Klarna CEO Sebastian Siemiatkowski led the rise from a profitable business to their peak $50 billion valuation, in which they were burning $150 million a month. In my latest episode, Sebastian shares how he turned Klarna back to profitability and discusses Klarna’s ongoing pursuit of creating a digital financial assistant. He also reflects on their recent boardroom drama with Sequoia and outlines the operating principles and the repaired mistakes that have made Klarna the company it is today.

(00:00) Intro

(01:45) Personal Reflections on Alcohol and Family

(03:03) The Journey to Sobriety

(05:57) Milestones and Achievements

(07:59) Understanding Company Success

(10:54) Challenges and Pivots in Business

(16:50) Building and Maintaining Company Culture

(26:16) Leadership and Motivation

(32:42) What Klarna Does

(41:33) Reflecting on Leadership and Self-Development

(41:48) Promoting Young Talent and Internal Growth

(44:52) Balancing Autonomy and Standardization

(46:29) Adopting Agile and Toyota's Influence

(55:05) Navigating Regulatory Challenges

(01:00:11) Klarna's Financial Journey and Market Expansion

(01:10:38) Handling Valuation Resets and Layoffs

(01:23:57) Evaluating Individuals in Business Relationships

(01:24:22) Stability of Institutions and Individuals

(01:25:40) Perverse Incentives in VC Firms

(01:26:50) Hands-On Leadership in VC Firms

(01:28:54) The Impact of Michael Moritz

(01:34:52) Leadership Evolution and Self-Reflection

(01:39:11) Facing Challenges and Finding Solitude

(01:42:19) AI Integration at Klarna

(01:52:03) Balancing Capitalism and Societal Impact

(02:00:53) Creativity and Constraints in Problem Solving

(02:05:41) Conclusion and Final Thoughts

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing 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/id1606770839

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About the Show

Logan 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.

Olivier Pomel built Datadog into a $40B company while burning only $25M in capital. In our conversation, he shares the fundraising lessons, operating principles, and core insights that made this possible. He also discusses the pros and cons of building a tech company in NYC, how early-career professionals should approach learning AI tools, how Datadog is building a trusted relationship with their users around AI features, and much more

(00:00) Intro

(01:30) Datadog's Early Challenges and Lessons

(04:32) The Core Insight Behind Datadog

(05:20) Building the Right Product

(07:46) Transitioning to Open Beta

(09:38) Expanding Datadog's Product Line

(11:26) Platform Vision and Modular Products

(18:12) Empowering Product Teams

(22:14) Acquisitions and Integration Strategy

(33:18) Customer-Centric Approach

(36:39) Bottom-Up Sales Strategy

(46:04) Navigating Founder Challenges

(46:37) Building a Collaborative Management Team

(48:32) Staying Close to Customers

(51:36) Maintaining a Culture of Discipline and Efficiency

(56:26) Pricing Strategy and Market Positioning

(01:01:24) Fostering a Low-Ego, High-Performance Culture

(01:06:32) Hiring and Promoting for Long-Term Success

(01:12:21) Fundraising and Investor Relations

(01:16:03) Deciding Whether to Sell or Scale

(01:18:26) The Impact of AI on Software Development

(01:23:24) Choosing New York Over Silicon Valley

(01:28:04) Final Thoughts and Reflections

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing 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/id1606770839

Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1

Google 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 Show

Logan 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.

Steve Kaufer led Tripadvisor to multi-billion dollar success over a 20+ year run as CEO. He discusses getting acquired and spun out from IAC, becoming a public company CEO, and his biggest operating lessons from his decades-long journey. Steve also shares behind-the-scenes of his new venture, Give Freely, and reflects on his entrepreneurial path.

(00:00) Intro

(01:00) Steve Kaufer's Journey with Tripadvisor

(03:18) Handling Negative Reviews and Legal Issues

(05:24) Psychology of Reviews and User Behavior

(10:01) Impact of AI on Review Platforms

(15:02) Graduation Speech and Key Lessons

(16:33) Speed Wins: The Importance of Agility

(22:46) Measuring Success and Embracing Change

(28:40) Hard Work and Personal Growth

(36:20) Management and Leadership Insights

(40:23) Setting Company Culture

(48:00) Adapting to Market Changes

(51:45) Hiring the Right People

(53:27) Identifying Red Flags in Interviews

(54:51) The Importance of Self-Improvement

(55:29) Curiosity and Adaptability in Candidates

(56:36) Managing Through Crises: 9/11 and COVID-19

(01:02:12) Lessons from Early Career and Centerline Software

(01:05:02) Founding Tripadvisor and Its Growth

(01:18:03) Tripadvisor's Acquisition and Integration with IAC

(01:25:23) Transitioning from Tripadvisor to Give Freely

(01:27:26) The Vision and Impact of Give Freely

(01:37:10) Conclusion and Final Thoughts

Show Notes:

https://givefreely.com/

Executive Producer: Rashad Assir

Producer: Leah Clapper

Mixing 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/id1606770839

Spotify: https://open.spotify.com/show/5WqBqDb4br3LlyVrdqOYYb?si=3076e6c1b5c94d63&nd=1

Google 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 Show

Logan 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.