Aaron Levie, every mention

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every year anyone Harry Stebbings 52Jason Lemkin 40Ted Blosser 5Rory O'Driscoll 4Mamoon Hamid 4Josh Stein 3Jeff Lawson 3Tyler Willis 2Martin Casado 2Jason Calacanis 2

Verbatim, from the transcripts: the passages where Aaron Levie comes up

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Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings Jul 2, 2026 · 3 mentions

  • ▶ 16:07 Jason Lemkin Even sometimes for a while, I would get tired of Aaron Levy's constant AI stuff. 3 times in the scene

Anthropic's Raise & What It Means for Potential IPO? Mag7: Google & Amazon Up, Meta & Microsoft Down · 20VC with Harry Stebbings May 7, 2026 · 2 mentions

SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings Apr 16, 2026 · 1 mention

  • ▶ 57:52 unnamed speaker You know, Aaron Levy had a, had a tweet this year, this week about his latest roadshow meeting with CIOs from box.

Thrive Raises New $10B Fund | OpenAI Buys OpenClaw | Stripe at $140B: Is Adyen Wildly Undervalued? · 20VC with Harry Stebbings Feb 19, 2026 · 2 mentions

  • ▶ 1:27:32 Harry Stebbings You know who deserves prizes for persistence and resilience, and I love, Drew from Dropbox, and Aaron from Box. 2 times in the scene

Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings Feb 12, 2026 · 1 mention

Will Cursor Kill Figma? Lightspeed Raises $9B & OpenAI’s $1B from Disney & #1 App in App Store · 20VC with Harry Stebbings Dec 18, 2025 · 2 mentions

  • ▶ 53:21 Jason Calacanis Now, I think I would argue Mark with his megaphone is actually like an Aaron Levy is doing a better job publicly of bridging the gap, but they have the same job. 2 times in the scene

Eventbrite Sold for $500M, Databricks $5B Raise at $134B Valuation & Why SaaS is Like Japan · 20VC with Harry Stebbings Dec 4, 2025 · 2 mentions

  • ▶ 26:51 Jason Lemkin How did the Aaron Levy's and the Drew Houston's and the others not figure out, and I love them, right? 2 times in the scene

OpenAI Restructuring: Who Wins and Who Loses & Mercor Raises $350M at a $10BN Valuation · 20VC with Harry Stebbings Oct 30, 2025 · 1 mention

  • ▶ 1:05:30 Jason Lemkin But I don't see the, the deep crows feet and, and like, you know, Aaron Levy going from, from going gray at 28 or whatever.

Thinking Machines Co-Founder Joins Meta for $3.5BN, Industry Venture's $665M Acquisition · 20VC with Harry Stebbings Oct 16, 2025 · 5 mentions

  • ▶ 42:06 unnamed speaker Oh my god, these, Aaron, Aaron and Dylan built a folder you could put a file in.
  • ▶ 45:01 unnamed speaker Um, we had Aaron talking to some of our LPs. 4 times in the scene

OpenAI's Multi-Billion Deal with AMD & Polymarket, Vercel and Supabase Raise Mega Rounds · 20VC with Harry Stebbings Oct 9, 2025 · 1 mention

  • ▶ 53:04 Harry Stebbings The astonishing thing for me about your Aaron Laveys, or your Drew Houstons, or your Mike Cannonbrooks,

OpenAI’s $10BN Secondary Sale, Ramp Hits $1BN ARR & Brex Hits $700M · 20VC with Harry Stebbings Sep 11, 2025 · 3 mentions

  • ▶ 1:11:02 Jeff Lawson Here's the thing I would say about both Dropbox and Box, both Aaron and Drew. 3 times in the scene

Sam Altman's Masterplan or a Gift to Anthropic? Palantir & Shopify Crush Earnings · 20VC with Harry Stebbings Aug 14, 2025 · 2 mentions

  • ▶ 1:21 Jason Lemkin But when I look at folks smarter than me, if Aaron Levy is running this through box and saying redline and document, conspiracy and term extraction is materially better. 2 times in the scene

a16z GP, Martin Casado: Anthropic vs OpenAI & Why Open Source is a National Security Risk with China · 20VC with Harry Stebbings Jul 28, 2025 · 2 mentions

  • ▶ 45:14 Martin Casado I mean, Aaron Levy said it so, Aaron Levy said it so beautiful. 2 times in the scene

