The Ledger

Every statement that passed quotation and attribution checks. Mix any filter with any other: certainty 1/5, debate potential 5/5, or both at once.

clear all ✕

why aren't all 39 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 1 checkable ones are still open, waiting for their date. predictions held up or didn't; assertions are supported or contradicted. on every card: ▮▮▮▮▮ certainty · ▮▮▮▮▮ debate potential. speakers are clickable

Prediction Open · timeframe Apr 2031
Levie: Box will have more software engineers in five years
“We will.”
Aaron Levie Apr 20, 2026 ▶ 5:23 Aaron Levie: Everyone is Wrong; We'll Have More Developers in 5 Years · 20VC with Harry Stebbings
Insight
Lemkin: If Box cannot re-accelerate growth, incumbent SaaS is hopeless
“If he can't get Box to 20 to 30% growth I'm giving up on, on the rest of the world.”
Jason Lemkin Apr 16, 2026 ▶ 1:02:12 SpaceX's Financials Leaked: Is it Worth $2TN | Meta Debuts Muse Spark: Are They Back in the AI Race? · 20VC with Harry Stebbings
Assertion Supported
Lemkin: SaaS incumbents see no revenue boost from AI features yet
“So far the evidence is no. So far it says the incumbents are gonna, they're gonna do great things with AI, great, great things. The product's gonna be much better, but it's not clear they're gonna get any revenue boost from it. No one's saying that none of the…”
Jason Lemkin Jun 3, 2024 ▶ 24:36 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Opinion
Levie: Box's 4x valuation multiple is way undervalued and should be 6-8x
“Now, now Forex is clearly way, way too undervalued. It, you should be in the kind of, you know, six or eight X range.”
Aaron Levie May 22, 2024 ▶ 57:42 Aaron Levie: How the Business Model of SaaS Changes Forever & Startups vs Incumbents:Who Wins?|E1155 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Levie: Box reinvests in headcount whenever AI boosts function productivity
“At least so far empirically, every time that we've done that, we will actually reinvest in that area of the business.”
Aaron Levie May 22, 2024 ▶ 16:16 Aaron Levie: How the Business Model of SaaS Changes Forever & Startups vs Incumbents:Who Wins?|E1155 · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Levie: Box API activity already dwarfs direct human user interactions
“The volume of API usage on our system is already enormous and already, you know, is outsized relative to any of the end user interactions in the system.”
Aaron Levie Apr 20, 2026 ▶ 17:39 Aaron Levie: Everyone is Wrong; We'll Have More Developers in 5 Years · 20VC with Harry Stebbings
Disclosure
Cannon-Brookes: Only four public CEOs remain from 2020 SaaS peer group
“In COVID in 2020, we formed a group of SaaS CEOs. I think there were 16 of us that got together, we'd meet on Zoom every single week, right? At one stage, 10, 11 of us were public, maybe more, we all had earnings calls, and you know, it was a really good thera…”
Mike Cannon-Brookes Feb 12, 2026 ▶ 24:28 Anthropic's Super Bowl Ad: Who Won & Lost? | Sierra Hits $150M ARR: Is Customer Support Too Crowded? · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Public SaaS companies are re-accelerating growth through AI
“I'm glad to see that just literally this week, we were seeing Mongo even Okta, which had been struggling, Box last, the other day, Zoom, which is, you know, which is not exactly a rocket ship anywhere, but seeing growth re-accelerate because of AI, it's like, …”
Jason Lemkin Aug 28, 2025 ▶ 45:52 Anthropic's $10B Round, Klarna's IPO, Inside a16z's 72 Deal Seed Investment Machine ft. Marc Benioff · 20VC with Harry Stebbings
Insight
Hamid: Aaron Levie's Box IPO dilution led VCs to re-up founder equity
“Aaron has done a great PSA for founders with his equity stake at the IPO, where I think we as investors, board members have done a way better job making sure that our founders get re-upped when, especially when they dip below a certain threshold.”
Mamoon Hamid Oct 21, 2024 ▶ 26:33 Mamoon Hamid: AI - Where Value Accrues, Startups vs Incumbents & Scaling Laws | E1217 · 20VC with Harry Stebbings
What-if
Khan: Box and Dropbox margin expansion required public market discipline
“Like, I don't think the margins that Box and Dropbox is generating, if they could have generated, if they would just stay private. Because the growth was slowing, they were forced to look at the business and run the business better.”
