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Latest Builds
PodToSite
Most podcasts are now created on YouTube — YouTube's own data has long-form audio/video uploads accelerating faster than any other category on the platform — but the public web that AI engines crawl still wants a *website* per podcast, not a YouTube channel. The result: shows that get hundreds of thousands of YouTube plays are invisible when somebody asks ChatGPT, Claude, or Perplexity for 'the best podcast about [thing].' The legacy podcast-website category (Podpage, Castos, Buzzsprout sites, generic WordPress builds) was designed to be a marketing site for human visitors clicking through from an RSS app — a homepage, a list of episodes, maybe a contact form. None of it was built to be *read by a model*. PodToSite is the structurally distinct entry: YouTube as the canonical source of truth, Astro-rendered episode pages with full transcripts and chapter timestamps, JSON-LD per-episode (`PodcastEpisode` + `Article` + `VideoObject` triple-typed), an `llms.txt` machine-readable index at the root, OG cards generated per episode, and an embed flow that pulls a new episode from YouTube the moment it publishes — so the LLM-discoverable version of the show exists the same hour the YouTube version does. Already in revenue with Tales From The Sky Lounge at tftsl.podtosite.com as the public reference deployment.
PlanCheck
Forsyth County, Georgia — one of the fastest-growing counties in the United States — processes roughly 885 planning applications a year across four departments (Engineering, Water & Sewer, GIS Addressing, Planning & Community Development), each application reviewed against a checklist that totals 47 items. Industry data says 40–60% of first submissions are incomplete; every incomplete submission becomes a rejection cycle that costs builders two to four weeks of carrying time and county planners a credentialed-staff hour they spent flagging the same missing-north-arrow they flagged on the last plan. The legacy permitting-software category (Accela, Tyler EnerGov, OpenGov) was built to track the application, not to read the drawing. CivCheck was acquired by Clariti in October 2025; that acquisition validated the market category — *AI plan review is a real category, not a niche.* PlanCheck is the structurally distinct entry in that category: a narrowly-scoped, builder-facing, self-service pre-qualification tool that runs on AI text + vision analysis, deploys with zero county IT involvement, and inverts the commercial model — counties get it free, builders pay per submission. Already live for Forsyth County, Georgia at plancheckers.com after the county evaluated 11 vendors and chose the narrowest one.
ChamberAdvance
A regional chamber of commerce runs 1,500–4,000 member businesses with a sales team of six to ten. Every new member gets the same welcome packet — the cupcake shop and the Fortune 500 anchor tenant get the same PDF. The chamber engagement coordinator hand-emails 800 members about an event nobody is the right fit for, then re-runs the same exercise next month for the next event. Members who don't see value in year one don't renew in year two; chambers lose 18–24% of new members inside the first 12 months on national averages. The tooling category (CMS / AMS) was built for membership records, not for member engagement. ChamberAdvance is the AI-generated, per-member engagement plan that turns a 5-minute survey into a chamber-branded PDF roadmap in 90 seconds — and into qualified sales intelligence for the chamber team in the same motion. Already in revenue with the Gwinnett Chamber of Commerce — the #1-ranked chamber in the U.S.
CounselExpress
In *United States v. Heppner* (S.D.N.Y., February 2026), a federal court held that information attorneys and clients put into consumer-tier AI tools — Claude desktop, ChatGPT, the $20-a-month subscription — is not protected by attorney-client privilege. Inputs to a public AI platform are shared with a third party; sharing waives privilege. The court explicitly preserved a different posture for enterprise-tier deployments with contractual confidentiality protections (Claude over AWS Bedrock, ChatGPT Enterprise, Claude commercial / government plans). Personal injury attorneys, who run 60–150+ open cases of 500–5,000-page document loads each, were already structurally outmatched on document-review time by defense counsel's paralegal teams. The obvious AI shortcut — paste the medical records into ChatGPT, ask for a timeline — just got ruled out for any matter where privilege matters. CounselExpress is the desktop application that gives PI attorneys the four analyses they need (medical timeline, case dashboard, police-report review, discovery review) over AWS Bedrock, with case files staying on the attorney's local machine.
CogleGroup
Mid-market customers have services lines being reshaped by AI faster than incumbent providers can keep up — and the structure of the firm that takes those engagements determines whether the work gets delivered. Sequoia's Julien Bek named the shape in March (*Services: The New Software*): the next legendary services firm sells the work, not the tool, by combining operator judgement with model intelligence. The structural answer is a GP-led, AI-native services firm — not a tooling vendor with a partner channel, not a consultancy bolting AI onto a managed-services contract, not a venture studio that pretends services and product live in the same P&L. Until today, CogleGroup was a services practice with a working operating model and the right two operators in front of it. The missing layer was the formal GP partnership and the partner-network firm structure that makes the model legible to customers, to Anthropic, and to the next set of operators we want to bring in.
30 years as a CTO. 2 years rebuilding everything around AI. This is what that looks like at speed.
Founder of Silverback CTO and Silverback Ventures. General partner at CogleGroup. Host of Tales From The Sky Lounge.
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