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PODCAST

Sunny"s Silver Linings

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

business entrepreneurship

All Episodes

44:51

How MSP Owners Can Lead with AI CMMC Level 2 Compliance

Sunny"s Silver Linings ·

2025/11/26

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

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31:42

Entrepreneur Mindset How MSPs Scale From Services to...

Sunny"s Silver Linings ·

2025/11/13

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32:09

MSP Leadership & Entrepreneurship: How Will Nobles...

Sunny"s Silver Linings ·

2025/10/30

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 collaboration beats competition in the MSP channel How "A Week with Will" is

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20:31

Red Helm CEO Michael Stratos | MSP + MSSP Leadership...

Sunny"s Silver Linings ·

2025/10/16

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 and perspective-driven decision making Whether you’re an MSP

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22:32

Alex Brandt: Why the Browser Is the New Endpoint for...

Sunny"s Silver Linings ·

2025/10/02

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 endpoint. How MSPs can monetize browser security and create strategic advantage.

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25:33

Kevin Blake: From Founder to Scalable MSP Leader & AI...

Sunny"s Silver Linings ·

2025/09/18

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 and empower your “number two” with business acumen, not just technical skills.

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16:48

Predict to Prevent: AI, Compliance & the Next Era of...

Sunny"s Silver Linings ·

2025/09/04

In this episode of Sunny’s Silver Linings, Sunny sits down with Al Alper, founder of CyberGuard360 and serial entrepreneur, to explore how MSPs can evolve beyond tools and quick fixes to deliver real client value. Al reveals why the future of cybersecurity isn’t just detection; it’s prediction. By anticipating where attackers are headed, MSPs can shut them down before they strike. Along the way, he explains why compliance is the true backbone of reliability, and why empathy: knowing your clients’

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35:50

From Break-Fix to Boardroom: Chris Day's Blueprint...

Sunny"s Silver Linings ·

2025/08/21

In this compelling episode, MSP legend Chris Day shares his transformative journey from an IT services entrepreneur to a software visionary who helped solve the industry's biggest documentation problem. Join us as we discuss: Why a plumber role is a dangerous posture for an MSP and how to pivot to a strategic advisor. The birth of IT Glue: How solving a core business problem led to a multi-million-dollar software company. The importance of relentless perseverance and why the

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20:28

Building Community, Automating Impact: The ImmyBot...

Sunny"s Silver Linings ·

2025/07/24

What if automation wasn’t about replacing people—but freeing them up to do what matters most? In this episode, Tara Rummer of ImmyBot shares how her team is helping MSPs scale smarter, eliminate revenue leaks, and reclaim valuable time—without losing their human touch. We uncover: The real origin of ImmyBot (from a 20-year-old MSP!) Why automation ≠ AI, and why that distinction matters Fixing revenue leakage through smart PSA integrations How freeing up engineers

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22:46

Ryan Bowman Unfiltered: Cybersecurity, AI & the MSP...

Sunny"s Silver Linings ·

2025/07/17

In this episode, Ryan Bowman of ThreatLocker joins Sunny Kaila for an insightful conversation on what it takes to defend today’s MSPs from modern cyber threats. From his time in the trenches as an MSP operator to his current work helping partners at ThreatLocker, Ryan shares powerful insights on: Why “Zero Trust” isn’t a buzzword: it’s a necessity How attackers are using AI to rewrite and bypass defenses Why familiar tools, when misused, are the most dangerous What

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20:11

Baxter Lanius: Why Cash Confidence Is the Hidden...

Sunny"s Silver Linings ·

2025/07/10

What’s stopping your MSP from scaling? Hint: it’s not sales, it’s cash flow. In this episode of Sunny’s Silver Linings, I sit down with Baxter Lanius, CEO of Alternative Payments, to unpack why cash confidence is the true growth engine for modern MSPs. From Wall Street investing to launching a fintech built for the channel, Baxter shares how automation, clarity, and a shift in mindset can transform your operations — and your EBITDA. Key Takeaways: Why most MSPs unknowingly bleed value

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29:34

Kendra Lee: Boost MSP Sales ROI & Build Authentic...

Sunny"s Silver Linings ·

2025/07/03

Struggling to get real ROI from your MSP sales efforts? In this episode of Sunny Silver Linings, Kendra Lee: sales strategist, HubSpot Gold Partner, and AI-for-sales expert: shares how MSP leaders can use AI to drive smarter prospecting, tighter follow-ups, and repeatable revenue growth. We cover everything from sales consistency and CRM discipline to the right way to use AI without losing your authenticity. This is your playbook for building a sales machine that works without sounding like a

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34:40

Jamison West: The MSP Owner's Blueprint to Time...