Imran Khan Aug 26, 2024 ▶ 16:52 Imran Khan: Why the IPO Market is Not Closed & Lessons From Taking Snap & Alibaba Public | E1194 · 20VC with Harry Stebbings
Opinion
Lemkin: Dropbox and Box have settled into low single-digit growth
“I think we are seeing some great companies like Dropbox and box settle into that and just feel that they without, unless they have a huge market cap and then go buy something that it is the world, right?”
Jason Lemkin Jun 3, 2024 ▶ 19:23 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Opinion
Lemkin: Box and Dropbox Were Very Late to Go Multi-Product
“When we look at the boxes and the drop boxes, and I think both Aaron and Drew are honest here. They were very late to go multi-product and arguably drop boxes and multi-product at all. Arguably it's one product boxes kind of getting there, but I would say it's…”
Jason Lemkin Jun 3, 2024 ▶ 22:10 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Levie: Users Will Wire Into Specific AI Models Rather Than Abstracted Selection
“I don't think you're going to have complete commoditization of sort of the personality of the models for the sort of style and the response to the point where then, you know, if you're a user, you know, any given response could come from Gemini, Versus GPT-IV …”
Aaron Levie May 22, 2024 ▶ 5:29 Aaron Levie: How the Business Model of SaaS Changes Forever & Startups vs Incumbents:Who Wins?|E1155 · 20VC with Harry Stebbings
Insight
Levie: Goal setting must be ambitious but decoupled from harsh accountability
“Whenever possible, have as ambitious of a goal as possible, and so goal setting should be sort of ambitious and idealistic in terms of what you're trying to achieve. That is, needs to be separate, though, from sort of like what maybe we would consider like har…”
Aaron Levie Feb 11, 2022 ▶ 15:55 20VC: Box's Aaron Levie on Why Founders Cannot Hedge Their Bets, The 2 Categories of Wrong Decision and How To Avoid Them & The Biggest Dangers of Being Over-Funded as a Startup
Insight
Levie: Founders scale only by avoiding solving problems directly
“As you're scaling, you have to attempt to not solve, hopefully, as many problems as possible in the business directly, and that's your only way of scaling”
Aaron Levie Feb 11, 2022 ▶ 7:21 20VC: Box's Aaron Levie on Why Founders Cannot Hedge Their Bets, The 2 Categories of Wrong Decision and How To Avoid Them & The Biggest Dangers of Being Over-Funded as a Startup
Disclosure
Suster passed on Uber and Box due to personal biases
“The obvious example, Harry, is Uber, where having lived in London and seen the taxi lobby and how strong the taxi lobby was in London, that clouded my vision for what was possible. Having lived in Los Angeles and seeing how few people ever use taxis, that clou…”
Mark Suster Apr 20, 2020 ▶ 34:13 20VC: Upfront's Mark Suster on COVID Redefining What A Great Company Looks Like and What Valuations Look Like, Why Pay-To-Play Is Back On The Table & Why We Will See The Death of Party Rounds
Assertion Supported
Lemkin: AI features helped Box return to double-digit growth
“It has led to a boost at Box. It hasn't turned Box into a hundred percent grower. It's gotten it back to double digit growths.”
Jason Lemkin Jul 2, 2026 ▶ 16:12 Coinbase Cuts AI Spend by 50% | Kalshi's $40B Valuation & Impending IPO | The Year for SaaS Roll-Ups · 20VC with Harry Stebbings
Insight
O'Driscoll: Legacy SaaS giants have lost high-valuation growth premium
“These companies, they're in a much more bounded world now. They might grow 15%. They might grow five percent. They might trade at six times revenues. They might trade at four times revenues. You know, if you look at the stock chart, the area of magic is gone, …”
Rory O'Driscoll Nov 6, 2025 ▶ 53:07 Is a $4.5BN Exit Enough in VC? & Harvey Raises $150M & Why Google is a Buy and Amazon is a Sell · 20VC with Harry Stebbings
Disclosure
O'Driscoll: I passed on Box in 2010 before investing nine months later
“Same thing on Box. I passed at the start of 2010. The round didn't even get done, and nine months later, I literally woke up and said, what's the dumbest thing I did all year? I didn't do that deal, and I went down and did it.”
