Sunny's Silver Linings

Oct 16, 2026

AI Governance as an MSP Revenue Opportunity | Josh Coke and Sunny Kaila

Clients are already asking their MSPs about AI. Josh Coke of Enforcer joins Sunny Kaila to explain why AI governance is becoming a clear revenue opportunity in the channel, and why identity, data and configuration have to come before the tools. In this conversation: ➥ Why adding more products misses what customers actually need ➥ Why end clients are coming to MSPs asking about AI ➥ What happens when Copilot is turned on without guardrails ➥ How Microsoft Purview can be set up in an afternoon using tools already inside Microsoft 365 Business Premium ➥ Why a 90-day AI activation plan starts with

Sep 29, 2026

Attackers Aren't Breaking In, They're Logging In | Wilfredo Santiago on Sunny's Silver Linings

Attackers are walking through the front door with legitimate credentials, and most MSP security stacks still treat identity as a hygiene checkbox. In this episode of Sunny's Silver Linings, Sunny Kaila sits down with Wilfredo Santiago of Blackpoint Cyber. Wilfredo shares his path from the US Navy to the NSA to the MSP space, then breaks down why identity is now the primary attack surface, why MFA is only the beginning, what separates true managed detection and response from reporting, and how MSPs should approach AI governance. Timestamps 00:00 Welcome 01:45 From hacking video games to the US

Sep 3, 2026

The Agentic MSP Revolution: Shahin Pirooz on AI, Cybersecurity, and Digital Employees

In this episode of SSL, IT By Design's Sunny Kaila sits down with Shahin Pirooz, cybersecurity veteran and founder of White Dog Cyber, to unpack what it really takes for an MSP to become agentic. Shahin traces his path from enterprise software developer to CTO at Centerbeam to building a unified security platform for MSPs, and shares why "not invented here" thinking is one of the biggest silent killers of good business decisions. The conversation moves into shadow AI, why most security vendors that claim to "do it all" are worth a second look, and a framework for treating AI agents as digital

Aug 19, 2026

Why Most MSPs Have a Knowledge Problem, Not a Growth Problem

I sat down with Greg Jones, SVP at Kaseya, for this episode, and it stayed with me long after we stopped recording. Greg has spent his career across government, MSP, and vendor roles, and he's watched thousands of MSPs make the same mistake: collecting more knowledge instead of executing on what they already have. We talk about his book, The Best of One Minute Wednesday, the knowledge action gap I fell into myself back in 2003, and what it takes to scale without losing yourself in the process. Timestamps: 00:56 – Welcome and guest introduction 01:15 – Greg's journey into the MSP and vendor wor

Jul 23, 2026

168 Hours. Same for Everyone. Automation Decides the Rest.

Sunny Kaila sits down with David Powell of Liongard, a channel veteran and two-time CRN Channel Chief, to unpack why MSPs keep buying tools instead of outcomes. David breaks down the visibility gap most MSPs don't know they have, why AI automation is only as good as the data behind it, and how Liongard's new MCP integration with Claude is changing how MSPs interact with their own asset data. The conversation covers everything from shadow IT to outcome-based billing to what a 90-day AI action plan actually looks like for an MSP owner. Timestamps 00:00 Welcome and Liongard partnership 01:23 Davi

Jul 9, 2026

AI Won't Just Change Jobs. It Will Redesign How Work Gets Done.

Jun 25, 2026

Browser Security and the AI Blind Spot MSPs Are Missing in 2025

On this episode of Sunny's Silver Linings, Sunny Kaila sits down with Daniel Gallancy, CEO of Atakama, to examine the browser security gap that most MSPs have yet to address and why shadow AI has made that gap significantly more dangerous. Daniel's career trajectory ran through engineering, finance, and the cryptocurrency world before arriving in cybersecurity. Atakama itself began as encryption software and executed a full pivot to browser security purpose-built for the MSP channel. That pivot and how Daniel led his team through it with clarity and conviction is one of the most instructive le

Jun 11, 2026

Serge Bukhar, Founder & CEO of Atlas Technica, on Scaling to 400 Employees

Serge Bukhar spent ten years inside an MSP, watched it grow from 80 to 400 people, then built something of his own. Ten years later, Atlas Technica is a 400-person pure-play MSP serving the alternative investment industry exclusively. In this episode, Sunny Kaila sits down with Serge to unpack what drove that growth, how Atlas Technica is approaching AI adoption internally and for clients, and why creating space for your team to talk may be the most important leadership move right now. TIMESTAMPS 00:37 From Engineer to Entrepreneur: The Atlas Technica Story 01:22 The Mistake Most MSPs Make: Pr

May 28, 2026

The MSP Who Waits to Feel Ready Will Lose to the One Who Already Moved

The MSPs who resisted the cloud in 2013 didn't disappear overnight, but they became last year's business fast. The same shift is happening right now with AI, and it's moving at a speed that won't give anyone a decade to catch up. In this episode, Sunny sits down with various MSP leaders to unpack what it takes to lead a business through this moment, financially, mentally, and operationally. Timestamps: 00:00 — Why embracing AI is non-negotiable for MSPs right now 01:29 — Running a weekly AI Accelerator for MSP leaders 02:08 — "AI won't replace MSPs. AI-powered MSPs will replace MSPs" 03:20 — W

