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

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.