Welcome to another episode of The MSP Security Playbook, brought to you by Heimdal Security, the unified, AI-powered cybersecurity solutions provider. 

In this episode, host Jacob Hazelbaker sits down with Austen Clark, CEO of Jera IT Limited, a fast-growing Scottish MSP known for its resilience, innovation, and commitment to client trust.

Under Austen’s leadership, Jera IT has integrated multiple firms, guided clients through real-world ransomware incidents, and achieved key cybersecurity certifications, including Cyber Essentials Plus, IASME, and ISO 9001.

Together, Jacob and Austen dive into how Jera IT helped a client recover from the AKIRA ransomware strain without paying a ransom or losing a day’s work, why certifications matter and how to prove, not just promise, your security posture, and finally, the art of communication during a crisis: why “telling people seven times, in seven different ways” keeps trust intact.

Plus, don’t miss this week’s Threat Brief with Heimdal Cybersecurity Advisor Adam Pilton, who unpacks how a convincing deepfake campaign targeted Ireland’s presidential election and what it signals for the future of digital trust.

If you enjoyed this episode, follow MSP Security Playbook on your favourite podcast platform, leave us a review, and share it with another MSP leader who’s serious about scaling securely. Got a question for the MSP Hot Seat or a topic you’d like covered? Drop us a line; we’d love to hear from you.

Chapter Markers:

(02:03) – Threat Brief: Deepfake disinformation targets Irish election

(06:00) – Surviving the AKIRA ransomware attack without paying ransom

(11:00) – The importance of communication “seven times, in seven ways”

(12:00) – Why every MSP should hold Cyber Essentials Plus

(17:00) – The biggest challenges facing UK MSPs: talent, regulation, and AI

(19:30) – The coming shift in MSP business models

(21:00) – MSP Hot Seat: How to prepare for a merger or acquisition

(23:00) – Play-by-Play: Jacob’s takeaways from the conversation

Useful Links:

Connect with Austen Clark on LinkedIn

To learn more about Jera IT, visit their website

Follow Jacob for more cybersecurity insights on LinkedIn

For more from Adam, connect via LinkedIn

Explore Heimdal’s platform at heimdalsecurity.com

Welcome to another episode of The MSP Security Playbook, brought to you by Heimdal Security, the unified, AI-powered cybersecurity solutions provider. 

In this episode, host Jacob Hazelbaker sits down with Alice Violet, Marketing Leader in Cyber & Tech, Speaker, Storyteller, and Host of Cyber Made Human.

After an unexpected leap from luxury travel marketing into cybersecurity, Alice has built a reputation for helping cyber brands communicate complexity with clarity and tell stories that connect on a human level.

Together, Jacob and Alice explore how MSPs can turn technical messaging into relatable storytelling, why trust is the ultimate differentiator in cybersecurity marketing and how to stand out in a saturated industry by being human first

Plus, don’t miss this week’s Threat Brief segment with Heimdal’s Adam Pilton, who breaks down a zero-day exploit targeting Oracle E-Business Suite and what MSPs can do right now to stay ahead.

If you enjoyed this episode, follow MSP Security Playbook on your favorite podcast app, leave us a review, and share it with an MSP who needs to hear it.

Got a question for the MSP Hot Seat or a topic you’d like covered? Drop us a line, we’d love to hear from you.

Chapter Markers:

(02:03) – Threat Briefing: Oracle zero-day exploited in Harvard breach

(11:38) – Building trust and thought leadership as an MSP

(22:00) – Why long-form content still matters for MSPs

(24:00) – Turning cybersecurity from a cost into a business opportunity

(27:05) – Creative storytelling beyond padlocks and buzzwords

(29:00) – MSP Hot Seat: Building real trust, not just saying it

(30:00) – Play-by-Play: Jacob’s takeaways from the conversation

Useful Links:

Connect with Alice Violet on LinkedIn

To learn more about Alice's work visit her website Alice Violet Creative

Listen to the Cyber Made Human Podcast

Follow Jacob for more cybersecurity insights on LinkedIn

For more from Adam connect via LinkedIn

Explore Heimdal’s platform at heimdalsecurity.com

Welcome back to the MSP Security Playbook, brought to you by Heimdal Security, the unified, AI-powered cybersecurity platform that helps MSPs cut through the noise, streamline operations, and grow more profitable security businesses.

