Podcast artwork thumbnail for Sunny's Silver Linings

Sunny's Silver Linings

Sunny Kaila

Booking Overview

This is an interview-led business and technology show focused on managed service providers, cybersecurity, artificial intelligence, automation, and channel growth, typically featuring MSP executives, technology vendors, cybersecurity specialists, and business authors. Credible pitches include MSP founders, cybersecurity and AI leaders, IT channel executives, automation experts, and authors with practical expertise; booking difficulty is medium because guests generally hold senior industry positions but are not necessarily mainstream public figures.

Metrics

Episodes: 163

Frequency: Irregular

Rating: 5.0/5.0

Estimated listeners: < 100

Gender skew: Male

Listener location: USA

YouTube: 1.8k subscribers

Instagram: 1.1k followers

Contact Information

Publicly listed emails

james.ruiz@itbd.net

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Host

Sunny Kaila - CEO of IT By Design and an executive focused on the managed services provider and IT channel ecosystem.

Booking Intelligence

Booking Requirements

medium
Typical Credentials:  
Senior MSP, IT channel, cybersecurity, software, or technology executives; founders of relevant companies; recognized channel leaders; and authors or practitioners with actionable expertise for MSP operators.
Required Achievements:  
Executive leadership at MSP, cybersecurity, software, or IT channel companies, Founding or leading a technology or cybersecurity business, Recognition as an IT channel leader, Publication of a business or leadership book

Recent Guest Discussions

Wilfredo Santiago - Identity Security, Managed Detection And Response, Multifactor Authentication, Least-privilege Access, AI Governance, And Protecting Small And Midsize Businesses.

Shahin Pirooz - Agentic MSP Operations, Cybersecurity Strategy, Build-versus-buy Decisions, Unified Security Data, Shadow AI, And Governance Of AI Agents.

Greg Jones - Execution, Leadership, MSP Growth, Delegation, Scaling, Go-to-market Strategy, Peer Groups, And Closing The Knowledge-action Gap.

David Powell - MSP Automation, Asset Intelligence, Data Visibility, AI Strategy, Outcome-based Pricing, Cybersecurity Documentation, And Operational Scaling.

Recent Topics

Business, Managed Services, Cybersecurity, Artificial Intelligence, It Channel

Episodes

Here's the recent few episodes on
Sunny's Silver Linings
:

AI Governance as an MSP Revenue Opportunity | Josh Coke and Sunny Kaila

October 16, 2026

Clients are already asking their MSPs about AI. Josh Coke of Enforcer joins Sunny Kaila to explain why AI governance is becoming a clear revenue opportunity in the channel, and why identity, data and configuration have to come before the tools. In this conversation: ➥ Why adding more products misses what customers actually need ➥ Why end clients are coming to MSPs asking about AI ➥ What happens when Copilot is turned on without guardrails ➥ How Microsoft Purview can be set up in an afternoon ...

Attackers Aren't Breaking In, They're Logging In | Wilfredo Santiago on Sunny's Silver Linings

September 29, 2026

Attackers are walking through the front door with legitimate credentials, and most MSP security stacks still treat identity as a hygiene checkbox. In this episode of Sunny's Silver Linings, Sunny Kaila sits down with Wilfredo Santiago of Blackpoint Cyber. Wilfredo shares his path from the US Navy to the NSA to the MSP space, then breaks down why identity is now the primary attack surface, why MFA is only the beginning, what separates true managed detection and response from reporting, and how...

The Agentic MSP Revolution: Shahin Pirooz on AI, Cybersecurity, and Digital Employees

September 03, 2026

In this episode of SSL, IT By Design's Sunny Kaila sits down with Shahin Pirooz, cybersecurity veteran and founder of White Dog Cyber, to unpack what it really takes for an MSP to become agentic. Shahin traces his path from enterprise software developer to CTO at Centerbeam to building a unified security platform for MSPs, and shares why "not invented here" thinking is one of the biggest silent killers of good business decisions. The conversation moves into shadow AI, why most security vendor...

Similar Podcasts

Podcast(s) similar to
Sunny's Silver Linings
:

Tate Talks - The MSP Podcast · Medium booking difficulty · 100 - 1,000 listeners

Frequently asked questions

Here's some frequently asked questions for
Sunny's Silver Linings
:

How do I get in touch with Sunny's Silver Linings?

Sunny's Silver Linings is hosted by Sunny Kaila. Its publicly listed email is james.ruiz@itbd.net. For guest bookings, the host or producer is usually the best person to reach. Podseeker helps you find direct host and producer contacts and pitch from your own inbox.

What is the email for Sunny's Silver Linings?

The publicly listed email for Sunny's Silver Linings: james.ruiz@itbd.net.

How many listeners does Sunny's Silver Linings have?

Podseeker estimates Sunny's Silver Linings reaches fewer than 100 listeners per episode. Only the publisher has exact numbers.

Who is an ideal guest for Sunny's Silver Linings?

Sunny's Silver Linings typically books industry leaders. Typical guest background: Senior MSP, IT channel, cybersecurity, software, or technology executives; founders of relevant companies; recognized channel leaders; and authors or practitioners with actionable expertise for MSP operators. Common among recent guests: Executive leadership at MSP, cybersecurity, software, or IT channel companies; Founding or leading a technology or cybersecurity business; Recognition as an IT channel leader. Recent guests include Wilfredo Santiago, Shahin Pirooz, and Greg Jones.

How hard is it to get booked on Sunny's Silver Linings?

Medium. Guests usually need solid credentials in the topic and an idea that fits the show.

What topics does Sunny's Silver Linings cover?

Recent episodes cover Business, Managed Services, Cybersecurity, Artificial Intelligence, and It Channel. Pitch an idea tied to one of these topics and mention a recent episode.

Publicly listed emails

james.ruiz@itbd.net

Looking for the right person? Join Podseeker to find direct host and producer contacts and manage your podcast outreach.

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