248 - Why Simplicity Wins - James Elliman’s Blueprint for Small Business IT Leadership

James Elliman planned to be a Marine officer, following a family legacy of military service. But a last-minute medical disqualification forced a hard pivot. Instead of serving in uniform, he leaned into his lifelong love of tech and launched Elliman Technologies to simplify IT for small businesses.

In this episode, James shares how leadership isn't just about titles—it’s about clarity, adaptability, and serving others, even when plans fall apart. He opens up about the early days, charging $14 an hour and fixing printers via Facebook. Over time, he learned how to price value, not time, and transitioned to a scalable MSP model. That shift not only stabilized his business—it turned him into a more strategic leader.

James discusses how overwhelming tech stacks taught him the importance of standardization, the role of empathy in customer service, and why flexible pricing models build trust. He also unpacks the chaos from recent tech outages, and how proactive leadership helped clients stay calm while the internet burned.

Want to learn more about James Elliman's work? Check out their website at https://ellimantech.com.

Connect with James Elliman on LinkedIn at https://www.linkedin.com/in/james-elliman-a7667212a/.

Think you'd be a great guest on the show? Apply at https://podcast.allies4me.com/podcast-guest/.

Want to learn more about Craig Andrew's work at allies4me? Check out his website at https://allies4me.com/.