Richard Greenberg, a well-known Cyber Security leader, evangelist, advisor, and speaker, has over 30 years of management experience, including 15 years as a CISO. He is an ISSA International Distinguished Fellow and has been inducted into their Hall of Fame. He is president of the ISSA LA Chapter. Richard is the Founder and CEO of Security Advisors LLC, offering security risk assessments, software security testing, and penetration testing, allowing organizations to continuously assess their cyber risk posture and meet compliance requirements.
In a recent interview with CIO Magazine, Richard Greenberg discussed his experience with IT and Cybersecurity. He shared his views on the entrepreneurial landscape, innovation, decision-making, and many more.
What are the most exciting trends currently reshaping the field of IT and Cybersecurity, and how should leaders adapt?
The landscape of IT and cybersecurity is changing rapidly, shaped by several technological advances and shifts in regulations. One of the biggest drivers is AI. We’re seeing its application moving beyond basic tasks and into critical areas like advanced threat detection and automated response systems. This creates both an opportunity and a challenge, as the same tools that enhance security can also be used by cybercriminals for more sophisticated attacks. As leaders, we must be proactive in adopting AI, but also prepare for AI-driven threats that might evolve faster than we can predict. This means not only integrating AI but setting up frameworks for its governance and ethical use.
Another key change is the dissolution of the traditional security perimeter. With cloud computing, edge devices, and remote work, the idea of a “secure boundary” no longer applies. We’re now living in a world where Zero Trust is becoming a necessity, where constant verification is built into every part of the organization. This doesn’t just mean technical changes; it’s a mindset shift that demands cultural alignment as well. For leaders, this means developing a strategy that’s as much about people as it is about technology.
There’s also the growing concern around supply chain security. Given the rise in interconnected systems, we’re seeing the vulnerabilities in third-party networks. Security can no longer be siloed within an organization but must extend to include third-party risk management. We’re seeing practices like Software Bills of Materials (SBOMs) become more essential to keep track of the software supply chain and reduce the risk of compromise.
Lastly, cyber resilience is becoming the new standard. It’s not just about prevention anymore, but about being able to respond to and recover from attacks quickly. Leaders need to focus on creating systems that can detect threats early and adapt quickly to new risks.
How do you approach decision-making when leading through uncertainty?
When leading through uncertainty, I focus on clarity of vision while maintaining flexibility. The world is constantly changing, and situations can evolve quickly. The key to navigating uncertainty is not relying solely on predictive models or gut instinct, but instead, having a clear sense of the long-term objectives and being willing to adapt the tactics that get us there.
During times of ambiguity, I lean on data-driven insights as much as possible, but I also understand the importance of intuition. Business decisions often have a human element that cannot be quantified. I trust my team’s collective experience and insights, making sure we remain aligned with our mission while being agile enough to pivot when new information presents itself.
A big part of decision-making in uncertain times is embracing the notion that failure is a part of the process. Every setback or wrong turn provides data that helps us make better decisions next time. I ensure my team understands this, which fosters an environment where people are not afraid to take calculated risks, knowing that learning and iteration are just as important as success.
How do you differentiate between meaningful innovation and change for the sake of change?
For me, the distinction between meaningful innovation and just change for the sake of it comes down to purpose and impact. Meaningful innovation solves real-world problems or makes a tangible improvement. It’s driven by customer needs, market gaps, or a specific pain point that we’re working to address. It’s always about improving something—whether that’s enhancing user experience, increasing efficiency, or creating something entirely new.
On the other hand, change for the sake of change often arises from external pressure—keeping up with competitors or following a trend. This kind of change may seem exciting on the surface, but it doesn’t always address any fundamental issue. It can even lead to unnecessary complexity, diverting focus away from the core mission. When innovation doesn’t have a clear purpose, it can create confusion and distract from what really matters.
The best innovations are the ones that align with strategic goals, solve a problem, and add measurable value. For me, the question always comes down to: How does this make things better, and for whom?
How do you see technology — such as AI, automation, or digital transformation — impacting the entrepreneurial landscape in the next five years?
