Glenn Fogel

CEO of Booking Holdings, leading its strategic expansion into a multi-vertical travel platform with a core focus on AI.

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Appeared in

Discussed in

Key positions and views

Generative AI represents a fundamental, industry-redefining shift for travel, enabling a proactive, automated 'connected trip' experience that will function as a personal travel advisor [11, 25].

Technological complacency is an existential threat to established businesses. Leaders must be willing to disrupt their own models to avoid the fate of companies like Blockbuster, which recognized the threat from Netflix but failed to act [6].

Successful international acquisitions require empowering local leadership and avoiding the forced integration of a US-centric corporate culture, as demonstrated by the successful acquisition of Booking.com [8].

Strategic diversification is critical for sustained growth. The company's evolution from a hotel-only agency to a multi-vertical platform with its own payments infrastructure was a necessary step to build a more resilient and comprehensive business [15, 22].

Delivering exceptional long-term shareholder value, such as a 30% CAGR over 25 years, sometimes requires making extremely difficult short-term decisions, including significant workforce reductions during a crisis [14, 16].

Podcast consensus on Fogel

Points of consensus

▶Both sources highlight Glenn Fogel's belief that AI is the next major frontier for the travel industry, specifically mentioning the launch of an 'AI trip planner' on Booking.com to create conversational itineraries [1, 20].Apr 2026

▶Fogel consistently states that Booking Holdings has been utilizing machine learning for over a decade, indicating it's a long-standing part of their technology stack, not just a recent development [5, 17].Apr 2026

▶Across both appearances, Fogel articulates a clear vision for the future of travel centered on a sophisticated, AI-powered personal travel advisor that can proactively manage and adjust a user's entire trip [21, 25].Apr 2026

▶Fogel emphasizes the development of AI that can automatically and proactively adjust a traveler's itinerary based on real-time data like weather, a concept he explains in detail in both podcasts [4, 25].Apr 2026

Points of debate

▶Fogel presents a narrative of immense, long-term financial success, citing an 800x stock price increase and a 30% CAGR over 25 years [16, 18], which contrasts sharply with the drastic decision to lay off 25% of the company's workforce during the COVID-19 pandemic [14].Apr 2026

▶There is a contrast between the historical 'hands-off' acquisition strategy that empowered local teams to operate independently [8] and the current strategic push towards a deeply integrated, multi-vertical 'connected trip' platform [15, 25].Apr 2026

▶Fogel's forward-looking focus is on sophisticated, generative AI creating a 'connected trip' [25], which stands in contrast to his acknowledgment that a key historical differentiator was a much simpler, yet highly effective, strategy of being an early adopter of Google ads [24].

▶The company's history shows a tension between high-risk, high-reward ventures, such as its 1999 IPO that led to a $15 billion valuation followed by near-bankruptcy [10, 13], and its current status as an established market leader making strategic, long-term investments in payments and AI [22, 4].

Key themes

▶AI as the Next Frontier in TravelApr 2026

Fogel consistently frames Generative AI as a revolutionary force poised to transform the travel industry from a transactional booking process into a seamless, 'connected trip' experience. He details specific product launches like AI trip planners and envisions a future where an AI acts as a proactive, personal travel agent for every user [1, 11, 25].

Booking Holdings is betting its future growth on becoming an AI-native company, moving beyond its legacy in search and aggregation to create a new competitive moat based on personalized, automated travel management.

▶Strategic Evolution from Agency to PlatformApr 2026

Under Fogel's leadership, the company has deliberately evolved from a simple hotel agency model to a comprehensive, multi-vertical travel platform. This includes integrating flights, car rentals, and attractions, and crucially, building a large-scale payments program to control the transaction from end to end [15, 22].

This strategic shift increases customer touchpoints and lifetime value while capturing more of the travel ecosystem's revenue, transforming the company from a mere intermediary into a central hub for travelers.

