Episode 109 - Honest Security with Jason Meller

In this episode of Hacker Valley Studio podcast, Ron and Chris are joined by Jason Meller, Founder, and CEO of Kolide. Jason has over 10 years of experience in managing and leading security organizations. Jason’s interest in technology and cybersecurity began in the 1990s when he began programming in Visual Basic and building AOL Instant Messenger bots. Building offensive tools accelerated Jason’s interest in defending networks and helped him learn how much honesty plays part in building security solutions.  Jason mentions that the security monitoring software at most organizations have the same functionality as spyware or surveillance tools. In addition, these tools are designed to scrutinize all the actions that occur on a device. COVID-19 has increased the rate of organizations going through a digital transformation; as a result, users at an organization are not in a cubicle but at their home. This could mean that security teams have an extremely elevated level of access to devices without transparency as to what is being monitored to protect an organization. This is why Honest Security was created - to create a transparent relationship between security teams and end-users.  Jason has collaborated with Jesse Kriss from Netflix who is actively working towards incorporating user-focused security. Jason describes that organizations should build a culture based on trusting users, treating them like adults, giving them the tools that they need to do their job, and not treating them as suspects from day one. Instead, organizations and security teams should seek teachable moments by giving recommendations and educating users. Throughout the episode, Jason describes situations that involve users and security team members maneuvering around security tooling obstacles to get their job done. Since working at home, traditional tools have created friction in the user experience. For instance, not having the ability to use USB ports on work devices, disabling corporate VPN to watch a YouTube video, and having to create a ticket to install software to help them with their job. When this friction is created, users will resort to using their personal devices for work activities and miss the opportunity to benefit from security. In some cases, there are “evil” applications found on a device created by a user - but often bad applications installed by users are Chrome extensions or helper utilities that are sending browsing history to a marketing firm. In the Honest Security manifesto, there’s a section on empathetic intelligence, Jason describes this concept as thinking of the daily life users, thinking of what challenges are users attempting to solve in their workflow, and what part of that workflow could pose a risk to the organization. An example of this would be a security team member trying to empathize with someone who is a developer- and thinking of their daily workflow. When empathizing the security team may realize that the developer is attempting to fix issues on a production application. While fixing the production application, the developer may try to bring a copy of the application database to their local device. Creating a local copy of the database could pose a security risk the copy of the database is not deleted in a reasonable time or the user has their device auto-backup folders to their corporate or personal cloud storage solution (ie. Google Drive). Creating education for avoiding this mistake is a prime example of empathic intelligence when practicing Honest Security. As the episode progresses, Jason goes into depth and explains more tenants of Honest Security - The goal is not to give unlimited power to the user or security team but to enable everyone to be in the position to make the right decisions and give appropriate recommendations. When consequences are articulated, users can understand that when maneuvering around security tools can pose a risk to their device and organization. Ie) disconnecting from