Eliminate Tech

Frustration for Good.

Stop struggling with confusing settings, endless passwords, and "Storage Full" warnings. Discover a calm, patient, and jargon-free way to make your Mac, iPhone, and iPad work together in perfect harmony.

Learn More About The Academy

The MacWhisperer Academy Plans

One Map. Three Paths to Total Tech Confidence.

Choose the perfect level of support for your lifestyle or business. Get continuous, live instruction from Dylan, real-time troubleshooting, and an entire community backing you up—with absolutely no hidden costs.

Pro

$ 3000 / year

Ideal for professionals and business owners building serious tech fluency

All Student benefits +

Attend both Friday & Saturday classes

2 monthly Pro Workshops (advanced workflows, shortcuts, productivity systems)

Attend all 4 live monthly Q&A sessions

20% off courses and webinars

Access to exclusive resource packs

Get started

Student

$ 100 / month

Perfect for committed learners who want structured, consistent education and regular access to Dylan's guidance

Attend either Friday or Saturday biweekly classes (live on Zoom)

Participate in 2 monthly Live Q&A sessions to get real-time answers from Dylan

Full access to the Class Replay Library

Full access to the SmartGuide Library, updated weekly with new downloadable guides

Patreon Community Access for ongoing support and discussion

10% off all courses and webinars

Get started

Mac Masters

$ 995 / month

Designed for VIPs, execs, or creatives needing tech mastery + dedicated support

All Pro benefits +

2 monthly, private one-on-one Zoom calls with Dylan

Direct chat / email support (concierge style)

Personalized Apple ecosystem audit

Priority email and phone support

24-Hour priority response time

Get started

Pro

$ 3000 / year

Ideal for professionals and business owners building serious tech fluency

All Student benefits +

Attend both Friday & Saturday classes

2 monthly Pro Workshops (advanced workflows, shortcuts, productivity systems)

Attend all 4 live monthly Q&A sessions

20% off courses and webinars

Access to exclusive resource packs

Get started

Student

$ 100 / month

Perfect for committed learners who want structured, consistent education and regular access to Dylan's guidance

Attend either Friday or Saturday biweekly classes (live on Zoom)

Participate in 2 monthly Live Q&A sessions to get real-time answers from Dylan

Full access to the Class Replay Library

Full access to the SmartGuide Library, updated weekly with new downloadable guides

Patreon Community Access for ongoing support and discussion

10% off all courses and webinars

Get started

Mac Masters

$ 995 / month

Designed for VIPs, execs, or creatives needing tech mastery + dedicated support

All Pro benefits +

2 monthly, private one-on-one Zoom calls with Dylan

Direct chat / email support (concierge style)

Personalized Apple ecosystem audit

Priority email and phone support

24-Hour priority response time

Get started

Pro

$ 3000 / year

Ideal for professionals and business owners building serious tech fluency

All Student benefits +

Attend both Friday & Saturday classes

2 monthly Pro Workshops (advanced workflows, shortcuts, productivity systems)

Attend all 4 live monthly Q&A sessions

20% off courses and webinars

Access to exclusive resource packs

Get started

Student

$ 100 / month

Perfect for committed learners who want structured, consistent education and regular access to Dylan's guidance

Attend either Friday or Saturday biweekly classes (live on Zoom)

Participate in 2 monthly Live Q&A sessions to get real-time answers from Dylan

Full access to the Class Replay Library

Full access to the SmartGuide Library, updated weekly with new downloadable guides

Patreon Community Access for ongoing support and discussion

10% off all courses and webinars

Get started

Mac Masters

$ 995 / month

Designed for VIPs, execs, or creatives needing tech mastery + dedicated support

All Pro benefits +

2 monthly, private one-on-one Zoom calls with Dylan

Direct chat / email support (concierge style)

Personalized Apple ecosystem audit

Priority email and phone support

24-Hour priority response time

Get started

I’ve been a paper planner user since the late ’70s and was afraid of technology. Thanks to Dylan, I now confidently use my iPhone, iPad. My life is more organized and backed up, and I love having Dylan’s expertise available when I need help. His humor and passion make learning fun.
Pamela Elliott
Thanks for your time and valuable experience. Using the computer is now so much easier!
Ted Mahoney
Your classes are so well organized and easy to follow—especially with replays. I can’t imagine how anyone over 70 manages an iPhone without someone like you. You're doing a fantastic job for us elderly kindergarten iPhoners. Cheers, and see you in class!
Lea
Dylan’s classes have been a game-changer. As a retired person struggling to keep up with tech, I found him on YouTube and joined the Academy. His teaching is clear, fun, and incredibly helpful. I now use Notes, Calendar, and Reminders daily, and I finally feel in control of my digital life.
Marcy Stebbins

