LLM systems · Cloud solutions

Signal. Everything else is noise you've learned to live with.

I build the systems that help good organizations prove their impact — LLM tools, cloud infrastructure, and web platforms shaped around how the work actually happens, not how software vendors wish it did.

LLM systemsCloud solutionsWeb platformsAutomation
StewardConnect — production
StewardConnect donor reporting, live in production

Live donor reporting · partner organization

LLM systems  •  Donor CRM  •  Case management  •  Grant data  •  Cloudflare Workers  •  Secure intake  •  Web design  •  Family constitutions  •  Automation  •  LLM systems  •  Donor CRM  •  Case management  •  Grant data  •  Cloudflare Workers  •  Secure intake  •  Web design  •  Family constitutions  •  Automation  • 

The Steward platform

Built for how small organizations actually work.

A growing suite — donor CRM, case management, intake and grants, compliance training, and legacy planning. Not a demo. Not a roadmap. Running in production with partner organizations today.

StewardConnect donor CRM reporting interface

Donor CRM

StewardConnect™

Donor management with a built-in LLM assistant — giving history, automated acknowledgments, and insights that used to need a data analyst.

StewardFlow resident budget planner — auto-calculated allocations from take-home pay

Case management

StewardFlow™

Case management, outcomes tracking, and resident budget planning — built so the reporting comes out of the work instead of on top of it.

StewardPulse resident intake and grant data interface

Intake & grants

StewardPulse™

Intake and grant data, captured once and reused everywhere — from first contact through final reporting.

StewardFlow™ · Proprietary methodology

Not the percentage. Not the amount. The same order, every time money arrives.

First

Give

Off the top, before anything else is allocated.

Second

Save

Set aside before spending starts — not from what survives it.

Third

Bills

Housing and obligations paid in their turn.

Fourth

Live

What remains is genuinely free to live on.

Most budgeting starts with the bills and hopes something is left. This starts with what matters and works down, so the first two are never what gets squeezed. Built into StewardFlow™ — income in, allocations calculated, the sequence held by the tool instead of by willpower. It works the same for a household that has never missed a payment and for someone rebuilding from zero.

Selected work

A few other things I've shipped.

The Steward suite is the flagship, but the same approach — understand the real workflow, then build the smallest thing that fixes it — shows up everywhere else too. Select an entry to read the detail.

Plus a handful of smaller builds: grant-reporting tools, member portals, and the site you're looking at right now.

Not a philosophy — a procedure

Praxis

πρᾶξις

Greek — practice. Knowledge that only counts once it's acted on.

Signal

Listen for the signal.

Alpha

Find the alpha.

Agency

Take agency.

Finance & arbitrage

Capital systems, built to run without you.

The same systems-first approach applied to capital instead of casework — automated arbitrage tooling, the models to track it, the sequencing and tax structure to keep more of it, and the basis planning that decides what your heirs actually receive. Work becomes optional, not required — and what's left transfers on purpose.

01

Arbitrage engines

Automated arbitrage systems

Software that finds and executes on pricing inefficiencies — spread capture and signal-driven execution logic that runs on its own schedule, not yours.

02

Modeling & data

Financial modeling & dashboards

Forecasting models and real-time dashboards that turn raw transaction data into a number you can actually manage — yield, drawdown, and runway, always current.

03

Sequencing & structure

Sequencing & tax sheltering

Withdrawal sequencing and entity structuring built into the model from day one — tax-advantaged wrappers designed in, not bolted on after the fact.

04

The outcome

Work optional

Multiple systems compounding in parallel, each hands-off by design. When the infrastructure carries the income, retirement stops being a deadline and becomes a choice.

Transfer & basis · passing it on

A plan that ends at retirement is only half a plan. How assets are held, titled, and timed determines what an heir actually receives after tax.

§1014

Stepped-up basis at death

Most appreciated assets included in a decedent's gross estate receive a basis adjustment to fair market value as of the date of death. Capital gain that accrued during the owner's lifetime is eliminated rather than inherited — heirs take the asset at the adjusted basis and may sell with little or no capital gains tax.

§1015

Carryover basis on lifetime gifts

Assets transferred during life generally carry the donor's original basis. The embedded gain travels with the asset to the recipient. The planning question is therefore which positions to gift, which to hold for the step-up, and which to donate outright — highly appreciated holdings usually favor the last two.

Title

Titling, portability & the double step-up

How property is titled governs what actually steps up. Community property regimes can produce a full double step-up on the first spouse's death, where separate property adjusts only the decedent's share. Portability of the deceased spousal unused exclusion must be elected on a timely filed Form 706.

Basis rules, exemption amounts, and portability elections are set by statute and change with legislation. Every structure is confirmed with your CPA and estate attorney before anything is titled or transferred.

Sample pages · client deliverable

Two pages from a capital deployment plan built for a private client — the toolkit page and the three-year outlook, showing how the modeling actually gets presented.

