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Chris Sereno · Co-founder & CTO, Cowboy Christian

The widest search.
The shortest path.

I build companies and work through complex systems. Today, my focus is Cowboy Christian, a health cost sharing platform.

My approach comes from twenty years at Caterpillar, AWS, and in my own practice: start with the outcome, explore the options, and let evidence narrow the path.

See how I work Read the writing
Chris Sereno in profile, hand at his chin, looking out of frame

Building Cowboy Christian

My primary focus today.

More about me →

  • 20 + yrs

    Reading systems at scale

  • 15 +

    Small businesses helped

  • 4

    Pieces published by AWS

  • 2

    Ventures founded

Actual State · the method

Define the outcome. Explore the routes. Find what holds up when you measure it.

How a decision gets made Four stages left to right. One target state on the left opens into nine candidates, more than feels efficient. Evidence eliminates five of them. The four that survive converge on a single answer at the right.
  1. 01 · Outcome

    Name the decision.

    What needs to be true when we finish?
  2. 02 · Options

    Draw the routes.

    Include the ones already dismissed.
  3. 03 · Evidence

    Go and measure.

    Test assumptions against real conditions.
  4. 04 · Decision

    Write the answer.

    Include what would change it.
The full framework →

The common thread

The same method, at every altitude.

A packet capture and a P&L are the same kind of object: a record of what a system actually did.

  1. Packet What is this application actually doing? 13 years, Caterpillar
  2. Service Will video and control survive 5,000 miles, live, on a machine that can kill? Command for Dozing
  3. Architecture Does a global estate stay up when a region doesn’t? Lead SA, McDonald’s · 5 years
  4. Organization Is the org chart describing how the work actually moves? Mentoring, exam authorship
  5. Industry Does anyone here know what care costs before they consent? Cowboy Christian

Recent writing

Working it out in public.

All writing →

Aug 2026 · Article

There Is Always a Middle Account

I spent months designing a system around "person to person" before I drew how a dollar actually moves. Every transfer is two instructions with an account in between.

Read →

May 2025 · Article

Thoughts on AI from an Infrastructure Guy

An infrastructure architect’s perspective on AI-managed networks, changing technical roles, and keeping business outcomes at the center of the work.

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May 2019 · Article

Imprints

Two worn spots on a pillow, pressed in by the same two small heads over months. We leave imprints on people whether or not we intend to.

Read →

Apply the method

Work through it. Or learn to run it.

Select advisory

An outside perspective.
A decision in writing.

Alongside Cowboy Christian, I take on select advisory engagements. Three working sessions on one consequential decision, with your team gathering evidence between them.

  1. Frame
  2. Test
  3. Decide

A decision brief, the evidence, a written recommendation, and working files your team keeps.

Explore advisory

Small-business learning · In development

Your business.
A guided path.

I’m building a guided path for small-business owners: practical lessons, ready-to-use templates, AI guidance, and checks on your own business.

  1. Purpose
  2. Foundations
  3. Automate
  4. Improve

Define what you sell. Build the foundations. Connect the work. Measure what improves. Each step leaves you with something usable.

Ask about learning