a16z Board Partner Steven Sinofsky and Box CEO and co-founder Aaron Levie discuss findings from a study of the information economy that has been built on cloud and mobile. The findings were based on workflow data collected anonymously from a subset of 25 million users, 225,000 businesses, and five industries (you can see the report here: blog.box.com/2014/06/mapping-th…f-five-industries/). It all amounts to big shifts in enterprise IT. But what are the implications of these findings for everyone’s business ... beyond Silicon Valley and the software industry? And finally -- shared in a live brainstorm at the end -- what’s the future of the cloud?
What exactly is an AI agent, and how will agents change the way we work? In this episode, a16z general partners Erik Torenberg and Martin Casado sit down with Aaron Levie (CEO, Box) and Steven Sinofsky (a16z board partner; former Microsoft exec) to unpack one of the hottest debates in AI right now. They cover: - Competing definitions of an “agent,” from background tasks to autonomous interns - Why today’s agents look less like a single AGI and more like networks of specialized sub-agents - The technical challenges of long-running, self-improving systems - How agent-driven workflows could reshape coding, productivity, and enterprise software - What history — from the early PC era to the rise of the internet — tells us about platform shifts like this one The conversation moves from deep technical questions to big-picture implications for founders, enterprises, and the future of work. Timecodes: 0:00 Introduction: The Evolution of AI Agents 0:36 Defining Agency and Autonomy 1:39 Long-Running Agents and Feedback Loops 4:27 Specialization and Task Division in AI 6:04 Anthropomorphizing AI and Economic Impact 9:10 Predictions, Progress, and Platform Shifts 11:31 Recursive Self-Improvement and Technical Challenges 13: 13 Hallucinations, Verification, and Expert Productivity 16:16 The Role of Experts and Tool Adoption 22:14 Changing Workflows: Agents Reshaping Work Patterns 45:55 Division of Labor, Specialization, and New Roles 48:47 Verticalization, Applied AI, and the Future of Agents 54:44 Platform Competition and the Application Layer Resources: Find Aaron on X: https://x.com/levie Find Martin on X: https://x.com/martin_casado Find Steven on X: https://x.com/stevesi Stay Updated: Let us know what you think: https://ratethispodcast.com/a16z Find a16z on Twitter: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Subscribe on your favorite podcast app: https://a16z.simplecast.com/ Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details, please see a16z.com/disclosures.
Steven Sinofsky, board partner at a16z, Aaron Levie, CEO of Box, and Martin Casado, general partner at a16z, discuss the reality of AI inside enterprises. They cover the gap between Silicon Valley and the rest of the world, why most AI initiatives fail in large organizations, and how agents, infrastructure, and workflows are evolving beyond the hype. Timestamps: 00:00 - Trailer 01:05 - Introductions & The Silicon Valley vs Enterprise Gap 04:30 - Why Enterprise AI Efforts Keep Failing 09:16 - The Architectural Shift: Treating AI as a User, Not Software 14:38 - The Integration Wall Agents Can't Climb 20:12 - Should Agents Be Treated Like Humans? 24:40 - Salesforce Goes Headless & What It Means for SaaS 39:16 - Scale, Entropy & Why AI Coding Creates as Many Problems as It Solves 47:53 - Will AI Kill Jobs or Create More of Them? Resources: Follow Aaron Levie on X: https://twitter.com/levie Follow Steve Sinofsky on X: https://twitter.com/stevesi Follow Martin Casado on X: https://twitter.com/martin_casado Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see http://a16z.com/disclosures.
a16z General Partner Martin Casado sits down with Box cofounder and CEO Aaron Levie to talk about how AI is changing not just software, but the structure and speed of work itself. They unpack how enterprise adoption of AI is different from the consumer wave, why incumbents may be better positioned than people think, and how the role of the individual contributor is already shifting from executor to orchestrator. From vibe coding and agent UX to why startups should still go vertical, this is a candid, strategic conversation about what it actually looks like to build and operate in an AI-native enterprise. Aaron also shares how Box is using AI internally today, and what might happen when agents outnumber employees. Timecodes: 00:00 Introduction to AI in the Enterprise 00:31 Aaron Levy, CEO of Box 01:32 AI in the Enterprise: Challenges and Opportunities 03:07 The Evolution of AI Adoption 04:54 AI's Role in Workflow Automation 05:55 Faster Buy-in Than Cloud: CIO Attitudes Have Changed 08:08 SaaS vs. AI-Native: Who Wins? 10:00 Is AI Just a Consumption Layer? 12:00 Business Models and the COGS of AI 15:00 New AI-First Categories Are Emerging 19:25 Box's Journey and AI Integration 21:39 The Future of Software and AI 27:41 AI in Decision-Making Processes 29:53 The Impact of Memo-Oriented Meetings 31:03 AI in Research and Strategy 32:18 AI's Role in Enterprise Budgets 43:03 The Future of Entry-Level Engineers 48:28 AI's Influence on Small Businesses 55:36 Predictions for the Next 5-10 Years Resources: Find Aaron on X: https://x.com/levie Find Martin on X: https://x.com/martin_casado Stay Updated: Let us know what you think: https://ratethispodcast.com/a16z Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Subscribe on your favorite podcast app: https://a16z.simplecast.com/ Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see a16z.com/disclosures.
