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 113 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 7 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
Bouaziz claims Rippling engaged in three years of poor competitive behavior
“Well, I think you should read our lawsuit in Delaware. You know, three years of poor way of competing in the market.”
Alex Bouaziz Oct 20, 2025 ▶ 1:08:05 Deel CEO, Alex Bouaziz on Raising $300M+ at a $17BN Valuation · 20VC with Harry Stebbings
Opinion
Bouaziz claims rival Rippling tries to compete through media headlines
“I think it's unfortunate that the way they're trying to compete is through media and through headlines and things like that.”
Alex Bouaziz Oct 20, 2025 ▶ 3:56 Deel CEO, Alex Bouaziz on Raising $300M+ at a $17BN Valuation · 20VC with Harry Stebbings
Prediction Open · timeframe May 2030
Lemkin: Rippling will 100% win its trade secret lawsuit against Deel
“There's no chance they'll lose you know, it could get settled, right? Which is, they're always the right outcome, even when there's emotion. The right outcome is always to settle it, right? There's no way they lose a hundred percent. The facts are too bad. The…”
Jason Lemkin May 22, 2025 ▶ 52:50 Rippling vs. Deel Lawsuit: WTF Happens Now? The Future of the Late Stage Private Market · 20VC with Harry Stebbings
Assertion Not checkable as stated
In-office SDRs significantly outperform remote peers, says Ashley Kelly
“We pivoted about nine months ago, I want to say, and started hiring in office more. And you do see the in office SDRs perform much higher than the ones that are remote, especially for outbound, just because there's so many learnings sitting next to each other.”
Ashley Kelly Jun 7, 2024 ▶ 49:40 Ashley Kelly: The Playbook to Start and Scale Your SDR Team | E1162 · 20VC with Harry Stebbings
Opinion
Petersen: Parker Conrad was wrongly scapegoated at Zenefits
“I think Parker was wrongly scapegoated and run out of town at benefits. Then he, and he proved it by going to build rippling into a business that's much bigger and better than reference benefits ever was in the exact same space.”
Ryan Petersen Nov 13, 2023 ▶ 52:04 Ryan Petersen: Why Velocity not Speed is Most Important in Company Building | E1081 · 20VC with Harry Stebbings
Insight
Lemkin: Bootstrapped SaaS startups risk falling behind venture-backed rivals
“Maybe it's not even until after five or ten million where if you don't have capital, you can't all be Atlassian or Qualtrics. Or, and they fall behind competitively. And I think that's the trap of the fallacy of the lifestyle-esque business, right? Where media…”
Jason Lemkin Aug 11, 2023 ▶ 32:24 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
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
Prediction Not checkable as stated
Lewis: Rippling will dominate globally without leaving room for European clones
“Why does some of these European payroll and HR, workforce management companies, not knocking on Europe, but why do you need a rippling for Europe? There's no Airbnb for Europe. There's no Google for Europe. Why do you need a rippling for Europe? Why do you nee…”
Geoff Lewis Oct 5, 2022 ▶ 15:09 Geoff Lewis: Why I Put $200M into Rippling; Uncapped Notes; "Compound Startups" | 20VC #933 · 20VC with Harry Stebbings
Insight
Parker Conrad: Compound startups building parallel products outperform single-focus startups
“Most you know, most companies there, there's sort of a conventional wisdom around startups that you ought to do like one extremely narrow thing. And that focus is like the way to build companies. And I think that at least for Rippling, we've sort of taken the …”
Parker Conrad Oct 3, 2022 ▶ 17:08 Parker Conrad: How I Got Ousted from Zenefits and Came Back with a Vengence | 20VC #932 · 20VC with Harry Stebbings
Assertion Partly supported
Scaleups acqui-hiring failing YC startups for AI talent is no longer viable
“When rippling is hoovered up 30, and owners hoovered up 20, and Revolut's hoovered up 10, you just, that strategy worked three years ago. Like, it's too late. Like, everyone is just sitting there hitting refresh, hoping these smart YC companies fail so they ca…”
Jason Lemkin Aug 12, 2026 ▶ 1:29:11 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Prediction Open · timeframe Apr 2029
O'Driscoll: Canva and Rippling won't fetch 30x revenue premiums
“Good SaaS companies that aren't AI first are going to trade at fair value, which means if you've created value, you'll get value. And I think Canva and Rippling have both created enormous value. So they'll get value, but what they won't get is that stupid, 30 …”
Rory O'Driscoll Apr 30, 2026 ▶ 18:27 Anthropic Raises $45B but Falls Short on Compute & Thoma Bravo Hand Back Medallia Keys to Creditors · 20VC with Harry Stebbings
What-if
Clements: Breaking VC rules for Rippling would have been worthwhile
“And I think like, I don't regret not breaking the rules in general, but you know, this would have been a time when it could have been worthwhile.”
