10 Best Aaron Levie Podcasts in 2026

1. Why Default AI Will Fail, and What Will Win Instead with Box CEO Aaron Levie

Follow Play Oct 28, 2025 48:45
Website Apple
About Episode Box Cofounder and CEO Aaron Levie joins Cameron Adams to explore how AI is transforming creativity, scale, and ambition inside organizations. Aaron shares how teams can turn data into a superpower, reinvent their ways of working, and unlock new opportunities to multiply their impact, all while keeping human creativity and judgment at the center. He also discusses how startups can now compete at scale from day one and how abundance thinking should shape what comes next. Cam’s notes on Substack: promptedwithcam.substack.com   Key Quotes “If you're in any creative role, the impact and leverage you have is truly 10 to a hundred times more than it was five or 10 years ago.” “A three or five person company now has the impact of a 50 person company.” “We should just start to think about this more as a technology for delivering abundance.” Timestamps 00:40 — Welcome + Intro to Aaron Levie 01:25 — The Prompt: Magic Camp and the spark of creativity 05:41 — What “being human” means in the age of intelligent tools 16:47 — Why intentional workflow design is essential 17:37 — The rise of prompt-driven companies 19:04 — Data is back: turning unstructured information into an advantage 28:02 — Abundance thinking and removing long-standing bottlenecks 28:31 — Creativity in every corner of the enterprise 30:47 — Failing fast and building a culture of experimentation 32:44 — Being more ambitious with what you ask AI to do 36:14 — Starting Box today: how AI changes what’s possible 40:05 — Differentiation and the importance of human spirit 41:48 — All-star creative team picks 42:56 — Magic Camp designer reveal 44:44 — Rapid-fire questions Links See Japes, Aaron and AI’s creative collaboration  Subscribe to the Prompted Newsletter Cam on LinkedIn: https://www.linkedin.com/in/themaninblue/ Aaron on LinkedIn: https://www.linkedin.com/in/boxaaron/ Aaron on X: https://x.com/levie Hosted by Simplecast, an AdsWizz company. See pcm.adswizz.com for information about our collection and use of personal data for advertising. MORE Podcast Title Prompted: AI, People and the Creative Spark
Podcast Description As AI evolves from just a tool to a trusted collaborator, the creative process is being rewritten. Prompted: AI, People and the Creative Spark is a show about this new era, when human inspiration meets artificial intelligence, and new forms of creativity, leadership, and invention take shape. Hosted by Canva’s Co-founder and Chief Product Officer, Cameron Adams, each episode brings you insight and direction from the leading voices at the intersection of AI and human ingenuity. These are the thinkers and builders reimagining what’s possible when we start treating AI as a co-creator. If you're curious about the future of creativity, and the people bold enough to shape it, you're in the right place.MORE Guest Aaron Levie
Apple Rating 4.0/5 Avg Length 37 min Format Medium form Get Email Contact Get access to full database of 2.7M podcastsCreate podcast lists, export in spreadsheet or CSV file with email contacts and start your podcast outreach in minutes.Sign Up for Free with Email Continue with Google

2. Aaron Levie | He Cold Emailed Mark Cuban To Invest in His Startup (Now..

Follow Play Oct 17, 2025 45:34
Website Apple Spotify
About Episode Episode #18 of Yesterday:Aaron Levie is the co-founder and CEO of Box (NYSE: BOX), a cloud storage company used by over 100,000 businesses worldwide, including 67% of the Fortune 500. He co-founded Box in 2005 while a student at USC, initially funding it with online poker winnings before securing an investment from Mark Cuban off a cold email. Under Aaron’s leadership, Box grew from a dorm-room startup to a publicly traded company with more than $1 billion in annual revenue and over 2,000 employees. In this episode, Aaron shares the unfiltered journey behind that growth: The early pivot from a consumer product to an enterprise-first model, to navigating the “innovator’s dilemma” He also discusses how the iPhone and the broader mobile revolution reshaped Box’s product strategy and accelerated enterprise adoption. TIMESTAMPS: 00:00 Intro 01:34 Box Origin Story 04:24 Funding the Company with Online Poker 05:46 The Cold Email That Landed Mark Cuban 07:06 Dropping Out of College for the Dream 09:52 Advice From Mark Cuban 11:12 Enterprise vs. Consumer 12:50 Using the “Innovator’s Dilemma” 15:59 The iPhone Launch 17:46 The ChatGPT Moment 21:02 AI Pivot 26:05 SORA Video Generation 29:45 Why Most Companies Are Failing 33:12 Agents Automating Everything 35:50 Jack Dorsey’s Favorite Entrepreneur 38:13 Advice for Young Founders Presented by Rho: Rho is the all-in-one banking platform for startups, used by Perplexity, Product Hunt, and thousands of other companies. You get everything you need to manage your startup’s cash & a team that’s obsessed with helping founders beat industry giants. Learn more at rho.co/yesterday Sponsored by The Cannon Project (TCP): TCP recruits founding GTM and engineering teams for startups like Ramp, Cursor, and Decagon while investing through their flagship venture fund, TCP 1. Apply for roles and learn more at thecannonproject.com This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit yesterdayy.substack.comMORE Podcast Title Yesterday Podcast
Podcast Description Interviews on inspiring life stories. yesterdayy.substack.com
Guest Aaron Levie
Apple Rating 5.0/5 Avg Length 54 min Format Long form Get Email Contact