For nearly two decades, Box co-founder and CEO Aaron Levie has been at the frontlines of how technology reshapes work—guiding the company through the rise of mobile, the cloud, and now the age of AI. In his fireside with YC General Partner David Lieb at AI Startup School, Aaron reflects on what it means to adapt a company over the long term, the hard lessons of staying relevant across multiple technology waves, and why he believes AI represents the most transformative shift yet. Chapters: 00:00 – AI hype vs. reality inside companies 01:00 – Early days: starting Box in 2005 03:30 – Pivoting from consumer storage to enterprise cloud 05:45 – Cloud transition lessons vs. AI today 07:10 – Why unstructured data is AI’s biggest opportunity 09:05 – Will AI replace jobs or create more work? 13:15 – Startups vs. incumbents in the AI era 15:20 – Finding the next “nouns and verbs” for startups 20:25 – Rethinking SaaS business models for AI agents 27:05 – Why companies won’t just build everything in-house 31:15 – Advice to young founders 35:40 – Fulfillment and meaning of life 36:40 – Enterprise design and craft in SaaS 39:00 – Competing with incumbents like Workday
Erik Torenberg, Steven Sinofsky, and Martin Casado speak to Aaron Levie, CEO at Box, about what happens to enterprise software when agents become the primary users. They discuss why coding agents succeed where other knowledge work agents struggle, what abstraction layers mean for the workforce, and how data access and systems of record must change in an agent-first world. Timestamps: 0:00—Intro 0:51—Building software for agents vs. humans 2:10—Can non-technical workers actually use AI agents? 14:31—CFO/CIO pushback: the real fear of agents doing integration 18:39—Treating agents like employees and why it breaks down 27:35—Diffusion gap: startups vs. enterprises 42:53—Wall Street's economics are off by an order of magnitude Read the full transcript here: https://www.a16z.news/s/podcast Resources: Follow Aaron Levie on X: https://twitter.com/levie Follow Steve Sinofsky on X: https://twitter.com/stevesi Follow Martin Casado on X: https://twitter.com/martin_casado Follow Erik Torenberg on X: https://twitter.com/eriktorenberg Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://twitter.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details please see http://a16z.com/disclosures.
Lecture Transcript: http://tech.genius.com/Aaron-levie-lecture-12-sales-and-marketing-annotated Aaron Levie - founder of Box, enterprise master, Twitter comedic genius. In this lecture, he'll convince you to Build for the Enterprise. See the slides and readings at http://startupclass.samaltman.com/courses/lec12 Discuss this lecture: http://startupclass.co/courses/how-to-start-a-startup/lectures/64041
The Lightcone hosts sit down with Aaron Levie, the co-founder & CEO of Box, to hear reports from the front of how large enterprise and Fortune 500 companies are adapting to the AI age. Apply to Y Combinator: https://ycombinator.com/apply Chapters (Powered by https://bit.ly/chapterme-yc) - 0:00 Intro 1:15 Why the GPT wrapper was a bad meme 4:44 Enterprise users just care about getting workflow done 8:38 What does it mean for startups as intelligence becomes a commodity? 12:47 Do Fortune 500’s have any interest in underlying models? 20:19 What are enterprise execs thinking about AI right now? 27:04 Is Box investing in internal AI tools? 28:17 What will enterprises build internally and what will they buy solutions for? 34:50 Is enterprise concerned with third-parties and security? 36:16 Shout-outs to Aaron! 39:46 The transition from cloud to AI 48:38 Outro
Should the US put a price on H-1B visas, or would that block the flow of new talent? Are AI coding agents actually making teams way more productive, or is it just hype? And in the AI platform shift, will the big winners be incumbents or new AI-native startups? Erik Torenberg is joined by Box co-founder and CEO Aaron Levie, a16z board partner Steven Sinofsky, and a16z general partner Martin Casado to debate the biggest questions in tech. They unpack pricing vs lottery for H-1Bs and what we’re actually optimizing for, why Box now ships a third of its code from AI, the shift from writing to reviewing code, and why bottom-up personal AI tools succeed where top-down “AI pilots” struggle. Timecodes: 0:00 Introduction 0:55 Latest immigration policy and who benefits 2:46 Salary bands as a solution for tech talent allocation 5:39 Optimizing immigration policy for wages, jobs, or merit 8:08 Market dynamics and policy changes in tech hiring 12:52 AI effects on labor productivity and developer output 19:25 Drivers of large AI productivity gains vs plateaus 24:40 Measuring AI’s impact on productivity and what’s missing 31:32 Human Taste and AI Tools 37:47 Young founders building companies differently with AI 41:34 Platform shifts: startups vs incumbents 49:01 AI opening new markets beyond software 55:54 Incumbents vs disruptors in the next decade of AI Resources: Find Aaron on X: https://x.com/levie Find Steven on X: https://x.com/stevesi Find Martin on X: https://x.com/martin_casado Find Erik on X: https://x.com/eriktorenberg Stay Updated: If you enjoyed this episode, be sure to like, subscribe, and share with your friends! Find a16z on X: https://x.com/a16z Find a16z on LinkedIn: https://www.linkedin.com/company/a16z Listen to the a16z Podcast on Spotify: https://open.spotify.com/show/5bC65RDvs3oxnLyqqvkUYX Listen to the a16z Podcast on Apple Podcasts: https://podcasts.apple.com/us/podcast/a16z-podcast/id842818711 Follow our host: https://x.com/eriktorenberg Please note that the content here is for informational purposes only; should NOT be taken as legal, business, tax, or investment advice or be used to evaluate any investment or security; and is not directed at any investors or potential investors in any a16z fund. a16z and its affiliates may maintain investments in the companies discussed. For more details, please see a16z.com/disclosures.