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
Episodes
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.
What if automation wasn’t about r...
In this episode, Ryan Bowman of ThreatLocker joins Sunny Kaila for an i...
What’s stopping your MSP from scaling? Hint: it’s
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 ...
Are you an MSP owner feeling indispensable? In this episode, Jamison West, a serial entrepreneur
Struggling to scale your MSP with the right
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:
- Wh...
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 ...
What does it take to scale a visionary business? In this episode, Sunny Kaila and Chad Willardson ...
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 cultur...
What does it take to build a high-performing MSP? In this episode, discover how Kayvan Yazdi and Iman
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 ...
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’...
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...
In this episode of Sunny's Silver Linings Podca...
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 firs...
Join Sunny Kaila, CEO of IT By Design, and cybersecurity expert Maggie MacAlpine
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