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

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

Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg

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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

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🎬 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

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🎬 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.

Since 2017, Bill Shufelt (CEO, Athletic Brewing) went from hedge fund trader to the CEO of the leading producer of non-alcoholic craft beer. Unlike the typical tech-focused chats, this one centers around a product many have fallen in love with. In the conversation, Bill tells stories of the unscalable but crucial strategies he used to build a brand, push past rejection, and redefine the non-alcoholic beer industry.

(00:00) Introduction to Athletic Brewing

(00:52) The Early Days and Breakthrough Moments

(01:15) Celebrity Partnerships and Brand Building

(03:16) The Philosophy of Brand and Movement

(07:33) The Non-Alcoholic Beer Market

(10:46) The Entrepreneurial Journey and Personal Sacrifices

(18:22) Scaling the Business and Marketing Strategies

(28:20) Navigating Regulations and Health Trends

(39:07) The Importance of a Tech Co-Founder

(39:31) Home Brewing Beginnings

(40:13) Innovative Brewing Process

(41:13) Food Safety Challenges

(43:24) Raising Funds and Building a Brewery

(44:24) Vertical Integration Benefits

(45:33) Early Sales Efforts

(46:56) Investor Relations and Accountability

(51:14) Long-Term Vision and Focus

(01:00:10) Cultural Differences in Non-Alcoholic Beer

(01:02:35) Health Considerations and Alcohol

(01:10:38) The Sensation of Drinking

(01:12:50) Reflections on the Entrepreneurial Journey

(01:14:46) 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

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

Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg

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🐦 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.

In the midst of meme stock craziness, Robinhood CEO Vlad Tenev shared his most eye-opening insights from running the company that transformed the game for retail investors. He talks about Robinhood’s new Gold Card, his views on crypto, the media side, how artificial intelligence could change finance, and more.

(00:00) Intro

(03:27) The Origin of the Name 'Robinhood'

(08:43) Navigating the GameStop and Meme Stock Saga

(10:52) Rebuilding Trust and Brand Impact

(19:10) Crisis Communication and Leadership Lessons

(23:54) Industry Insights and Future of Trading

(31:00) AI and Financial Services

(33:34) Crypto and Regulatory Challenges

(40:14) The Viral Launch of Robinhood

(47:01) The Gold Card Launch and Customer Strategy

(50:08) The Vision Behind Robinhood's Credit Card

(53:50) Building vs. Buying: The X1 Acquisition

(56:12) Integrating X1 into Robinhood

(57:11) The GM Structure and Its Benefits

(58:42) Challenges and Trade-offs of Decentralization

(01:01:08) Financial Modeling and Customer Economics

(01:04:48) Navigating Remote Work and Returning to the Office

(01:09:14) Managing Stock Price Expectations

(01:13:23) Hiring and Retaining Talent

(01:17:11) Fundraising and Investor Relations

(01:31:09) Launching Sherwood Media

(01:38:56) Reflections and Future Aspirations

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.

On the day of the ChatGPT-4o announcement, Sam Altman sat down to share behind-the-scenes details of the launch and offer his predictions for the future of AI. Altman delves into OpenAI's vision, discusses the timeline for achieving AGI, and explores the societal impact of humanoid robots. He also expresses his excitement and concerns about AI personal assistants, highlights the biggest opportunities and risks in the AI landscape today, and much more.

(00:00) Intro

(00:50) The Personal Impact of Leading OpenAI

(01:44) Unveiling Multimodal AI: A Leap in Technology

(02:47) The Surprising Use Cases and Benefits of Multimodal AI

(03:23) Behind the Scenes: Making Multimodal AI Possible

(08:36) Envisioning the Future of AI in Communication and Creativity

(10:21) The Business of AI: Monetization, Open Source, and Future Directions

(16:42) AI's Role in Shaping Future Jobs and Experiences

(20:29) Debunking AGI: A Continuous Journey Towards Advanced AI

(24:04) Exploring the Pace of Scientific and Technological Progress

(24:18) The Importance of Interpretability in AI

(25:11) Navigating AI Ethics and Regulation

(27:26) The Safety Paradigm in AI and Beyond

(28:55) Personal Reflections and the Impact of AI on Society

(29:11) The Future of AI: Fast Takeoff Scenarios and Societal Changes

(30:59) Navigating Personal and Professional Challenges

(40:21) The Role of AI in Creative and Personal Identity

(43:09) Educational System Adaptations for the AI Era

(44:30) Contemplating the Future with Advanced AI

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

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📸 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.

