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 66 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 2 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
Salesforce Is No Longer the Best CRM on the Market
“Salesforce isn't the best CRM now.”
Jake Saper Mar 10, 2025 ▶ 47:28 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Opinion
Saper: Focused startups are outpacing incumbents in capturing AI value
“The thing I've changed my mind on is I'm less fearful that incumbents will be able to accrue most of the value. The reality is, like, it still early days in this game, and things could change, but thus far, the startups are outpacing, the focus startups are ou…”
Jake Saper Mar 10, 2025 ▶ 57:38 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Opinion
If Jake Saper Were to Short a Public Stock, It Would Be IBM
“If I were to short a stock publicly, it'd be IBM.”
Jake Saper Mar 10, 2025 ▶ 1:01:34 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Opinion
Saper: Multi-stage VC seed programs create signaling risk for founders
“Most multi-stage firms treat their seed programs as an option program, right? They write small checks. Often it's their junior people writing these small checks and they use it as a way to track the company to see if it breaks out. If it does, then they try to…”
Jake Saper Mar 10, 2025 ▶ 1:07:34 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Insight
All PLG companies eventually need to layer on enterprise sales motions
“As exciting as bottoms up PLG is, all PLG companies eventually need to layer on enterprise software motions to be sustainable and enduring.”
Jake Saper Mar 10, 2025 ▶ 5:42 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Prediction Not checkable as stated
Saper: AI web app builders will disrupt Squarespace and Webflow
“But those businesses will clearly disrupt the square space and the web flows and et cetera.”
Jake Saper Mar 10, 2025 ▶ 12:57 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Insight
Saper: Market pull is more important than founder quality in startup investments
“The first one is market pull. Like that is the most important thing, I think, when you're evaluating a potential investment or starting a company. The second is the founder, because it's the founder's job to figure out how do you build something defensible in …”
Jake Saper Mar 10, 2025 ▶ 20:22 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Supported
Jake Saper Has Never Had a VC Investment Go to Zero
“No, what you mean is I've never none of my deals have ever gone to zero.”
Jake Saper Mar 10, 2025 ▶ 29:28 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Supported
Together.ai Scaled From $2M to Over $100M Revenue in 15 Months
“Together is a good one, where we were in the A in 15 months ago, they were at two million revenue. The business is now north of a hundred million revenue.”
Jake Saper Mar 10, 2025 ▶ 40:06 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Insight
The New SaaS Benchmark for the AI Era Is 'Quadruple 120'
“If I were to posit a replacement for the triple, triple, double, double phrase, Maybe it's something like quadruple one 20. And what I mean by that is, yes, you should be growing very quickly, perhaps quadrupling year over year, triple quadrupling, et cetera. …”
Jake Saper Mar 10, 2025 ▶ 41:16 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Prediction Not checkable as stated
Saper: Average AI startup retention cohorts will disappoint, but outliers will excel
“On the average, I think they'll disappoint. And I think there'll be outliers that are better than we expect.”
Jake Saper Mar 10, 2025 ▶ 46:45 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Prediction Not checkable as stated
Saper: Specialized LLMs will proliferate and mostly originate from open source
“I do think that you're going to see a lot of specialized LLMs. And I think that a lot of them will come from open source back to the earlier point.”
Jake Saper Mar 10, 2025 ▶ 48:40 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Insight
Saper: Domain-specific LLMs will derive insights frontier models like OpenAI cannot match
“And if you build domain specific large language models using that data, you're going to have insights that even an open AI won't be able to have.”
Jake Saper Mar 10, 2025 ▶ 49:42 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Prediction Not checkable as stated
Saper: B2B software vendors will survive AI-enabled internal code generation
“I believe that B to B software, I believe software vendors have an important role in the future, even if the bolts of the world, the curses of the world make coding cheap, easy, in some cases free.”
Jake Saper Mar 10, 2025 ▶ 50:26 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Insight
Enterprise AI Buyers Are Using Tools to Freeze Hiring, Not Fire
“Most buyers of this stuff aren't firing people. What they're doing is not hiring new people. And so they're trying to be more efficient with whatever they currently have.”
Jake Saper Mar 10, 2025 ▶ 1:00:24 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Supported
Saper: 75% of Fortune 500 companies still run core applications on mainframes
“75% of the fortune 500 still run their core applications on refrigerators in their closet.”
