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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

28:03

M&A Secrets for MSPs: Maximize Value & Navigate Growth

Sunny"s Silver Linings ·

2025/02/20

In this episode of Sunny’s Silver Linings Podcast, IT By Design CEO Sunny Kaila sits down with M&A expert Hartland Ross to break down the evolving MSP M&A landscape. Hartland shares key insights on: ✅ Why it’s a seller’s market & what it means for MSP owners ✅ How to maximize business value before selling ✅ The biggest red flags that scare off buyers ✅ Strategies to scale & stay competitive in a consolidating industry If you’re considering an acquisition or planning an exit, this conversation

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43:32

Unlocking High-Performing Teams: Leadership...

Sunny"s Silver Linings ·

2025/02/07

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51:15

Building Winning Teams: Strategies for MSP Success

Sunny"s Silver Linings ·

2024/12/26

In this episode of Sunny's Silver Linings Podcast, IT By Design CEO Sunny Kaila dives into the evolving MSP ecosystem with Paul Hamilton and Tim Barton-Wines from Halo. Discover how teamwork, innovation, and delivering exceptional value are reshaping the industry. Key highlights: The power of collaboration in navigating challenges and opportunities in the MSP space. How Halo's innovative credit-back policy and customer-first approach redefine value. Strategies for building

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21:41

From Homeless to COO: Beth Leonard’s Inspiring...

Sunny"s Silver Linings ·

2024/12/12

In this episode of Sunny's Silver Linings Podcast, IT By Design CEO Sunny Kaila sits down with Beth Leonard, COO of R3, to discuss her incredible journey from earning $8 an hour in retail to leading a thriving IT company. Beth opens about overcoming significant challenges, including homelessness and a life-altering cancer diagnosis. In this inspiring conversation, she shares: -How resilience shaped her path to success. -The importance of diverse talent in the IT industry. -Effective strategies for

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22:01

To Sell or Not to Sell: Navigating the MSP Exit...

Sunny"s Silver Linings ·

2024/11/28

In this episode of Sunny's Silver Linings Podcast, IT By Design CEO Sunny Kaila sits down with Mit Patel, a seasoned MSP entrepreneur, to explore the tough decision every business owner faces: Should you sell your MSP or hold on for the long haul? Learn from Mit’s two decades of experience as he shares: How to define your personal and financial “enough.” Why timing and preparation are key for a successful sale. The dangers of chasing trends and the power of refining existing

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07:57

Empowering Teams & Expanding Horizons: Success...

Sunny"s Silver Linings ·

2024/11/14

In this episode of Sunny’s Silver Linings, CEO Sunny Kaila sits down with MSP leaders Chris Caprio and Michael Hornby to share powerful strategies for team empowerment and growth. From making impactful first impressions to unlocking the full potential of your tools, they discuss how to build a culture of trust, expand talent pools, and align personal and professional goals. Get ready for actionable insights to elevate your MSP business through collaboration and strategic expansion.

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19:42

Defending the Kingdom: MSPs vs. Modern Cyber Pirates

Sunny"s Silver Linings ·

2024/10/31

Join Sunny Kaila, CEO of IT By Design, and cybersecurity expert Maggie MacAlpine in this eye-opening episode of Sunny’s Silver Linings as they tackle the evolving landscape of cybersecurity threats facing Managed Service Providers (MSPs). Explore the parallels between historical piracy and today’s cybercrime and learn why MSPs are now prime targets for hackers. Discover essential strategies for enhancing cybersecurity hygiene and simplifying your security tools to effectively protect your

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40:29

People First: Building a Winning Culture in MSPs with...

Sunny"s Silver Linings ·

2024/10/17

Join IT By Design CEO Sunny Kaila in this episode of Sunny’s Silver Linings podcast as he chats with EOS Worldwide experts Kelly Knight, CJ Dubé, and Mark O'Donnell. Together, they delve into the crucial role of a people-first culture in driving business success and overcoming challenges. Here are the key takeaways from the enlightening session: • Discover how IT By Design's journey with the Entrepreneurial Operating System (EOS) transformed their approach to scaling while prioritizing team

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23:16

Beyond Competition: The Power of MSP Communities...

Sunny"s Silver Linings ·

2024/10/10

In this episode of "Sunny Silver Linings," I interview Brad Schow about the transformative power of MSP communities. We explore the idea that one plus one isn't just two; it’s equal to eleven. By embracing an abundance mindset and a Go-Givers approach, we can unlock limitless potential in the total addressable market. Instead of viewing other MSP platforms and communities as competitors, we should see them as collaborators. Together, we can create greater value for our partners. Join us as we

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25:23

Embracing Failure: Redefining Leadership with Sunny...

Sunny"s Silver Linings ·

2024/10/03

In this episode of Sunny’s Silver Linings podcast, IT By Design CEO Sunny Kaila engages in a thought-provoking conversation with James Hwang, author of Dare to Fail, about the transformative power of embracing failure in leadership. Discover how to redefine failure as a stepping-stone for growth and innovation. Hear James’s perspective on shifting mindsets to view setbacks as valuable lessons. Learn about the Actionable Leadership Framework and how it can elevate your leadership

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14:37

Building a Purpose-Driven MSP: Insights from Johan...

