Twenty years building digital businesses globally. A decade at Google. An $80M+ media portfolio bootstrapped without VC. Now in code daily, rebuilding my own operation with AI at the core and writing about what's actually 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 opening doors we couldn't see a few years ago.
My career started at Google in 2006, when the company was just 12,000 people strong. Over a decade there, I worked across Europe, North America, the Middle East, and Asia. In my last position, I was managing a $1B+ advertising business and a 25-person team across four continents. 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 without raising a dollar. 90%+ profit margins and a global organisation of 20+ people.
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, and it's what I write about.
Operations scaled. Global SMB P&L led across four continents at Google.
Bootstrapped cumulative sales at mOOnshot digital. Zero external capital.
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 moreI'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+ in cumulative sales, then rebuilt from zero with AI as the foundation.
Read more →A recent dinner in Dubai with senior publishers. Most ask how to use AI to produce more content — I'm increasingly convinced the bigger lever is rebuilding the organisation around AI, not integrating it onto separate functions.
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 that caters to the needs of AI readers, with the same attention to detail as the human-facing layer.
llms.txtagent-skillsThe same publishing operation, rebuilt from zero around AI. A full rewrite of how the work gets done.
Cited by AI65mentions across AI toolsGemini16Claude14Perplexity13ChatGPT12Grok7Copilot3
“Once digital transformation starts gaining momentum, we can develop the right marketing strategy for luxury brands to grow.”
Best way to reach me is email. I read everything but reply selectively. If you're an operator rebuilding your business around AI, an institution working through operational AI deployment, or a founder bootstrapping with AI-first infrastructure, I'd like to hear from you.