đź”’ Patreon Special

IT Pros: exclusive shows await you on Patreon, focusing on the more challenging aspects of running your practice and working with clients and employees.


665: Apple’s 50th Anniversary Old Shortcuts, and What Still Delights - Part 2

The hosts revisit early Apple and Mac experiences and discuss first keyboard shortcuts, focusing on “Command Control Power” after a photographer client referenced it while troubleshooting a MacBook Pro that died on location from a drained battery. They debate the proper shortcut key order versus Apple’s conventions, recall Apple II shortcuts like Control–Open Apple–Reset, and reflect on floppy-drive workflows and multi-disk backups. The conversation shifts to Apple’s attempts to break into business hardware, Steve Jobs’ impact and management style, and a perceived reversal where hardware fit-and-finish improved while macOS feels buggier, with annual OS releases and settings moving cited as problems. They note Rapid Security Response/Background Security Improvements placement changes, praise Apple Watch and AirPods, share audience photos and Apple memorabilia, and close with gratitude to Apple, colleagues, and listeners.

00:00 Apple 50th Kickoff

00:27 Shortcut Origin Story

01:08 Photo Shoot Panic

02:17 Shortcut Order Debate

03:27 Open Apple Keys

05:16 Save Changes Shutdown

07:33 Floppy Boot Days

09:02 Apple In Business

12:22 Jobs Magic And Myth

14:03 Modern OS Buggy Era

19:27 Settings Search Problem

23:17 Yearly OS Cadence

26:04 Planned Obsolescence Talk

27:46 Software Sells Hardware

28:07 Mac CPU Transitions

29:12 Snow Leopard Lessons

31:37 Intel Era Reality Check

33:11 Security Updates Moved

34:22 Throwback Mac Photos

35:52 Daily Delight Devices

40:12 Old iPhones and iPods

42:29 Apple Employee Card

44:37 Startup Office Memories

46:13 50 Years of Apple

664: Apple at 50 - First Macs, HyperCard, iPod Halo, and Memories from the Early Days - Part 1

Apple at 50: First Macs, HyperCard, iPod Halo, and Memories from the Early Days - Part 1

CHM Live | Apple at 50: Five Decades of Thinking Different

The hosts celebrate Apple’s 50th anniversary (recorded April 1) and recommend David Pogue’s book “Apple at 50,” including his Computer History Museum interview. They invite listener stories and discuss first Apple computers (Apple IIe/IIc/II Plus), early BASIC programming habits, and Apple’s influence in schools via HyperCard/HyperTalk. Jerry recounts starting on PC compatibles in a tool-and-die business, moving into Macs for music/MIDI and Finale, and shows a 1989 receipt for a Macintosh IIx system costing about $7,000 (roughly $14,730 in 2026 dollars). Listener Dwayne Moss shares memories working at Apple, concerts at sales conferences, seeing Steve Jobs introduce the iPod at Town Hall, and being hired and laid off three times. The group reflects on the iPod’s Windows support, the “digital hub” era, early CD burning, Airport cards, Macworld/iPhone displays, Newton hardware, and transitions from PowerPC to Intel to Apple silicon. 

00:00 Apple Turns 50

00:40 David Pogue Book Pick

01:59 First Apple Computers

03:56 Learning BASIC Early

06:34 Jerry’s First Macs

09:25 Sticker Shock Pricing

11:55 From Punch Cards to AI

13:42 HyperCard Magic

15:38 Listener Story Dwayne

18:30 iPod Halo Effect

20:37 Digital Hub Creativity

24:15 CD Burning Nostalgia

26:31 Iconic iPhone Sounds

27:26 First Business Macs

28:49 Early WiFi Upgrades

30:35 Offline Computing Era

31:45 Macworld iPhone Memories

36:09 Newton Surprise Find

39:12 Early Influences

39:55 Jerry Career Pivot

46:23 Vintage Server Rooms

50:33 G4 to Intel Shift

50:55 Wrap 

663: No Slam Dunk: Apple Setup Snags & Compliance Hoops

Joe and Jerry discuss Apple’s redesigned online store, noting that Mac configuration choices are now embedded in the URL, making it easier to share exact specs with clients. Jerry describes upgrading from an M3 MacBook Air to an M5 Air via trade-in and 0% financing, then they compare experiences with Migration Assistant failures during remote migrations, including restarts, antivirus removal, and workarounds like migrating via an external drive. They talk about battery-life and thermal concerns on smaller MacBook Pros, using Low Power Mode, and consider how an entry-level “Neo” Mac might expand education or large deployments. Joe warns Apple’s Partner Network locator has worse search and may mishandle reviews, recommending saving reviews via Claude-generated HTML. They gripe about post-update “Welcome to Mac” and Apple Intelligence prompts disrupting remote access, share an iPhone brightness mishap, cover RingCentral shared-inbox texting requiring opt-in/terms/privacy compliance, and Jerry previews a job cleaning mouse contamination from a network closet using protective gear.

