🚀 Mac Masters – $995/month

For visionary professionals, entrepreneurs, and high-performing individuals who want a true Apple strategist by their side—this is your personal tech concierge service with Dylan Stewart.

Includes Everything in Apple Architect, Plus: 

✅ Private 1:1 Strategy Sessions (2x/month) 

•  Two 45-minute Zoom calls per month directly with Dylan.

•  Sessions are tailored to your specific needs: workflow redesign, system clean-up, device setup, or advanced tech coaching.

•  Perfect for getting unstuck, exploring new Apple tools, or optimizing complex environments across Mac, iPhone, iPad, Watch, and more.

✅ Priority Personal Tech Support 

•  Skip the line—get access to Dylan’s priority inbox for support between calls.

•  Dylan or a senior team member will respond to your questions or troubleshoot your issue within 24 hours (M–F).

•  Ideal for quick check-ins, emergencies, or “Is this the best way to do this?” moments.

✅ Custom Apple Ecosystem Audit 

•  Onboarding begins with a full review of your devices, software setup, file systems, and daily habits.

•  Dylan designs a customized action plan to align your digital life with your goals—less tech stress, more flow.

✅ VIP Access to All Events, Webinars & Courses 

•  You’re automatically enrolled in all live webinars, courses, and public masterclasses at no additional charge.

•  Never miss a training. Always have the front-row seat.

✅ Annual MacWhisperer Swag Pack 

•  Each year you remain a Vanguard member, receive a curated physical gift box including:

•  TMW mug, stickers, or T-shirt

•  Exclusive Smart Guide print editions

•  Bonus tech tools or productivity accessories handpicked by Dylan

✅ Vanguard-Only Check-In Option 

•  Quarterly (optional) check-in form where you can request Dylan’s review of new workflows, ask strategic questions, or set fresh digital goals.

•  Dylan personally replies with feedback and resources.

The Apple Vanguard tier is for those who don’t want to waste time Googling answers—they want a trusted expert in their corner, available on-demand to guide, solve, and elevate.