Sunny's Silver Linings

Sunny Kaila
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Sunny's Silver Linings is a Top MSP Channel Podcast hosted by the CEO of IT By Design, Sunny Kaila. Sunny and his guests cover a wide range of MSP and Talent-based topics, including MSP services, cybersecurity, customer service, and strategies to achieve growth and success in the channel. Listen now to take your business to the next level!

https://hubs.ly/Q02DrxnQ0

  1. 2d ago ·  Video

    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 world 06:21 – The origin story behind One Minute Wednesday 11:09 – Why every leader should write down what they've learned 13:01 – Execution over consumption in the AI era 15:06 – Choosing the right idea and building a 30 day action plan 18:39 – Closing the knowledge action gap 21:05 – Building the capabilities SMBs actually need 22:28 – Becoming a go to market business, not just a tech business 27:03 – Scaling without owner burnout 30:10 – Why peer groups matter, and letting go of the grenade 34:48 – The charity behind the book 36:21 – Where to find The Best of One Minute Wednesday Who this is for: Any MSP owner who has walked out of a conference inspired and walked back into the same routine a week later. Leaders who know they need to delegate more but haven't figured out how. What you will learn: Why knowledge without action is just a hobby How to reverse engineer a plan into weekly execution steps The mindset shift from tech-led to go to market-led How letting go of control is what actually lets a business grow

  2. Jul 23

    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 David Powell's background and industry recognition 01:53 Tools vs. outcomes: what the industry keeps selling MSPs wrong 02:09 The quarter-inch drill bit story 04:47 Why MSPs need actionable ideas, not more good ideas 05:11 The box of Legos problem 07:36 The MSP visibility gap explained 07:54 Windows and doors: the apartment building analogy 10:45 Shadow IT, shadow AI, and what RMMs miss 11:29 Why RMMs are ephemeral and Liongard keeps 18 months of history 12:57 Why AI only works when the underlying data is right 14:09 The chocolate chip cookie robot: why source of truth matters 17:16 Aunt Evelyn's caramel cake and the MSP documentation problem 19:36 Dirty data and how AI amplifies it 20:55 Liongard's new MCP capability explained 21:15 Demoing Liongard through Claude instead of logging in 22:35 Is Claude becoming the real single pane of glass? 24:11 Data accuracy and the 10x effect on decisions 24:41 Provability and cybersecurity insurance 26:03 Breach liability and the historical record 26:59 The managed intelligence provider maturity model 27:06 Scaling without linear headcount 28:53 The barbell effect: private equity and MSP market polarization 29:18 The shift to outcome-based pricing 31:05 The physician analogy: procedure-based vs. visit-based pay 32:32 A history of MSP billing models, from break-fix to outcomes 34:46 The PC imaging example and efficiency at scale 35:21 David's 90-day action plan for AI-native MSPs 36:24 Why every MSP needs a dedicated AI automation day Who this is for: MSP owners, operators, and technical leaders who are trying to move past tool sprawl and build a real AI automation strategy. Also relevant for anyone evaluating asset intelligence platforms, RMM/PSA data gaps, or outcome-based pricing models. What you will learn: Why MSPs get sold tools instead of outcomes, and how to spot the difference What the "visibility gap" is and why most MSPs don't know what's actually in their environment Why AI automation fails without a reliable source of truth How Liongard's MCP integration with Claude changes how MSPs access their own data Why outcome-based billing is replacing time-based and device-based models A practical, low-cost way to start building an AI automation practice in 90 days #MSP #ManagedServiceProviders #AIforMSPs #AssetIntelligence #ITChannel #MSPGrowth #AIAutomation #ClaudeAI #ITByDesign #Liongard

  3. Jul 9

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

    Sunny's Silver Linings

  4. Jun 25

    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 leadership threads in this conversation. The episode covers shadow AI as a present operational reality inside SMB environments, not a theoretical future risk. It also explores how browser-level visibility reshapes the MSP sales conversation and what it looks like to lead through product transformation without losing team alignment. 00:00 Introduction and guest welcome 01:14 Daniel's entrepreneurial journey from engineering to cybersecurity 02:50 The origin of the Atakama name 04:55 The blind spot in traditional endpoint security stacks 07:08 How AI has changed the security threat landscape for MSPs and their clients 10:33 Shadow AI: what MSP leaders are encountering every week 12:36 How Atakama addresses shadow AI at the browser level 16:56 How browser security helps MSPs grow, sell, and retain clients 20:25 The opening question MSPs can use to start a browser security conversation 23:41 Leadership lesson: communicating through a major product pivot 29:10 Looking ahead: where the MSP security stack is heading 30:05 Life lesson from Daniel: the discipline of responding rather than reacting Who This Is For: MSP owners and CEOs evaluating browser security as a new practice area, technology leaders assessing shadow AI visibility and data governance controls, and MSP operators who want a firsthand account of how a cybersecurity company navigated a full product pivot while maintaining team alignment and market momentum. What You Will Learn: Why the browser is the current blind spot in most MSP security stacks and why endpoint tools alone are not enough What shadow AI is, why its non-malicious nature makes it harder to govern, and why that distinction matters for MSP conversations How Atakama surfaces shadow AI activity and client data uploads to MSPs in real time What browser visibility data looks like in a client-facing or prospect-facing conversation The single question MSPs can ask an SMB decision-maker to open a browser security discussion How Daniel maintained team focus and operational momentum through a complete product pivot What the distinction between responding and reacting means at both the leadership and personal level #MSP #CyberSecurity #ShadowAI #BrowserSecurity #AIGovernance #ManagedServices #MSPGrowth #SunnySilverLinings #ITByDesign #ManagedIntelligence