After 18 years leading Guidewire (~$10B), Marcus Ryu made the transition from CEO to partner at Battery Ventures. In the episode, Marcus shares his journey of co-founding Guidewire in 2001, steering the company through its IPO in 2012, and building one of the largest vertical software businesses in the world. He shares his insights on how to build a durable company in troubling times, what he looks for in entrepreneurs, the future of vertical software, and much more.

(00:00) Intro

(01:31) The Philosophical Approach to Investing and Strategy

(03:27) Unpacking the Strategy: Diagnosis, Market Definition, and Execution

(04:31) The Intricacies of Investment Decisions and Entrepreneurial Insight

(10:39) From Philosophy to Silicon Valley: A Personal Journey

(12:29) The Dot-com Bubble and Lessons Learned

(26:19) Guidewire's Founding: Identifying a Niche in the Insurance Industry

(37:13) The Early Days: Building from Scratch

(37:34) The Founder's Balance Sheet: Energy, Time, and Market Demand

(37:54) Starting with Nothing: The Humble Beginnings of a Startup

(38:14) The Power of Insight and Precision in Startup Success

(39:58) Product Development and Market Strategy: The Binder's Role

(40:37) The Brutal Reality of Go-to-Market: Rejection and Resilience

(42:59) The Parable of the Horse: Navigating Startup Highs and Lows

(45:23) Overcoming Legal Battles and Finding a Moral Purpose

(48:37) The CEO Transition: Learning from Leadership Changes

(50:49) Foundational Principles for Sustaining Founder Relationships

(53:41) Cultivating a Company Culture Based on Core Values

(01:01:31) The Journey from Founder to Investor: A New Chapter

(01:03:53) The Role of a Board and Achieving Founder-Investor Alignment

(01:08:25) Managing Founder Psychosis and Scaling as a Leader

(01:12:52) The Founder's Journey and Commitment

(01:13:27) The Philosophical Underpinnings of Insurance

(01:14:03) Insurance: A Civilizational Necessity

(01:15:01) The Impact of Insurance on Society and Innovation

(01:19:32) Navigating the Complexities of Insurance Regulation

(01:21:07) The Dark Side of Ad Tech and Its Societal Impact

(01:28:41) The Challenge of Communication and Leadership

(01:31:46) The Future of Software: Vertical Specialization

(01:42:05) Evaluating Founders and the Essence of Entrepreneurship

(01:45:56) Emerging Opportunities and the Specificity of Markets

(01:48:53) Concluding Reflections on Authentic Leadership

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

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🐦 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.

After last week’s announcement that IBM is acquiring HashiCorp for $6.4B, HashiCorp co-founder Armon Dadgar discussed a few behind-the-scenes elements of the acquisition and HashiCorp’s full journey from the early days. Armon shares some of his biggest lessons from the journey, from fundraising to community building and more.

(00:00) Intro

(01:17) Explaining HashiCorp: Simplifying Cloud Infrastructure for Enterprises

(03:24) Navigating the Acquisition: Emotions, Expectations, and the Future with IBM

(09:01) The Founding Story: Choosing the Path of a Venture-Backed Business

(10:59) Challenging Silicon Valley Wisdom: HashiCorp's Multi-Product Strategy

(17:54) The Importance of Being Pragmatic: Adapting Products to Market Needs

(32:27) Customer Trust and Commitment: The Foundation of HashiCorp's Success

(36:27) Organizational Evolution: Adapting Structure to Strategy at HashiCorp

(38:36) Exploring Product Verticals and Team Structures

(39:16) The Evolution of Product Portfolio

(40:46) Strategic Product Development and Market Fit

(41:51) Transitioning from Product Expansion to Monetization

(43:27) The Impact of Docker on Fundraising and Strategy

(50:31) Navigating the Challenges of Multi-Product Strategy

(55:33) The Significance of Branding and Product Naming

(01:00:46) Understanding User vs. Buyer Dynamics in Open Source Monetization

(01:09:17) The Founders' Journey: From University to HashiCorp

(01:16:39) Navigating Leadership and Hiring Challenges

(01:17:14) The Search for the Right Leadership: A Journey of Discovery

(01:17:57) Realizing the Need for Specialized Roles

(01:18:24) The Turning Point: Hiring Key Executives

(01:19:57) Overcoming the Ego: Embracing Change for Company Success

(01:21:18) The Final Decision: Bringing in New Leadership

(01:22:45) Reflecting on the Hiring Process and Its Impact

(01:28:27) Building a Culture of Execution and Communication

(01:50:51) The Importance of Airline Loyalty for Busy Executives

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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Google Podcasts: https://podcasts.google.com/feed/aHR0cHM6Ly9mZWVkcy5zaW1wbGVjYXN0LmNvbS9zb0hJZkhWbg

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🎬 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.

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.