3. Why AI companies are cutting Trump a deal

Follow Play Sep 04, 2025 21:04
Website Apple Spotify
About Episode The federal government is buying artificial intelligence technology at deeply discounted rates — part of an effort to bring agencies into modern times. And for companies like OpenAI and Anthropic, it’s a chance to get the government hooked on their products. On POLITICO Tech, Box CEO Aaron Levie joins host Steven Overly to discuss his own bargain for the Trump administration, why these deals are happening now and what an AI-powered government could look like. Steven Overly is the host of POLITICO Tech and covers the intersection of politics and technology.  Nirmal Mulaikal is the co-host and producer of POLITICO Energy and producer of POLITICO Tech.  Learn more about your ad choices. Visit megaphone.fm/adchoicesMORE Podcast Title POLITICO Tech
Podcast Description The POLITICO Tech podcast is your download on the disruption that technology is bringing to politics and policy. New episodes on Thursdays.
Host Steven Overly
Guest Aaron Levie
Producer/Network POLITICO
Email ****@gmail.com
Apple Rating 4.2/5 Avg Length 24 min Format Medium form Get Email Contact

4. Betting on the Cloud Before it was Cool: The Rise of Box w/ Aaron Levie

Follow Play Jul 07, 2025 1:08:23
Website Apple Spotify
About Episode With an insatiable appetite for “what’s the new model,” Aaron Levie, Co-founder and CEO of Box, grew up chasing ideas without hesitation: performing magic at birthday parties, building websites, and making short films. In this episode of HD in HD, he shares how a curious mind from early ages became his greatest strength, and how staying slightly uncomfortable kept him ahead of the biggest tech shifts, from SaaS to AI. Today, Box powers content for 100k+ organizations and 68% of the Fortune 500, and is still driven by the same restless energy Aaron had as a teenager, always chasing what’s next. In this episode, we also get into: overcoming critical challenges when scaling storage capacity the move that set Box apart from Dropbox how AI is becoming the next major accelerator for Box 00:00 Intro 00:57 Brex Sponsorship 01:44 Aaron Levy's Early Years 02:24 High School 13:04 College 17:29 The Early Days of Box 23:17 Technological Shifts and Challenges 29:39 Navigating Competition 30:00 Enterprise Differentiation 32:24 Brex Sponsorship 33:12 AI’s Impact on Software and Work 44:51 AI's Role in Enterprise Knowledge Management 48:07 Future of Organizational Design 55:50 AI's Influence on Sales and Marketing 01:03:50 Reflections on Luck, Strategy, and Mistakes ABOUT US: We’re proudly sponsored by Brex—a brand I co-founded, now supporting over 30,000 businesses like Anthropic, DoorDash, and Scale AI, helping them make every dollar count. I’m grateful for their continued support as I bring you all conversations with some of the most exceptional founders of our generation. For more information, please go to: https://www.brex.com/?ref_code=bmk_audio_HDinHD Connect with us here: 1. Aaron Levie- https://www.linkedin.com/in/boxaaron/ 2. Brex- https://x.com/brexHQ 3. Henrique Dubugras- https://x.com/hdubugras This episode was produced and distributed by our friends at Atomik Growth: https://atomikgrowth.com/MORE Podcast Title HD in HD
Podcast Description Henrique Dubugras founded fintech giant Brex when he was twenty-one years old. In his journey from São Paulo to Stanford to the heights of Silicon Valley he made connections with some of the biggest names in the ecosystem. Now, they’re not just business connections, but friends.MORE Guest Aaron Levie
Producer/Network Henrique Dubugras
Avg Length 95 min Format Extended Get Email Contact

