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

We confirm coaching bookings by email within 24 hours.