Twenty years building digital businesses globally. A decade at Google. A bootstrapped $80M+ media portfolio. Now in code daily, rebuilding my own operation with AI at the core and writing about what's happening from inside the transformation.
I've been building digital businesses for twenty years, and AI is the biggest shift I've seen since Google changed online advertising. AI is squeezing our existing revenue and creating new streams at the same time.
My career started at Google in 2006. The company was 12,000 people and felt like a startup that had accidentally become enormous. Over a decade, I worked across Europe, North America, the Middle East, and Asia, eventually running a 25-person international team and a $1B+ advertising business. I left in 2017 to build something of my own. Together with my wife, we bootstrapped a portfolio of online publications to $80M+ in sales with 90% profit margins, 20+ people across the world, and without raising a dollar.
Today, I spend most of my time rebuilding our operations on AI infrastructure, designing production AI systems for new ventures, and understanding what drives real business results.
That space between what AI promises and what actually works in production is what I'm most interested in.
Global operations led across four continents at Google.
In sales at mOOnshot digital. Zero investors, zero pitch decks.
Net profit margins. High-margin operations rebuilt from zero around AI.
International talents managed across remote and in-office teams worldwide.
Business exit to a private investment group.
Global users reached across the mOOnshot digital portfolio.
Recommendations from people who worked with me directly, mostly during my decade managing international teams at Google.
Hye In Kim
APAC Growth Lead, Google Play Games
“He cares about people very much and he also knows how to push people beyond their comfort zone.”
Maiko Fujita
Consumer Marketing Manager
“Simon had led the team by showing clear vision and goals, always giving actionable feedback.”
Pratik V Udeshi
Head of Amazon Ads, Asia-Pacific
“Simon also has very good product knowledge and displays an amazing sense of ownership towards all his projects.”
How AI is reshaping content creation, monetisation, and the economics of online publishing. Written from inside the transformation, not from the sidelines.
Read moreBuilding without VC, achieving 90%+ margins, and the discipline of profitable-first growth. The frameworks behind scaling a portfolio to $80M without external capital.
Read moreWhere online publishing, audience attention, and content monetisation are heading. Why the advertiser-first model won't survive AI. Industry analysis grounded in 20 years of operating data.
Read moreThe daily practice of building AI-powered products. Build logs, architecture decisions, and what AI-assisted development actually feels like in production.
Read moreInstead of wondering how often AI models cite my work, I built a custom little weekly automation that gives me a real number on every page of this site.
Read more →I'm updating this site with just a few taps on my phone: a small Shortcut, the iPhone share button, and a workflow doing the heavy lifting on the server. See exactly how it works.
Read more →AI is great at sounding confident, even when it's completely wrong.
Read more →We have hundreds of articles ready to publish across our portfolio. The slow part of our operation isn't the AI any more. It's the human time around it, and that's where most publishers are under-investing.
Read more →How I bootstrapped mOOnshot digital to $80M+, then rebuilt from zero with AI as the foundation.
Read more →
$80M+ bootstrapped, rebuilding AI-first
Two-arm media operation: an owned publications portfolio plus an agency serving premium brands. Currently rewriting the production stack from zero around AI agents and orchestration.
100M+ readers, agent-driven editorial
Flagship luxury lifestyle publication. The 15-person manual editorial team is being replaced by a quality-gated AI agent pipeline: 4-week cycles down to 4 hours.
Directory + networking, scaling globally
Directory and networking platform connecting senior luxury professionals from world-class companies. Members-only network of executives across every luxury industry.
Sustainable luxury travel guide
Curated guide to ethical hotels, vegan restaurants, and sustainable destinations for conscious travelers. Editorial built on the same AI publishing rails as Luxe Digital.
Stealth, on Shopify
Direct-to-consumer home design brand. Curated objects for considered interiors, with the catalog and merchandising loop run end-to-end by AI.
Stealth, regional pilot
News aggregator with zero noise. Only verified and trustworthy sources.
Stealth, internal tooling
End-to-end content framework powering the mOOnshot publications: research, drafting, editorial review, SEO, and publishing as a single agent loop with human quality gates.
Stealth, testing on myself
A multi-tenant personal-brand publishing system. This site is the first tenant — the framework drafts, this repo publishes, and the same rails will serve other operators next.
Stealth, live on 2 domains, scaling to 10+
Templated directory platform for niche business categories. Shared Next.js + Supabase core, AI-generated entries, designed to scale across verticals from one codebase.
Most websites are written for humans. This one is built for AI agents too. There's an entire hidden layer of content and signals underneath what you see, built for AI readers with the same care and attention to detail as the human-facing one.
llms.txtagent-skillsBased on seven years of experience bootstrapping mOOnshot digital to $80M+ in sales, and validated as we rebuilt the entire operation around AI.
This is my system to incorporate AI into existing operations or build new business from scatch with AI as a foundation.
Healthy margins from day one, no outside money. AI has removed the need for large start-up capital.
The idea and expertise are yours, but AI shortens the path from conception to implementation.
Rethink your business with AI from the start. Don't try to force AI onto old infrastructures. Redesign the team around what AI actually changes.
AI models converge to the same output. Human experience, opinions, and data are what sets you apart.
Best way to reach me is email. I read everything but reply selectively. If you're an entrepreneur building your business around AI or an institution working through AI deployment, I'd like to hear from you.