Ashkaan Hassan, Esq.

AI Systems Architect

Building production AI systems, not prototypes. 14 years of company-building meets 50+ Claude automations.

LVL 1487% to next level

About

Time as CEO14 years, 4 months, 29 days(and counting)

I built an AI-native platform that runs a real company. Not a weekend hack β€” a production system managing $1.09M in annual revenue across 25+ clients with a 6-person team. 50+ Claude-powered automations handle everything from news curation to compliance monitoring to client reporting.

The orchestration layer is Windmill β€” an open-source workflow engine where every automation is version-controlled, observable, and connected. Claude Code hooks, SSH-based API calls, and structured prompts turn business processes into reliable pipelines.

Before the AI pivot, I spent 14 years building We Solve Problems from a solo IT consultancy into a managed services firm with enterprise clients like MannKind Corporation. Along the way, I earned a law degree, passed the bar, got my CKA, went to DEF CON, and did a stint at Marvel Studios.

The FDE role is the convergence of everything I've built. I don't just understand AI systems β€” I've deployed them in production, sold them to enterprises, and operated them at scale. I can talk to a CTO about architecture and a CFO about ROI in the same meeting.

Ask Claude About Me

Powered by a real Claude Haiku endpoint. Ask anything about my background.

Contextium

Open-Source AI-Native Knowledge Management

A framework for making Claude Code deeply project-aware. Structured context routing, governance rules, and domain-organized memory β€” all in Markdown, all version-controlled. This site itself is powered by Contextium.

All Contexts

integrations/windmill/README.md
preferences/style_guides/code-conventions.md
preferences/rules/governance.md
preferences/rules/behavior.md
integrations/README.md
preferences/user/preferences.md
knowledge/growth/goals/current-focus.md
projects/README.md

Loaded

integrations/windmill/README.md
preferences/style_guides/code-conventions.md
preferences/rules/governance.md

AI Portfolio

Production systems, not toy projects.

Experience

We Solve Problems

14 Years Building a Technology Company

$0.00M
Annual Revenue
0+
Active Clients
0
Team Size
0%
SDE Margin

Founded in 2011 as a solo IT consultancy, We Solve Problems has grown into a full-service technology firm delivering managed services, cybersecurity, and AI transformation. The 2023 AI pivot deployed 50+ Claude-powered automations on Windmill, achieving a 40% SDE margin β€” 2x the industry average. Today the company operates with a 6-person team serving 25+ enterprise and SMB clients.

Timeline

Why This Matters for Anthropic

  • β–ΈBuilt and scaled a real company β€” not a side project. 14 years of operational complexity.
  • β–ΈLed an AI transformation from the inside β€” 50+ Claude automations replacing manual workflows.
  • β–ΈEnterprise client delivery experience β€” MannKind AI audit, multi-year managed services contracts.

Skills

TypeScriptPythonDockerProxmoxCF Workers/Pages/KVAstroReactTailwindWindmillAI/MLClaude API/SDKCoreMCPGitLinuxZFS/TrueNASKubernetesHome Assistant
DEF CONEliteSOC 2CIS Controls178-Control AuditMSSP Ops
CloudflareGitHubWindmillAutotaskNinjaOneQuickBooksKomodo

Leadership

After-School All-Stars LA

Board Chair

Leading the board of a nonprofit providing free after-school programs to 10,000+ students across Los Angeles.

Entrepreneurs' Organization LA

6 Leadership Roles

Engagement Co-Chair, Learning Co-Chair (incoming), and four other leadership positions across chapter operations.

CA Commission on Judicial Nominees Evaluation

Commissioner

Evaluating qualifications of judicial nominees for the California State Bar.

Games for Love

Advisory Council

Advising a nonprofit that uses gaming and technology to improve children's lives in hospitals and underserved communities.

Education & Credentials

Juris Doctor (JD)

Degree

USD School of Law

2008 -- 2011

B.S. Business Law

Degree

CSUN

2003 -- 2008

Minors in Metaphysics & Psychology. Started in Astrophysics.

Certified Kubernetes Administrator (CKA)

Certified

CNCF

2024

California State Bar

Licensed

Bar #381138

Admitted 2012

California Real Estate Broker

Licensed

DRE

Since 2014

Mortgage Loan Originator

Licensed

NMLS

2014

Certified Mediator

Certified

NCRC

2009

Google Workspace Administrator

Certified

Google

2019

Let's build something together.

Β© 2026 Ashkaan Hassan. Built with Astro, React, Tailwind & Claude.