Plans built to run your business
Every plan includes a dedicated Winston working 24/7 — pick the level of autonomy and scale you need.
Winston Venture
$350/mo
$2,500 one-time activation
- Outbound AI sequences for cold email
- Meta ad management with AI-built creative
- AI content generation across formats
- Executive Hub — KPI dashboard & client management
- Branded client portal
- Real-time analytics and reporting
- 24/7 AI Butler assistant
Winston Executive
Most popular$999/mo
$5,000 one-time activation
- Everything in Venture, plus:
- AI voice calling for lead qualification
- Ad creative generation with performance scoring
- Newsletter platform for audience building
- Priority support
Winston Enterprise
$1,800/mo
$10,000 one-time activation
- Everything in Executive, plus:
- CRM integration with pipeline management
- Advanced AI calling, higher volume
- End-to-end Meta and Google Ads management
- Monthly executive strategy report
- White-label client portal
- M&A deal flow tracking
- Dynasty Trust and IUL consultation access
- Dedicated monthly strategy sessions
New in Winston
The latest upgrades to the Winston that runs your business, and what each one does for you.
- Council of three AIs. Big decisions get a second and third opinion, so one model's blind spot doesn't become your mistake.
- Deep Research. Every plan starts from today's prices, benchmarks, rules and competitors, and you can check every fact.
- 32 AI assistants. You get a whole department's advice, refreshed in the background, without hiring one.
- Winston's memory. Winston gets more like you every week, and each rule reaches only the work it belongs to.
- Talk to Winston. Ask a question while you drive or cook, and never start from a blank box.
- Lead database and sequences. Outreach becomes a daily list to work through, and fewer emails bounce.
- One CRM for everything. Nothing about a customer lives in someone's head or a stray spreadsheet.
- Marketing dashboards and Launch Center. You see what's working, and your plan actually gets done instead of sitting in a document.
- Studio. Campaign creative in minutes, without a designer or video crew.
- Drafts that sound human. Your posts and emails sound like a person wrote them, so customers keep reading.
- Launch check. You find the problems that cost customers and trust before anyone else does.
- Finance overview. You know how long your cash lasts and where it goes, without an accountant on call.
- Trading desk (paper money). You can learn and test an investing approach without risking real money. Not investment advice.
- Life insurance calculator. You understand the numbers before you talk to a licensed professional. Hypothetical, not a quote.
- Company Overview hub. Run several businesses, or your clients' businesses, without losing track of any of them.
- Alerts wherever you are. Work never sits waiting for you, and problems reach you the moment they happen.
- Free AI engine. Winston keeps working through outages and never runs up a surprise AI bill.
- Desktop app. Winston is one click away all day, and every update arrives without a reinstall.
- Key redaction. Your accounts stay safe even when something goes wrong.
Add-ons
AI SDR$300/mo
AI Video$200/mo
SEO Content Engine$250/mo
Video Repurposing$150/mo
LinkedIn Personal Brand$150/mo
Extra AI calling minutes$100/mo
1-on-1 Business Coaching$350 per 60-minute session
Free lesson
Watch a free business lesson before you buy.
Get a quick sample of the Winston point of view before committing to a plan.
Standalone service
$350
per 60-minute session
1-on-1 Business Coaching & Consulting
Work directly with Justin Joslin on strategy, systems, sales, positioning, or operational decisions.
What you get
- 60-minute 1-on-1 video coaching session
- Pre-session intake form to focus the conversation
- Action plan delivered within 24 hours
Common topics
- Business strategy & growth planning
- Sales system design
- Operational efficiency
- Marketing and positioning