Jake Saper Mar 10, 2025 ▶ 1:01:44 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Prediction Open · timeframe Mar 2030
A Major Enterprise Will Suffer a Damaging AI Agent Failure
“In fact, likely that some big enterprise is going to deploy an agent and the agent's going to do something really bad”
Jake Saper Mar 10, 2025 ▶ 1:03:17 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Insight
Saper: VC partner turnover creates orphaned deals that harm founders
“And it is really, really bad for our founders. Because what happens is these founders become orphaned deals.”
Jake Saper Mar 10, 2025 ▶ 1:05:52 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Insight
Saper: VCs have no defensible reason to hold public stock without board inside info
“If we didn't have inside information, we'd have no defensible reason to hold the position. But as long as we're on the board, we have that information, you know, we can hold it.”
Jake Saper Mar 10, 2025 ▶ 1:10:41 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Insight
Saper: Revenue growth without high margins isn't product-market fit
“What that doesn't tell you is have you used AI to provide a high margin service, right? You can sell a lot of something, but if you haven't figured out a way to have a good business model around it, then it's not really product market fit.”
Jake Saper Mar 10, 2025 ▶ 1:16:50 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Disclosure
Emergence Capital Founders Forfeit Their Carry Upon Retirement
“Our founders made the very generous choice to when they step away from the business and retire to forfeit their carry.”
Jake Saper Mar 10, 2025 ▶ 1:29:41 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Disclosure
Emergence Invested in Zoom at a 100x Revenue Multiple in 2014
“It would have been, it was going to be priced at two hundred million dollar post money valuation, and this, again, remember the company was at around two million in revenue, And this was a hundred X revenue in 2014, right?”
Jake Saper Mar 10, 2025 ▶ 3:07 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Supported
Zoom Founder Eric Yuan Originally Miscalculated Churn by Counting Upgrades
“Eric himself was miscalculating churn. Specifically, he was counting upgrades from, you know, low tier to high tier as churn. He was counting pausing as a churn. And so he was unnecessarily burdening the business with churn.”
Jake Saper Mar 10, 2025 ▶ 4:37 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Opinion
Saper: No VC Firm Makes All Its Money from 'Prepared Minds'
“The reality is, I don't think any venture firm makes all their money on prepared minds. I just think that that is bullshit.”
Jake Saper Mar 10, 2025 ▶ 8:15 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Disclosure
Emergence Capital's Fund III Has Reached a 16x DPI
“That fund, I believe was fund three, which is the same fund that has Zoom. It's the same fund that has some other really large outcomes. And so that fund is already at a, I think it's a 16 times DPI.”
Jake Saper Mar 10, 2025 ▶ 10:08 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Supported
Salesloft Was the Highest Multiple Ever Paid by PE for Software
“Which was the biggest outcome that it was the highest multiple ever paid by private equity for a software company. Companies required for 2.3 billion dollars.”
Jake Saper Mar 10, 2025 ▶ 10:34 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Disclosure
Saper: Emergence Capital's Fund III Is Top Decile Even Without Zoom
“The cool thing about that fund, though, is even if you took Zoom out, it would still be a top to sell fund.”
Jake Saper Mar 10, 2025 ▶ 11:03 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Prediction Open · timeframe Mar 2030
Saper: Private equity will consolidate most legacy website builders
“I think there will be consolidation, there will be private equity, and there will be a few that reinvent themselves. There will be a few that are nimble enough to figure out how to adapt to the new era, but I think most will get consolidated.”
Jake Saper Mar 10, 2025 ▶ 13:34 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Disclosure
Emergence Capital backed Gusto over faster-growing rival Zenefits
“We had just invested in Gusto, which was a competitor that was growing not quite as quickly as Zenefits. But the reality is Gusto has endured and become a massive company, and Zenefits didn't.”
Jake Saper Mar 10, 2025 ▶ 18:24 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Supported
Bolt Scaled From Zero to $20M Revenue in Two Months
“We're seeing examples like Bolt, you know, which went zero to 20 in two months”
Jake Saper Mar 10, 2025 ▶ 40:06 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Disclosure
Emergence Capital Sold Its Position in Salesforce Too Early
“Yeah we sold Salesforce too early.”
Jake Saper Mar 10, 2025 ▶ 1:09:54 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
What-if
Selling Stocks at Lockup Would Have Lost LPs $2 Billion
“If we had sold them all at lockup, we would have returned two billion dollars less to our LPs.”
Jake Saper Mar 10, 2025 ▶ 1:13:18 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
What-if
Emergence Missed Out on $2 Billion by Not Selling Stocks at Peak
“What's interesting, and this just is like totally coincidental, if we had sold all of our shares at peak price of whatever, whenever the peak price proposed for that stock, we would have made two billion dollars more for our LPs.”
