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.

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why aren't all 19 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 0 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

Opinion
Rippling Wins by Copying Vertical SaaS Features Into a Suite
“Rippling's building like the next work day and they've taken like, oh, this company does HR analytics. We'll like copy 90% of their good features and we'll make an integrated version that works with your employee directory. Oh, you want to do like global billi…”
Jean-Denis Greze Jul 21, 2023 ▶ 36:15 Jean-Denis Greze: CTO of Plaid, the $18B Fintech Startup; How to Hire, Fire & Build Great UX | E1038 · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Silver Lake Prepares $43B Take-Private Bid for Workday
“Silver Lake circles a forty three billion dollar take private bid for Workday.”
Harry Stebbings Aug 20, 2026 ▶ 48:27 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Insight
Lemkin: Being a software system of record prevents churn but doesn't drive growth
“I don't think system of record is, I think it's a moat, but I don't think it's a ticket to growth. This is, I think, super important. And it's something that everyone on X gets wrong. It's great to have a system of record, which Workday has. It means churn eve…”
Jason Lemkin Aug 20, 2026 ▶ 51:23 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Insight
O'Driscoll: Price hardly matters in winning VC deals unlike PE buyouts
“In venture deals, if you're in the right thing, it almost doesn't matter what you paid. You see cursor for details, see open router for details, right? This is the exact opposite. This is fine, precise financial engineering. If you're wrong by 20%, 30% on pric…”
Rory O'Driscoll Aug 20, 2026 ▶ 50:40 Stripe's $8B OpenRouter Bet | Anthropic's First Profit & The Math Behind Reaching $600B in Revenue?
Disclosure
Mitchell Green: Lead Edge Capital is buying public software stocks like Procore, Workday, Appian
“We are buyers. We're buying software stocks right now. You know, a portion of our funds can be invested in public equities, so we're buying companies like Procore, Workday, Appian.”
Mitchell Green Mar 7, 2026 ▶ 1:45 Mitchell Green: Why 50% of VCs Should Not Exist · 20VC with Harry Stebbings
Insight
Bookman: Vertical SaaS startups must build multi-product suites to support viable ASPs
“In a lot of these verticals, you've got to get to like workday level product or, you know, rippling compound multi-product company to get the ASPs working.”
Zachary Bookman Dec 6, 2024 ▶ 24:48 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Demand environment is worsening for Salesforce, MongoDB, and Workday
“Yamini got on the last call a couple of weeks ago and said, yeah, we saw a little bounce at the end of the year and HubSpot had a great quarter, but it's not any easier. She said, it's not one lick easier right now. So HubSpot, not any easier Mongo worse. Sale…”
Jason Lemkin Jun 3, 2024 ▶ 36:55 Jason Lemkin: PluralSight S*** the Bed & The Next IPO Candidates | E1160 · 20VC with Harry Stebbings
Insight
Kerrest: Successful Enterprise Software Founders Are Industry Veterans, Not 20-Somethings
“I think if you look at successful enterprise software founders, whether it was Mark Benioff and Parker Harris, Salesforce, or whether it was Anil Bushri, And Dave Duffield at Workday or whether it was Fred Luddy at ServiceNow, these are all folks who did not s…”
Frederic Kerrest May 3, 2019 ▶ 10:37 20VC: Okta Founder Frederic Kerrest on Why You Want To Be A Monopolist In A Small Market, The Biggest Challenges in Scaling Okta To IPO and Being a16z's First Ever Fund Check
Opinion
Rampell: Workday and NetSuite are impervious to AI disruption
“There are the ones that are almost impervious to everything that's happening with AI. And if anything, it's a huge tailwind because they're going to start being, they have the distribution, they're going to start adding features. And that's things like Workday…”
Alex Rampell Jan 12, 2026 ▶ 1:04:39 Alex Rampell: The Best Founders Materialise Capital, Customers & Labour | The Future of Venture · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Workday acquired Sana Labs for $1.1B at $50M ARR
“Workday acquiring Sana Labs for 1.1 billion dollars. They were at like, 50 in ARR.”