▶Learning from Corporate HistoryApr 2026

Fogel frequently uses historical business cases to illustrate his strategic principles, citing Blockbuster's failure to adapt to Netflix as a cautionary tale against complacency [6]. He also reflects on Priceline's own near-bankruptcy after its IPO and the successful 'hands-off' acquisition of Booking.com to inform his current leadership decisions [8, 13].

Fogel's leadership style is heavily influenced by a 'student of history' mindset, suggesting a focus on long-term resilience and adaptability over short-term trends.

▶Resilience Through Extreme Volatility

Fogel's narrative highlights a history of navigating extreme market cycles, from the dot-com bust that nearly bankrupted Priceline [13] to the COVID-19 pandemic that necessitated laying off a quarter of the workforce [14]. This is juxtaposed against the company's extraordinary long-term performance, including a 30% compound annual growth rate for investors [16].

The company's ability to make severe operational cuts during crises while maintaining a long-term growth trajectory indicates a battle-hardened leadership team comfortable with making difficult, high-stakes decisions.

Source episodes

Sentiment over time

Not enough data for timeline

Changes over time

Spring 1999

Priceline.com, the predecessor to Booking Holdings, conducts its Initial Public Offering [10].

Late 2000

After reaching a market capitalization of approximately $15 billion, Priceline.com's value collapses, and the company nearly goes bankrupt [13].

Early 2000s

The company acquires Booking.com, which was an early and effective adopter of Google advertising. The acquisition is managed with a 'hands-off' approach, allowing the local team to operate independently, a strategy that proves highly successful [8, 23, 24].

Circa 2010-2012

Booking Holdings begins utilizing machine learning in its operations, a practice that has now been in place for over a dozen years [5, 17].

Post-2017 (During Fogel's CEO tenure)

Fogel leads a strategic expansion of Booking.com from a hotel-only agency model to a multi-vertical platform including flights, cars, and attractions, supported by the creation of a large, internal payments program [15, 22].

Early 2020 - Pandemic

At the start of the COVID-19 pandemic, the company has 26,000-27,000 employees. It subsequently lays off 25% of its workforce to navigate the crisis [14, 19].

Present

Fogel announces the launch of generative AI products, such as Booking.com's 'AI trip planner' and Priceline's 'Penny,' signaling a major strategic push into AI-driven travel services [1, 3, 20].

Suggested prompts

How does Glenn Fogel's 'hands-off' acquisition philosophy for Booking.com reconcile with the current strategy of creating a deeply integrated 'connected trip' across all company verticals? &nearr;What specific risks does Booking Holdings face if its significant investments in generative AI do not yield the expected user adoption or competitive advantage Fogel predicts? &nearr;How has the experience of near-bankruptcy in 2000 and the COVID-19 crisis shaped Fogel's current approach to financial management and risk mitigation? &nearr;Beyond customer-facing features, how is Booking Holdings leveraging AI and machine learning internally to improve operational efficiency and profitability, as hinted by the customer service automation example? &nearr;

Key concepts

Artificial Intelligence (AI) 2 ep Business Strategy 2 ep Corporate History 2 ep Machine Learning 2 ep Travel Industry 2 ep Leadership 2 ep Product Development 2 ep Financial Performance 1 ep Acquisition Strategy 1 ep COVID-19 Impact 1 ep

Notable quotes

“So that's from $6 to $4,800 over 25 years. So that, think about that, 800 times.”

Glenn Fogel · The Leadership Moves That Drives a Billion-Dollar Brand

“During the pandemic, we let go 25% of our employees.”

Glenn Fogel · The Leadership Moves That Drives a Billion-Dollar Brand

“we know though the weather on thursday when you're supposed to take this boat ride it's going to probably rain... we'd like to change this for you put you on the boat on the sunny day wednesday go to the museum on the rainy thursday and we're doing that automatically through ai”

Glenn Fogel · The Leadership Moves That Drives a Billion-Dollar Brand

“One of the easiest ways to really wreck a non-US company that is operating outside the US, one of the best ways to wreck it is parachuting a bunch of Americans who don't know anything about it.”

Glenn Fogel · The Leadership Moves That Drives a Billion-Dollar Brand

Report last updated: Apr 21, 2026

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