In this episode, host Jacob Hazelbaker sits down with Kevin Walker, owner of Black Swan Cyber, an MSP with a mission: to protect schools and educational institutions from the growing wave of cyber threats. With nearly 30 years in IT, two decades of which have been dedicated to education, Kevin shares how specialising in a niche has sharpened his business focus and driven both purpose and profit.

From decoding the UK Department for Education’s new cybersecurity standards to building a security-first culture, Kevin reveals what MSPs need to know to serve schools effectively and how those lessons extend far beyond the classroom. We also explore the evolution of multi-academy trusts, why Cyber Essentials is opening new business opportunities, and why focusing on why you do what you do matters more than chasing MRR.

Whether you’re an MSP looking to carve out a niche or simply want to build a business that truly protects people, this episode is packed with actionable insights, strategies, and inspiration.

Before the main interview, Heimdal’s Adam Pilton breaks down three newly discovered vulnerabilities in Google’s Gemini platform and what MSPs must do now to protect clients from AI-enabled attack surfaces.

If you enjoy this episode, be sure to follow the MSP Security Playbook on your favourite podcast app, leave us a review, and share it with a fellow MSP leader who needs to hear this.

Chapter Markers:

(02:25) – Threat Brief: AI in the crosshairs – 3 critical Gemini vulnerabilities you need to know about

(10:27) – Foundations First: Essential controls every MSP needs before serving schools

(16:00) – Beyond MRR: Why purpose matters more than monthly recurring revenue

(18:02) – Multi-Academy Trusts: Engaging C-suite stakeholders and speaking their language

(22:25) – Cyber Essentials Everywhere: How compliance is expanding into construction, trades, and beyond

(27:06) – MSP Hot Seat: The #1 security control every school should implement tomorrow

Useful Links:

Connect with Kevin Walker on LinkedIn

To learn more about Black Swan Cyber, visit the website

Follow Jacob for more cybersecurity insights on LinkedIn

For more from Adam connect via LinkedIn

Explore Heimdal’s platform at heimdalsecurity.com

Welcome back to the MSP Security Playbook, brought to you by Heimdal Security, the unified, AI-powered cybersecurity solutions provider. 

In this episode, host Jacob Hazelbaker sits down with Dave Sobel, former MSP owner, vendor leader, and now the voice behind the Business of Tech podcast, one of the most influential voices in the IT space.

Dave pulls back the curtain on how he distills the overwhelming flood of industry news into the most valuable ten minutes of an MSP’s day. He shares why the future of MSPs lies not just in infrastructure, but in driving productivity and business processes that deliver measurable ROI. 

We explore how AI and automation can unlock real value without erasing the human element and how MSPs can reposition themselves from cost centers into growth enablers for their clients.

Finally, in the MSP Hot Seat, Dave takes on a tough question: when resources are tight, should a growing MSP prioritise tools, talent, or revenue? His answer may surprise you.

But before that, this week’s Threat Brief, where Heimdal Security advisor Adam Pilton breaks down a new phishing-as-a-service platform called Void Proxy and how MSPs can defend against it.

If you enjoy this episode, be sure to follow the MSP Security Playbook on your favourite podcast app, leave us a review, and share it with a fellow MSP leader who needs to hear this.

Chapter Markers:

(02:10) – Threat Brief: Void Proxy and the evolution of phishing-as-a-service

(09:15) – Cutting Through the Noise: How MSPs should filter industry news

(13:56) – Cybersecurity as Expense vs. Growth Driver

(22:03) – Building Trust and Audience: Lessons from the Business of Tech

(25:41) – MSP Hot Seat: Prioritising tools, talent, or revenue?

(28:41) – Play-by-Play: Jacob reflects on the conversation with Dave Sobel

Useful Links:

Connect with Dave Sobel on LinkedIn

To learn more about Dave Sobel visit his website

Follow Jacob for more cybersecurity insights on LinkedIn

For more from Adam connect via LinkedIn

Explore Heimdal’s platform at heimdalsecurity.com

Welcome back to the MSP Security Playbook, brought to you by Heimdal Security — the unified, AI-powered cybersecurity solutions provider. 