Sunny"s Silver Linings ·

2024/09/19

In this episode of Sunny's Silver Linings podcast, IT By Design Founder & CEO Sunny Kaila interacted with Johan Hammerstrom, CEO of Community IT Innovators, to discuss the power of purpose-driven leadership in the MSP space. Johan shared valuable insights on aligning business goals with customer needs, building a strong organizational culture through trust and fostering talent development by focusing on individual strengths. Whether you're an MSP leader or a business owner, these lessons will help

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22:00

Building Winning Teams as an MSP: Lessons from Omega...

Sunny"s Silver Linings ·

2024/09/05

In this special episode of Sunny’s Silver Linings, host Sunny Kaila interacted with Ben Tercha, COO of Omega Systems, to explore his 19-year journey in the managed service provider (MSP) industry. From building strong customer relationships to leading high-performing teams, Ben shares actionable insights for growing your MSP business. Key takeaways include: The importance of innovation to stand out in a competitive MSP landscape How to build meaningful, long-lasting relationships

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38:39

The Future of MSPs: Maximizing Profits & Embracing a...

Sunny"s Silver Linings ·

2024/08/23

In this episode of Sunny’s Silver Linings, IT By Design CEO Sunny Kaila talks with Sumeet Sabharwal, CEO of Netgain, and Frank DeBenetto, General Manager of MSP Suite at Kaseya, about the challenges MSPs face with profitability and share actionable strategies for expanding beyond regional boundaries and maximizing value. Key Topics Covered: Overcoming Profitability Challenges in the MSP Industry Expanding MSP Operations Beyond Regional Boundaries The Power of Focus and

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13:41

Building a People-First Culture: Insights from...

Sunny"s Silver Linings ·

2024/08/09

In this episode of Sunny's Silver Linings, IT By Design CEO Sunny Kaila sat down with Max Kaplan, Director of Engineering at Machado Consulting, Inc., to discuss the importance of a people-first culture in business. Max shared how adopting IT By Design's talent operating system, Team GPS, transformed their team's dynamics by improving goal setting, enhancing peer recognition, and streamlining one-to-one meetings. Tune in to learn how these strategies can help you foster a more engaged and

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23:58

Unlocking Relationship Success With Ann Sheu

Sunny"s Silver Linings ·

2024/07/25

In this insightful episode of Sunny's Silver Linings podcast, IT By Design CEO Sunny Kaila is joined by Ann Sheu, Founder & CEO of Mpowered Families, to explore the keys to relationship success at home and work. Ann shares her personal journey, the founding of Mpowered Families, and practical strategies for improving relationships through intentionality and self-care. Key Topics Covered: The inspiration behind Mpowered Families The importance of "me work" and self-care Strategies for overcoming

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17:44

Mastering the MSP Business: Strategic Insights with...

Sunny"s Silver Linings ·

2024/07/11

In this episode of Sunny's Silver Linings, hosted by IT By Design CEO Sunny Kaila, we have an engaging and insightful conversation with Brian Hoppe, a strategic coach for MSPs. Brian shares his entrepreneurial journey, offering valuable advice for new and existing MSP owners. From the importance of finding your niche to the critical role of company culture and the common mistakes MSPs make, Brian's wisdom is a must-hear for anyone in the managed services industry. The key highlights include:

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26:56

MSP M&A Trends: Insights from Christopher...

Sunny"s Silver Linings ·

2024/06/27

Join IT By Design CEO Sunny Kaila as he chats with Christopher Vollmond-Carstens, Chief M&A Officer at Ntiva Inc., about the latest trends in the MSP mergers and acquisitions (M&A) landscape. Discover strategic advice, future predictions and the role of global teams in this insightful episode of Sunny's Silver Linings. Don’t miss out on expert tips for staying competitive and growing your MSP business!

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30:28

Exploring MSP Evolution with 1Path’s Lori Patrick and...

Sunny"s Silver Linings ·

2024/06/13

Welcome to the latest episode of "Sunny's Silver Linings" podcast, hosted by IT By Design CEO Sunny Kaila. In this episode, Sunny engaged in insightful discussions with Lori Patrick, Vice President of Central Services at 1Path, and Luca Jacobellis, Chief Operating Officer at 1Path. Join us as we explore their perspectives on leadership, technology trends and navigating the challenges of the managed service providers (MSP) industry. Don’t miss out on this enriching conversation!

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31:26

Damien Stevens: From a High School Dropout to a Tech...

Sunny"s Silver Linings ·

2024/05/30

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35:44

MSP Leadership & Growth Lessons From Wolf...

Sunny"s Silver Linings ·

2024/05/16

The latest episode of the "Sunny’s Silver Linings" podcast featuring Jonathan JB Lamb, CEO of Wolf Consulting is out, and you must listen to it now! Tune in to hear JB’s inspiring leadership journey, unique insights on the MSP industry, and his strategies for driving growth and innovation. Don't miss this deep dive into effective MSP leadership and the importance of people-centric, proactive approaches. #SunnysSilverLinings #SSLPodcast #MSPGrowth #MSPLeadership #PeopleCentricCulture

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