Ashkaan Hassan

Esq.

AI Systems Architect

Experience14 years
View My Work

About

The short version.

I'm a CEO, attorney, and engineer who builds production systems β€” not prototypes. For 14 years, I've run We Solve Problems, a technology consulting firm now doing $1.09M ARR with a 40% SDE margin (2x industry average). In 2023, I led an AI transformation that replaced manual workflows with 50+ Claude-powered automations running on Windmill. I hold a JD, a CKA, and three professional licenses. I attend DEF CON. I built the 178-control AI governance framework deployed at MannKind Corporation. This site β€” every interactive element, the terminal, the API β€” was built with the same stack Anthropic uses.

Time as CEO

Portfolio

8 production systems. Not toy projects.

Experience

CEO + Attorney + Engineer.

We Solve Problems

14 years of building, scaling, and now automating with AI.

$0M
Top-Line Revenue
$0M
Annual Revenue
0+
Active Clients
0
Team Size
0%
SDE Margin

Timeline

2011

Founded We Solve Problems

2014

Expanded into managed services

2018

Launched cybersecurity practice

2020

Remote-first transformation

2023

AI pivot β€” Claude + Windmill

2024

50+ automations in production

2025

Enterprise AI consulting launch

2026

$1.09M ARR, AI-native operations

Why This Matters for FDE

  • 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.

Contextium

Open-source AI-native knowledge management. Powers this site.

Context Router

Trigger-based lazy loading of context files. Only loads what's needed for the current task.

Governance Rules

Behavioral rules, deployment guardrails, and credential management policies.

Structured Memory

Knowledge organized by domain β€” people, projects, integrations, preferences.

Session Management

Every AI session follows structured protocols β€” context loading, delegation rules, and session-end governance. No rogue agents.

Integration Hub

24 external services connected β€” from Windmill automation to 1Password secrets to Cloudflare deployments. All orchestrated through one repo.

Quality Enforcement

Aegis runs 15+ automated health checks. Deno lint, shellcheck, gitleaks, deployment drift detection. Nothing ships broken.

Context Router Demo

Select a task type to see which context files get loaded.

βœ“preferences/style_guides/app-development.md
βœ“integrations/daedalus/README.md

Skills

CKA + DEF CON + State Bar. Not many people have all three.

TypeScriptPythonDockerProxmoxCF Workers/Pages/KVAstroReactTailwindWindmillAI/MLClaude API/SDKCoreMCPGitLinuxZFS/TrueNASKubernetesHome AssistantActive DirectoryMicrosoft 365Azure ADNetworking (TCP/IP, DNS, DHCP)VPN/FirewallBackup & DR
DEF CONEliteSOC 2CIS Controls178-Control AuditMSSP Ops
CloudflareGitHubWindmillAutotaskNinjaOneQuickBooksKomodo
RMM (NinjaOne)PSA (Autotask)ITIL/ITSMPatch ManagementEndpoint SecuritySOC OperationsClient OnboardingSLA Management

Leadership

Board Chair, Commissioner, 6 EO roles.

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

JD + BS + CKA + 5 licenses.

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.

I'm looking for the Forward Deployed Engineer role at Anthropic.

Built with Astro, React, Tailwind, and Claude. Deployed on Cloudflare Pages.