Leadership Rooted in Innovation and Real-World Experience

David Mililli’s journey into hospitality began unexpectedly while he was in business school. After a friend suggested he “go to any hotel” to find work, he rode his bike to the downtown Hyatt in Pittsburgh and was hired as a union busboy - a moment that sparked his love for the hotel environment. Though he knew food and beverage wasn’t for him, he felt drawn to the energy inside hotels. This early experience led him to FIU, then to New York, where he became one of the youngest general managers in the city.

The rise of the internet transformed his career path. After joining an early startup that ultimately failed, Mililli and his partners pivoted and built one of the first booking engines for independent hotels, helping properties take online bookings during a time when many doubted consumers would ever enter their credit cards on the internet. He later led several companies, including Open Hospitality and Pegasus, while focusing on innovation and helping hotels drive more direct business. Throughout, he relied on curiosity, industry insight, and a willingness to embrace new ideas long before they became mainstream.

Notable Quotes/Highlights 

• “Surround yourself with… people that you can trust and you know that are gonna have your back and support you.”
• “You spend all this time with a founder… and they just don’t take the advice.” (a reminder of the humility required to listen and grow)
• “Nobody’s ever gonna put their credit card on the internet… and I just saw past that.” (reminder that we must think out of the box)
• “AI is really gonna help enhance, in many cases, the guest experience and the staff’s experience.”
• “If you keep your intelligence over your emotions, you’ll always be successful.”

Closing Reflection

Mililli’s journey demonstrates the power of belief, resilience, and the courage to embrace new ideas before others see their potential. His reflections remind us that great leadership requires listening deeply, staying open to change, and helping others grow by understanding their aspirations. He reinforces that innovation is not just about technology. It is about people, curiosity, and the willingness to challenge old assumptions. His story encourages every leader to take chances, trust their instincts, and remain humble enough to learn along the way. It’s a powerful reminder that with purpose and perseverance, each of us can shape a meaningful and impactful path forward.