Jake Saper Mar 10, 2025 ▶ 1:13:26 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Opinion
Jake Saper Would Sell Grok at a $50 Billion Valuation
“So I sell Grok, and I think the reason I sell Grok is I don't yet know how, what niche they've carved out in the market.”
Jake Saper Mar 10, 2025 ▶ 1:26:20 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Opinion
Saper: OpenAI feels expensive at $300 billion valuation
“OpenAI feels expensive, but they have a strong consumer brand.”
Jake Saper Mar 10, 2025 ▶ 1:26:29 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Opinion
Saper: Buy Anthropic at $60 billion valuation if application layer improves
“I probably buy Anthropic assuming they can figure out the app, you know, the app stuff more.”
Jake Saper Mar 10, 2025 ▶ 1:26:33 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Not checkable as stated
Jake Saper: Most VC founders retain firm ownership after retiring
“The vast majority of founders of firms, when they retire, they retain a meaningful portion of the ownership of that firm.”
Jake Saper Mar 10, 2025 ▶ 1:30:07 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Supported
Emergence Capital Has Returned Over $8 Billion in Cash
“The dollars in capital, we've returned a little over eight billion dollars in cash.”
Jake Saper Mar 10, 2025 ▶ 0:00 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Partly supported
20% of Emergence Capital Investments Hit $1B+ Valuations
“One out of five have gone on to raise rounds at north of a billion dollars.”
Jake Saper Mar 10, 2025 ▶ 30:35 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Not publicly verifiable
10% of Emergence Capital's Early-Stage Deals Go Public
“One out of 10 of our early stage investments have gone public.”
Jake Saper Mar 10, 2025 ▶ 30:41 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Supported
Zoom was profitable when Emergence Capital invested in 2014
“It was competitive both because the, there was early growth, but also because the company was profitable. And so we didn't have to raise capital.”
Jake Saper Mar 10, 2025 ▶ 5:21 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Disclosure
Saper: Zoom Returned Emergence Capital's Fund III Over 10x
“Zoom returned it, you know, more than 10.”
Jake Saper Mar 10, 2025 ▶ 10:53 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Supported
Saper: Private equity typically pays 3x to 5x ARR for acquisitions
“Savior is too strong of a word because most private equity outcomes don't generate incredible returns for the VC. So savior is not the right. It may be savior in the sense that like would get your money back. The sales loft outcome was an awesome one, but that…”
Jake Saper Mar 10, 2025 ▶ 13:52 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Insight
Saper: True market pull requires buyers having tried hacking DIY solutions
“It's not a desperate problem if someone hasn't, if your buyer hasn't tried to hack together something on their own to solve it, or if they haven't bought an inferior product to solve it, or if they're not spending countless hours themselves dealing with it. Ot…”
Jake Saper Mar 10, 2025 ▶ 19:12 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Disclosure
Saper: Top Emergence investments like Zoom were expensive, but Veeva wasn't
“They are not always expensive, but they are often expensive. So if I look back at our portfolio, Gusto was expensive. Zoom was expensive. Yammer was expensive. A lot of the good ones, Ironclad was expensive. But some of them weren't. Viva wasn't expensive beca…”
Jake Saper Mar 10, 2025 ▶ 24:25 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Not checkable as stated
Every Emergence Capital partner does reference calls on every investment
“So what it means is that for every investment we make, every partner does reference calls. Every partner calls customers. Every partner calls management references. Every partner does backchannel references.”
Jake Saper Mar 10, 2025 ▶ 31:23 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Assertion Not checkable as stated
Saper: Emergence's AI Application Portfolio Companies Seeing Gross Margin Increases
“Most of our application layer companies that are providing applications on top of these products are seeing gross margin increase over time because of that competitive dynamic.”
Jake Saper Mar 10, 2025 ▶ 42:50 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
Disclosure
Saper: Emergence Invested in Together.ai Believing Open-Source LLMs Will Become Dominant
“The clearest what you have to believe for that investment was that open source LLMs will be a dominant part of the market over time. That enterprises, that businesses are going to want to buy and use open source models and not just anthropic open AI and the cl…”
Jake Saper Mar 10, 2025 ▶ 43:38 Jake Saper, GP @ Emergence Capital: "We Sold Salesforce Early and Lost Out on Billions" · 20VC with Harry Stebbings
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