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 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.

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 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.

What does it take to scale a company from an idea to a $13B industry leader? In my latest episode, Okta CEO Todd McKinnon dives into the essential lessons he’s learned on high-stakes decision-making, managing up to the board, and competing against tech giants like Microsoft.

Todd also reflects on his journey to founding Okta, his bold choice to team up with a co-founder he hardly knew, and the motivations that have fueled him for over seven years as a public company CEO. Some key takeaways…

[0:00] Intro[0:33] Todd McKinnon's Early Career and Founding Okta[1:38] Challenges and Psychological Shifts in Leadership[2:49] Decision Making and Company Culture[6:10] Milestones and Early Successes[18:03] The Importance of Market Timing[30:34] Hiring and Building a Strong Team[39:22] Setting Expectations with Board Members[40:50] The Shift in Board Dynamics[41:41] Maintaining Context and Strategic Input[43:15] Navigating Public Company Governance[45:21] Trusting Instincts and Founder Mode[47:11] Breaking Out of the Echo Chamber[51:00] The Importance of Prioritization[53:05] The Loneliness of Innovation[1:05:33] The Role of a CEO in Decision Making[1:18:17] The Journey to IPO and Beyond

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.

Nine months into his role as Snowflake’s CEO, Sridhar Ramaswamy sat down for a candid discussion on the journey so far & what’s ahead.

He uncovered details about his transition to Snowflake CEO, the operational changes he’s put in place to accelerate product development, and his bold predictions for AI’s future—along with how he’s guiding a vision for Snowflake to fit into that landscape.

Sridhar also reflects on how his leadership has evolved, from leading a major Google unit to founding Neeva (acquired by Salesforce) and now running Snowflake.

[0:00] Intro

[0:56] Sridhar’s Journey to Snowflake

[3:37] Snowflake's AI Vision and Cortex AI

[10:35] Innovative Uses of AI at Snowflake

[15:49] Challenges and Future of AI in Business

[21:27] Snowflake's Long-Term AI Aspirations

[25:04] Predictable and Unpredictable Aspects of AI

[26:20] Autonomous Agents and AI Predictions

[27:01] Market Consolidation in AI

[29:54] Journey into AI and Early Experiences

[31:21] The Evolution of AI Models

[32:06] Building Neeva and AI Search Engines

[36:16] Leadership and Product Development at Snowflake

[40:45] Setting Goals and Accountability

[43:25] Leadership Style and Cultural Foundations

[47:25] Career Advice and Finding Your Path

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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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.

Evan Goldberg has been leading NetSuite for 26 years and counting. In this episode, Evan reflects on the journey of building NetSuite—from launching it with Larry Ellison’s support, to scaling through its IPO, and eventually being acquired by Oracle for $9.3B. He shares his leadership philosophies around humor and empathy, lessons learned from Larry Ellison and Marc Benioff, and why he still feels passionate about the business after all these years.

[0:00] Intro[1:13] Lessons from Economic Crises[2:22] The Importance of Existing Customers[4:24] Founding and Early Days of NetSuite[6:32] The Pivot to Business Software[10:26] NetSuite's Growth and Customizability[20:26] AI and the Future of NetSuite[32:24] The Role of Customizability in NetSuite's Success[38:49] Balancing Profitability and Growth[40:46] Leadership Evolution and Management Philosophy[46:59] The Importance of Empathy in Leadership[48:42] Navigating Hypergrowth and Tough Decisions[51:11] Consumer Quality in Enterprise Software[52:31] Oracle's Transformation and Redwood Design System[55:57] Maintaining Focus Amid Distractions[59:39] Company Culture and Humor[1:03:03] NetSuite's Unique Position within Oracle[1:10:15] Involvement with the V Foundation[1:13:52] Reflections on Founding and Leadership[1:16:38] 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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🎬 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.