The next five years will be crucial for entrepreneurs, and technology will be their greatest ally. AI and automation are transforming the way businesses operate, especially in terms of efficiency and scalability. For example, AI can help entrepreneurs access insights faster than ever before, making it easier to identify opportunities and make data-backed decisions. With automation, businesses can streamline operations, allowing small teams to focus on high-level strategy rather than getting bogged down with repetitive tasks.
Digital transformation is opening up entrepreneurship to a wider audience. It’s no longer necessary to have huge capital to start a tech-driven business. The cloud, SaaS platforms, and AI tools give anyone with an idea the tools they need to launch and scale a business from anywhere. We’re seeing more entrepreneurs able to compete globally with minimal upfront costs, which is creating a more diverse and inclusive entrepreneurial ecosystem.
However, the growing reliance on these technologies also means entrepreneurs will need to be vigilant about security and ethics. As businesses become more digital, the risks associated with data privacy and cybersecurity are higher. Entrepreneurs will need to stay ahead of these challenges, ensuring they are equipped with the knowledge and tools to protect their companies and customers.
In short, AI and automation will enable more entrepreneurs to scale faster and smarter, but they must also be conscious of the ethical implications and potential pitfalls that come with emerging technologies.
For organizations aiming to foster a more entrepreneurial culture internally, what best practices or mindsets are essential for success?
Building an entrepreneurial culture within a company requires shifting from a traditional mindset to one that values creativity, autonomy, and risk-taking. One of the key mindsets is empowering employees to take ownership of projects and ideas. When people feel trusted to innovate and experiment, they take more initiative and are more likely to contribute to the organization’s growth in unique ways.
A growth mindset is also essential. Employees should be encouraged to learn from failure rather than shy away from it. The best innovations come from taking risks, and if people feel they can fail without fear of retribution, they’re more likely to think outside the box.
Cross-functional collaboration is another important practice. Breaking down silos within an organization allows people to share ideas and solutions across departments, leading to greater creativity and faster problem-solving. The more teams collaborate, the more innovation flourishes.
Lastly, celebrating small wins is crucial. Entrepreneurial organizations understand that progress, no matter how incremental, adds up. Acknowledging achievements—even if they seem small—helps maintain momentum and keeps everyone focused on the bigger picture.
What advice would you offer to the next generation of innovators and entrepreneurs who are just getting started?
My biggest piece of advice for new entrepreneurs is to stay curious and never stop learning. The best innovations come from constantly asking questions and seeking out new perspectives. Don’t be afraid to challenge assumptions, and always look for ways to improve existing ideas or processes.
Another key point is to focus on solving real problems. Starting a business isn’t just about coming up with the next big idea; it’s about addressing a need that people have. Make sure you understand your customers deeply and tailor your product or service to their specific pain points.
Also, embrace failure as part of the journey. You’re going to face setbacks—everyone does—but what matters is how you respond. Every failure is an opportunity to learn and grow. It’s not about avoiding mistakes but about being resilient enough to bounce back and keep moving forward.
Lastly, build a support network around you. Surround yourself with people who believe in your vision, challenge you to think bigger, and provide honest feedback. Entrepreneurship can be a lonely road, but having the right people around you can make all the difference.
What keeps you inspired during the inevitable setbacks that come with ambitious goals?
During setbacks, I draw inspiration from remembering why I started. Having a clear sense of purpose helps me stay grounded when things get tough. Whether it’s a product vision, a problem I’m passionate about solving, or a personal goal, that vision keeps me focused on the long-term.
Setbacks also remind me of the learning opportunities they present. Every challenge is a chance to reflect, adjust, and improve. I think of setbacks not as failures, but as feedback—information that helps me refine my approach and get closer to success.
I also find inspiration in the people around me. My team, mentors, and even friends provide encouragement and perspective when I need it most. Their belief in the mission motivates me to keep pushing forward, even on tough days.
Lastly, resilience is a big part of staying inspired. Setbacks are part of the entrepreneurial journey, and each time I overcome one, I come out stronger and more determined.