Entrepreneurs in Residence
The plan: Document the entire process as I go through startup number four, so you can follow along and see behind the curtain on how a bootstrapped product gets built from the ground up. I’m not gonna sugarcoat it — this Skool group is a massive experiment, so I’m relying on you to tell me what works, what doesn’t, what’s shit, what’s not.The Promise
When I built my first business back in 2016, I made a promise to myself that I would stick at it for six months no matter what. I reasoned that, even if it completely flopped, it would still be a learning experience and CV piece I could be proud of. Not gonna lie - it was f*ckin’ annoying, and I nearly quit about a million times… but I stayed true to the promise and ended up bootstrapping it to £10,000 per month, and sold it twice. So I want you to make that same promise to yourself. Whatever your idea, your goal, whether you’re working on it now or you’re looking for a problem to solve, stick around for six months and I’ll make this the resource I wish I had when I was going through that, too.What You Get
Weekly Sessions
- Tuesday & Thursday at 7 PM GMT: Co-working sessions
- Weekly Show & Tell: Share your progress, get feedback, learn from others
Access to All My Resources
Every boilerplate, starter kit, and tool I’ve built to ship products faster:Withseismic MCP Server
TypeScript MCP server template for building AI agents. Zero-config setup with production-ready transport layers.
React Tailwind Chrome Extension Template
Start coding Chrome extensions in 30 seconds. React 18, Tailwind CSS, TypeScript, and Vite with hot reload.
Site to Swagger
Turn any website into documented API. Extract endpoints from DevTools and generate complete Swagger/OpenAPI docs.
Definitely Not a Robot
Make browser automation undetectable. Natural mouse movements, human-like typing, and behavioral patterns.
Cursor Tools
Supercharge Cursor IDE. Instant project scaffolding, AI rules, pattern learning, and automated refactoring.
GTM Crawler
Bridge cloud automation platforms to local code. Run specialized tools from Clay.com, N8n, or Make.com.
Who Am I and Why Should You Care?
I’m Doug Silkstone, a British software engineer based in Prague. Over the past 10 years, I’ve built production systems for companies like Contra, Groupon, Motley Fool, Sky, and MIT. I’ve also built and sold three of my own products. I combine full-stack engineering with growth, product, and marketing experience. This rare blend comes from years of building revenue-generating software - first as a bootstrapped founder, then as Head of Growth managing multi-million dollar budgets, and now as an engineer building systems that directly impact business metrics. My background:- Built my first business in 2016, scaled to $100k ARR, and sold it twice
- Worked across engineering, growth, and product with teams at Contra, Sky, Groupon, The Motley Fool, and MIT
- Helped early-stage startups collectively raise $20M+ USD
- Course contributor for MIT’s Generative AI & LLM course
- Previous Head of Growth, managing systems that drove $10M+ in spend and over 1 billion product sessions
- Open-source contributor to TanStack, Mastra, and various tools
The Mission
The aim here is to collect 100 entrepreneurs, builders, and promise makers in six months, whilst I launch another product and walk you through the whole process. Over the next six months, I’m going to share EVERYTHING I know about:- Building products from zero to one
- Acquiring customers without massive budgets
- Engineering for revenue, not vanity metrics
- The mistakes I’ve made and how to avoid them
- The systems and tools that actually work
Join the Community
Join Entrepreneurs in Residence on Skool
Become part of the community and follow along as I build startup #4
Are you in? Whether you’re working on your idea now or looking for a problem to solve, make the promise. Six months. Let’s build something worth being proud of.