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Dinners With Friends

Hosted dinners that help people make friends

CTO · Built the brand, booking platform, apps and search programme

Dinners With Friends brings people together to make friends over hosted meals at local venues across South West England. As CTO for the relaunch, the role covered the website, mobile apps, bookings, payments and host tools, alongside the brand, customer acquisition and analytics needed to run the business.

Relaunched a Social for Good concept that seats strangers around one table, first run twenty years ago by Pamela Silkstone.
Took the relaunch from a napkin sketch to an operating events business: brand, digital products, ticketing, operations and acquisition.
Built and ran the web product, the mobile apps and the internal operations platform.
Shipped the apps to the iOS App Store and Google Play with Expo.
Built ticketing and payments on Stripe Connect.
Built guest messaging, lifecycle email and AI-assisted admin tools.
Built search-led landing pages and event-filling campaigns.
Measured the whole journey, from first visit to booked seat.
Hosted 500+ guests across 50 events across South West England, selling out six to eight weeks ahead with waiting lists longer than the seats available.
Grew organic search from under 100 visitors a month to over 1,500 in one quarter, with impressions up from ~1.8k to ~950k and a million within six months.
Took first place for competitive local searches covering events, restaurants, spas, breaks, days out and regional guides.

dinnerswithfriends.co.uk

#typescript #react #reactnative #expo #nextjs #hono #postgres #gcp #stripe #seo #lifecycle #growth

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Doug Silkstone

From a napkin sketch to a year of full tables

In November 2024, Dinners With Friends was a revived idea and a napkin sketch. By the start of September 2026, it had welcomed more than 500 guests across 50 dinners. Dates were routinely selling out six to eight weeks ahead, and nearly all of the remaining 2026 calendar was booked.

Pamela Silkstone first ran the concept twenty years earlier: put people who have never met around one table, give them a host, and make the first conversation easier. I took the relaunch from idea to first version, first paying customers and a business with more demand than seats. Along the way I built the brand, website, booking system, internal tools, mobile app and the search programme that now brings new people in.

The search programme delivered 5,530 Google clicks in June–August 2026, up 66.1% on the previous three months, alongside 381,345 search impressions. Building and maintaining a library of local guides gave the business a way to be discovered by people looking for food, activities and places to meet across Exeter and Devon.

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dinnerswithfriends.co.uk

#typescript #react #reactnative #expo #nextjs #hono #postgres #railway #stripe #seo #ai #lifecycle #attribution #growth

Dinners With Friends homepage showing the event-discovery and booking experience — The live product joins discovery, social proof, availability and booking in one path.

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Doug Silkstone

Benson

Coupon-extension and AI-agent control for ecommerce

Founder & technical lead · Rebuilt and relaunched in ten days with AI agents

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Benson shows online stores which coupon extensions and AI shopping agents are in their sessions and what they cost, then lets them hide, cap or replace them with a holdout behind every change. The founder and technical lead role covered building, operating and selling the original getBenson platform, then reacquiring the brand and rebuilding it for the relaunch at trybenson.com.

Rebuilt Benson from an empty repository to a public relaunch at trybenson.com in ten days, against an original roadmap of 14 to 18 weeks.
Wrote the product as 44 PRDs and ran the build as an orchestrator, with AI agents delivering each task through tests, adversarial review and simplification: 836 commits and 785 test files in under two weeks.
Shipped ten apps and fifteen packages: a 2.5KB storefront loader, ingest on Redis Streams, Postgres with row-level security, a dashboard, an embedded Shopify admin, a WooCommerce plugin, a Cloudflare edge detector and an MCP server.

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trybenson.com How Benson was rebuilt

#typescript #react #nextjs #nodejs #hono #postgres #llms #architecture #zerotoone #attribution #ecommerce #growth

Doug Silkstone

Benson is back

On 24 September 2026, the Benson repository was an empty Turborepo starter. Ten days later, on 4 October, I relaunched Benson at trybenson.com with a Shopify app, a WooCommerce plugin, a dashboard, a marketing site, a press release and a series of explainer films behind it. By the end of the second week, the repository held 836 commits, 44 product specs and about 655,000 lines of TypeScript, with 785 test files among them.

The original roadmap for the same scope estimated 14 to 18 weeks. I built it with a team of AI agents doing most of the typing while I did the deciding.

Benson is still a work in progress. It's also the piece of work I'm proudest of, because it's the first time I haven't had to cut an idea down to fit the hours I had.

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trybenson.com

#typescript #nextjs #hono #postgres #llms #architecture #zerotoone #attribution #ecommerce #growth

The Benson dashboard overview in a demo store, showing protected value, live controls and insights — The Benson overview in a demo store with sample data. It shows what's protected, which controls are live and the next step in the recommended playbook.

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Doug Silkstone

Hogsend

Lifecycle messaging for software teams

Founder & CTO · Built the product, journey engine and cloud platform

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Hogsend lets software teams automate onboarding, customer messaging and retention in TypeScript rather than a visual workflow builder. The founder and CTO role covered the whole product: strategy, design, the journey engine, developer tools, cloud infrastructure and launch.

Built lifecycle marketing as code, with journeys reviewed in pull requests and tested before release.
Shipped the TypeScript development kit, journey engine, automated tests, Studio, command-line tools and MCP tools.
Built journeys that survive restarts, provider failures and releases while running for days or weeks.

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hogsend.com