EP 125: Glenn Fogel (CEO, Booking Holdings) Building a $170B Travel Empire: On AI, Acquisitions, and Shaping Travel’s Future

Yamini Rangan, CEO of HubSpot (a $40 billion leader in the CRM space) shares how AI is transforming go-to-market strategies, the key lessons Yamini has learned as a first-time CEO, and the sales tactics she’s mastered.She also discusses the challenges of navigating major business pivots, including how companies can successfully transition into AI-first businesses and what it takes to stay competitive in an evolving landscape.(00:00) Intro(00:56) Yamini Rangan's Background and Career Journey(02:33) Joining HubSpot and Early Challenges(03:49) Transition to CEO and Leadership Insights(07:33) Strategic Planning and Long-Term Vision(15:15) AI Transformation and Product Innovation(18:57) AI's Impact on CRM and Future Prospects(28:51) Content Strategy and Customer Engagement(37:34) Contextual AI Features for Better Usage(38:13) Human Expectations and AI(39:36) AI in Daily Productivity(42:54) The Art and Science of Sales(51:05) The Role of Curiosity and Resilience in Sales(53:23) Evolving Company Culture(55:27) Leadership Style and Management Lessons(58:27) Scaling Startups: Lessons from Workday(01:02:54) The Future of AI and Incumbents(01:14:10) Concluding Thoughts Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow📱 X - https://twitter.com/loganbartshow🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the ShowLogan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.Tap follow and enable notifications to stay ahead of the game.

Andy is the founder of Artisanal Ventures and Artisanal Talent, one of Silicon Valley’s top search firms. He’s helped build leadership teams at companies like Databricks, Snowflake, Confluent, Abnormal Security, AcuityMD, and many more.In this episode, he shares…- How founders can differentiate in the talent war today- Maximizing the success rate of executive hires- Why interviews are a waste of time- The best ways to do references- How to choose the right search firm& more (00:00) Intro(02:02) Andy Price's Background and Career Journey(03:20) The Role of Founders in Hiring(04:32) Challenges in Early Stage Hiring(10:08) Importance of Venture Capital Brand(12:14) Effective Search Processes and Candidate Evaluation(23:27) Backchannel References and Networking(29:10) Identifying Key Players in Sales Growth(29:44) The Importance of Minimal Disruption(30:40) Effective Founder-Executive Relationships(30:57) The Role of Soak Time in Differentiation(31:52) Hiring Strategies for Rapid Growth(33:42) Common Failure Modes in Hiring(34:32) Aligning Founder and Executive Expectations(38:26) Building a Strong Talent Acquisition Team(40:51) The Talent Wars and Hiring Choke Points(44:24) Balancing Skill Sets and Company Culture(47:29) Evaluating and Upleveling Team Members(49:59) The Importance of Forecasting and Planning(51:34) Handling Executive Transitions Smoothly(59:09) The Art of Firing: Best Practices(59:32) Handling Employee Terminations with Dignity(01:02:19) Negotiating with Candidates: Tips and Tricks(01:06:31) Understanding Compensation Trends(01:08:18) Avoiding Common Founder Mistakes(01:11:28) Scaling Operations in Hypergrowth(01:15:00) Navigating the Current VC and Talent Ecosystem(01:23:34) The Importance of Specialized Search Firms(01:28:03) Adapting to the New Market Realities(01:30:46) Final Thoughts and Reflections Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow📱 X - https://twitter.com/loganbartshow🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the ShowLogan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.Tap follow and enable notifications to stay ahead of the game.

The recent controversy between WordPress and WP Engine put Matt Mullenweg (Co-Founder of WordPress, CEO of Automattic) under intense online scrutiny. In our conversation, he shared lessons from the controversy and managing through crisis, as well as this thoughts on the future of open source AI and more.(00:00) Intro(01:17) Controversy with WP Engine(03:36) Understanding Open Source and Trademarks(04:36) Automattic's Role and Contributions(08:26) Navigating Legal Battles and Community Relations(18:27) Leadership and Personal Resilience(21:49) The Impact of Social Media on CEOs(31:22) Future Outlook and Reflections(32:42) Exploring the Quinn Model and Open Source Innovations(33:17) The Evolution of AI Interfaces and User Interactions(35:36) AI as a Writing and Coding Partner(38:07) The Power of Open Source in AI Development(40:00) Commoditizing Complements: A Business Strategy(41:39) The Battle with Shopify and Open Source Models(42:33) The Impact of Open Source on Market Dynamics(43:55) USB-C Transition and Gadget Recommendations(47:53) The Benefits of Sabbaticals(53:34) The Future of WordPress and Automattic(59:12) Employee Ownership and Liquidity Programs(01:04:33) Conclusion and Final Thoughts Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎙 Listen to the show Apple Podcasts: https://podcasts.apple.com/us/podcast/the-logan-bartlett-show/id1606770839Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials📸 Instagram - https://www.instagram.com/theloganbartlettshow🐦 Twitter - https://twitter.com/loganbartshow🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the ShowLogan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode, Logan goes behind the scenes with world-class entrepreneurs and investors. If you're interested in the real inside baseball of tech, entrepreneurship, and start-up investing, tune in every Friday for new episodes. Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow📱 X - https://twitter.com/loganbartshow🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the ShowLogan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.Tap follow and enable notifications to stay ahead of the game.

