had to survive widgets being added later. This is the same safety-gated core that requires three separate environment acknowledgements before it will place a live order.

Agent Michael trading dashboard wireframe in colour
Dashboard · the whole desk, one page
1 / 1 Tap to read

One sheet. Every number on the screen placed before anything was built.

Electric 600 — EV rental, built as components

Product design · "My goal is to make EVs more accessible than gas"

Specified component by component before any code: the EV tile, the data card, the money menu, the rent action. Each one its own unit with a pressed and unpressed state, light and dark mode, and a defined flip, fade and blur. Think microservice.

Then the parts most people skip. Per-charge against per-weekend against membership pricing. The add-on menu that writes to a digital invoice. The security deposit, split to a second card if you want. ID onboarding that has to match the payment address. And the adverse path — the branch where no rental can happen — drawn out in full rather than left for later.

Rent and redeem scheduler flow on a whiteboard
Scheduler · now / later, pickup, filters
EV placard component study
The placard · one component
EV placard component study, annotated
The placard · states and hover
Component breakdown and money menu
Money menu · per charge to membership
Add-on menu and digital receipt flow
Add-ons · receipt and deposit
Payment, identity onboarding and the adverse path
Payment & ID · and the adverse path
1 / 6 Tap to read

Six boards. Components first, then pricing, then the invoice, then the path where the rental fails.

Art

$250K
In commissions
1/1
Every piece
0
Galleries, agents, prints

A quarter-million dollars of it, sold direct

Acrylic on canvas · 1 of 1 · Certificate of authenticity

Hard-edge portraiture — flat planes, vectorized rendering, color-block and currency grounds, Detroit and Chicago iconography. Every piece is a one-off, signed, with a certificate. No prints, no editions, no reorders.

Commissioned by recording artists and their families across Atlanta and Detroit, and carried on the collectors' own channels — including a piece Lil Baby took to the wall on the My Turn press run, in the first frame below. Priced, pitched, sold and delivered by me. No gallery took a cut and no agent booked a client.

Post Malone portrait on a smiley-face ground, signed nvmbr
Post Malone · acrylic on canvas, signed nvmbr
Lil Baby holding the commissioned canvas at the My Turn press wall
Delivered · My Turn press run
Portrait on a colour-splat ground
Commission · acrylic on canvas
Man of the Year portrait, finished
Man of the Year · the finished canvas
Man of the Year portrait, acrylic on canvas
Man of the Year · finished
Man of the Year canvas on the studio floor
Man of the Year · in the room
Portrait on a currency ground, framed
Currency ground · Detroit
Detail of the currency ground portrait
Currency ground · detail
Child portrait in overalls on a currency and colour-block ground
Commission · signed nvmbrr
Close detail of the child portrait
Commission · detail
Child portrait, hands at the cheeks
Commission · acrylic on canvas
Portrait in sunglasses on a currency ground
Currency ground · commission
Detail of a portrait against a colour-block ground
Hard edge · flat planes, detail
Pop-art lettering canvas
Lettering · pop ground
Sealing a finished canvas with spray
Finishing · sealing a commission
Underpainting in progress
Underpainting · in progress
Graphite drawing of a dog on raw canvas
Romeo · drawing on raw canvas
Painting the Romeo commission
Romeo · brush in hand
Hand-built cloud set piece in progress
Set build · clouds, by hand
1 / 19

Hard-edge portraiture on currency and colour-block grounds. Painted, sealed, signed and delivered by hand.

Vendors don't bluff me and engineers don't have to translate. Why the two halves were never two people

Twenty-two years

The order matters more than any single line in it.

Credentials

Every credential is verifiable by link.

8
Certifications
25+
Further credentials
2026
B.S. Information Technology

Technical

  • CompTIA Security+
  • CompTIA Network+
  • CompTIA A+
  • AWS Certified Cloud Practitioner
  • LPI Linux Essentials
  • Google Cloud
  • Google IT Support Professional

Practice & education

  • ITIL Foundation
  • CAPM · PMI #3924111
  • Leadership MicroMasters
    University of Michigan, Ross School of Business
  • B.S. Information Technology
    Western Governors University, 2026

Résumés

One page each. Same person, written for the room.

→ Technical Project ManagerPDF → Founder & Operating PartnerPDF → Operations LeaderPDF → Software & AI EngineerPDF

Contact

No booking links, no scheduling forms — write to me and I'll answer.

mike@michaelrmcguire.com
github.com/knwvmbrr