The Logan Bartlett Show

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

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

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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

🎥 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 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.

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

Follow on Socials

📸 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.