Colin shares how his leadership has evolved over 12 years at IHG and the additional leadership skills he's developed through board service, his own curiosity, and lessons from his support system and mentors. He discusses using self awareness to overcome self doubt, his strategies for public speaking and building relationships, and the importance of feedback. Colin talks about wellness, something people don't know about him, and the important impact of knowing everything will turn out okay.

Clarity, Discipline, and Global Perspective in Technology Leadership

Duane Overgaard’s leadership journey is grounded in a powerful combination of operational depth and global systems expertise. His formative years at Hilton provided a foundation in how hotels operate and how commercial systems function in practice, while his experience at Sabre expanded his perspective on connectivity, distribution, and the broader travel ecosystem. Together, these experiences shaped an end-to-end understanding of how the industry works, positioning him to lead at DerbySoft.

As Divisional CEO, Overgaard is known for a leadership style rooted in clarity, discipline, and trust. He believes direct communication is essential, particularly in global environments where ambiguity can slow execution, and he prioritizes aligning teams around what truly matters. His approach is grounded in listening to his team, customers, and the realities of the market, with a focus on translating ideas into practical, scalable solutions while maintaining humility and accountability.

Notable Quotes

• “Clarity is a leadership responsibility—be direct so teams can move faster.”

• “Ideas are everywhere—execution is what actually matters.”

• “I’ve never forgotten where I came from—treat people the right way.”

• “Segmentation is gone—everything is visible in today’s market.”

• “AI is only as strong as the content behind it.”

Closing Reflection

Overgaard’s journey reflects leadership grounded in clarity, discipline, and trust. His experience demonstrates how operational depth and global perspective shape effective decision-making. By focusing on execution and alignment, he creates consistency across complex environments. His approach reinforces that leadership is built through experience, listening, and accountability.

His story highlights the importance of combining experience with continuous learning. By staying focused on what matters and translating ideas into action, leaders can navigate complexity. He emphasizes respect, clarity, and practical thinking in every interaction. Through discipline and alignment, teams can move faster and perform better. Ultimately, his journey shows that effective leadership is both grounded and forward-looking.

I recently sat down with Chris Hemmeter, Co Founder and Managing Director of Thayer Investment Partners, and one part of our conversation stood out because it applies to all of us, not just entrepreneurs.

Chris pushed back on the idea that there is a perfect formula for success. Instead, he shared three qualities he consistently sees in high potential leaders:

Integrity: A commitment to truth and accuracy, even when the facts are not as strong as you would like them to be. People can feel that honesty, and it builds the connection necessary to do something together.

Persistence: This is not about long hours alone, but about tenacity and the willingness to take multiple at bats. If you do not get up and swing again, you will never figure it out.

Progress: A relentless focus on moving forward. Every leader should be able to show what they have accomplished in the last 90 days. Momentum is the ultimate indicator of excellence.

What struck me is how simple, and how difficult, these are to practice consistently. We also explored why focus can be a defining inflection point, how to avoid getting stuck, and what it really means to be comfortable in your own skin.

If you are working toward something meaningful, I think you will find this conversation both practical and thought provoking.

Adi’s career demonstrates that lasting success comes from deliberate choices, not shortcuts. He calls us to reinvent ourselves from within, advocate for our value with facts and preparation, and invest in relationships that deepen over time. His advice to seek honest mentors — people who tell you the truth and challenge your blind spots — is a reminder that growth requires honest counsel. Play the long game, because the compounding side of it is very hard to replicate.

Curiosity, Adaptability, and Leadership Across Hospitality’s Evolving Landscape

Andrew Rubinacci’s career reflects a journey shaped by curiosity, adaptability, and a willingness to embrace unexpected opportunities. Beginning in operations with a goal to become a general manager, he moved into revenue management after being identified for a new initiative, becoming the first revenue manager at IHG. His path expanded into distribution, digital, and e-commerce roles across major organizations, including Bristol, Maristar, and IHG, where he led early OTA negotiations and gained global experience in Europe.

Across brand, ownership, management, and now technology at FLYR, Rubinacci emphasizes understanding the three core stakeholders in hospitality—brand, owner, and manager—each with competing priorities that shape decision-making. He highlights the contrast between large organizations requiring rigor and alignment, and smaller or integrated businesses that can move quickly. In technology and AI, he stresses staying current through networks, continuous learning, and adaptability, noting that innovation often comes from those able to move fast without legacy constraints. His perspective underscores that while technology is transforming the industry, success still depends on understanding fundamentals and navigating complexity.

Notable Quotes

• “You just work hard. Stay true to yourself.”

• “Speed sometimes helps you win.”

• “You should do revenue management.”

• “You can't get too far behind because it's changing that rapidly.”

• “Work your ass off in your twenties.”

Closing Reflection

Rubinacci’s journey reflects leadership grounded in adaptability, resilience, and continuous learning. He demonstrates how diverse experiences across operations, commercial strategy, and technology shape a broader perspective. By embracing change and staying curious, he navigates complexity with clarity. His approach highlights that success comes from understanding both people and systems.

His story reinforces that careers are rarely linear and often shaped by unexpected opportunities. By working hard, staying curious, and building relationships, new paths emerge. He encourages future leaders to seek knowledge, create opportunities, and remain adaptable. As technology reshapes the industry, those who evolve will remain relevant. Ultimately, his journey shows that growth comes from action, curiosity, and a commitment to learning.

Leonard discusses his lifelong hospitality career journey, how mentors from his career have shaped his current leadership, and his mantras that guide him. He shares the importance of nurturing relationships, how his curiosity has influenced him, and how he has developed new skills while evolving many existing ones. Leonard talks about the future of hospitality as seen through the eyes of hospitality school education, one thing about him that would surprise everyone, and his advice to his younger self.

Harmeet’s insights reinforce that success is built through systems, support, and a commitment to continuous improvement. Her approach encourages leaders to empower others by providing structure and guidance rather than relying solely on motivation. She reminds us that respect and strong relationships are foundational to sustainable growth. Her perspective on learning highlights the importance of staying curious and adaptable in a changing world. Ultimately, her message is clear: with the right mindset and support, challenges can always be worked through and transformed into progress.

For decades, Jeff Weinstein told the stories of others. This time, it’s his story.

A deeply personal conversation about leadership, integrity, fatherhood, and the perspective gained from raising a son with autism. A reminder that success is one thing, but who we become along the way matters far more.