In this episode, host Jacob Hazelbaker sits down with Adam Pilton, Cybersecurity Advisor at Heimdal and former Detective Sergeant in the UK police cybercrime unit. 

With 15 years of frontline policing and digital investigations under his belt, Adam brings a rare perspective that blends law enforcement, consultancy, and cybersecurity advisory work.

The episode kicks off with our latest threat brief, which details how attackers are weaponising AI through Hex Strike AI to automate exploitation at scale, shrinking the window from disclosure to compromise down to minutes. Adam explains what this means for MSPs and the steps providers must take to defend faster.

Further in the episode, Jacob and Adam explore why simplifying cyber is more than a personal mission — it’s a business imperative, the biggest mistakes MSPs make when it comes to incident response and why storytelling and social selling are secret weapons for MSPs looking to build trust.

Adam also goes on to share how his own online presence has helped him grow influence, credibility, and trust — lessons that every MSP can apply to their own business. 

And during the MSP Hot Seat, he answers a critical question from a small but growing MSP: how do you land your first five clients and stand out in a crowded market?

If you enjoyed this episode, make sure to follow MSP Security Playbook on your favourite podcast app, leave us a review, and share it with a fellow MSP who needs to hear this. 

Got a question for the MSP Hot Seat or a topic you want covered? Drop us a line — we’d love to hear from you.

Chapter Markers:

(02:05) Threat Briefing: The rise of AI-driven exploitation with Hex Strike AI

(08:12) Simplifying Cyber: Trust, clarity, and storytelling for MSPs

(13:39) Tabletop Exercises: Practicing chaos before it strikes

(21:00) Social Selling: Building credibility and trust through LinkedIn

(23:30) Cybersecurity Awareness as a Service: Making training engaging and billable

(30:58) MSP Hot Seat: How to land your first five clients and stand out

(33:20) Play-by-Play: Jacob reflects on key lessons from Adam

Useful Links:

For more from Adam connect via LinkedIn

Explore Heimdal’s platform at heimdalsecurity.com

Follow Jacob for more cybersecurity insights on LinkedIn

Welcome back to the MSP Security Playbook, powered by Heimdal Security, the unified, AI-driven cybersecurity platform designed to help MSPs streamline operations and scale profitably.

In this episode, host Jacob Hazelbaker is joined by Luis Giraldo, Chief Evangelist at ScalePad and seasoned MSP operator, to tackle a crucial mindset shift: moving beyond tools and tickets toward customer success.

Luis shares why MSPs can no longer afford to think only about their stack or efficiency. Instead, the future belongs to those who deeply understand their clients’ businesses, align technology with outcomes, and position themselves as strategic advisors.

Plus, Luis takes on the MSP Hot Seat, answering how to start implementing customer success without a dedicated role.

You’ll also hear from Adam Pilton in the Threat Briefing, where he breaks down how the Interlock ransomware group crippled St. Paul, MN, and why MSPs are a prime target for double-extortion attacks.

If you’re ready to elevate your MSP from “the IT guy” to trusted business partner, this episode is a playbook you won’t want to miss.

Got a question for the MSP Hot Seat or a topic you’d like covered? Drop us a line; we’d love to hear from you.

Chapter Markers:

02:10) Threat Briefing: Interlock ransomware cripples St. Paul, MN

(07:08) Why Customer Success Matters More Than Sales

(13:30) Breaking Out of the Commoditisation Trap

(18:20) Shifting Cybersecurity Conversations from Tools to Risk

(25:48) What Thriving MSPs Do Differently

(27:50) MSP Hot Seat: How to Implement Customer Success Without Hiring a Role

(29:37) Play-by-Play: Jacob’s Key Takeaways

Useful Links:

Connect with Luis Giraldo on LinkedIn 

Visit the ScalePad Website

Explore Heimdal’s platform at heimdalsecurity.com

Follow Jacob for more cybersecurity insights on LinkedIn

For more from Adam connect via LinkedIn

Welcome back to the MSP Security Playbook, brought to you by Heimdal Security, the unified, AI-powered cybersecurity solutions provider helping MSPs streamline operations and grow stronger security businesses.

In this episode, host Jacob Hazelbaker is joined by Michael Bakaic, founder of Iceberg Cyber, to tackle one of the most dreaded yet most critical parts of running a successful MSP: sales.