Capital plan sample page: the toolkit, with vehicle names redacted
01 — The toolkit
Capital plan sample page: three-year outlook table
02 — Three-year outlook

Investment vehicles & client details redacted

Not financial or tax advice — every engagement starts with your numbers, your risk tolerance, and your CPA. Start the conversation.

StewardPlanner™ · Legacy

Money transfers on its own. Values don't.

The Family Constitution is a written covenant — not a legal instrument, a moral one. It answers the questions an estate plan was never designed to ask.

An estate plan decides where assets go. It has nothing to say about why the family built them, what an heir is actually inheriting, or what that heir is expected to demonstrate before receiving access to any of it. That gap is where most generational wealth quietly comes apart — not through bad markets, but through unspoken assumptions.

The Family Constitution closes it. Eleven articles carry a family from its core values through its immutable capital laws, inheritance philosophy, financial-literacy milestones, governance structure, giving commitments, succession, and conflict resolution — ending in a letter to future generations and a signature page every generation re-signs.

It is built to be filled in together, read aloud, reviewed on a schedule, and passed down. Delivered as a designed, print-ready document your family can actually sign.

Who it's for

Families with a business, a portfolio, or a first meaningful liquidity event — and anyone who would rather their children inherit a standard than a surprise.

The Family Constitution cover page — a charter of values, stewardship, and legacy

The eleven articles

ICore personal & family values
IIVision for the family's future
IIIThe immutable laws of family capital
IVCore financial principles
VWealth distribution principles
VIEducation, development & mentorship
VIIFamily governance
VIIIPhilanthropic commitments
IXSuccession planning
XConflict resolution & amendments
XIA letter to future generations
Interior page: vision for the family's future and the immutable laws of family capital
Interior — Articles II & III
Adoption and signatures page, with reaffirmation lines for future generations
Adoption & signatures

Not a will, a trust, or a substitute for either — it sits alongside them and tells your attorney, your heirs, and your future self what the plan is actually for. Prepared with your family, in your language.

Creative

Long-form pieces, start to finish.

Each one researched, written, illustrated, and built — not templated. The same care that goes into a donor CRM goes into a design history or a travel feature.

The whole body of work

Everything, in one frame.

A combined contact sheet of the Cali Gato sculpture collection, editorial site builds, and Steward platform interfaces
Cali Gato collection · G-Shock · Small Museums · Credo · Basquiat · Capital plan · Steward suite Photography, editorial & builds · Benjamin Stafford

Credentials & stack

Credentialed for both the care and the code.

Fifteen-plus years of revenue and team leadership, credentialed on both sides of the work — the human side and the technical side.

Certified Peer Support Specialist

FAVOR Lowcountry — Faces and Voices of Recovery

MIT Professional Education (CSAIL)

AI & LLMs solving business outcomes

Cisco Meraki CMNA

Cisco Meraki Network Associate

Programs & systems in active use

Everything below is running in production on a client engagement or on this site — not a list of things I've read about.

Cloud & infrastructure

Cloudflare Workers·Pages·D1·KV·DNS·direct-upload deployments·Wrangler CLI·Edge caching & CDN·Netlify

Email, DNS & deliverability

Cloudflare Email Routing·Custom-domain forwarding·MX·SPF·DKIM·DMARC·TXT & CNAME verification·Resend·FormSubmit·SMTP relay & send-as·Transactional templates

AI & automation

Anthropic API·Agent SDK·Model Context Protocol·Agentic tool orchestration·Retrieval-augmented generation·Prompt & context engineering·Structured output & JSON schemas·Browser automation·Scheduled workers & cron·Webhook pipelines

Web build & delivery

Semantic HTML5·CSS Grid & Flexbox·Custom properties·Responsive & mobile-first·SVG filters & procedural texture·IntersectionObserver·Fetch API·Progressive enhancement·ARIA & keyboard accessibility·prefers-reduced-motion·Schema.org JSON-LD·Open Graph & Twitter Cards·Canonical URLs·Google Fonts·Core Web Vitals & lazy loading

Document & image pipeline

Python imaging (Pillow)·PyMuPDF·PDF rendering & extraction·Programmatic redaction·Compositing & color grading·Asset optimization

Google Workspace & Apps Script

Apps Script·Sheets automation & custom functions·SpreadsheetApp·DocumentApp·GmailApp·DriveApp·CalendarApp·FormApp·UrlFetchApp·PropertiesService·Time-driven triggers·Custom menus & sidebars·Sheets·Docs·Drive·Forms·Looker Studio

Development

Node.js·Electron·JavaScript·HTML & CSS·Python·SQL·Git·PowerShell·REST APIs·JSON-LD & structured data

Operations, finance & creative

QuickBooks Online·Zeffy·Canva Professional·Meta Business Suite·Google Business Profile·LinkedIn Pages·Trello·Sling·RouteXL·Adobe PDF workflows·SaaS administration

Get in touch

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