Rory O'Driscoll Sep 4, 2025 ▶ 1:08:19 Anthropic Raises $13BN & OpenAI Buys Statsig for $1.1BN All Stock · 20VC with Harry Stebbings
Disclosure
Scale Venture Partners invested in HubSpot, Box, DocuSign, and RingCentral in 2009
“Yes, I remember that was in O-Nine. We did HubSpot, Box, DocuSign, and I think RingCentral.”
Rory O'Driscoll Aug 7, 2025 ▶ 45:37 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Opinion
O'Driscoll: Box's valuation suffers from competing against free Microsoft and Google
“The reason the stock price is always hard is we're competing against Microsoft and Google who give it away for free.”
Rory O'Driscoll May 1, 2025 ▶ 51:41 What Does it Take to Be Good at Series A and B Today? · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Hamid: Box raised 2008 bridge financing at a $25M valuation
“We got to invest more dollars in the box at a twenty-five million dollar valuation. More, like, every incremental dollar or, you know, two, three million dollars in bridge that was being done was done at that valuation.”
Mamoon Hamid Oct 21, 2024 ▶ 25:48 Mamoon Hamid: AI - Where Value Accrues, Startups vs Incumbents & Scaling Laws | E1217 · 20VC with Harry Stebbings
Assertion Supported
Hamid: Box was one week from running out of cash before IPO
“I've had companies that are one week away from cash out become public companies.”
Mamoon Hamid Oct 21, 2024 ▶ 24:09 Mamoon Hamid: AI - Where Value Accrues, Startups vs Incumbents & Scaling Laws | E1217 · 20VC with Harry Stebbings
Insight
Annie Pearl: New products inside established companies take longer to impact revenue
“It always takes much longer for the sort of payoff of that investment to really start to materially lift and impact the business.”
Annie Pearl Sep 1, 2022 ▶ 45:07 Calendly CPO Annie Pearl: Hiring Advice for Product; Calendly's Second Product | 20VC #921 · 20VC with Harry Stebbings
Disclosure
Levie: Box secretly built a peer-to-peer file sharing product in 2005
“And we actually developed another product that we don't talk about publicly, which was going to be a peer to peer file sharing technology that we were going to introduce in the market.”
Aaron Levie Feb 11, 2022 ▶ 10:43 20VC: Box's Aaron Levie on Why Founders Cannot Hedge Their Bets, The 2 Categories of Wrong Decision and How To Avoid Them & The Biggest Dangers of Being Over-Funded as a Startup
Disclosure
Levie: Box centralizes software design like Apple while keeping engineering autonomous
“So for design, as an example, we probably more have the Apple ethos. So our software design is extremely centralized and that ensures that everything we put out in the market, we believe is going to have the same look and feel the same great user experience. C…”
Aaron Levie Feb 11, 2022 ▶ 18:39 20VC: Box's Aaron Levie on Why Founders Cannot Hedge Their Bets, The 2 Categories of Wrong Decision and How To Avoid Them & The Biggest Dangers of Being Over-Funded as a Startup
What-if
Levie: Pursuing a peer-to-peer architecture in 2005 would have failed Box
“So if we had chosen the peer to peer path as an example, that would not have worked just based on the architecture of the web went.”
Aaron Levie Feb 11, 2022 ▶ 11:32 20VC: Box's Aaron Levie on Why Founders Cannot Hedge Their Bets, The 2 Categories of Wrong Decision and How To Avoid Them & The Biggest Dangers of Being Over-Funded as a Startup
Disclosure
Levie delegates everything outside product, strategy, culture, and customers
“And so I've designed my schedule, my time to be able to support, you know, spending time in those areas, which then by definition means you need to delegate all of the other important aspects of the business as much as humanly possible.”
Aaron Levie Feb 11, 2022 ▶ 9:33 20VC: Box's Aaron Levie on Why Founders Cannot Hedge Their Bets, The 2 Categories of Wrong Decision and How To Avoid Them & The Biggest Dangers of Being Over-Funded as a Startup
Insight
Levie: Product bets fail when teams prioritize technology over customer problems
“And when certain features or products don't work and often they frequently have a, an element of Us as sort of product managers and people within the company brainstorming about how amazing it would be if we could do X thing with Y technology, as opposed to th…”
Aaron Levie Feb 11, 2022 ▶ 14:21 20VC: Box's Aaron Levie on Why Founders Cannot Hedge Their Bets, The 2 Categories of Wrong Decision and How To Avoid Them & The Biggest Dangers of Being Over-Funded as a Startup
Disclosure
Shirazi Passed on Early-Stage Investment Opportunities in Box and Waze
“I remember making a bad decision not to advise or invest in box or join box because I just thought that the business was so young and so early, and it was basically when it was just three people. And I also made a mistake on Waze, too. And, you know, I met the…”
Darian Shirazi Apr 6, 2018 ▶ 9:21 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
Assertion Supported
Box and Twilio Reached $200M ARR Prior to Going Public
“In fact, the last two IPOs that we've seen at DFJ over the last couple years, Box and Twilio, were both companies that were on nearly two hundred million dollar annual revenue run rates before they got public.”