Harry Stebbings Sep 18, 2025 ▶ 1:08:13 Opendoor CEO, Kaz Nejatian: OpenAI and Oracle, How Can Either Afford to Do This · 20VC with Harry Stebbings
Insight
Grady: Early SaaS was a business model shift, not a UX revolution
“If you look at the last decade or so of software, the transition has been from on-premise to SaaS or on-premise to cloud, and that's been a wonderfully impactful transition, but at a very fundamental level, it's been a transition in the business model, not a t…”
Pat Grady Mar 13, 2017 ▶ 8:23 20VC: Sequoia Partner, Pat Grady on Why Data Is The New Oil, Why We Will See The Return of The Apprenticeship Model in VC & The Defining Characteristics of The Next Generation of Great Software
Assertion Partly supported
Lemkin: Workday's standard enterprise contract terms effectively total eight years
“Workday does three year contracts up front and five year renewal. So the average Workday customer effectively signs up for an eight year contract. Three and five is their standard term.”
Jason Lemkin Apr 30, 2026 ▶ 10:30 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
Assertion Not checkable as stated
Plank: Upmarket is Rippling's fastest-growing segment, competing with Workday
“The fastest growing segment, for sure, is like our upmarket segment, like our, you know, we're moving that market, like very quickly and, you know, used to not compete with the workdays of the world. And now that's weren't a lot of deals with them.”
Matt Plank Dec 20, 2024 ▶ 48:15 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Opinion
Cahn: Rational AI strategy is unclear for non-cloud giants like Salesforce
“I mean, I do think the like tier below those three big companies are scared right now. I think there's probably like those boardroom conversations are probably tense, right? I think on the one hand, huge opportunity, right? Make the product better. You already…”
David Cahn Aug 5, 2024 ▶ 27:06 David Cahn: Why Servers, Steel and Power Are the Pillars Powering the Future of AI | E1186 · 20VC with Harry Stebbings
Assertion Contradicted
George: Salesforce, Workday, and ServiceNow command market cap in B2B
“In B to B, you know, Salesforce, Workday, ServiceNow, they command almost all the market cap in their respective markets.”
David George Feb 9, 2024 ▶ 24:58 20VC: Doug Leone, Bill Ackman, Bill Gurley and Orlando Bravo on "Does Price Matter"; When to Pay Up vs When to Stay Disciplined, The Biggest Lessons on Price Discipline from 8 of the World's Best Investors
Assertion Supported
Adaptive Insights took a $1.6B Workday acquisition three days pre-IPO
“Including Adaptive Insights, by the way, last year, who was three days away from going public, and then instead chose to take the Workday offered a 1,000,000,006 instead.”
Byron Deeter Jul 8, 2019 ▶ 15:30 20VC: Bessemer's Byron Deeter On Lessons From Investing in 14 $Bn Companies, What The Heck Is Going On In Cloud Today and Why Cloud IPO Floodgates Are About To Burst Open
Disclosure
Viswanathan: Workday's 2009 pitch was his most straightforward in 20 years
“When we heard the pitch, it was probably one of the most straightforward pitches I've ever heard in 20 years of venture, meaning we just had to fund that company, and the reason for that is there's the numbers, but you really have to see what is this company d…”
Ravi Viswanathan Apr 6, 2020 ▶ 17:32 20VC: Raising A $1.35Bn Fund I, The Emerging Secondary Opportunity For Early Stage Managers and Founders & What It Takes To Win The Best Growth Deals Today with Ravi Viswanathan, Founder & Managing Partner @ NewView Capital
Assertion Supported
NewView Capital's $1.35B debut fund yielded three major exits within two years
“Launched in 2018 with their 1.35 billion dollar debut fund, They've already set themselves as leaders in the world of growth funding, with three massive exits in less than two years, in the form of, check this out, Plaid sold to Visa for 5.3 billion dollars, A…”
Harry Stebbings Apr 6, 2020 ▶ 0:24 20VC: Raising A $1.35Bn Fund I, The Emerging Secondary Opportunity For Early Stage Managers and Founders & What It Takes To Win The Best Growth Deals Today with Ravi Viswanathan, Founder & Managing Partner @ NewView Capital
Opinion
Viswanathan: Tom Bogan is the best board member he has worked with
“I would say Tom Bogan. Tom is a senior exec at Workday now. He was CEO of Adapted Insights. I was on a board with him. I was on the Acquia board with him, and I would say just the best board member I've ever worked with just had incredible credibility. He was …”
Ravi Viswanathan Apr 6, 2020 ▶ 34:56 20VC: Raising A $1.35Bn Fund I, The Emerging Secondary Opportunity For Early Stage Managers and Founders & What It Takes To Win The Best Growth Deals Today with Ravi Viswanathan, Founder & Managing Partner @ NewView Capital
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