Deepfakes, Disguises, and Deliveries: How Rob Shapland Hacks Human Weakness to Build Stronger Security

Now That's IT: Stories of MSP Success

Modern cyberattacks aren’t just technical—they’re personal. And Rob Shapland knows how to exploit the human element better than anyone.

In this episode, Chris Massey sits down with Rob to unpack the wild world of social engineering—from sneaking into corporate offices disguised as a delivery driver to using AI voice clones to bypass MFA. With over 200 successful break-ins (all authorized, of course), Rob shares what IT leaders and MSPs are still getting wrong—and how to fix it.

They cover:

• Why the human layer is still the biggest vulnerability in security
• How attackers are already using AI for voice and video deepfakes
• What companies can do today to strengthen their weakest links

If your clients think MFA alone is enough, this episode proves otherwise.

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'Now that's it: Stories of MSP Success,' dives into the journeys of some of the trailblazers in our industry to find out how they used their passion for technology to help turn Managed Services into the thriving sector it is today.
Every episode is packed with the valuable insights, practical strategies, and inspiring anecdotes that lead our guests to the transformative moment when they knew….. Now, that's it.
This podcast provides educational information about issues that may be relevant to information technology service providers.

Nothing in the podcast should be construed as any recommendation or endorsement by N-able, or as legal or any other advice.

The views expressed by guests are their own and their appearance on the podcast does not imply an endorsement of them or any entity they represent.

Views and opinions expressed by N-able employees are those of the employees and do not necessarily reflect the view of N-able or its officers and directors.

The podcast may also contain forward-looking statements regarding future product plans, functionality, or development efforts that should not be interpreted as a commitment from N-able related to any deliverables or timeframe.

All content is based on information available at the time of recording, and N-able has no obligation to update any forward-looking statements.

Chapters

1. From School Hacker to Ethical Intruder (00:00:00)

2. Physical Break-ins and Social Engineering (00:08:37)

3. Extreme Sports and Competitive Drive (00:18:01)

4. Voice Cloning and MFA Bypass (00:22:14)

5. Future of Social Engineering Attacks (00:28:36)

6. The Simple Things Still Work (00:34:44)