Sunny's Silver Linings

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 wh...

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...

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 ki...

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...

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 c...

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 s...

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...

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. Timest...

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...

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...

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...

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,...

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 faste...

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,...

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'l...

From the fields to the fast lane, this is the story of Will Nobles, CEO of Vector Choice, whose journey from bulldozers to boardrooms redefines what leadership and resilience mean in the MSP world. In this candid conversation with Sunny Kaila, Founder & CEO of IT By Design, discover: How Will built Vector Choice from the ground up The 3 leadership lessons every entrepreneur should know Why collabo...

Michael Stratos, CEO of Red Helm, shares his journey from Ideal Integrations to building a leading MSP + MSSP cybersecurity company. In this video, Sunny Kaila and Michael discuss: The story behind Red Helm's rebrand Turning competitors into collaborators in the MSP channel How AI and cybersecurity drive growth for MSPs Red team, pen testing, and continuous security strategies Leadership lessons a...

Join Sunny Kaila as he talks with Alex Brandt, cybersecurity expert and MSP strategist, about the next revolution in the industry: browser security. Learn why the browser is the new endpoint, how MSPs can turn it into revenue, and how AI provides actionable insights to protect clients and boost productivity. Key Highlights: Why SMBs are leading the cloud revolution and the browser is the next endp...

What does it take to transform from an indispensable founder to a scalable leader? In this episode, Kevin Blake shares his powerful journey from building ICS and selling it, to guiding MSPs on leadership, delegation, and the next big frontier: AI. Key Highlights: Kevin's story of building and eventually selling ICS. The pivotal lesson: why being replaceable increases enterprise value. How to find...