From Dial-Up to AI: Lessons for Leaders to Stay Current or Get Left Behind

Episode Description

Technology has transformed dramatically over the past 30 years — from dial-up connections and floppy disks to AI tools that can rewrite how we work. The lesson is clear: leaders who don’t stay current risk getting left behind.

In this episode of Engineer Your Success, Dr. James Bryant sits down with Nathan Whittacre, CEO of Stimulus Technologies and author of The CEO’s Digital Survival Guide. Since 1995, Nathan has been helping businesses adapt to every major tech wave. He shares stories from his early days sending emails through university mainframes, to guiding companies through today’s AI-driven workplace.

Together, James and Nathan explore:

• Lessons learned from three decades of tech evolution — and how they apply today
• Why leaders must focus on ROI before adopting new technology
• How process-mapping prevents wasted effort and failed implementations
• The growing importance of cybersecurity and compliance for every business
• Practical ways engineering leaders can leverage AI as a tool, not just hype

Whether you’re leading a small team or a whole organization, this conversation will help you see how technology can serve as an asset — if you stay intentional, strategic, and current.

⏱️ Episode Timestamps

• 01:00 – Meet Nathan Whittacre– From founding Stimulus Technologies in high school to leading through today’s AI-powered workplace
• 04:00 – Lessons from 30 Years of Tech – How the industry evolved from Windows 95 to AI and what leaders can learn
• 06:00 – ROI Over Hype – Why leaders must set baselines and ask “why” before adopting new tech
• 09:30 – Process Mapping in Action – The “wasted reports” story and how to avoid automating the wrong work
• 12:30 – Writing The CEO’s Digital Survival Guide – Why leaders need trusted guides for technology decisions
• 18:00 – Cybersecurity & Compliance – The next big threats and how structure strengthens organizations
• 21:00 – Key Takeaway – Stay current with technology, or risk getting left behind

Connect with Nathan Whittacre

LinkedIn: Nathan Whittacre | Website: https://www.stimulustech.com/

• Resources
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