Miles Clements Mar 9, 2026 ▶ 22:20 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Opinion
Clements: Nobody builds ARR compounding levers better than Parker Conrad
“And I think nobody in the world does that better than Parker Conrad.”
Miles Clements Mar 9, 2026 ▶ 20:52 "Cursor is Dead" is Total BS: Here is Why | Miles Clements · 20VC with Harry Stebbings
Opinion
Stebbings claims Silicon Valley elites protect and anoint Rippling
“Rippling have the Silicon Valley Illuminati around them, and in the same way for me, like, there are some media companies, which I'm not going to name because they'll hate me for it, but, like, they just have the Silicon Valley, the Collison's, and the YC's ar…”
Harry Stebbings Oct 20, 2025 ▶ 4:43 Deel CEO, Alex Bouaziz on Raising $300M+ at a $17BN Valuation · 20VC with Harry Stebbings
Prediction Open · timeframe Aug 2027
Lemkin: Rippling will not go public for at least two more years
“Rippling needs another two years is my guess in the oven to get to that.”
Jason Lemkin Aug 21, 2025 ▶ 1:33:04 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lemkin: Buyers will demand AI software from single vendors within 12 months
“We're already seeing this consolidation in e-commerce if we want to chat about where they're becoming one tool already. I think it's a real risk for all these cool ones. Like we just don't need five of them going to Rory's point. We may, Rippling's a good exam…”
Jason Lemkin Aug 21, 2025 ▶ 1:17:26 Databricks at $100BN, CoreWeave’s $11B Debt Bet & Nubank’s $2.5B Profit Shocker - Ep.19 · 20VC with Harry Stebbings
Prediction Open · timeframe Jul 2030
Lemkin: Initialized Capital's Fund II will achieve a 10x return
“Their fund two is going to be a 10 X fund, I think with flock safety rippling and others.”
Jason Lemkin Jul 10, 2025 ▶ 11:29 Daniel Gross and Nat Friedman: Acquired by Meta | Microsoft Layoff 9000 People | OpenAI's Bombshell · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lemkin: A hundred corporate espionage and founder fraud cases will surface
“I think you're going to hear a hundred, just like fraud. Like every day now we pull up the media and there's another founder that stole thirty million from the investors and we shrug it off. Right. There's going to be a hundred of these in this environment.”
Jason Lemkin Apr 17, 2025 ▶ 1:23:24 a16z's $20BN Fund & Founders Fund's $4.6BN & Why Josh Kushner Has Mastered the Game · 20VC with Harry Stebbings
What-if
Plank: Rippling couldn't compete in niche verticals without specialized reps
“Had we not done that, We never would have been able to compete in these kind of, like, hyper-competitive, like, vertical spaces like finance and global payroll”
Matt Plank Dec 20, 2024 ▶ 1:10:13 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Disclosure
Plank: Rippling account executives have zero outbound prospecting targets
“Outbound SDRs own the quota. Like they schedule the demos. If you're a rep at Ripley and you have zero, like actual prospecting targets.”
