Gilad Berenstein
Artificial Intelligence Strategist, Entrepreneur, and Investor Shaping the Future of Travel and Consumer Technology
- AI entrepreneur and venture capital investor with three decades of technology leadership
- Founder and Managing Partner of Brook Bay Capital, an AI-focused investment firm
- Founder and CEO of Utrip, the world’s first AI-powered trip planning company
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About Gilad Berenstein Orenstein
Download ProfileGilad Berenstein is an AI entrepreneur, Board Director, and Venture Capital investor with three decades of experience at the intersection of technology, travel, hospitality, and lifestyle businesses. Based in Seattle, Gilad leads Brook Bay Capital, an AI-focused investment firm backing category-defining companies across travel, hospitality, fintech, and experiential consumer platforms. He serves on the boards of both large, established organizations and high-growth startups, including Virtuoso, Faye, Mindtrip, and ResortPass, and advises CEOs and institutional Investors navigating technological disruption, platform strategy, and long-term growth.
Gilad is widely regarded as one of the industry’s leading thinkers on artificial intelligence, personalization, and what he has termed the “Great Commoditization”; the structural shift reshaping competitive advantage, product differentiation, and power dynamics across industries. His perspective is grounded not in theory alone, but in operating experience: he founded Utrip in 2011, the world’s first AI trip-planning company, which helped more than 200 million travelers and pioneered the first large-scale integrations of AI into many global hospitality brands. Earlier exposure to AI through his father, a machine-learning pioneer in the 1990s, shaped a lifelong focus on applying advanced technology in practical, human-centric ways. In addition to his board and investment work, Gilad is a frequent keynote speaker at major global conferences (including Skift, Phocuswright, Arival, Forbes Travel, etc.), co-hosts the Travel Tech Insider podcast, and mentors founders through platforms such as Plug and Play.
Known for strategic nuance, long-term thinking, and calm leadership in moments of change, Gilad brings boards a rare combination of AI depth, operating experience, and sector-specific insight. Helping organizations build resilient advantage in an increasingly intelligent, dynamic economy.
Video Gallery
Gilad Berenstein: Ask Me Anything Travel Investment Outlook
Gilad Berenstein: Aigentic AI for Travel and Hospitality CEOs and Business Owners. At Virtuosos Euro & UK Forums 2026
Gilad Berenstein: The Investor View
Gilad Berenstein: Ask Me Anything Travel Investment Outlook
Gilad Berenstein: Aigentic AI for Travel and Hospitality CEOs and Business Owners. At Virtuosos Euro & UK Forums 2026
Gilad Berenstein: The Investor View
Speech Topics
Download Topics- AI for (non-technical) Business Leaders and CEOs – all about the times we are in, the impact on business strategy and leaders, Mental Models, and more. Versions of this have been my most requested speech over the past year. This is industry agnostic and focused on senior leaders, owners, CEOs, and the like.
- Innovation Thinking & Mental Models in the Age of AI – this is a similar topic but a bit broader and typically requested when there are more commercial leaders in the audience.
- AI in Travel & Hospitality – this is probably my second most given set of talks over the past year. At Utrip, I built the world’s first AI Travel Platform and had most of the largest travel brands as clients, so this is one I am asked for a lot within the industry. A brief history of travel tech, how we got here, where we should go from here, and what I am paying attention to.
- Gilad’s Mental Models – this is often for more sophisticated audiences who already have a strong AI framework. This is digging into some of the theses I (and some of my friends) write about. Much deeper thinking about how the new reality can be utilized within business.
- The Impact of AI on _____ – in panels and short talks I have been asked to play a futurist role and try to help leaders imagine how the Great Commoditization is going to impact their sector or business. I have done this in Finance, Real Estate, Retail, Lifestyle, and similar industry sectors.
- Venture Capital & Startups – this is not a talk I give very often anymore, but in the early 2020s I was hired a few times to help traditional industries understand how Venture Capital, the Startup Ecosystem, and the Innovation Economy work.
- Big Questions for the AI Age – this is an overview or survey of many of the key ethical questions faced by business leaders and society in this age that I coined as the Great Commoditization of AI.
- AI History – this is a short talk that is often combined with other topics about the history of AI, how we got here, and the major questions created by the rollout of AI into every element of Human Life.
- AI Ethics for Business & Society – this is a version of the first talk narrowly focused on the specific questions faced by CEOs, politicians, and similar leaders in society.
- Consciousness, Sentience, & Intelligence – this is for people who really want to nerd out and dive deep into the philosophy of AI and the future of the human experience. This is more for academic and intellectual events than business-focused events.
Related Links
Travel Tech Insider: Gilead Bernstein
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