Drew Houston has now been CEO of Dropbox for over 17 years. In my latest conversation, he opens up about the pivotal leadership lessons he's learned, the mistakes that shaped the company, and the true challenges of going head-to-head with big tech. We also dive into the highs and lows of fundraising, how valuations can make or break a company trajectory, and discuss the opportunities AI presents for the future of work.

[0:00] Intro

[0:44] AI Opportunities for Dropbox

[5:57] Dropbox's AI Principles

[7:52] Introducing Dropbox Dash

[9:18] AI Enhancements in Search

[12:33] Personal Productivity with AI

[17:10] Memo-First Culture at Dropbox

[22:15] Reflections on Leadership and Growth

[31:21] Early Challenges and Viral Growth

[48:22] Facing Fierce Competition

[51:51] Strategic Shift to Collaboration

[53:20] Navigating Internal Challenges

[55:18] Reevaluating Productivity

[1:03:07] The Birth of Dash

[1:16:32] You Don't Want to Feel Like a Victim

[1:30:29] Closing Thoughts and Lessons Learned

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.

Will Gaybrick joined Stripe as CFO after investing in the company at Thrive Capital. Over the past 9 years, now as President, he's helped grow Stripe's into one of the world's largest private startups. In this episode, we explore his impressive career journey—from Harvard Math to software engineering, Yale Law, venture capital, and now his leadership role at Stripe. Will shares key insights on capital allocation, crypto, AI, investing, leadership, and more. Some takeaways:

(00:00) Intro

(01:09) From Academia to Venture Capital

(02:01) Joining Stripe: The Unexpected Journey

(02:09) Career Philosophy and Decision Making

(05:23) Building Hack Yale and Teaching

(08:15) The Role of a Polymath at Stripe

(09:31) Learning Techniques and AI Insights

(16:15) Operational Shifts and Growth Strategies

(20:36) Hiring and Leadership at Stripe

(28:08) Organizational Systems and Processes

(31:40) Migrating Users to New API Versions

(32:07) Challenges in API Refactoring

(33:57) The Rise of Stablecoins

(34:07) Stripe's History with Crypto

(35:51) Stablecoins: Use Cases and Adoption

(41:30) AI and Machine Learning at Stripe

(47:59) Risk Management and Compliance

(53:21) Empowering Innovation with AI

(57:14) Decision-Making Frameworks at Stripe

(01:04:07) Stripe's Product Evolution

(01:09:31) Exploring the Fun and Challenges of Product Space

(01:10:20) Stripe's Organizational Structure and Strategy

(01:12:12) The Importance of Technical Unification

(01:13:13) User Demands and Capital Allocation

(01:14:18) The Role of ROI in Early Projects

(01:15:53) Stripe's Unique Approach to Titles and Levels

(01:18:36) Insights on Organizational Design

(01:21:36) Effective Leadership and Decision-Making

(01:24:18) Reflections on Influential Leaders

(01:33:25) The Value of Venture Capital

(01:38:29) Future Prospects and Motivation at Stripe

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.

Parker Conrad has spent the last 8 years building Rippling into a $13B company, marking his redemption after being ousted from Zenefits. In his second appearance on the podcast, Parker and I discussed Paul Graham's "founder mode" essay and how he operationalizes it at Rippling. He also reflected on the key lessons he's learned throughout his career, highlighting the differences in how he ran Zenefits compared to Rippling today. Additionally, Parker shared his candid views on the challenges of having investors as board members and why he believes much of VC "value add" is overrated.