Randy Glein Feb 8, 2017 ▶ 14:11 20VC: The Radical Changes In Public Market Expectations, The Right Way To Assess Valuation & What It Means To Be A Disciplined & Diligent Investor with Randy Glein, Partner @ DFJ Growth
Assertion Supported
Box's post-2008 revenue ramped from $5M to $125M
“They went rough revenue ramp was five, 10, 25, 55, one, 25, and so just, you know, exploding out of the gate on the heels of that.”
Josh Stein Jan 9, 2017 ▶ 14:10 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
What-if
Seibert: Dual-tracking M&A and funding yields stronger acquisition deal terms
“If we had started in January and had a full six months to sort of side by side pursue funding and partnerships or acquisition, I think we would have been in a much stronger position.”
Jeff Seibert Jan 29, 2016 ▶ 9:15 20 VC FF 032: Jeff Seibert on Lessons From Being Acquired By Twitter & Box and Now Leading Twitter's Consumer Product
Assertion Supported
Lemkin: Box Generates Over $1B Annually With $800M Gross Margin
“Box is doing a billion-ish a year, a little bit more, right? So, twenty million goes to, two hundred million goes to COGS, to servers and support, and he's got eight hundred million to play with each year.”
Jason Lemkin Jun 3, 2024 ▶ 1:07:34 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Assertion Partly supported
Lemkin: Box, HubSpot, and Shopify IPO'd under $1B valuations
“Box IPO did eight hundred million. HubSpot IPO did eight hundred million valuation. Shopify IPO did a seven hundred and fifty million dollar valuation.”
Jason Lemkin Jan 4, 2024 ▶ 52:23 Jason Lemkin: Predictions for 2024 - What Does a Trump Administration do for Startups? | E1099 · 20VC with Harry Stebbings
Assertion Supported
Deeter: Box had over 130% net upsells in its IPO prospectus
“Was the fact that they had over a 130% net upsells, meaning if you stopped closing any new business and essentially fired your sales and marketing team, the business would still grow 30%.”
Byron Deeter May 2, 2016 ▶ 17:07 20VC: Bessemer's Byron Deeter on The Commonalities Of Truly Great Founders and Learnings From Investing In Box, Twilio and GainSight
Assertion Not checkable as stated
Levie: Early investors thought the concept for Box was stupid
“And it never felt like an epiphany because the moment I started pitching people on the idea, they thought it was stupid.”
Aaron Levie Feb 11, 2022 ▶ 3:58 20VC: Box's Aaron Levie on Why Founders Cannot Hedge Their Bets, The 2 Categories of Wrong Decision and How To Avoid Them & The Biggest Dangers of Being Over-Funded as a Startup
Assertion Supported
Willis: Aaron Levie had no enterprise experience when he founded Box
“At the same point, Aaron Levy didn't know anything about the enterprise before he started box. And that worked out brilliantly well.”
Tyler Willis Feb 17, 2016 ▶ 13:30 20VC: Tyler Willis on How To Be Innovative With Customer Acquisition and The Future Of Innovation
Assertion Supported
Stebbings: Box's first-ever acquisition was InCrayo in 2009
“Before Crashlytics, Jeff was the founder of InCrayo, which was Box's first ever acquisition in 2009.”
Harry Stebbings Jan 29, 2016 ▶ 0:37 20 VC FF 032: Jeff Seibert on Lessons From Being Acquired By Twitter & Box and Now Leading Twitter's Consumer Product
Made with StarZero

Turn any episode into a week of clips.

This entire site, over 1,200 episodes transcribed, diarized, checked and made playable, runs on the StarZero media pipeline. Drop in your own episode and the podcast clipper finds the moments worth sharing, cuts them, captions them, and reframes them for every feed.