If your Macs live in a Windows world, this episode is your playbook. Rob Calvert, President & Founder of Second Son Consulting shares how his team became Los Angeles’s largest Apple Partner Network member by aligning IT decisions with real user workflows, not just shiny tools.

From “zero-touch” deployments and managed Apple IDs to practical security training that actually sticks, Rob shows MSPs and IT leaders how to harden endpoints without wrecking productivity. We also dive into recession-era lessons, hiring for soft skills, and why being the “mortar between SaaS bricks” is the future.

Whether you manage 20 Macs inside a 100-PC org or run a hybrid fleet across states, you’ll leave with concrete ways to cut friction, boost security, and ship devices anywhere - ready to work on first boot.

Episode Highlights

• [00:00] Origin story: From pre-press and “translator” between IT and the business to launching Second Son in 2003.

• [03:10] Finding the niche: Making Macs play nicely with Windows—VPNs, RAID, file servers, and Windows-only apps.

• [06:45] Weathering downturns: What 2008–09 and 2020 taught Rob about getting lean and growing via outsourced IT.

• [10:20] Security starts at the endpoint: Why network-first thinking fails in a WFH world; Foundations Plan basics.

• [14:05] Prevention over cure: Managed Apple IDs, device ownership proof, and avoiding iCloud lockouts.

• [18:30] Culture & training that works: Ongoing micro-education, targeted simulations, and “don’t shoot the messenger.”

• [22:40] Zero-touch at scale: Open-source Baseline to decouple deployments from any single MDM (Jamf, Mosyle, Intune, JumpCloud).

• [27:15] Packaging & pricing: Modular services—device mgmt, help desk, onboarding, cybersecurity, BCDR, and infra.

• [31:00] Hiring that sticks: DISC for role fit, live troubleshooting over written tests, and front- vs back-of-house engineers.

• [35:20] Go-to-market: 95% referrals via Apple, Microsoft partner communities, and telecom allies.

• [38:15] What’s next: SSO everywhere, SaaS “mortar,” privacy-safe on-device AI (Apple Intelligence), and shadow-IT done right.Tags/Keywords

AI for IT ops, Apple device management, zero-touch deployment, managed Apple ID, MSP growth, hybrid Mac/Windows, endpoint security, cybersecurity training, single sign-on (SSO), SaaS integration, Mac admins, Apple Partner NetworkGuest

Rob Calvert, President of Second Son Consulting
LinkedIn: https://www.linkedin.com/in/robcalvert/
Website: https://secondsonconsulting.com/about/our-team/Call to Action (CTA)

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