#93 Matt Holland: Zero Day

Sep 29, 2020
Overview

Matthew Holland, founder and CEO of Field Effect Security and a leading cybersecurity authority, discusses the state of cybersecurity, attacker mindsets, and defending against threats. He shares insights from his intelligence agency background and advises businesses on navigating the complex cyber landscape.

At a Glance
24 Insights
1h 27m Duration
16 Topics
8 Concepts

Deep Dive Analysis

Introduction to Matthew Holland and Cybersecurity Background

Early Career at an Intelligence Agency

Transition to Private Sector and Founding Linchpin Security

Lessons Learned from Growing and Selling Linchpin Security

Motivation for Starting Field Effect Security

The Current State and Pillars of the Cybersecurity Industry

The Attacker's Mindset and Exploitation Process

Challenges and Nuances of Mobile Operating System Security

Understanding Ransomware: Mechanics, Impact, and Prevention

Critique of Cybersecurity Vendor Sales Strategies and Jargon

Key Questions to Ask Cybersecurity Vendors

Discussion on Huawei and National Security Concerns

Reflections on Edward Snowden's Actions and Impact

Recruiting and Empowering Talent in the Private Sector

Scaling a Company and the Importance of Execution

Final Advice on Cybersecurity Preparedness for Businesses

Offensive Cybersecurity

This pillar encompasses traditional hacking, ransomware, and intelligence agency operations. It exists largely because humans are generally poor at writing secure software and is driven by economic incentives.

Defensive Cybersecurity

This pillar focuses on protecting against cyberattacks, offering solutions like antivirus, anti-spyware, firewalls, and endpoint detection. The industry often presents these as fragmented, requiring businesses to cobble together multiple, often ineffective, solutions.

Faux Cybersecurity

This refers to activities like election interference or organized social media influence campaigns that are often categorized under cybersecurity but are not directly related to traditional computer security or network defense.

Zero-day Exploit

A vulnerability in software that is unknown to the vendor and the public, allowing attackers to exploit it before any patch or fix is available. These are highly valuable to attackers as they can bypass existing defenses.

One-click vs. Zero-click Attack

A one-click attack requires user interaction, such as clicking a malicious link, to compromise a device. A zero-click attack can exploit a device without any user action, making it extremely stealthy and dangerous.

Sandbox Escape

A technique used by attackers to break out of a restricted execution environment (a sandbox) where an application is designed to run safely. This allows them to gain broader access to the underlying operating system.

Privilege Escalation

The process by which an attacker gains higher-level access permissions on a computer system. This often involves moving from a standard user account to an administrative or even kernel-level access, effectively taking full control of the system.

Ransomware

A type of malware that encrypts a victim's data or locks them out of their systems, demanding a ransom (often in cryptocurrency) for decryption or restoration of access. It can also involve exfiltrating data to further extort the victim.

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Why did Matthew Holland leave his intelligence agency role?

He left because he perceived a ceiling on his growth and the group's vision, feeling that arbitrary limitations were placed on innovation, which was not an environment where he could continue to grow.

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How did Matthew Holland's first company, Linchpin, gain initial attention?

Linchpin made a splash by releasing a tool called 'Den Whip Atsiv' (Vista pooned in reverse) that demonstrated how to load an unsigned driver on Windows Vista, circumventing its mandatory driver signing feature, which Microsoft had heavily promoted as a security silver bullet.

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What are the primary ways attackers profile and exploit a target company?

Attackers initially profile online services, email addresses, and social media presence, then typically launch social engineering campaigns (like phishing emails) or brute-force passwords for basic email setups to gain initial access, then escalate privileges and potentially redirect finances.

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How does a sophisticated attack on a Windows machine typically unfold?

An attacker might send an email with a malicious link, exploiting the web browser to gain code execution. This is followed by a sandbox escape to break out of the browser's restricted environment and then a privilege escalation to achieve kernel-level execution, effectively taking full control of the operating system.

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Why is Android's security posture generally considered worse than iOS, despite its open nature?

While Android's fragmentation makes mass attacks harder, individual vendors often customize the OS and may miss critical security fixes from the main Android branch, making targeted attacks against specific Android versions more successful. iOS, having a uniform OS across devices, allows a single vulnerability to affect all devices.

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Why is ransomware considered easy to detect and stop by cybersecurity experts?

Ransomware typically has a very basic attack profile, making it relatively easy to identify and block with sophisticated on-host (endpoint) security solutions and proper cybersecurity tradecraft, though network-only monitoring solutions are insufficient.

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What questions should businesses ask cybersecurity vendors to genuinely assess their solutions?

Businesses should ask, 'How are you protecting my company?' and 'What happens when something goes wrong?' They should look for clear, straightforward answers that explain the actual protection mechanisms and incident response, rather than vague jargon like 'next generation,' 'seamless,' 'AI,' or 'machine learning.'

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What is Matthew Holland's stance on Huawei's involvement in critical infrastructure?

He agrees with banning Huawei from critical infrastructure due to documented ties to the Chinese government, past use of leaked intellectual property, and a fundamental lack of trust. He argues that the rapid pace of software development makes it impossible to reliably vet their code for backdoors or vulnerabilities.

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What is Matthew Holland's primary criticism of Edward Snowden's actions?

His main criticism is not just the exposure of potentially illegal surveillance but the mass release of legitimate, legal intelligence-gathering programs and techniques. This action damaged trust in agencies working to keep countries safe and exposed people's names, setting back critical operations.

1. Proactively Secure Your Company

If your company lacks a cybersecurity vendor or assistance, immediately seek one, as every company, regardless of size, is a target for attackers.

2. Prioritize Preventative Cybersecurity

It is significantly easier and cheaper to implement preventative cybersecurity measures and harden your systems against attacks than to react to a breach, a reality that businesses must accept.