May 14, 2026

What the Best MSP Leaders Actually Do Differently

Most MSP leaders are busy. But busy is not the same as building. In this video, Sunny Kaila breaks down different conversations that reveal the habits, mindsets, and practices that separate leaders who scale from those who stall. Who this is for: MSP owners, founders, and leaders who want to build something that lasts, not just manage what they already have. What you will learn: Why planning more than you think you need to is the foundation most MSPs skip How the shiny toy syndrome quietly kills momentum in growing businesses Why bad decisions are always better than indecision, and how to buil

Apr 2, 2026

How MSP Leaders Can Scale Their Business Without Becoming the Bottleneck

Scaling an MSP isn't a technology problem - it's a leadership one. In this SSL Recap, I sit down with MSP leaders to unpack what holds businesses back: founder bottlenecks, overthinking, lack of clarity, and the inability to let go. From building a leadership mindset to creating scalable systems, this conversation goes deep into what it really takes to grow a Managed Service Provider in today's AI-first world. If you're trying to scale your MSP, build a stronger team, or shift from being in the business to building the business, this is the leadership lens you need. Chapters 00:00 – Why everyt

Mar 18, 2026

How the 5 Ps Framework Helps MSPs Scale Faster in 2026 MSP Growth AI for MSPs

Scaling an MSP isn't about working harder: it's about building a business that runs without you. In this episode, Sunny Kaila breaks down the mindset shift from being indispensable to becoming replaceable, and how the 5 Ps framework (People, Process, Priorities, Performance, Perspective) helps MSP leaders scale faster, eliminate bottlenecks, and prepare for the AI-driven future of managed services. Chapters 00:00 – The mindset shift: Replaceable vs indispensable 00:40 – The 5 Ps of scaling a business 01:30 – Why People come first 02:10 – Process: Eliminating tribal knowledge 03:00 – Guardrails

Mar 3, 2026

The Hard Truth About Scaling an MSP Leadership AI Private Equity Letting Go

Scaling an MSP isn't about working harder - it's about thinking differently. In this powerful conversation, we break down the real challenges behind MSP growth strategy, selling to private equity, leadership blind spots, and why AI is reshaping the managed services industry faster than cloud ever did. If you're an IT services entrepreneur navigating MSP operations, considering an MSP acquisition, or preparing for IT services M&A, this episode delivers the hard truths most leaders only learn the expensive way. Chapters 00:00 Greatest Life Lesson in Business 01:15 Perspective vs Perception 03:05

Feb 18, 2026

How to Get Unstuck in Life Business 8-Step Framework

Jan 30, 2026

How MSPs Scale by Building Trust Community Sunnys Silver Linings

Jan 22, 2026

Why Connectivity Drives MSP Growth in the AI Era

AI isn't just about tools; it's about data, speed, and connectivity. In this episode of AI By Design, Sunny Kaila explains why connectivity is the next growth lever for MSPs in the AI era. Chapters 00:00 – AI, data explosion & why MSPs must adapt 03:12 – How connectivity became a growth lever for MSPs 07:45 – Enterprise digitization & multi-cloud demand 12:30 – Edge computing and data moving faster than ever 17:10 – How MSPs grow EBITDA through service diversification 22:05 – AT&T Partner Exchange explained for MSPs 27:40 – MSP margins, tier-one support & resale opportunities 33:15 – Ideal cus

Jan 8, 2026

Why Profitable MSPs Fix Processes Not People AI EBITDA Valuation MSP Growth

Profitable MSPs don't scale by fixing people; they scale by fixing processes. In this Sunny Silver Linings recap episode, we unpack the biggest insights shaping the MSP space today: why process-driven MSPs outperform rockstar-dependent teams, how profitability, EBITDA, and cash flow drive real MSP valuation, and why AI in managed services should be treated as an exoskeleton that amplifies people, not replaces them. This conversation brings together leadership lessons, financial reality checks, and practical growth strategies every MSP leader needs as the industry shifts from IT support to busi

Dec 23, 2025

Future of MSPs 2026 AI Strategy Automation MSP Growth

Dec 11, 2025

Cashflow Is Reality How to Fix Cashflow Problems in Small Business

Nov 26, 2025

How MSP Owners Can Lead with AI CMMC Level 2 Compliance

How can MSP owners lead stronger, adopt AI safely, and meet CMMC Level 2 requirements? In this episode of Sunny's Silver Linings, Sunny Kaila interviews Tobias (Toby) Musser, co-leader of MNS Group, a rare CMMC Level 2 assessment MSP and C3PAO. Together they break down leadership development for MSP owners, CMMC compliance explained, and how MSPs can use AI without sacrificing security. What You'll Learn: Leadership development for MSP owners: grit, lifelong learning, mindset, culture. CMMC compliance explained: what Level 2 requires, what tools MSPs can/can't use, and how to stay compliant. H