(00:00) Intro

(01:31) Parker's Leadership Principles at Rippling

(02:16) The Importance of Anecdotal Evidence

(04:09) Balancing Founder Mode and Team Collaboration

(05:08) The Risks of Over-Extrapolating Founder Mode

(06:56) The Reality of Sales Compensation

(08:15) Hiring Founders for New Products

(11:10) The Pace of Execution in a Company

(11:21) The 'C on a Box' Dilemma

(12:07) The Speed vs. Quality Debate

(13:56) The Viral Tweet Incident

(16:51) Governance and Board Dynamics

(20:04) Choosing the Right Investors

(29:57) The Role of Career VCs as Board Members

(33:43) Misaligned Incentives Between Founders and Investors

(35:43) Navigating Business Challenges

(36:27) Sam Altman's Crucial Support

(38:45) The Role of Venture Capitalists

(40:06) The Value of Y Combinator

(43:16) Fundraising and Valuations

(01:00:39) Lessons from Past Ventures

(01:06:05) Building Compound Software

(01:09:33) The Future of Compound Software Businesses

(01:10:04) Microsoft's Unassailable Approach

(01:10:40) Building Narrow vs. Compound Software

(01:12:16) Investment Decisions in New vs. Existing Products

(01:14:42) Platform Development and Resource Allocation

(01:16:32) The Journey from Chem Major to Software Visionary

(01:18:34) Challenges and Strategies in Multi-Product R&D

(01:25:32) Improving Customer Support Metrics

(01:28:50) The Role of a Founder in Product Management

(01:31:23) Hiring and Cultivating Executive Talent

(01:39:07) The Motivation Behind Rippling's Success

(01:41:58) 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.

Many know Celsius as a top energy drink brand today, but few are aware of the tumultuous journey CEO John Fieldly took to get it here. In the episode, John shared how the company nearly went bankrupt multiple times, lost 50% of its revenue overnight and even got delisted from the NASDAQ.

Despite these challenges, John stepped up to rebuild the brand to the nearly $10B company it is today. We discuss how he shifted focus from weight loss to broad-based energy, secured key distribution deals, landed a major partnership with Pepsi, and much more.

(00:00) Intro

(01:34) The Origins of Celsius

(03:30) Going Public: The Early Days

(06:07) Challenges and Lawsuits

(09:17) Rebuilding and Rebranding

(13:18) Strategic Shifts and Market Positioning

(30:40) The Role of Influencers and Social Media

(32:03) John Fieldly's Leadership Journey

(33:34) Reflecting on the Stock Price Journey

(34:12) Navigating Public Company Challenges

(35:25) Distribution Deals and Market Perception

(38:00) Strategic Moves and Competitive Advantage

(44:08) Marketing Strategies and Consumer Engagement

(52:35) Leadership and Company Culture

(01:02:01) International Expansion and Future Goals

(01:06:01) 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.

Josh Wolfe, co-founder and managing partner at Lux Capital, is a master at quickly understanding complex, emerging technologies. In our conversation, Josh shared how he identifies the next big thing, his contrarian views on nuclear energy, biotech, and robotics, as well as his thoughts on the state of the venture capital market today.

(00:00) Intro

(01:02) Daily News Routine

(05:28) Geopolitical Insights

(07:03) Competitiveness and Curiosity

(11:01) Investment Strategies and Risks

(26:07) The Control Labs Story

(33:48) The Founder’s Dilemma: Financial vs. Strategic Motivations

(34:33) Geopolitical Concerns: Iran and Global Politics

(36:31) Investments in Defense: Controversies and Convictions

(37:36) The State of Society: Happiness and Social Dynamics

(48:07) Artificial Intelligence: Trends and Predictions

(01:02:22) The Future of Robotics: Beyond Humanoids

(01:06:46) Ethical Implications of AI and Defense Technologies

(01:11:29) Lux Capital’s Investment Strategy and LP Relations

(01:12:43) ESG and Moral Impositions

(01:13:30) Defense and Complex Moral Valences

(01:14:19) Investment Ethics and Decision Making

(01:16:46) Venture Capital Market Outlook

(01:17:56) Challenges in Venture Capital

(01:37:12) The Role of Storytelling in Venture Capital

(01:43:20) Personal Reflections and Background

(01:51:34) Partnership Dynamics and Trust

(01:53:48) 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

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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.