Sunny's Silver Linings

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 au...

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. Jamiso...

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'...

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 servi...

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 innovatio...

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 t...

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 st...

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...

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...

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...

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-ba...

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 shape...

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 su...

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 actionabl...

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 en...

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 Entre...

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...

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. Lea...

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 focus...

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 ou...

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 E...

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-...

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 inspi...

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'...