How Do All Providers Deal with Anthropic Dependency Risk & Figma IPO Breakdown: Where Does it Price? · 20VC with Harry Stebbings Jul 24, 2025 · 2 mentions

  • ▶ 5:23 Jason Lemkin As Aaron Levy pointed out, you know, enterprises are terrified because an agent will just go out and change things in his database without telling you it will, it will take data. 2 times in the scene

Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings Jun 5, 2025 · 17 mentions

  • ▶ 35:32 Jason Lemkin Harry, you should have asked Aaron Levy when you interviewed him yesterday, if he mattered. 10 times in the scene
  • ▶ 52:58 Rory O'Driscoll I give Aaron huge credit. 3 times in the scene
  • ▶ 55:43 Jason Lemkin Like if I'm Aaron or Yamini, like these are S tier SaaS CEOs. 3 times in the scene
  • ▶ 1:21:17 Jason Lemkin So I would say the one thing, you know, from these guys going even there in Levy's, but, but Zuck's on another level, hyper competitive, right?

Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings May 22, 2025 · 2 mentions

  • ▶ 45:54 Jason Lemkin So Aaron Levy, he's, you know,
  • ▶ 1:01:05 Jason Lemkin You know, um, the biggest takeaway, I think, um, you know, you've had both of them on, I think what, what Yamini from HubSpot and Aaron Levy both said is, um, I'm super excited, but I'm anxious.

What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings May 1, 2025 · 7 mentions

  • ▶ 48:03 unnamed speaker And like Aaron's all over AI, right? 7 times in the scene

Mamoon Hamid: AI - Where Value Accrues, Startups vs Incumbents & Scaling Laws | E1217 · 20VC with Harry Stebbings Oct 21, 2024 · 12 mentions

Eiso Kant, CTO @Poolside: Raising $600M To Compete in the Race for AGI | E1211 · 20VC with Harry Stebbings Oct 7, 2024 · 1 mention

  • ▶ 59:17 Eiso Kant There was a tweet, and if I recall correctly, it's from Aaron, Levi from Box, early on in post-ChatGPT moment, and he wrote something along the lines of, if you feel like you're working extremely hard on reasonable hours as AI is now…

Ara Mahdessian: ServiceTitan Would Not Be the Success if We Raised VC Earlier | E1175 · 20VC with Harry Stebbings Jul 10, 2024 · 1 mention

  • ▶ 51:56 Harry Stebbings It's the hardest thing, my friend, Aaron Levy said, you know, if you do hiring well, you get one out of two, right?

Andrew Bialecki: Is Klaviyo the Most Under-Priced Public Company? | E1170 · 20VC with Harry Stebbings Jun 26, 2024 · 1 mention

Michael Eisenberg: How China Could Overtake the US in the AI Race | E1167 · 20VC with Harry Stebbings Jun 19, 2024 · 1 mention

  • ▶ 20:16 Harry Stebbings They need to upsell a new product, which they've been, Aaron will admit this, so I'm not shitting on him, but too slow to do.

Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings Jun 3, 2024 · 14 mentions

  • ▶ 3:43 Jason Lemkin Uh, I think, you know, you had Aaron Levy here the other day too, right?
  • ▶ 19:13 Jason Lemkin It feels like draw and maybe even as much as I love, maybe even Aaron Levy settled into that too. 5 times in the scene
  • ▶ 22:10 Jason Lemkin When we look at the boxes and the drop boxes, and I think both Aaron and Drew are honest here.
  • ▶ 23:01 Harry Stebbings They can integrate generative AI or you name it, like Aaron on the show talked about integrating AI into their storage solution so you could extract knowledge way more efficiently from the docs you have. 3 times in the scene
  • ▶ 26:04 Harry Stebbings When I had Aaron on the show, and live in the show, I was like, damn, checking his market cap. 2 times in the scene
  • ▶ 1:07:14 Jason Lemkin And then the third one, this, this I learned from, um, from Aaron Levy. 2 times in the scene

Keith Rabois & Eric Glyman: The Tools, Tips, Secrets and Process That Drive Efficiency | E1148 · 20VC with Harry Stebbings May 3, 2024 · 2 mentions

  • ▶ 17:24 Harry Stebbings I think it's Aaron Levy says you need five turnovers before you go to a public company in the trajectory of company scaling. 2 times in the scene

Daniel Dines: From a Dollar a Day to Romania's Richest Man| Happiness, Wealth, Risk and more | E1143 · 20VC with Harry Stebbings Apr 22, 2024 · 1 mention

  • ▶ 43:14 Harry Stebbings And Aaron Levy actually at Box, the famous enterprise software founder, says it takes actually five exact teams churning to go to a public company, I think is his statement.

Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings Jan 4, 2024 · 3 mentions

  • ▶ 1:22 Jason Lemkin Yeah, I was, uh, I was an early SaaS founder with the generations of, uh, Aaron Levy at Box and Renee LeCert and Drew Houston.
  • ▶ 48:35 Jason Lemkin I mean, I asked Aaron Levy when I talked to him, when you talk with your biggest customers, what's their AI budget? 2 times in the scene

Lori Jiménez: How to Increase Sales; Hiring Tips from Google; Best Way to Grow Sales Teams | E1043 · 20VC with Harry Stebbings Aug 2, 2023 · 2 mentions

  • ▶ 7:20 Lori Jiménez And that's really something Aaron just, um, has built and made core to the culture and I've carried it forward, um, in every place I've been since.
  • ▶ 7:58 Harry Stebbings I loved having Aaron on the show.

Miki Kuusi: How I Scaled Wolt to $8B; Why I Sold to DoorDash | 20VC #953 · 20VC with Harry Stebbings Nov 28, 2022 · 1 mention

  • ▶ 46:49 Harry Stebbings You're seeing it with Elon more than ever, but you're seeing it with your Aaron levies and CEOs are now public figures.

20VC: Why the Traditional Seed Fund Model No Longer Works, Why Multi-Stage Funds Investing at Seed Bring Signaling Risk but also Less Pressure, The One Criteria All Potential Sales Hires Need to Have and The Clear Signs of 10x Sales Hires with Jason Lemki May 6, 2022 · 1 mention

  • ▶ 3:36 Jason Lemkin Yeah, I mean, it's a long time ago now, but literally 10 years ago, my cohort of Sasta founders, the Aaron Levy's, the David Sachs's, the others,

20VC: Scaling to $122M ARR IPO with $6M in Net Burn, Olo. The Ultimate Journey of Capital Efficiency, What Worked, What Did Not Work and How Leaders Need To Reshape Thinking Around Resource and Attention Allocation Apr 29, 2022 · 1 mention

  • ▶ 12:32 Noah Glass The ability to, to delegate, I picked this up from what Aaron said from the box episode, it is so critical as you scale the organization.

20VC: Sweetgreen Founder Jonathan Neman on Leadership Lessons from Managing Through COVID, The Importance of Failing Fast and Iterating & How the Best Leaders Bring Together Brand, Capital Allocation and Strategy Jan 26, 2022 · 1 mention

20VC: 23andMe's Anne Wojcicki on How To Approach Trust in Business and Personal Relationships, Leadership Lessons from Sheryl Sandberg and Reflections on How The Best Founders Manage Their Boards Jan 24, 2022 · 2 mentions

  • ▶ 17:56 Harry Stebbings Aaron Levy recently said about management become a team churn and how you need a new leadership team with every stage of the company. 2 times in the scene

20VC: Unity Founder David Helgason on The Hypergrowth Early Days of Unity, Why Running A Company Is Like A Liberal Art, The Secret To A Successful CEO Transition and What Makes Roelof Botha Such A Special Board Member Oct 29, 2020 · 1 mention

  • ▶ 23:09 Harry Stebbings Because Aaron Levy at Box is always very pronounced in terms of saying, like, management churn is the most inevitable thing of startups.

20VC: Plaid's Zach Perret on Why You Have To Hire For Spikes and What That Really Means, Fintech Predictions From Incumbent Entrants To The Rise of Europe & The 2 Big Questions That CEOs Should Ask Themselves Jun 7, 2019 · 1 mention

  • ▶ 17:34 Harry Stebbings In the past, you've also tweeted, as we said earlier, you should always be running an exec search, and I had Aaron Levy at Box on the show, and he said, on the way to IPO, you can have five cycles of exec churn.