Two weeks after Oura CEO Tom Hale started tracking and improving his sleep, he recalls, “It was like walking out of a black-and-white movie into a 4K technicolor movie… I’ve been missing this for 30 years.” The experience of feeling 20 again every day inspired him to apply for the Oura CEO role. Now, nearly 3 years into the job, he sat down to discuss what all founders and CEOs should consider when it comes to avoiding burnout and maximizing health and productivity. We covered his experiences with tools like continuous glucose monitoring, his thoughts on the future of wearables, and how AI insights will help us take better control of our health. (00:00) Intro(00:53) The Journey with Oura Ring(01:47) Sleep Optimization and Health Trends(05:06) Behavioral Changes for Better Sleep(09:33) Tom Hale's Professional Background(12:47) Challenges and Opportunities at Oura(22:50) The Importance of Sleep(26:05) Health Benefits of Quality Sleep(28:38) Oura's Unique Position in the Market(36:47) Consumer Choice and Healthcare Disruption(40:59) Unexpected Insights from HSA and FSA Spending(41:36) The Future of Insurance and Wearable Data(44:40) Preventative Care and Employer Incentives(47:21) The Impact of Small Choices on Health(48:52) Artificial Intelligence in Healthcare(54:08) The Role of Continuous Glucose Monitors(59:50) Expanding Oura's Market and Product Strategy(01:12:04) Navigating Leadership and Company Culture(01:19:22) Future Opportunities and Global Expansion(01:23:43) Closing Remarks and Reflections  Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow📱 X - https://twitter.com/loganbartshow🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the ShowLogan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.Tap follow and enable notifications to stay ahead of the game.

Jay Chaudhry is the definition of a self-starter. Born in the Himalayas with no running water or electricity until high school, Jay has now scaled Zscaler to a $30B public company. He and his wife went all in many times over—betting their life savings and quitting their jobs to launch their first venture, Secure IT, which became a huge success. Jay then parlayed that into building multiple more self-funded, successful cybersecurity companies before founding Zscaler.In this episode, Jay shares his playbook for building disruptive companies, how he picks a market, and insights on using AI to combat modern breaches—plus his perspectives on life, family, and money. Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow📱 X - https://twitter.com/loganbartshow🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the ShowLogan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.Tap follow and enable notifications to stay ahead of the game.

In this episode, Marc Benioff (CEO, Salesforce) responds to Satya Nadella’s recent predictions and shares his thoughts on the current reality of Agi. He dives into the rise of digital labor, the multi-trillion-dollar potential of agentic technology, and what the future split between software and agentic revenue might look like. Marc also discusses why CEOs need to stay grounded in delivering actionable solutions, and he emphasizes the moral obligation businesses have to retrain employees and invest in communities as AI continues to evolve.(00:00) Intro(01:45) Salesforce's AI Impact on Business(03:03) The Future of Digital Labor(05:28) Agentic AI and Customer Success(07:42) Salesforce's Competitive Edge(11:48) Marc Benioff's Response to Satya Nadella(14:16) The Role of AI in Enterprise Software(20:14) The Balance of AI and Human Labor(28:34) Salesforce's Philanthropic Efforts(36:24) The Future of AI and Regulation(40:24) Conclusion and Farewell Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow📱 X - https://twitter.com/loganbartshow🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the ShowLogan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.Tap follow and enable notifications to stay ahead of the game.

Eran Zinman entered a crowded category, out-executed everyone, and scaled monday.com into a $14B public company. In my latest conversation with him, he details their unique metric tracking system (dubbed Big Brain) that allows them to do the same amount of work with ½ the people, along with their relentless focus on cash over other metrics, and the little tactics that brought significant ROI (like sending everyone—including investors—a daily SMS with yesterday’s metrics).(00:00) Introduction to the Logan Bartlett Show(01:12) The Philosophy Behind Monday.com(01:29) Building a Flexible Platform(04:12) Competing in a Crowded Market(06:21) The Evolution of Monday.com(13:43) The Importance of Cash Efficiency(14:22) Big Brain: The In-House Analytics Platform(23:54) Performance Marketing Strategies(29:47) AI Integration and Future Prospects(38:51) Founder Mode and Company Philosophy(40:53) Learning from Mistakes and Adapting(43:04) Customer Success and Service Philosophy(46:53) Building a Strong Company Culture(51:10) Interviewing and Hiring Best Practices(54:49) Going Public and Investor Relations(01:03:38) Co-CEO Model and Partnership(01:08:34) Future Vision for Monday.com(01:11:07) Embracing Failure and Continuous Improvement Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow📱 X - https://twitter.com/loganbartshow🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the ShowLogan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.Tap follow and enable notifications to stay ahead of the game.

