What does it take to transition from commanding 350 people in military aviation to flying commercial aircraft while simultaneously building technology companies?
In this episode of The Digital Diaries, Peter Woods sits down with Rob Wright, a former U.S. Army Special Operations Aviation commander, commercial airline pilot, and entrepreneur. Together they explore leadership under pressure, making difficult decisions, the realities of entrepreneurship, and how AI is changing the way businesses operate.
Rob shares lessons from military leadership, explains why execution beats ideas every time, and discusses how his company, Waffl, helps organisations build AI-powered software that solves real business problems—not just shiny technology.
Whether you're leading teams, building a startup, or trying to understand where AI creates genuine business value, this conversation is packed with practical insights.
Why military leadership is built on trusting the people around you
The biggest adjustment from Army command to commercial aviation
Why time—not money—is your most valuable resource
How Rob balances multiple businesses alongside a flying career
The story behind Waffl and building custom AI solutions for businesses
Why AI alone isn't a competitive advantage
The difference between automation and creating real business value
How businesses can identify hidden inefficiencies in their operations
Why execution consistently beats great ideas
The importance of validating customer demand before building a product
Great leaders don't make decisions in isolation—they rely on experienced teams and proven processes.
AI should create new value or remove unnecessary costs, not simply make existing tasks slightly faster.
Every business has operational bottlenecks that become opportunities when they're properly measured.
Owning your own software and intellectual property can become a long-term competitive advantage.
Entrepreneurs often overestimate ideas and underestimate execution.
Positive feedback doesn't equal paying customers—market validation is everything.
"The best ideas don't win. The best execution does."
"Time is the most valuable resource."
"You're not really using the power of AI unless you're creating new value for your company or eliminating unnecessary spend."
"There's a big difference between someone saying your idea sounds great and someone writing you a cheque."
Rob Wright is a former U.S. Army aviation commander, commercial airline pilot, and entrepreneur. Alongside his aviation career, he helps organisations build custom software and AI solutions through Waffl, focusing on practical technology that delivers measurable business outcomes.
LinkedIn: Robert Wright
Website: GoWaffl.com
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