Box CEO Aaron Levie joined the show to share his perspective on how AI is reshaping the enterprise landscape. He shared what his customers are actually thinking about when it comes to AI, the shift from closed to open-source models, and why the biggest opportunities might not be in flashy consumer tools but in workflow automation and data-rich enterprise applications.

Aaron also shares his take on the changing business model dynamics in B2B, including the rise of usage-based pricing, and what it means for the next wave of software companies.

00:00 Introduction to AI in B2B and Consumer Worlds

00:32 Conversation with Aaron Levy: AI in the Enterprise

01:10 Defining a Model Company and AI's Role

02:19 Challenges and Opportunities in AI for Enterprises

03:44 Open Source vs. Commercial AI Models

05:40 The Future of AI Agents

11:42 AI's Impact on Business Models and Pricing

15:16 AI's Potential to Transform Industries

27:14 Comparing AI and Cloud Adoption

30:05 Strategizing AI Implementation

31:08 Customer Adoption and Resistance

32:59 Practical Considerations and Challenges

34:58 Building Flexible AI Architectures

37:57 Exploring Agentic Workflows

41:57 Future of AI in Enterprises

43:36 Rapid Fire Questions on AI Impact

53:20 Exciting AI Features at Box

55:53 Conclusion and Final Thoughts

After unveiling 45 new product announcements this week, Zoom CEO Eric Yuan joined the show to share how he’s thinking about the future of work. He shared how he prioritizes which features to build, his approach to rebuilding company culture, what he’d do differently if he were starting Zoom today, and much more.

(00:00) Intro

(01:14) Eric Yuan on Zoom's Recent Innovations

(02:02) AI Companion and Its Capabilities

(03:23) Zoom's Open Platform and AI Features

(04:36) Customer-Centric AI Development

(06:21) Innovative Features and Real-World Applications

(11:15) Balancing Core and Future Innovations

(13:32) Zoom's AI-First Transformation

(25:05) Security and Data Privacy in AI

(27:46) Customer Feedback Driving Innovation

(29:36) Eric Yuan's Leadership Style

(33:22) Navigating the Pandemic: Rapid Growth and Cultural Challenges

(34:44) Rebuilding Company Culture: The Culture Playbook

(35:45) Continuous Improvement: Daily Self-Reflection

(37:25) Hybrid Work: Embracing the New Normal

(40:31) Founding Zoom: Insights and Challenges

(48:50) Lessons from Early Days: Perseverance and Timing

(53:12) Hiring and Leadership: Building the Right Team

(57:05) Reflections and Future Planning

(01:01:27) Choosing the Right Investors

(01:03:04) The Future of AI and Industry Transformation

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.

As tariff drama continues to heat up, Ryan Petersen, CEO of Flexport (one of the hottest freight forwarders in the world) came on the show to unpack the impact. Ryan also dives deep into the hidden world of US shipping, opportunities for AI automation in logistics, reflections on building Flexport, and some supply chain conspiracy theories.

(00:00) Intro

(01:16) Flexport's Mission and Operations

(02:28) Impact of Tariffs on Businesses

(05:15) Navigating New Duties and Regulations

(09:19) Flexport's Strategic Response

(14:39) Challenges in U.S. Shipping Policies

(28:21) Union Influence on Port Automation

(40:35) National Security and Trade Negotiations

(41:06) Tariffs and Business Planning Challenges

(42:16) Investment Opportunities in Ports

(44:02) Port Automation and AI Integration

(45:09) Flexport's Big Tech Launch

(47:02) AI's Role in Supply Chain Management

(53:14) Digitizing Freight Contracts

(58:18) Lessons from Flexport's Growth

(01:09:13) Conspiracy Theories in Shipping

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

🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=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 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.

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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 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

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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 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.

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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 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

🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1

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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 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.

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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 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.

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

🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1

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📸 Instagram - https://www.instagram.com/theloganbartlettshow

📱 X - 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 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 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

🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=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 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.

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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 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

🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1

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📱 X - 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 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.

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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 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

🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=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 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.

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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 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

🎥 Subscribe on YouTube: https://www.youtube.com/channel/UCugS0jD5IAdoqzjaNYzns7w?sub_confirmation=1

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📱 X - 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 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.