Podcasts by IT By Design

Your weekly scoop of the conversations driving MSP leadership and scale.

Conversations Worth Your Time

Three podcast series. One through-line: helping MSP leaders think more clearly, lead more confidently, and build businesses that scale.

No fluff. No filler. Just real conversations with the people building and running successful MSPs.

Podcast 01

AI by Design

MSP innovation in practice, not in theory
Hosted by Sunny Kaila, AI by Design features short, unscripted conversations with MSP and AI leaders who are actively building AI into their operations. Each episode is focused: what’s working, what isn’t, and what other MSP leaders can take directly back to their business.
No academic overviews. No vendor pitches. Just practitioners talking through the real challenges of putting AI to work inside a managed service environment.

PODCAST 02

Sunny's Silver Linings (SSL)

What 30 years of building businesses actually teaches you
Leadership isn’t a destination. Sunny Kaila has built companies, navigated hard seasons, and spent decades working alongside MSP leaders at every stage of growth. This series is where he shares what he’s learned.
Each episode pulls from real experience: decisions that worked, calls that didn’t, and the mindset shifts that made the difference. Whether you’re scaling your first MSP or running a mature operation, there’s something in these conversations worth sitting with.
Topics include: Leadership development | Building resilient teams | Decision-making under pressure | Growth and self-awareness

PODCAST 03

Culture and Career Corner (CCC)

Where people, growth, and performance intersect

Your team is your delivery model. How you hire, develop, and retain people determines what you can actually build. The Culture and Career Corner series explores the human side of running an MSP, from setting expectations and building career paths to creating the kind of culture where people want to stay.
Practical conversations for leaders who know that team performance isn’t just a metrics problem. It’s a people problem, and it deserves focused attention.
Topics include: High-performing teams | Career development | Culture by design | Manager effectiveness | Retention

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AI by Design

Where MSP innovation becomes business impact

Hosted by Sunny Kaila, AI by Design features short, unscripted conversations with MSP and AI leaders who are actively turning innovation into real-world outcomes.

Sunny’s Silver Linings (SSL)

Leadership perspective from Sunny Kaila

Through candid reflections and conversations, Sunny Kaila shares insights on leadership, growth, resilience, and decision-making, drawn from decades of building businesses and working closely with MSP leaders.

Culture and Career Corner (CCC) Podcast

Where people, growth, and performance intersect

This series explores how culture, careers, and leadership development shape long-term success, covering everything from building high-performing teams to creating clarity around growth paths and expectations.