Michael shares how he went from hating sales to building an entire business around helping MSPs fall in love with it. You’ll hear a proven playbook for generating leads from scratch, warming up cold outreach, and getting your sales message to land, all while staying true to your founder-led brand.

If sales has ever felt like guesswork, rejection, or a necessary evil, this episode is your reset.

As always, we kick things off with the latest Threat Briefing from Heimdal’s cyber advisor and former cyber detective, Adam Pilton, who breaks down the evolution of ransomware into full-blown quadruple extortion attacks and how to protect your MSP from becoming the next headline.

If you enjoy the show, be sure to follow MSP Security Playbook on your favorite podcast platform, leave us a review, and share this episode with a fellow MSP who’s ready to close more deals.

Got a question for the MSP Hot Seat or a topic you’d like covered? Drop us a line; we’d love to hear from you.

Chapter Markers:

(02:08) Threat Briefing: Ransomware’s quadruple extortion playbook 

(08:48) Why MSPs need to love sales 

(11:35) Michael’s 3 lead magnet types for converting cold leads

(15:53) Scaling sales without losing your founder touch

(23:47) Why cold emails fail 

(24:11) How to leverage LinkedIn to build lukewarm leads

(26:57) MSP Hot Seat: Breaking through outbound fatigue

(33:05) Play-by-Play: Jacob reflects on the big takeaways from Michael’s approach

Useful Links:

Connect with Michael Bakaic on LinkedIn 

Visit the Iceberg Cyber Website

Explore Heimdal’s platform at heimdalsecurity.com

Follow Jacob for more cybersecurity insights on LinkedIn

For more from Adam connect via LinkedIn

Welcome to another episode of the MSP Security Playbook, brought to you by Heimdal Security — the unified, AI-powered cybersecurity platform that helps modern MSPs win.

This week, host Jacob Hazelbaker is joined by Dan Di Pisa, President & CEO of Fusion Cyber Group, for a powerful and eye-opening conversation about the realities of cybersecurity in the MSP space.

Dan shares the moment that changed everything — a client ransomware breach that not only jeopardised business operations but also led him to absorb the ransom cost himself. What followed was a complete transformation of his business model, evolving from a traditional MSP into one of Canada’s most cyber-forward MSSPs.

From dealing with threat actors on the dark web, to identifying the biggest red flags MSPs miss, to building a truly layered security strategy — this episode is a masterclass in what it means to take ownership, learn hard lessons, and come back stronger.

Whether you're just starting to explore cybersecurity services or you're in the trenches every day, Dan's story will challenge you to rethink your own approach — and inspire you to lead with resilience.

Also on this episode, Adam Pilton breaks down a pair of high-priority SharePoint exploits that allow attackers to execute code with zero user interaction. Learn what’s at risk, how threat actors are already abusing these flaws, and the urgent steps MSPs must take to secure client environments — including patching, rebooting, and rotating machine keys.

If you found value in this episode, don’t forget to follow MSP Security Playbook on your favorite podcast platform, leave a review, and share it with a fellow MSP.

Got a hot seat question or a topic you want covered? We’d love to hear from you.

Chapter Markers:

(02:04) Threat Briefing: Critical SharePoint vulnerabilities

(03:52) Meet Dan Di Pisa: From IT service manager to MSP founder

(06:15) The 2015 Ransomware Breach That Changed Everything

(10:27) Paying the Ransom: Taking responsibility and earning client trust

(16:59) Hiring & Tools: Finding the right people and the right platforms

(20:31) Speaking in ROI: How to communicate value to your clients

(24:19) MSP Hot Seat: The most overlooked red flag in client environments

(25:57) Play-by-Play: Jacob reflects on Dan’s insights and story

Useful Links:

Connect with Dan Di Pisa on LinkedIn 

Visit the Fusion Cyber Group Website

Explore Heimdal’s platform at heimdalsecurity.com

Follow Jacob for more cybersecurity insights on LinkedIn

For more from Adam connect via LinkedIn

Welcome back to the MSP Security Playbook, brought to you by Heimdal Security — the unified, AI-powered cybersecurity solutions provider that helps MSPs grow stronger and more secure.

In this episode, host Jacob Hazelbaker is joined by Dustin Bolander, founder of Beltex, a specialist in insurance and compliance for professional service providers. Together, they tackle one of the most dreaded — yet potentially most powerful — aspects of running an MSP: compliance.