Matt Plank Dec 20, 2024 ▶ 44:18 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 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
Insight
Lemkin: Passing on Great Founders Over Competition Misses Out on Category Winners
“I believe the best opportunities find you at the end of the day. It's not that you don't find them. Okay. But they also find you by the same token. And if you're gonna pass on an amazing binary set of founders, an amazing CEO, CTO, just because they're in a co…”
Jason Lemkin May 27, 2024 ▶ 19:59 Jason Lemkin: Why Pricing is Worse Than Ever and There is More Funding Than Ever | E1157 · 20VC with Harry Stebbings
Insight
Blond: Do Not Hire Initial Sales Reps From Salesforce or Rippling
“If you are hiring your first AE, first AEs number one and two, They need to have seen an early stage startup environment. Do not hire from an extreme example, be Salesforce, but gosh, even today, you know, don't hire from a rep who came from rippling. And join…”
Sam Blond Apr 12, 2024 ▶ 13:45 Sam Blond: Why Startups are Doing Outbound Wrong and How to Fix It | E1139 · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2029
Blond: Parker Conrad Will Build a $100 Billion Business With Rippling
“I just wanted to join this guy's company because he was going to build a hundred billion dollar business. You know, we didn't realize that outcome with Zenefits. He's going to with Rippling.”
Sam Blond Apr 12, 2024 ▶ 6:58 Sam Blond: Why Startups are Doing Outbound Wrong and How to Fix It | E1139 · 20VC with Harry Stebbings
Disclosure
Lewis: Bedrock lost Rippling's Series B after trying to lower agreed valuation
“We agreed on evaluation with Parker. He's like, send me the term sheet. I'm ready to sign. And we were like, wait, Like all of their business at the time was SMBs. Now, since then they've extended, expanded surface area phenomenally into mid-market. They're st…”
Geoff Lewis Oct 5, 2022 ▶ 26:38 Geoff Lewis: Why I Put $200M into Rippling; Uncapped Notes; "Compound Startups" | 20VC #933 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lewis: Rippling's preferred stack will grow linearly or sublinearly relative to revenue
“Because of their approach to product building and go to market, I believe the preferred stack Grows either linearly or sub linearly versus revenue over time versus hyper linearly.”
Geoff Lewis Oct 5, 2022 ▶ 19:16 Geoff Lewis: Why I Put $200M into Rippling; Uncapped Notes; "Compound Startups" | 20VC #933 · 20VC with Harry Stebbings
Disclosure
Bedrock exited Bitcoin and Ethereum to fund its investment in Rippling
“And so we traded out of Bitcoin and Ethereum via our second fund and for it, right before the crash for a great multiple and recycled those proceeds to fund our rippling investment.”
Geoff Lewis Oct 5, 2022 ▶ 34:28 Geoff Lewis: Why I Put $200M into Rippling; Uncapped Notes; "Compound Startups" | 20VC #933 · 20VC with Harry Stebbings
Opinion
Lewis: Parker Conrad is the most vengeance-driven founder he has backed
“And Parker has that in spades more than any entrepreneur I've backed. He's got it.”
Geoff Lewis Oct 5, 2022 ▶ 8:14 Geoff Lewis: Why I Put $200M into Rippling; Uncapped Notes; "Compound Startups" | 20VC #933 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lewis: Rippling will become the AdWords for SaaS software distribution
“In March of twenty-twenty-two, Parker and the company articulated a very specific and detailed product roadmap around how they can really become, through their employee graph, over time, I don't think he would phrase it this way, but I'm going to, the AdWords …”
Geoff Lewis Oct 5, 2022 ▶ 13:34 Geoff Lewis: Why I Put $200M into Rippling; Uncapped Notes; "Compound Startups" | 20VC #933 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Conrad: Non-Rippling companies employ double the HR, IT, and finance staff
“At almost every stage of growth, you know, companies between zero to 25 employees, companies, you know, like between 500 and a thousand employees, they have almost double the number of people in HR, IT, and finance for companies that don't use Rippling than co…”
Parker Conrad Oct 3, 2022 ▶ 26:25 Parker Conrad: How I Got Ousted from Zenefits and Came Back with a Vengence | 20VC #932 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Conrad: Rippling aims to match competitors with 20% of R&D cost
“Our goal is, is to be able to, you know, match or really exceed in a lot of ways, the capability of the current sort of best in class products in the market with like, 20% of the R and D investment.”
