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Book 1:1 Tech Coaching & Consulting with Dylan Stewart

Get personal help with your Apple devices and technology. We'll troubleshoot issues, build better workflows, and answer your questions step by step.

Why 1:1 Coaching?

Every tech situation is different. Instead of generic advice, you get personalized guidance tailored to your specific devices, workflows, and goals. Whether you're struggling with a stubborn Apple device issue, want to streamline your productivity, or need hands-on help navigating new software—Dylan works directly with you to solve problems and build confidence with your technology.

No group calls. No waiting. Just focused, one-on-one attention.

HOW IT WORKS

Step 1 - Choose Your Session "Select the session length that matches your needs. Whether you need a quick 1-hour troubleshooting session, a deeper 2-hour deep dive, or ongoing support with bulk hours—pick what works for you."

Step 2 - Complete Your Payment "Securely pay through our checkout. Your coaching session is confirmed immediately, and you'll receive a confirmation email with next steps."

Step 3 - Schedule & Get Reminders "Choose your preferred date and time using our online scheduler. You'll get automatic email and text reminders before your session so you're never left wondering when Dylan will call."

Choose Your Coaching Session

1-Hour Coaching Session

Perfect for focused troubleshooting, quick questions, or getting unstuck on a specific tech problem. Dylan will walk you through solutions step-by-step and answer your questions in real time

What's Included:

  • Direct 1:1 time with Dylan
  • Live troubleshooting and hands-on guidance
  • Personalized advice for your specific situation
  • Follow-up notes via email  

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2-Hour Coaching Session

Ideal if you have multiple issues to work through or want deeper, project-based support. Two hours gives Dylan time to really dig in, explore your workflows, and create a plan for ongoing success.

What's Included:

  • Extended 1:1 time with Dylan
  • Multiple issues covered in one session
  • Personalized advice for your specific situation
  • Follow-up notes via email  

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Bulk Coaching Hours

Know you'll want ongoing support? Save money with bulk hours and schedule multiple sessions as needed. Perfect for longer-term projects, continuous learning, or having a tech expert on call.

What's Included:

  • Use your hours across multiple sessions
  • Flexible scheduling
  • Ongoing support for your tech needs
  • We'll track your hoursil  

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Your Digital Traveler Special Offer for a Limited Time!

Unlock the Full Power of Your Apple World — Month After Month

Join the MacWhisperer Academy for just $100/month and get the MacMasterclass (a $397 value) FREE!

This offer ends Monday, December 3 at midnight PT.

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Dylan's way of teaching is full of humor combined with such enthusiasm that it made learning the iPhone so enjoyable for me. By the end of each session I was enjoying using my iPhone more. I would never have found interest in the full range use of my phone without Dylan's class. the best the best the best the best the best the best 

STEVEN KIRALLA

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When I first found The MacWhisperer's classes I was pretty clueless about how to use my devices. Dylan walked me through my resistance to change with good humor and explained things in terms that made sense to me! I never thought I would get to this place, but I'm actually teaching the people around me how to use their devices now (at least I'd like to think so)!! Thank you!

TANYA RAGIR

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Before The MacWhisperer's Classes I was intimidated to use Siri or fully explore my phone's capabilities. But Dylan's class was empowering. His explanations are clear and concise and the pace is just right. You learn some really cool stuff. I bet most of the students didn't know what happens when you shake the iPhone vigorously. I certainly didn't.

THOMAS CLAFLIN

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Dylan's way of teaching is full of humor combined with such enthusiasm that it made learning the iPhone so enjoyable for me. By the end of each session I was enjoying using my iPhone more. I would never have found interest in the full range use of my phone without Dylan's class.

STEVEN KIRALLA

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When I first found The MacWhisperer's classes I was pretty clueless about how to use my devices. Dylan walked me through my resistance to change with good humor and explained things in terms that made sense to me! I never thought I would get to this place, but I'm actually teaching the people around me how to use their devices now (at least I'd like to think so)!! Thank you!

TANYA RAGIR

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Before The MacWhisperer's Classes I was intimidated to use Siri or fully explore my phone's capabilities. But Dylan's class was empowering. His explanations are clear and concise and the pace is just right. You learn some really cool stuff. I bet most of the students didn't know what happens when you shake the iPhone vigorously. I certainly didn't.

THOMAS CLAFLIN

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Ready to Get Expert Help?

Stop struggling with tech on your own. Book your session with Dylan today and get the personalized support you deserve. Whether you need a quick fix or ongoing guidance, Dylan is here to help you master your Apple devices and build workflows that actually work for you.

Learn From Someone Who Makes Technology Feel Easy

Dylan Stewart has spent over 20 years helping people unlock the full potential of their Apple devices. His warm, practical teaching style makes everything easier to understand—and even easier to apply.

Let's Solve Your Tech Problems

You don't have to figure this out alone. Dylan is ready to help you troubleshoot, optimize, and build confidence with your technology. Choose your session above and book your time today.

Choose your session