Six live products. One AI-first founder.

Hard problems. Simple products.

A portfolio of commercial apps, each aimed at a specific, stubborn problem that big software either overcomplicates or ignores. They are built to last, priced to be fair, and every one has a free tier.

Explore the apps How one person runs six

6live commercial apps
6 of 6with a free tier
1founder, working AI-first
1lean platform runs them all

The portfolio

Pick the problem you have. Each app has its own site, its own customers, and a free way to start.

01Schedule a CoachBooking, payments, and video for independent coaches, with zero session feesFree tierscheduleacoach.com
02CalTogetherThe community calendar people actually trust and useFree tiercaltogether.com
03StreetHighlighterWildfire evacuation maps that neighborhood volunteers can buildFree tierstreethighlighter.com
04ContextUpdaterKeeps AI agents current on the world outside your companyFree tiercontextupdater.com
05ScriptTunerA voice-driven AI script consultant that keeps the writer in chargeFree tierscripttuner.com
06MailJollyEmail that small organizations can run and that actually landsFree tiermailjolly.com

01Coaching platformFree tier

Schedule a Coach

For independent coaches, trainers, tutors, and consultants

The challenge: Solo coaches stitch together a booking tool, a payment processor, and a video app. Marketplaces take a cut of every session and keep the client relationship.
The simple answer: One white-label site on your own domain that books the session, takes the payment, and hosts the call.

Zero session feesA flat monthly price. Coaches keep every dollar their clients pay.
Your brand, not oursClients book, pay, and meet on your site, with no marketplace steering them elsewhere.
AI that coaches the coachSessions are analyzed to suggest follow-ups, improvements, and ways to grow.

Start free at scheduleacoach.com

Screenshot of the Schedule a Coach website

02Community calendarFree tier

CalTogether

For nonprofits, schools, HOAs, and faith groups

The challenge: Community events live in spreadsheets, PDFs, and social posts. Nobody knows which version is current, so people stop checking.
The simple answer: Publish once and it shows up everywhere: a polished public page, an embed for your website, and a feed people can subscribe to.

Pages that look finishedMonth and list views with a photo on every event, so the calendar earns trust.
Teamwork without shared passwordsOwners, editors, and viewers each get the right level of access.
Reminders that reach peopleText message alerts for events, not just another email.

Start free at caltogether.com

03Wildfire preparednessFree tier

StreetHighlighter

For Firewise communities and neighborhood emergency volunteers

The challenge: Evacuation planning means knowing which streets belong to which zone and how people get out. Spreadsheets cannot draw a map, and GIS software takes training volunteers do not have.
The simple answer: Paste in addresses and get highlighted street segments, grouped by POD, with evacuation routes drawn on an interactive map.

From address list to mapU.S. addresses are geocoded into points and street segments automatically.
Organized the way neighborhoods planSet up PODs, mark drive-out and walk-out routes, and save views to share.
Built by a Firewise chairDesigned by the person who runs a Firewise association in the Santa Cruz Mountains, and used there.

Start free at streethighlighter.com

Screenshot of StreetHighlighter showing an evacuation route on a neighborhood map

04API for AI agentsFree tier

ContextUpdater

For teams running AI agents in production

The challenge: AI agents act on what they knew at training time. Keeping them aware of new regulations, market moves, and competitors usually takes analysts and a pile of feeds.
The simple answer: One API call returns a ranked, deduplicated briefing your agents can use right away.

Made for agents, not dashboardsAgent-ready output from a single endpoint, with no analyst in the loop.
Many signals, one integrationMacro, regulatory, competitor, and supply-chain news arrive together, ranked by materiality.
Fresh twice a dayScheduled sweeps of news and filings keep briefings from going stale.

Start free at contextupdater.com

Screenshot of the ContextUpdater website

05ScreenwritingFree tier

ScriptTuner

For screenwriters revising a draft

The challenge: Revising a screenplay with AI usually means pasting pages into a chat box, losing the formatting, and hoping the edits keep your voice.
The simple answer: Talk through the draft with Riley, an AI script consultant who pitches changes inside your properly formatted script. You approve or reject each one.

A consultant you talk toDiscuss scenes by voice, the way you would in a writers' room.
The writer stays in chargeEvery edit is a pitch you accept or reject, with full history.
Fits your workflowImport your draft, autosave as you go, and export FDX when you are done.

Start free at scripttuner.com

Screenshot of ScriptTuner with a screenplay beside the Riley voice consultant

06Email for small organizationsFree tier

MailJolly

For small businesses, nonprofits, and community groups

The challenge: Email platforms are built for marketing departments: dense to learn, priced for scale, and easy to land in spam if you send it wrong.
The simple answer: One list, one message, done. Deliverability protection is built in, so the email you send actually arrives.

Paced sending, not blastingThrottled delivery and smart send windows protect your sender reputation.
List hygiene on autopilotBounces and spam complaints are suppressed automatically.
An AI deliverability checkLive delivery status and analysis for every list, campaign, and contact, plus tracking you own.

Start free at mailjolly.com

The operating model

AI changed the math. Now one person can serve the markets big SaaS skips.

A focused product for a few thousand customers used to need a team of ten to build and maintain. Working AI-first, it needs one person who understands the problem. That is what makes these apps viable as businesses, not side projects.

AI-first, end to end

Design, code, testing, and copy are built with AI agents, so one founder ships and maintains at team speed. Inside the products, AI does real work: coaching insights, deliverability checks, agent briefings, and a script consultant.

One lean platform

All six run on the same serverless stack, Vercel and Neon Postgres, which costs almost nothing when idle and scales when used. Low running costs keep pricing fair and free tiers sustainable.

Built to last

Each app is a business with its own domain, customers, and paid plans, maintained for the long term. The free tier is how you try it, not a demo that disappears.

The founder

I build where I have a stake in the problem.

I am Craig Winter. I chair a Firewise association, so I built StreetHighlighter. I write screenplays, so I built ScriptTuner. Every app in this portfolio started with a problem I or the people around me could not solve with existing tools.

I started my career writing assembly language for rocket control systems, then spent 11 years as a product manager on marketing cloud platforms. That combination, software that has to work and products people have to adopt, is what I bring to each app.

I also advise a small number of teams as a fractional CPO or CTO through GenAI Fuel.

Product management on marketing cloudsCheetah Digital, Revinate, MovableInk
Founder, six live appsBuilt and operated AI-first
Community workBoard director, Felton Fire Protection District. Chair, Forest Lakes Firewise.
WGA-registered screenwriterComputer science and physics background

Questions about an app?

The fastest way to see what an app does is its free tier. For anything else, such as a partnership, an integration, or a question before you sign up, send a note and I will reply by email.