Glenn Fogel, CEO of Booking Holdings, has built a $170B travel empire that includes brands like http://Booking.com, Priceline, Kayak, and OpenTable. Glenn shares insights into how Booking has grown into a global powerhouse, weathering challenges like tsunamis, wars, 9/11, and the COVID-19 pandemic. We dive into the strategy behind the transformative acquisition of http://Booking.com, which now drives 90% of the company’s revenue, and the key lessons Glenn has learned about M&A success. Glenn also discusses how AI could revolutionize travel, from automating customer service to creating seamless traveler-first experiences. (00:00) Intro(01:37) Overview of Booking Holdings(02:31) Early Days of Priceline and Joining the Company(03:33) Dot-Com Boom and Financial Challenges(07:28) Travel Industry Resilience(07:47) Cultural and Economic Factors in Travel(09:17) Stock Splits and Employee Incentives(13:34) Acquisition of Booking.com and Active Hotels(24:20) Growth and Integration of Acquired Companies(29:11) Artificial Intelligence in Travel(30:57) Future of Travel and AI Integration(38:54) The Greatest Acquirers in History(39:16) Teamwork in Business Acquisitions(40:48) Challenges in M&A and Regulatory Hurdles(41:49) Patterns in Successful and Failed Deals(46:06) Cultural Alignment in Mergers(50:31) Brand Management and Integration(54:14) Regulatory Environment and Smart Regulations(01:00:11) Post-COVID Business Travel Trends(01:08:24) Leadership Through Crises(01:15:33) Technological Advancements in Travel Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow📱 X - https://twitter.com/loganbartshow🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the ShowLogan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.Tap follow and enable notifications to stay ahead of the game.

Ali Ghodsi, CEO of Databricks (now a $61B company), has become one of the top minds in AI, evolving from researcher to leading one of the biggest AI-centered private companies. In our conversation, he broke down the AI hype cycle in detail and made bold predictions for the future. He also shared his biggest operating lessons from scaling Databricks to a market leader and pivotal moments in his journey. (00:00) Introduction to AGI and AI Challenges(01:00) Ali Ghodsi's Journey in AI(01:38) The Evolution and Impact of AI(03:59) AI in Enterprises and Consumer Adoption(05:25) Specialized AI Systems and Data Advantage(07:32) The Hype Cycle and Future of AI(08:22) Scaling Laws and Compound AI Systems(19:52) AI Use Cases and Industry Applications(28:29) Early Days of Databricks and Spark(38:43) Taking Over as Interim CEO(39:00) Focusing on Enterprise Sales(40:42) Innovating in Open Source(41:08) Challenges and Pivots in 2015(44:31) Building and Scaling New Products(47:57) Leadership Evolution and Advice(54:45) Hiring and Promoting Leaders(01:10:44) Future of AI and Databricks Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow📱 X - https://twitter.com/loganbartshow🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the ShowLogan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.Tap follow and enable notifications to stay ahead of the game.

Eoghan McCabe returned to the CEO seat at Intercom with a mission to shake things up. Over the past two years, he's been reinventing the company’s culture, leading with zero apologies, and transforming Intercom into an AI-driven powerhouse. In my latest conversation, we dive into Eoghan’s journey back to Intercom after a two-year break, his blueprint for turning a software company into an AI leader, and the tactics he uses to keep Intercom running like a high-intensity startup. Eoghan also shares his thoughts on personal freedom and his controversial endorsement of Donald Trump. [0:00] Intro[1:33] Eoghan McCabe's Return to Intercom[3:01] Challenges and Learnings[10:44] Cultural Reset at Intercom[29:23] AI and the Future of Customer Service[31:11] Adapting to AI and Market Changes[43:00] Competitive Landscape and Strategy[48:29] Future of AI in Customer Service[50:24] The Evolution of Work[52:18] Challenges and Rewards of Leadership[56:45] Media and Public Perception[1:00:40] Political Endorsements and Reactions[1:10:11] Freedom Club and Cultural Influence[1:12:33] HR and Company Culture[1:29:35] Fundraising and Investor Relations[1:33:01] Final Reflections and Advice  Executive Producer: Rashad AssirProducer: Leah ClapperMixing and editing: Justin Hrabovsky Check out Unsupervised Learning, Redpoint's AI Podcast: https://www.youtube.com/@UCUl-s_Vp-Kkk_XVyDylNwLA 🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1 Follow on Socials 📸 Instagram - https://www.instagram.com/theloganbartlettshow📱 X - https://twitter.com/loganbartshow🎬 Clips on TikTok - https://www.tiktok.com/@theloganbartlettshow About the ShowLogan Bartlett is a Software Investor at Redpoint Ventures - a Silicon Valley-based VC with $6B AUM and investments in Snowflake, DraftKings, Twilio, and Netflix. In each episode of The Logan Bartlett Show, we sit down with the people behind today’s most important startups and extract the tactics, lessons, and frameworks they’ve learned the hard way. Conversations span hiring to GTM, product, growth, fundraising and everything in between - collectively forming the ultimate playbook to make you a better CEO, investor or board member.Tap follow and enable notifications to stay ahead of the game.