Parker Conrad Oct 3, 2022 ▶ 21:30 Parker Conrad: How I Got Ousted from Zenefits and Came Back with a Vengence | 20VC #932 · 20VC with Harry Stebbings
Prediction Partly held up
Conrad: Rippling partner products will have equal distribution to internal SKUs
“No, I think, I mean, we have a really robust partner ecosystem, and I think you know, our goal is to have you know, companies that we partner with that, that compete against internal rippling products on even footing. And not just in the sense that, you know, …”
Parker Conrad Oct 3, 2022 ▶ 34:51 Parker Conrad: How I Got Ousted from Zenefits and Came Back with a Vengence | 20VC #932 · 20VC with Harry Stebbings
Disclosure
Geoff Lewis: Uncapped note in Rippling was one of Bedrock's best investments
“I think one of our best investments at Bedrock was doing an uncapped note investment in Rippling”
Geoff Lewis Feb 14, 2022 ▶ 16:09 20VC: Bedrock's Geoff Lewis on Whether VCs Actually Provide Value or Not, Why Bedrock Does Not Have An Ownership Focus and The Difference Between Principles and Rules When Building a Firm or Company
Disclosure
Conrad: Rippling exists to prove what Zenefits could have become
“A big part of how I think about Rippling is that this is a way for me to sort of prove, mostly to myself, But also to the extended community, to my friends and family, to the general public, and all that kind of stuff, that this is how things might have turned…”
Parker Conrad Apr 26, 2021 ▶ 22:56 20VC: Rippling's Parker Conrad on Why The VC/Founder Marriage Analogy is Weird, Why The Notion of Focus, Focus, Focus is Overrated, Why Narrow Point Solutions Are Not Best in Class Products & The Rise of the "Compound Startup"
Prediction Not checkable as stated
Conrad: Rippling will become the Salesforce for employee data
“I think Rippling is going to be the Salesforce for employee data.”
Parker Conrad Apr 26, 2021 ▶ 37:56 20VC: Rippling's Parker Conrad on Why The VC/Founder Marriage Analogy is Weird, Why The Notion of Focus, Focus, Focus is Overrated, Why Narrow Point Solutions Are Not Best in Class Products & The Rise of the "Compound Startup"
Insight
Conrad: Employee data is the ideal foundation for business management software
“But I actually think that, like, almost every business system a company uses is full of information about employees, and that because of that, employee data is the right foundation for sort of a broader business systems management platform.”
Parker Conrad Apr 26, 2021 ▶ 3:25 20VC: Rippling's Parker Conrad on Why The VC/Founder Marriage Analogy is Weird, Why The Notion of Focus, Focus, Focus is Overrated, Why Narrow Point Solutions Are Not Best in Class Products & The Rise of the "Compound Startup"
Opinion
Lemkin: Rippling's financial performance far surpasses Figma's
“It's better than Figma by the numbers, right? It's better than Figma by the numbers by far. By far.”
Jason Lemkin Apr 23, 2026 ▶ 1:12:44 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Rippling reached $1B ARR while accelerating growth past 70%
“So if they were at less than 511 months ago, which I do know. Right. And they're at a billion growing 70 something percent. Do the math with me, Rory. They're accelerating. It's not just 70, which is enough. They're accelerating.”
