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 17 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

Assertion Not checkable as stated
Lemkin: Coupa, Zendesk, and Anaplan may fail to repay their debt
“Coupa, New Relic, Anaplan, even Zendesk, Avalara, Smartsheet they all look like they may not be able to fully repay their debt”
Jason Lemkin Apr 30, 2026 ▶ 47:05 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Prediction Not checkable as stated
Rampell: AI could drive Zendesk's seat-based revenue down to zero
“On the other side, you have things like Zendesk, right? Where it's like, how many licenses per seat do you need of Zendesk? If now every customer support ticket can be answered automatically, you need zero license. Like their revenue could go down a hundred pe…”
Alex Rampell Jan 12, 2026 ▶ 1:04:55 Alex Rampell: The Best Founders Materialise Capital, Customers & Labour | The Future of Venture · 20VC with Harry Stebbings
Prediction Held up
O'Driscoll: PE firms will acquire AI startups to dress up legacy SaaS
“I'm willing to bet that all those PE shops have a, let's acquire some new AI Pixie Dust to put on top of Zendesk, to put on top of Anaplan so we can, you know, tart up the story with acquisitions.”
Rory O'Driscoll Apr 17, 2025 ▶ 24:12 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
Assertion Not checkable as stated
McCabe: Intercom AI resolution reaches 50%, beating Zendesk's high twenties
“When we first released our AI agent, the average resolution rate was in the high twenties to high 20%. So that's the rate at which it successfully closes tickets when it gets involved in the conversation. And now, like I said, it's approaching 50%. I think Zen…”
Eoghan McCabe Oct 11, 2024 ▶ 4:14 Eoghan McCabe, CEO @Intercom: Freedom of Speech, Censorship and Government Control | E1213 · 20VC with Harry Stebbings
Prediction Open · timeframe May 2029
Lemkin: Private Equity Firms Will Lose Money on Bubble-Era Software Buyouts
“Yeah. I think they'll lose money on, on, on these deals.”
Jason Lemkin May 27, 2024 ▶ 26:39 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Stebbings: Zendesk Is a $10B Company Overbid by Private Equity
“Come on, Zendesk is like a ten billion dollar company at best, overbid by PE providers.”
Harry Stebbings Jan 10, 2025 ▶ 11:41 Mikey Shulman, CEO @Suno: The Future of Music, What is Gonna Happen? | E1244 · 20VC with Harry Stebbings
Insight
Traynor: Focusing on beating a declining competitor risks ruling over a graveyard
“Oftentimes you can find yourself ruling over a graveyard. Right. Like if we just beat Zendesk, but Zendesk is like in the current state it's in, that won't be the full realization of what Intercom can be.”
Des Traynor Nov 15, 2023 ▶ 1:25:31 Des Traynor: How to Survive and Thrive in a World of OpenAI | E1082 · 20VC with Harry Stebbings
Insight
Des Traynor: Private equity software playbook increases prices and shrinks product roadmaps
“The PE cash cow playbook would look like raise prices, shrink roadmap, bring the register, package it up into a very efficient, like sort of cash producing machine and hand it over.”
Des Traynor Nov 15, 2023 ▶ 1:25:46 Des Traynor: How to Survive and Thrive in a World of OpenAI | E1082 · 20VC with Harry Stebbings
Assertion Supported
European enterprise software investors universally passed on Zendesk's early rounds
“Everybody in Europe, Who knew anything about enterprise software looked at Zendesk and passed because there were plenty of reasons why this would never work.”
Christoph Janz Nov 24, 2021 ▶ 15:04 20VC: The Contentful Memo: Point Nine's Christoph Janz on The Cold Email That Led to a Unicorn Investment, How To Approach Market Sizing and Timing & The Pros and Cons of Pre-Emptive Rounds, When To Do Them vs When Not To?
Opinion
Nelson: AI-native startups possess superior ML environments over legacy software firms
“I do think that there is an advantage to many of the younger companies that have started from their foundation with AI at the center of everything that it is that they're doing, because they have created much better environments to support machine learning the…”
Maren Nelson Jan 13, 2017 ▶ 15:37 20VC: Building An AI Company For The Long Term? How Humans & Machine Learning Can Work Together? What Applications Are The Conversational Interface Best Suited To with Maran Nelson, Founder & CEO @ Clara Labs
Assertion Supported
Jason Lemkin: Base Zendesk AI achieves 20% ticket automation without custom training
“The base version of Zendesk, which you get with AI, it's about 20% automated. That's about as well as you can do without training.”
Jason Lemkin Nov 27, 2025 ▶ 51:15 Anthropic Raises $30B from Microsoft & NVIDIA & NVIDIA’s Core Business Faces TPU Threat · 20VC with Harry Stebbings
Assertion Partly supported
Halligan: Zendesk never secured long-only investors due to shaky IPO timing
“Zendesk at the time went out. And it was just, it was timing, and it was just a shaky week that they went out, and they just didn't get, they didn't get the big long onlys, and they had a good story, and they didn't get them, and they never really got them. Th…”
Brian Halligan Aug 7, 2025 ▶ 17:07 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Insight
Brian Halligan: Activist investor horror stories are rare and public markets are rational
“Public investors, like there's so much written about what happened with Zendesk or Autodesk, or these really bad things that happen. It's pretty rare. And I have found that public investors be pretty rational.”
Brian Halligan Aug 7, 2025 ▶ 39:11 Figma's 250% Pop - The Greatest IPO Mispricing Ever? Meta & Microsoft Blowout Quarters: Broken Down · 20VC with Harry Stebbings
Assertion Not checkable as stated
Tunguz: Top data teams at Facebook and Zendesk focus on internal education
“The first is they have a data team, and there's this data, and that, this exists at Facebook, it exists at Zendesk, and these data teams, they, they're structured a little bit differently, but they all basically do the same thing. They're the experts. They kno…”
Tomasz Tunguz Sep 12, 2016 ▶ 6:41 20VC: Redpoint's Tom Tunguz on Winning with Data: How To Gain A Competitive Advantage & Dominate Markets with Data and 5 Steps To Create A Data Driven Company
Assertion Supported
Zendesk disproved the $1,000/month minimum pricing rule for enterprise software
“Five years ago, it used to be the case that You enterprise products had to be something you could sell for at least a thousand dollars a month. Otherwise you couldn't sell them economically. And then Zendesk comes along and completely rips that apart.”
Rob Moffat Jun 22, 2015 ▶ 5:29 20 VC 047: 4 Ways Investors Find Great Startups with Rob Moffat, Principal @ Balderton Capital
Disclosure
Mignot: Index Ventures passed on Zendesk early rounds before growth investment
“That was just before I started, but we did that with Zendesk, for example, where, you know, we passed on, on, on the seed and on DA especially You know, if you look at the memo and the valuation at the time, it's quite funny in retrospect, I don't remember exa…”
Martin Mignot Aug 11, 2025 ▶ 41:24 Index Ventures Partner, Martin Mignot: Figma, Scale, Wiz: Inside Index’s Decacorn Factory · 20VC with Harry Stebbings
Assertion Supported
Zendesk for Startups grew to 3,000 startups under Kimmel
“And prior to starting Worklife, Brianne spent two years at Zendesk on their go-to-market strategy, building Zendesk for startups, ultimately representing 3000 startups and 250 accelerators.”
Harry Stebbings Oct 14, 2019 ▶ 0:36 20VC: Worklife Ventures' Brianne Kimmel on Why More Operators Should Start Their Own Fund, How To Structure Your Round for the Highest Signal Round & What The Multi-Stage Funds Playing At Seed Means For The Rest of The Asset Class
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.