You changed my life with your lessons! Thank you 👏🏻
Patti Neuwirth
There’s so much information, but I love that I can learn at my own pace. Knowing I can reach out to Dylan or the team for support is incredibly reassuring. This program is worth every penny.
Dr. Henrietta Taylor Knight
The MacWhisperer has helped me unlearn years of bad tech habits and pinpoint exactly what I need to work on. It's saving me time and making everything more efficient.
Judy Stewart
I’ve been using Apple products for a decade, but I’ve learned more in one month with Dylan than I did in the last 10 years. I’m retired, so I don’t 'need' to know this stuff—but I enjoy it now. That says a lot.
David Stollmack

I’ve used Apple since the Apple IIc, but always by trial and error. Dylan has helped me embrace new features and tools I never explored before. It’s like seeing the Mac world with fresh eyes—simpler, more useful, and far less frustrating.
Jocelyn Kunkle
The iPhone Productivity course is pure magic! If you are constantly looking to improve your productivity game, this course is great for you. Dylan makes things look super simple and shares all great lessons without wasting your precious time. This course brings a hundred times more value than it's price.
Simeon Ivanov
Dylan Stewart is just the best. He keeps me up to date with new and helpful programs. He also cleans up my computer messes! Just the best!
Kaija Keel
Dylan Stewart, the Mac Whisperer, helped me big time when I had to upgrade my old MacIntosh operating system. He took the time to guide me on what software would be compatible and which would not. Within a minimum amount of time, he brought me current, and in the process incredibly boosted the speed of my programs.
Jim Ellis

Why The MacWhisperer Academy

With Dylan Stewart, the MacWhisperer, you’re not just learning, you're enhancing how you interact with technology daily.

Community Interaction:

Join a community of like-minded Apple users, share experiences, and learn from the collective wisdom of the group.

A safe space to ask any question

Support that grows with your confidence

Simple answers to everyday tech problems

Tech confidence fully unlocked

Apple devices organized and protected

Live masterclasses active and accessible

Tech confidence fully unlocked

Apple devices organized and protected

Live masterclasses active and accessible

Reassurance and peace of mind

Direct access to Dylan during live Q&A sessions

Step-by-step guidance tailored for everyday users

Reassurance and peace of mind

Direct access to Dylan during live Q&A sessions

Step-by-step guidance tailored for everyday users

Personalized Support:

Get direct answers to your specific questions during live Q&A sessions, making sure no issue goes unresolved.

Tech anxiety eliminated for good

Passwords and photos safely backed up

SmartGuides & class replays fully unlocked

Save Time:

Efficiently manage your digital environment, saving crucial hours each week.

Find any file or photo in seconds

Master timesaving Apple features

Automated setups so your devices handle the work for you

Digital clutter removed

File organization streamlined

Desktop and photo storage organized

Digital clutter removed

File organization streamlined

Desktop and photo storage organized

Step-by-step guides you can save and print

Two live interactive sessions every single month

No pressure or rigid deadlines—learn when it fits your day

Step-by-step guides you can save and print

Two live interactive sessions every single month

No pressure or rigid deadlines—learn when it fits your day

Continuous Learning:

With monthly updates and classes, stay on top of the latest Apple features and best practices.

Zero stress over new updates

New SmartGuides added to your vault

Passwords and photos safely backed up

Gain Confidence:

Elevate from tech-stressed to tech-savvy, mastering your Apple devices confidently.

No fear of ruining settings or losing data

Proven framework to build mastery over your tech

Reassurance and direct human backup whenever you get stuck

Tech anxiety replaced with control

Complete digital independence unlocked

Fear of clicking the wrong button removed

Tech anxiety replaced with control

Complete digital independence unlocked

Fear of clicking the wrong button removed

Daily tasks streamlined

Pro features made simple

Apple ecosystem fully connected

Daily tasks streamlined

Pro features made simple

Apple ecosystem fully connected

Reveal Tech Secrets:

Learn the lesser-known tricks of your devices to streamline your daily tasks and enhance your tech fluency.

Uncover built-in productivity features

Practical tips for iPhone, iPad, and Mac integration

Hidden settings that keep your devices fast and organized

Everything you need

for Total Tech Confidence

Designed to remove frustration, protect your personal data, and make using your Apple devices a truly enjoyable daily experience.

%

Plain English Zero tech jargon or complicated terms

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Plain English Zero tech jargon or complicated terms

%

Frustration No more getting stuck on confusing settings

%

Frustration No more getting stuck on confusing settings

X

More Confidence Feel comfortable exploring your Apple devices

X

More Confidence Feel comfortable exploring your Apple devices

Live with

more confidence

and less friction

Stop struggling with confusing settings and start enjoying your Mac, iPhone, and iPad today.

Learn More About The Academy