Jason Lemkin Apr 23, 2026 ▶ 1:10:56 Cursor Acquired for $60BN | Anthropic Hits $1TRN in Secondary Markets & Figma, Adobe, Canva Dead? · 20VC with Harry Stebbings
Opinion
O'Driscoll: Deel has more attractive market dynamics than Rippling
“At the margin, I'm, of those two choices, I would bet at the margin, despite a little distaste for what went on in terms of the de-espionage thing, I would say, maybe I want to say is the TAM and the, Competitive matrix is more attractive for deal.”
Rory O'Driscoll Oct 23, 2025 ▶ 1:28:38 Why VC Today is Worse than 2021 · 20VC with Harry Stebbings
Insight
Plank: Time-based discounts without trust are counterproductive in enterprise sales
“People do not sign contracts on the last day of the month because they're worried that their discount's gonna go away. Like, that's absolute bullshit. Like, if you ever bought software and it's the 31st of the month, and someone's like, you have this quarter-e…”
Matt Plank Dec 20, 2024 ▶ 34:07 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Disclosure
Rippling ties account manager compensation 70% to new business, 30% to retention
“I think, like, 70% of it is tied to selling new business, and 30% roughly is tied to retention, specifically, like, dollar retention, and it completely changed everything in our, you know, like, have just, like, out, completely outlier, like, off the charts, l…”
Matt Plank Dec 20, 2024 ▶ 24:09 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Insight
Plank: Early startups should never turn down any non-zero price deal
“I think the first one is when you're a, you know, zero to one company, whatever, you're a million bucks, two million bucks, like early, early stage, like nothing matters. The only thing that matters is winning customers. It doesn't matter what they pay. It doe…”
Matt Plank Dec 20, 2024 ▶ 28:09 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Insight
Plank: Discounting is a made-up concept and list prices do not matter
“Discounting is a completely like made up thing. Like at the end of the day, what the only thing that matters is like net price, right? And so discounting is simply a factor of like, where do you set your list price? Like list price doesn't matter, right? Like …”
Matt Plank Dec 20, 2024 ▶ 24:45 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Plank: Non-US HR software markets lag the US by a decade
“All of the U S non U S markets, like starting with Canada and for sure in Europe and, you know, an APAC, like their HR software landscape is at least a decade behind where the U S is”
Matt Plank Dec 20, 2024 ▶ 51:12 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Plank: Rippling will not fund inefficient top-of-funnel spend for growth
“No matter how much money we have, we could be sitting on a billion dollars of cash. Like we are not going to go invest in top of funnel that is inefficient just to grow faster.”
Matt Plank Dec 20, 2024 ▶ 53:03 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Insight
Plank: Sales deals delayed by stakeholder or budget changes start over
“There's no such thing as like delaying a deal for like those types of reasons. Like you're starting over from scratch. You might not know it, but you're starting over from scratch.”
Matt Plank Dec 20, 2024 ▶ 38:00 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Insight
Efficiency does not matter for early startups, but becomes the top constraint
“When you're in an early stage company, like efficiency, like doesn't really matter. Like you don't even have a business, right? Like it's not about how efficient are you? It's like, you're just trying to win any way possible and you're losing money and all tha…”
Matt Plank Dec 20, 2024 ▶ 49:42 Matt Plank, Rippling's CRO: How to Build an Enterprise Sales Machine | E1241 · 20VC with Harry Stebbings
Opinion
Bookman: Rippling executes acqui-hires whereas OpenGov acquires built products
“By the way, I think the guys at Rippling are doing something slightly similar. They're gathering founders, and they're, some of these have subject matter expertise, some don't, and it's a, they're acquihiring, and we're doing product acquisitions.”
Zachary Bookman Dec 6, 2024 ▶ 19:47 Zachary Bookman: Why Valuations and Fundraising are BS | E1235 · 20VC with Harry Stebbings
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.