5. How Box builds for Enterprise AI | Aaron Levie

Follow Play May 27, 2025 33:19
Website Apple Spotify
About Episode Welcome to the first episode of the Future Proof Podcast: Building AI Products That Last! In this episode, we chat with Aaron Levie, CEO and founder of Box, about what it takes to build successful Enterprise AI products. We cover: Why good data is a moat / flywheel for AI products The importance of access controls in RAG Building broad or building deep APIs, MCPs, A2A (00:00) Clips (00:30) Intro (01:40) Box's AI strategy (04:45) RAG use cases with proven value (09:05) Horizontal vs. deep product strategy (11:14) Prompts as IP (12:05) Importance of secure RAG in enterprise AI (16:28) Ingest vs. agentic queries (19:10) APIs, MCPs and Agent-to-Agent (21:20) Moats and network effects for AI companies (26:49) Risk of bad data (29:48) A few large AI agents vs. many niche AI agents Scale your AI product's integration roadmap with Paragon at https://useparagon.com/?utm_source=podcast/utm_campaign=ep1 MORE Podcast Title Future Proof: Building AI Products that Last
Podcast Description Future Proof brings top Product and Engineering leaders in B2B SaaS, working on AI products, to share learnings, discuss challenges and the latest developments in the future of B2B software. Producer: Forrest Herlick Host: Ethan LeeMORE Guest Aaron Levie
Apple Rating 5.0/5 Avg Length 32 min Format Medium form Get Email Contact

6. Inside Box’s AI playbook with founder & CEO Aaron Levie

Follow Play May 21, 2025 48:47
Website Apple Spotify
About Episode Aaron Levie, CEO & co-founder of Box, joins Azeem Azhar to explore how an “AI-first” mindset is reshaping every layer of Box – from product road-maps to pricing – and what that teaches the rest of us about building faster, smarter organisations. Timestamps: (00:00) Episode trailer (02:04) The "lump of labor fallacy" in sci-fi books (07:37) When individual productivity gains don’t translate to teams (12:32) Box’s Friday AI demos (21:23) How agents might redefine 100 years of management science (26:37) A lesson on AI innovation from the early days of Ford (29:52) Sundar Pichai, Satya Nadella, and Sergey Brin are coding again? (35:16) Pricing in a post-AI agent world (38:43) Cheaper tokens, heavier usage: AI’s margin math (43:02) Solving AI’s verifiability problem (48:24) How Aaron uses AI in his personal life Aaron's links: Box: https://www.box.com/ LinkedIn: https://www.linkedin.com/in/boxaaron/ X/Twitter: https://x.com/levie Azeem’s links: Substack: https://www.exponentialview.co/ Website: https://www.azeemazhar.com/ LinkedIn: https://www.linkedin.com/in/azhar X/Twitter: https://x.com/azeem This conversation was recorded for “Friday with Azeem Azhar”, live every Friday at 9 am PT / 12 pm ET. Catch it via Exponential View on Substack. Produced by supermix.io and EPIIPLUS1 Ltd MORE Podcast Title Azeem Azhar's Exponential View
Podcast Description How will the future unfold? What is the impact of AI and other exponential technologies on business & society? Join Azeem Azhar, founder of Exponential View, on his quest to demistify the era of exponential change.MORE Host Azeem Azhar
Guest Aaron Levie
Producer/Network Azeem Azhar
Email ****@azhar.co.uk
Apple Rating 4.9/5 Avg Length 32 min Format Medium form Get Email Contact

7. The enterprise AI revolution is underway, with Box’s Aaron Levie

Follow Play May 20, 2025 33:37
Website Apple Spotify
About Episode The buzz in Silicon Valley around AI agents has many asking: What’s real and what’s hype? Box’s co-founder and CEO, Aaron Levie, joins Rapid Response to help decipher between fact and fiction, taking listeners inside the fast-paced evolution of agents and its impact on the future of enterprise AI. Plus, Levie unpacks how AI is really being adopted in the workplace, what it takes to legitimately build an AI-first organization, and what political leaders across both parties misunderstand about creating the best environment for technology to thrive.  Visit the Rapid Response website here: https://www.rapidresponseshow.com/ See Privacy Policy at https://art19.com/privacy and California Privacy Notice at https://art19.com/privacy#do-not-sell-my-info. MORE Podcast Title Masters of Scale
Podcast Description On Masters of Scale, iconic business leaders share lessons and strategies that have helped them grow the world's most fascinating companies. Founders, CEOs, and dynamic innovators join candid conversations about their triumphs and challenges with a set of luminary hosts, including founding host Reid Hoffman (LinkedIn co-founder and Greylock partner). From navigating early prototypes to expanding brands globally, Masters of Scale provides priceless insights to help anyone grow their dream enterprise.MORE Hosts Bob Safian, Jeff Berman, Reid Hoffman
Guest Aaron Levie
Producer/Network Masters of Scale Network
Email ****@mastersofscale.com
Apple Rating 4.6/5Facebook 11.6KTwitter 30.5KInstagram 79.7K Avg Length 33 min Format Medium form Since Nov 2017 Get Email Contact