20VC: So You Want To Be Acquired? Instacart VP of Corp Dev, Dave Sobota on His Biggest Lessons From 10 Years in Google's M&A Team Working on The Acquisitions of Motorola, Waze & Android Apr 15, 2019 · 1 mention

  • ▶ 0:31 Harry Stebbings To date, the company's raised over 1.9 billion dollars in funding from some of the very best investors and operators in the industry, including the likes of Mike Moritz at Sequoia, Jeff Jordan at Andreessen, Aaron Levy at Box, Sam Altman,…

20VC: Elad Gil's High Growth Handbook on The Commonalities of The Truly Great CEOs, How To Hire The Very Best Execs, Why Cash is A Defensible Moat Today & The Pros and Cons of M&A and IPOs Jul 17, 2018 · 3 mentions

  • ▶ 0:28 Harry Stebbings General Catalyst, CRV, ATVC, Aaron Levy, and more incredible names.
  • ▶ 37:44 unnamed speaker I think Aaron Levy from Box would be a good example of that.
  • ▶ 43:29 Elad Gil But then I did interviews to supplement that with Reid Hoffman, Mark Andreessen, Miriam Nafisi, Aaron Levish, Shannon Stubo.

20VC: The Core Lessons From Building a 150 Startup Angel Portfolio, Why Founders Who Angel Invest Have Such Strong Advantages and Why The Lean Startup Makes Less and Less Sense Today with Adrian Aoun, Founder & CEO @ Forward May 25, 2018 · 1 mention

  • ▶ 0:27 Harry Stebbings To date, Adrian has raised funding from some of the true greats of the business, including Mark Benioff, Eric Schmidt, Joe Lonsdale, Aaron Levy, and Josh Kushner, just to name a few.

20VC: Why Facebook Will Be The Company To Succeed in Crypto, Why Founders Should Be Actively Angel Investing & Commonalities of Great Leadership From Mark Zuckerberg to Mark Pincus with Darian Shirazi, Founder & CEO @ Radius Apr 6, 2018 · 2 mentions

  • ▶ 7:35 Darian Shirazi When Aaron and Dylan were in a shack behind their uncle's house in Berkeley, these are all companies where I didn't realize until I had seen a few cases of these transition from the early stages until to a really big company and what that…
  • ▶ 8:06 Harry Stebbings You mentioned their kind of arrow in a box, you mentioned the Udemy team, you mentioned market Facebook, you've seen this cohort of incredible leaders.

20VC: Why You Should Build Your Investor Team Like A Sports Team & How To Leverage The Abilities Of Your Investors Effectively with Ted Blosser, Founder & CEO @ WorkRamp Jan 27, 2017 · 10 mentions

  • ▶ 3:40 Ted Blosser One was I was able to go learn from the best from the likes of Aaron Levy and Dylan Smith and understand how to build a hyper growth business.
  • ▶ 4:33 Harry Stebbings Now, you teed me up so nicely there with the learning from the best from Aaron and Dylan, but I'd love to ask them, with the incredible journey that you experienced with Box in their kind of period of hyper-growth, 5 times in the scene
  • ▶ 15:12 Ted Blosser I'll bring up a, I'll bring up a good story actually about Aaron Levy. 4 times in the scene

20VC: Why You Should Not Invest From Patterns, Why No Good Business Was Built As An Analogy Of Another & Why The Rise Of The 'Celebrity Investor' Is Concerning with Emily Melton, Partner @ DFJ Jan 11, 2017 · 1 mention

20VC: DFJ's Josh Stein on Why VCs Must Adapt To Their Founders, The Major Transition Points For Aaron Levie @ Box & Why SaaS Startups Are Growing At A Rate Never Seen Before Jan 9, 2017 · 16 mentions

  • ▶ 7:23 Josh Stein Aaron Levy at box is much more of a parallel processor and is much more also about, you know, I think he's more willing to make mistakes along the way because he sees, and I think pretty correctly in the sense of box, you know, a time… 3 times in the scene
  • ▶ 9:47 Harry Stebbings And so Greg Sands at Costa Noah asks you, what did you see in the early days of box with the young founder that was Aaron Levy that made you so excited? 13 times in the scene

20VC: The Best Determinant Of Product Market Fit & Why Prior Experience Is Not Required For Founder Success with Neeraj Agrawal, General Partner @ Battery Ventures Apr 18, 2016 · 2 mentions

  • ▶ 8:36 Harry Stebbings You know, your iron levies of the world who are coming in with no prior experience in enterprise.
  • ▶ 13:40 Neeraj Agrawal I think that, you know, with the enormous success folks like Anne Levy has had, or Zuckerberg's had, I don't think that that structure is an issue anymore.

20VC: Tyler Willis on How To Be Innovative With Customer Acquisition and The Future Of Innovation Feb 17, 2016 · 2 mentions

  • ▶ 13:30 Tyler Willis At the same point, Aaron Levy didn't know anything about the enterprise before he started box. 2 times in the scene
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