Far from being just a checklist headache or sales hurdle, Dustin argues compliance can become a catalyst for growth, deeper client engagement, and new revenue streams. Whether you’re wondering how to navigate HIPAA, avoid the pitfalls of CMMC, or use compliance frameworks to lock in client loyalty, this episode has you covered.

If compliance has ever felt like a burden, Dustin will help you see it as a strategic advantage that sets you apart from every “patch report” competitor in the market.

In this week's Threat Briefing, Adam unpacks a critical new Cisco vulnerability: a hardcoded root account in Unified Communications Manager (UC) servers that gives attackers instant SSH access — no passwords or MFA required. Tune in to hear why patching and isolating voice systems should be your top priority.

If you found this episode helpful, please follow MSP Security Playbook on your favorite podcast app, leave us a review, and share it with another MSP looking to turn compliance into their secret growth weapon.

Have a question for the MSP Hot Seat or a topic you want us to tackle next? Drop us a line — we’d love to hear from you.

Chapter Markers:

(02:04) Threat Briefing: Cisco UC server backdoor lets attackers log in with hardcoded root

(05:17) The compliance gold rush: CMMC, HIPAA, and overlooked opportunities

(08:58) Turning compliance from a checkbox into a sales differentiator

(13:14) Common compliance mistakes: DIY disasters and reinventing the wheel

(16:55) The insurance 101 for MSPs: Cyber vs. Tech E&O

(20:06) How to future-proof your MSP for compliance (without last-minute panic)

(25:35) Streamlining compliance without it becoming a full-time job or sales blocker

(28:32) Play-by-Play: Building client cadence & loyalty through compliance

Useful Links:

Connect with Dustin Bolander on LinkedIn

Visit the Beltex Website

Explore Heimdal’s platform at heimdalsecurity.com

Follow Jacob for more cybersecurity insights on LinkedIn

For more from Adam connect via LinkedIn

Welcome to another episode of the MSP Security Playbook, brought to you by Heimdal Security—the unified, AI-powered cybersecurity solutions provider that helps MSPs streamline operations and grow more profitable security businesses.

In this episode, host Jacob Hazelbaker sits down with Kevin Lancaster, founder of Channel Program, a platform designed to give MSPs and vendors the data they need to make smarter, faster decisions. Kevin’s seen this industry from all sides—as a founder, investor, and advisor—and today he pulls back the curtain on the operational headaches that are quietly draining MSP profits.

From why 97% of MSPs still rely on Excel spreadsheets to track their tech stacks to how AI attacks are evolving faster than ever, Kevin offers hard truths and practical insights that could save your MSP serious time, money, and stress.

Finally, on this week's Threat Briefing, Adam breaks down a chilling zero-click iCloud exploit that installs spyware on Apple devices without the user even tapping a link. Learn how it works, why it’s so dangerous, and the urgent steps MSPs must take to protect clients before the July 7th federal compliance deadline.

If you enjoyed this episode, make sure to follow MSP Security Playbook on your favourite podcast app, leave us a review, and share it with a fellow MSP who needs to hear this.

Got a question for the MSP Hot Seat or a topic you want covered? Drop us a line—we’d love to hear from you.

Chapter Markers:

(01:39) Threat Briefing: A zero-click iCloud exploit, spyware on iPhones, and urgent patch advice

(07:20) Tool Sprawl & Fatigue: Why hundreds of tools lead to chaos

(09:14) Kevin’s Top 3 Tips: Reducing redundancy, preparing for compliance, and mastering costs

(14:34) AI Attacks & The New Reality: From 18-hour persistence to 18-day nonstop intrusions

(17:01) The Next-Gen MSP: AI, commoditisation, and why platforms will dominate

(20:17) MSP Hot Seat: What’s the #1 metric to watch daily?

(22:27) Play-by-Play: Jacob’s key takeaways on outdated processes and the crushing complexity MSPs face

Useful Links:

Connect with Kevin Lancaster on LinkedIn

Visit the Channel Program Website

Explore Heimdal’s platform at heimdalsecurity.com

Follow Jacob for more cybersecurity insights on LinkedIn

For more from Adam connect via LinkedIn