3. Demand Holistic Cybersecurity Solutions

Seek a comprehensive cybersecurity solution that protects your data across all potential attack vectors, including endpoint, network, cloud, and IoT components, designed to adapt to future threats.

4. Don’t Fear Seeking Cybersecurity Help

When facing cybersecurity challenges, do not be afraid to ask for help from experts or vendors, as it’s crucial for protection.

5. Ensure Adequate Security Protections

Implement adequate security protections to avoid significant fines and legal obligations for reporting compromises in customer data, especially if it’s shown your company wasn’t taking the problem seriously.

6. Remove Barriers for High Performers

As a leader, remove bureaucratic barriers and quickly provide employees with the tools they need to excel, empowering them to produce amazing results.

7. Unleash Employee Potential

Empower employees by clearly stating goals and problems, providing necessary resources, and allowing them autonomy to solve issues, fostering an environment where they can unleash their full potential.

8. Align Team with Clear Company Goals

Ensure everyone in the company is aligned and moving in the same direction by being straightforward, frank, and honest about internal assessments and clearly communicating company goals to all employees.

9. Foster Team-Centric Entrepreneurship

Entrepreneurs should emphasize that success is a collective effort, not solely about their individual journey, by expressing appreciation for team members and reinforcing that ‘we’re all in this together’.

10. Cultivate Decisive, Confident Leadership

Develop the ability to make confident decisions and avoid paralysis by filtering out noise and focusing on what truly matters, which improves over time with practice.

11. Prioritize Aggressive Execution

In challenging times, prioritize aggressive execution over caution to gain a competitive advantage, understanding that turning great ideas into reality requires focused and effective implementation.

12. Share Knowledge Within Your Team

When you learn something new, share it with your colleagues to foster a strong team environment and mutual education.

13. Implement Multi-Factor Authentication

Use multi-factor authentication for email setups to prevent brute-force password attacks, which attackers use to gain access, profile your routine, and potentially execute financial redirection scams.

14. Limit Public Digital Footprint

Be aware that attackers profile targets by probing online services, identifying easily accessible email addresses on websites, and analyzing social media presence, so limit publicly available information.

15. Seek Problem-Solving Cybersecurity Partners

When choosing a cybersecurity vendor, look for partners who prioritize identifying and fixing your specific problems and helping you improve over time, rather than just selling a generic software solution.

16. Choose User-Friendly Cyber Solutions

Select cybersecurity systems designed for users without technical expertise, ensuring the solution works effectively even if the user doesn’t have a deep interest or background in cybersecurity.

17. Demand Guided Cybersecurity Action

Opt for cybersecurity solutions that provide clear, concise, and guided instructions on specific actions to take when an issue arises, rather than expecting users to research and implement complex technical fixes themselves.

18. Beware Cybersecurity Buzzwords

When evaluating cybersecurity vendors, be wary of buzzwords like ’next generation,’ ‘seamless,’ ‘AI,’ or ‘machine learning,’ as these are often red flags indicating sales jargon rather than substantive solutions.

19. Avoid Bundled Cybersecurity Overload

Do not fall for vendors pushing a multitude of disparate cybersecurity solutions as a single necessary package, as they often don’t work well together and are not all essential.

20. Choose Iterative, Future-Proof Solutions

Prioritize cybersecurity solutions that are iterative and engineered to handle future threats without relying on marketing buzzwords, as these indicate a more robust and adaptable defense.

21. Beware Cybersecurity Black Box

Be aware that the cybersecurity industry often operates as a ‘black box,’ where businesses may not fully understand what they are buying, which can be exploited by vendors.

22. Embrace Solving Hard Problems

Find enjoyment in tackling difficult problems, as this can be a strong motivator for entrepreneurial ventures and personal growth.

23. Pursue Impactful Entrepreneurship

When considering new ventures, choose to tackle significant, world-changing problems rather than simpler ones, as the effort required might be similar but the potential impact far greater.

24. Acknowledge Partner’s Support

Recognize and appreciate the crucial role your partner plays in your success, especially as a workaholic, as their support can be a significant factor in achieving your goals.

Everybody is a target at this point. Your company is not small enough to be off an attacker's radar. I have seen five-person companies. Actually, I've seen two-person companies attacked and hit.

Matthew Holland

The current state of the cybersecurity industry, to say it's a hard problem is an understatement. It is an unethical shit show, I would say.

Matthew Holland

The only true working cybersecurity solution is one that looks at it from where's your data. How are you going to be attacked across the board?

Matthew Holland

If somebody uses the word next generation, seamless, we'll stop everything. Yeah. AI, we've got machine learning, any of that, if any of that comes up, big red flags.

Matthew Holland

It's much, much easier and cheaper to be preventative and to harden your system and be ready for attacks.

Matthew Holland

A little part of me will die if he's pardoned.

Matthew Holland
Two-person companies
Smallest company size observed to be attacked Indicates that no company is too small to be off an attacker's radar.
2007 to 2018
Matthew Holland's first company (Linchpin Security) operational period Period of operation before its sale.
90 to 100 people
Number of employees at Linchpin Security when it was sold Globally, including a partner company.
December 2019
Matthew Holland's departure from the acquired company (Linchpin) Left a year after the company was sold.
Almost 100 people
Current number of employees at Field Effect Security Company is entirely self-funded to this point.
Six-figure fines
Potential fines for Canadian companies for customer data compromise Discussions pre-COVID-19 for companies not taking security seriously.
20 years
Years Matthew Holland has been in the cybersecurity industry His experience contributes to his perspective on ransomware sophistication.
15 years
Years Matthew Holland has been an entrepreneur Across two companies, witnessing the 'unleashing' process for employees.