In this episode of "The Free Lawyer" podcast, host Gary interviews Valentina Flores, CEO of Red Sentry. Valentina shares her journey from law enforcement to leading a proactive cybersecurity company, emphasizing the importance of ethical hacking and prevention for law firms. She offers practical tips—like enabling multi-factor authentication, limiting data access, and preparing response plans—to help lawyers protect sensitive information. Valentina also discusses the collaborative nature of cybersecurity, the human element in defense, and aligning security practices with core values, making cybersecurity accessible and actionable for legal professionals.

Valentina Flores is the CEO and Co-Founder of Red Sentry, a proactive cybersecurity company that breaks into your network, so hackers never get the chance. Before protecting companies, she served as a detective on joint federal task forces, tracking cybercriminals through digital back-alleys. Now a public speaker on hacker psychology, a two-time award-winning cybersecurity leader, and a fierce advocate for women in tech, Valentina is redefining what leadership looks like in the industry, championing smarter and more accessible security for all.

Transition from Detective to Cybersecurity (00:01:33)

What is Penetration Testing? (00:02:56)

Success Rate and Client Vulnerabilities (00:03:35)

Understanding Hacker Psychology (00:05:30)

Why Law Firms Are Targets (00:06:38)

Triggers for Law Firms to Seek Help (00:07:46)

Compliance vs. Proactive Security (00:09:09)

Human Element in Cybersecurity (00:10:16)

Making Clients Comfortable with Ethical Hacking (00:11:55)

Emerging Threats and the Future of Cybersecurity (00:13:25)

Cybersecurity for Small and Medium Businesses (00:14:43)

Diversity in Tech and Cognitive Diversity (00:16:37)

Awards and People-First Leadership (00:17:27)

Leadership in Cybersecurity vs. Traditional Business (00:18:20)

Role of Coaching and Mentorship (00:19:28)

Annual Testing and Follow-Up (00:20:21)

Prioritizing Cybersecurity in Law Firms (00:21:13)

Collaboration vs. Competition in Cybersecurity (00:22:17)

Top Three Cybersecurity Actions for Lawyers (00:23:29)

First Steps for the Unprepared (00:25:39)

What is Penetration Testing? (Clarification) (00:26:39)

Freedom and Work-Life Balance (00:27:06)

Aligning Practice with Values (00:27:51)

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