Bobby Acri is a cybersecurity analyst based in Winnetka, Illinois, whose career has been shaped by curiosity, discipline, and a long-term view of risk. From an early age, he was drawn to problem-solving and systems thinking, often more interested in how things failed than how they appeared to work on the surface.
That mindset led him to study information security and computer science, where he built a strong foundation in network architecture, operating systems, and applied cryptography. He learned early that strong security starts with understanding how systems are designed and how people actually use them.
Bobby began his professional career in IT support and systems administration. These roles gave him hands-on exposure to real enterprise environments and everyday user behavior. Over time, he noticed that many security issues came not from malicious intent, but from unclear systems and small gaps in the process. That insight pushed him toward cybersecurity.
As he transitioned into cybersecurity roles, Bobby focused on threat monitoring, incident response, and security assessments. Today, as a cybersecurity analyst, he works closely with cross-functional teams to detect risks early, investigate anomalies, and strengthen defenses before problems escalate.
Known for his calm decision-making and methodical approach, Bobby emphasizes documentation, learning from near misses, and continuous improvement. Outside of work, he enjoys endurance running along Lake Michigan, strategic board games, and reading history and behavioral science. These interests reflect the same principles that guide his work: patience, preparation, and thoughtful analysis.
What is your typical day, and how do you make it productive?
My day usually starts early. I review alerts, logs, and any overnight activity to see if anything needs attention. I look for patterns, not just individual events. Productivity for me comes from prioritization. I decide early what actually matters and what can wait. I also block time for documentation and review, because writing things down forces clarity and prevents repeated mistakes
How do you bring ideas to life?
I test ideas on a small scale first. In security, ideas that sound good can create risk if rolled out too fast. I start with one system or one process, measure the outcome, then adjust. If it improves visibility or reduces noise, it stays. If it adds complexity, it goes.
What’s one trend that excites you?
I’m encouraged by the growing focus on proactive security instead of reactive fixes. More teams are investing in detection engineering and prevention rather than waiting for incidents. That shift reduces long-term risk.
What is one habit that helps you be productive?
Consistent review. I look back at near misses and closed incidents regularly. Even small events usually reveal gaps worth fixing.
What advice would you give your younger self?
Slow down and document more. Early in my career, I solved problems quickly but didn’t always record the process. That made the same issues reappear later.
Tell us something you believe almost nobody agrees with you on?
I think most security problems are caused by unclear systems, not bad actors. When people understand tools and expectations, risk drops significantly.
What is the one thing you repeatedly do and recommend everyone else do?
Review near misses. Incidents that almost happened often provide more useful insight than confirmed breaches.
When you feel overwhelmed or unfocused, what do you do?
I step away from screens and go for a run along Lake Michigan. Physical movement resets my thinking and helps me return with better focus.
What is one strategy that has helped you grow your business or advance in your career?
Learning how systems interact. My time in IT support taught me how users, infrastructure, and processes connect. That context made my transition into cybersecurity much smoother.
What is one failure in your career, how did you overcome it, and what lessons did you take away from it?
Early on, I ignored documentation during a system change. Months later, no one remembered why decisions were made, including me. I fixed it by rebuilding the process and committing to documentation going forward.
What is one business idea you’re willing to give away to our readers?
Create a shared incident review template that focuses on process gaps instead of blame. It improves learning and reduces repeat issues.
What is one piece of software that helps you be productive? How do you use it?
A basic note-taking app. I log decisions, assumptions, and follow-ups daily. It becomes a personal knowledge base.
Do you have a favorite book or podcast you’ve gotten a ton of value from and why?
Books on history and behavioral science. They explain patterns that repeat over time, which is useful in understanding risk. For example, Thinking, Fast and Slow by Daniel Kahneman shows how human behavior and incentives repeat across different eras.
What’s a movie or series you recently enjoyed and why?
I enjoy slow-paced series that focus on systems and decision-making. They reward attention and patience. Shows like Succession, where power dynamics and long-term positioning matter more than action, are a good example of what I mean.
Key learnings
- Strong security comes from preparation, not reaction.
- Near-miss analysis reveals valuable insight into system weaknesses.
- Documentation prevents repeated mistakes and knowledge loss.
- Human behavior plays a major role in cybersecurity risk.