8. Aaron Levie: The Restless Founder Plotting the Future of Cloud Storage and AI

Follow Play Mar 31, 2025 40:49
Website Apple Spotify
About Episode When the team behind Box first went looking for funding back in 2005, they tried just about every trick in the book. They sent Bill Gates a fax. They dropped a prospectus off at Paul Allen’s house in Seattle. And they took a shot at convincing Mark Cuban to join two ambitious college kids  with a hunch the way businesses stored and collaborated around information was about to change. Two decades later Box is a cornerstone of the cloud era with $1 Billion in revenue, but co-founder and CEO Aaron Levie is as restless as ever. In this episode, Mike Maples, Jr. of Floodgate speaks with Levie about how he started Box when he was still in college at USC, why it’s fatal for startups to hire sales reps too slowly, and how he’s personally leading the way as the company looks to reinvent itself in the era of AI.Check out the Pattern Breakers Blog at patternbreakers.substack.com for even more Pattern Breaking content from Mike.   Mike's book Pattern Breakers is available now wherever you buy books.MORE Podcast Title Pattern Breakers
Podcast Description Host Mike Maples Jr. from venture capital firm Floodgate offers lessons from the rare startup super performers — BEFORE they were successful. Pattern Breakers features interviews with some of Silicon Valley’s most legendary entrepreneurs and thought leaders, including Netscape co-founder Marc Andreessen, LinkedIn founder Reid Hoffman, Instagram founders Kevin Systrom and Mike Kreiger, business maverick Mark Cuban, and Shopify co-founder Tobi Lütke.MORE Host Mike Maples Jr
Guest Aaron Levie
Producer/Network Floodgate
Email ****@floodgate.com
Apple Rating 4.9/5Twitter 96K Avg Length 40 min Format Long form Since Nov 2019 Get Email Contact

9. Between Two Founders (Episode 004) - Aaron Levie

Follow Play Dec 03, 2024 45:23
Website Apple Spotify
About Episode Episode 004 of Between Two Founders – Jeff Seibert, CEO and founder of Digits, sits down with Aaron Levie, CEO and co-founder of Box, a cloud-based content management company that allows companies to access information from anywhere and collaborate with anyone. In this episode, Jeff and Aaron chat about Aaron’s journey starting Box — from cold-emailing Mark Cuban to his decision to drop out of USC, and the current landscape of the cloud storage space. Between Two Founders is an enlightening series of interviews hosted by Jeff Seibert of Digits, featuring seasoned founders from VC-backed startups offering rare insights from their journeys and first-hand experience. MORE Podcast Title Between Two Founders
Podcast Description An enlightening series of fireside chats, hosted by Jeff Seibert of Digits, featuring seasoned founders from VC-backed startups. Gain rare insights from their journeys, and first hand experience.MORE Guest Aaron Levie
Producer/Network Digits
Apple Rating 5.0/5 Avg Length 66 min Format Long form Get Email Contact

10. How to Adapt and Win in Enterprise Software (Aaron Levie, Co-Founder &..

Follow Play Oct 11, 2024 42:40
Website Apple Spotify
About Episode Aaron Levie, co-founder and CEO of Box, has guided the cloud content management platform from a dorm room project into a publicly traded company with over $1B in annual revenue. In his second appearance on B2BaCEO, Aaron reflects on his founder journey, sharing how Box capitalized on cloud computing and their recent push to integrate generative AI. But our conversation goes far beyond Box. Aaron’s role has given him a unique vantage point on what the latest advances in AI mean for founders. We explore the AI applications that excite him most, where he sees opportunities for startups over incumbents, and the potential areas in AI that founders might be overlooking. (0:00) Intro (2:26) The Box journey (4:23) Transitioning to enterprise (8:26) Building a GTM flywheel (11:45) Lessons from the enterprise journey (15:16) Where AI is heading (18:14) Facing the innovator's dilemma (20:54) AI agents (26:15) Why AI is positive sum for the economy (30:24) The AI doomer debate (34:22) The evolving model ecosystem (40:30) Parting advice for foundersMORE Podcast Title B2BaCEO (with Ashu Garg)
Podcast Description B2B a CEO is the show about how to scale your enterprise startup and how to grow from founder to CEO. Hosted by Ashu Garg, general partner at Foundation Capital. Subscribe to the newsletter here: https://ashugarg.substack.com/MORE Host Ashu Garg
Guest Aaron Levie
Producer/Network Foundation Capital, Ashu Garg
Email ****@foundationcap.com
Apple Rating 5.0/5Facebook 149 Avg Length 49 min Format Long form Get Email Contact