Sunny"s Silver Linings ·

2025/06/12

Are you an MSP owner feeling indispensable? In this episode, Jamison West, a serial entrepreneur and MSP veteran, unveils his transformative "Five Ps" framework for building a business that thrives independently. Learn how to overcome the founder's fear, delegate effectively, and unlock unparalleled freedom. Key Highlights: The profound shift: from indispensable owner to replaceable leader. Jamison's "Five Ps" for building a scalable, high-value business. How to find and

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10:46

The HR Edge: How to Attract, Grow & Lead Top Talent...

Sunny"s Silver Linings ·

2025/05/30

Struggling to scale your MSP with the right people? You're not alone. In this powerful episode, IT By Design CEO Sunny Kaila talks with Ainsley Lump of Entech about the real HR strategies that drive growth, loyalty, and culture in today’s MSP landscape. From recruiting smarter to building magnetic culture and performance systems your team actually wants—this is the leadership masterclass you didn’t know you needed. Here’s a synopsis of what Ainsley shares: Why scalable processes are the

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38:24

From IT Fixers to Strategic Advisors: Reinventing the...

Sunny"s Silver Linings ·

2025/05/15

What’s the secret to building an unstoppable MSP in today’s fast-moving tech world? In this episode, Peter Melby, CEO of New Charter Technologies, breaks down how top MSPs are shifting from reactive IT support to proactive business problem-solvers. Discover why the future belongs to those who ask better questions, embrace AI with purpose, and treat their MSP like an innovation lab—not just a service desk. Key Highlights: Why solving business problems is the new MSP superpower The hidden cost of

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39:24

Decoding Thrive’s Success: The Power of People,...

Sunny"s Silver Linings ·

2025/05/01

What does it take to lead the next evolution of the MSP industry? In this episode, Bill McLaughlin of Thrive reveals how visionary leadership, a security-first approach, and a relentless focus on people and execution have fueled Thrive’s extraordinary growth. Key Highlights: The bold "Thrive 2.0" transformation strategy Why leadership and culture drive real MSP success How ServiceNow and innovation differentiate Thrive Private equity’s role in scaling without losing

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22:26

From Chaos to Clarity: Why Every Visionary Needs an...

Sunny"s Silver Linings ·

2025/04/17

What does it take to scale a visionary business? In this episode, Sunny Kaila and Chad Willardson reveal how visionary-integrator alignment can propel your growth and elevate your leadership. Discover the blueprint for creating a high-performing team that amplifies your vision and drives success. Key Highlights: The unique mindset of founders and why it’s different How to protect the visionary’s time for strategic growth Why every visionary needs an integrator to turn chaos

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27:22

Embracing the Entrepreneurial Journey: Lessons from...

Sunny"s Silver Linings ·

2025/04/04

What separates successful entrepreneurs from the rest? It’s not just vision—it’s resilience, adaptability, and the willingness to embrace discomfort. In this episode, Nick Recker shares his journey from running a small MSP to building Blue Alliance, an innovative platform company. The challenges of scaling a business Why the "messy middle" defines true entrepreneurs The power of self-audits and strategic pivots How culture and accountability fuel growth Why collaboration beats competition in

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41:01

Unlocking High-Performing Teams: Growth Mindset...

Sunny"s Silver Linings ·

2025/03/21

What does it take to build a high-performing MSP? In this episode, discover how Kayvan Yazdi and Iman Oskoorouchi of TruAdvantage transformed their business by embracing a growth mindset, prioritizing leadership, and investing in their people. Key Highlights: Shifting from IT consultants to business leaders The power of a people-first culture in driving success Overcoming distractions and staying laser-focused on growth How personal development fuels team performance

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11:06

MSP M&A Insights: Growth, Exit Strategies & Market...

Sunny"s Silver Linings ·

2025/03/07

The MSP M&A game is changing. Economic shifts, rising interest rates, and evolving deal structures are reshaping the landscape. But opportunity is still everywhere for those who are prepared! In this episode of Sunny’s Silver Linings, I sit down with Arlin Sorensen, Rob Stephenson, and Christopher Vollmond-Carstens to unpack: ✅ The current state of MSP M&A and market trends ✅ How rising interest rates impact valuations and deal structures ✅ What makes an MSP acquisition truly successful ✅ The

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45 results

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