  5. Jun 11

    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: Prioritizing Sales Over Service 02:44 Happy Employees Create Happy Clients 04:48 Building a Pure-Play MSP for Alternative Investment Firms 05:21 Why Measured Growth Beats Growth at Any Cost 05:55 Using AI to Improve Efficiency, Delivery & Client Outcomes 07:18 Why Governance, Compliance & Security Must Come Before AI 09:20 Helping Clients Separate AI Hype from Business Value 10:25 The Dot-Com Comparison: What Today's AI Market Can Learn 12:00 Why MSPs Should Avoid Betting on a Single AI Vendor 15:00 Securing Employee Buy-In for AI Adoption 16:24 How Atlas Technica Implemented Glean Across the Organization 17:32 Driving Adoption Through Communication & Internal Hackathons 19:21 The Reality Check: AI Won't Take Your Job, Someone Using It Better Might 20:24 How Client Demand for AI Changed Almost Overnight 21:27 Why Businesses of Every Size Can Benefit from AI Today 23:50 Turning AI Capabilities Into Growth & Upsell Opportunities 25:36 Serge's Top Leadership Advice: Listen to Your Employees 26:16 Creating Safe Spaces for AI Conversations & Innovation Who this is for: MSP owners and operators looking to scale with intention, leaders navigating internal AI adoption, and anyone working to turn AI into a real business practice. What you will learn: Why service delivery is the real growth driver for MSPs, not sales or technology How Atlas Technica used Glean to give 400 employees practical access to AI How to help clients navigate AI vendor selection without chasing hype Why hedging across multiple AI vendors matters more than committing to one How to identify and retain AI-forward thinkers already inside your organization #AIbyDesign #MSP #ManagedServices #AIAdoption #MSPGrowth #ArtificialIntelligence #ITByDesign #SunnyKaila #AtlasTechnica #AlternativeInvestments #ServiceDelivery #TechLeadership

  6. May 28

    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 — Why culture and cash are not in conflict 04:27 — Teaching your team the financials: the leadership move most skip 07:56 — DSO explained: the number that changes MSP cash flow overnight 07:59 — Readiness is not a state of being. It's what happens after you act 10:43 — The backwards confidence model: action first, confidence second 11:34 — Being stuck is not a problem. It's a signal Who this is for: MSP owners and operators who want to lead through the AI transition, improve financial health, and stop waiting for the "right moment" to make their next move. What you will learn: Why the AI transition will move faster than the cloud shift and what that means for MSPs who hesitate The difference between AI replacing MSPs vs. AI-powered MSPs outcompeting everyone else How to use DSO as a practical lever to improve cash flow and business health Why financial transparency with your team builds culture, not undermines it The backwards confidence model: why action creates readiness, not the other way around How to reframe being "stuck" as a signal for growth, not a failure state

  7. May 14

    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 build that muscle The difference between perception and perspective, and why it changes how you lead, hire, and close A reverse culture fit interview technique that builds buy-in before day one #MSP #ManagedServices #MSPLeadership #SunnyKaila #AIbyDesign #BusinessGrowth #LeadershipDevelopment #DecisionMaking #CompanyCulture #MSPBusiness

  8. Apr 2

    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 everything starts with courage in leadership 02:10 – How mindset and limiting beliefs impact MSP growth 05:00 – Clarity, confidence, and intentional decision-making 08:30 – Why founders become the bottleneck in MSPs 1 2:00 – Letting go: the shift from control to scale 15:20 – Entrepreneurs are wired differently—what that means 18:40 – Building vision and freeing the visionary 22:10 – Hiring the right team and empowering them 26:00 – Overthinking, perfectionism, and getting out of your own way 29:30 – Perspective vs perception in leadership 33:00 – Lessons for young MSP founders and operators 36:30 – Final thoughts on scaling, leadership, and growth Who This Video Is For · MSP owners looking to scale their business beyond founder dependency · Managed Service Provider leaders struggling with growth bottlenecks · Entrepreneurs working on leadership mindset and decision-making · MSP operators building teams, processes, and scalable systems · IT service providers transitioning toward AI-first MSP leadership What You'll Learn · Why MSP leadership not tools is the real driver of growth · How to overcome the founder bottleneck and scale with systems · The role of mindset, courage, and clarity in business decision making · Why perfectionism and overthinking slow down MSP growth · How to hire, trust, and empower teams to execute independently · The importance of perspective in leadership, relationships, and problem-solving · How to transition from doing the work to building a scalable MSP business MSP growth today is defined by how leaders think, delegate, and build systems not just how they deliver services. #MSP #ManagedServices #MSPLeadership #MSPGrowth #ITServices #AIforMSP #BusinessLeadership #EntrepreneurMindset #ScalingBusiness #LeadershipDevelopment #MSPCommunity #TechLeadership

    How MSP Leaders Can Scale Their Business Without Becoming the Bottleneck
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About

Sunny's Silver Linings is a Top MSP Channel Podcast hosted by the CEO of IT By Design, Sunny Kaila. Sunny and his guests cover a wide range of MSP and Talent-based topics, including MSP services, cybersecurity, customer service, and strategies to achieve growth and success in the channel. Listen now to take your business to the next level!

https://hubs.ly/Q02DrxnQ0

Information

  • Creator
    Sunny Kaila
  • Years Active
    2024 - 2026
  • Episodes
    158
  • Rating
    Clean
  • Copyright
    © Sunny's Silver Linings 2024
  • Show Website
    Sunny's Silver Linings