00:00 Show kickoff Sam missing

00:20 Apple Store URL configs

04:35 Jerry upgrades MacBook Air

05:29 Migration Assistant failures

07:21 Remote setup workflow

13:44 Trade in timing value

14:53 Battery life low power mode

16:29 Thermals 14 inch Pro

18:45 Mac Neo market wildcard

20:48 Partner locator review backup

24:23 Locator search broken

28:39 AI Bugs and Review Backups

30:03 Claude Recreates Review Page

31:34 Welcome Screen Update Rage

33:14 Remote Access Blocked by Prompts

35:22 Stability Over New Features

37:37 iPhone Brightness Disaster

40:19 Shared SMS Inbox with RingCentral

41:44 Business SMS Compliance Hoops

49:34 Hazmat Tech Closet Cleanup

54:41 Patreon and Wrap Up

662: Wildfire Warnings, Aging Clients, and AI’s Growing Impact

The hosts discuss unseasonably warm February weather in Boulder, a small wildfire near the Flatiron Mountains, and concerns about drought, low snowpack, and higher summer fire risk. Joe shares a soft launch of psikit.com to promote MeshTastic-based mesh communication devices for emergency preparedness. They then talk about a senior living network project requiring outside cabling certification due to unlabeled, problematic wiring, and how client crises can finally drive needed spending. Joe describes a long-term client’s aging Mac mini and 15-year-old Promise RAID enclosures, recent drive failures, and a likely refresh to newer Mac hardware with direct-attached RAID and faster networking while noting how client retirement timelines affect investment and business valuation. They preview ACEs (CCP discount code) and an MDM panel, debate AI’s near-term staffing impact, and warn that Synology C2 backups can’t be transferred from an MSP to a customer.

00:00 Welcome and Check In

00:07 Boulder Drought and Fire Scare

01:59 Mesh Comms and PSIKIT Launch

03:23 Getting Out Bossed on a Project

05:52 Why Network Certification Matters

09:15 Client Server Upgrade Warning Signs

12:26 Aging Hardware and Backup Plan

13:47 Longtime Client Origin Story

15:53 Retirement and Tech Spending Choices

18:49 Upgrade Proposal and Storage Strategy

21:21 Promise vs NAS and Other Vendors

24:35 Software RAID Pitfalls

25:33 SoftRAID Upsells

26:34 Client Aging Valuation

28:21 ACEs Discount Plug

29:19 MDM Panel Preview

31:07 Intune Reality Check

31:55 AI In Small Business

37:21 AI Workflow Quirks

44:40 Synology C2 Lock In

48:07 Wrap Up Thanks

660: Clouds of Doubt: Are We Crossing the Data Line?

When “Cloud-Only” Starts to Crack: Costs, Control, AI Risks, and Hybrid Reality

The hosts discuss an AI-suggested topic: why “cloud-only” thinking is cracking, focusing on broken cost predictability from usage-based pricing, vendor lock-in and loss of control, latency and dependency on internet uptime, and growing compliance and data-residency pressures. They explore how AI increases data exposure risk while also driving demand for integrations like Copilot and Gemini, debate ethical/environmental concerns and whether banning AI would matter, and note AI may reduce support work while increasing competition. They argue hybrid setups are becoming a practical middle ground, enabled by smaller local hardware like Mac minis. They also cover new Apple Magic Mouse and keyboard purchases, announce the UniFi Cloud Gateway Industrial (high-power PoE and SIM slot features), promote ACES 2026 with code CCP, and describe difficulty playing a purchased MP4 on Apple TV due to AirPlay audio dropouts.

00:00 Show Kickoff

00:40 Cloud Costs Rising

04:57 AI Data Exposure

08:34 Ethics And Environment

13:22 Jobs And Competition

15:42 Latency And Outages

18:26 Vendor Control Drift

23:15 Hybrid Middle Ground

24:34 Compliance And Risk

27:20 How We Use AI

31:49 AI Hits Support Work

32:21 Apple AI Troubleshooting Vision

34:16 Staying Valuable Beyond AI

35:29 New Magic Mouse Setup

37:50 Fixing Accidental Gestures

40:45 UCG Industrial Gateway

41:43 Starlink Mini Power Options

45:42 Remote SIM And WiFi 7

47:09 ACEs 2026 And Discount

48:23 MP4 To Apple TV Struggles

51:47 Wrap Up And Thanks