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 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

Prediction Not checkable as stated
Lessin: Universal Basic Income is inevitable
“I don't actually know what Tim Draper's view is on it, but I think there's no possible way that it won't happen.”
Sam Lessin May 25, 2016 ▶ 23:16 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Prediction Not checkable as stated
Lessin: Co-living communities will inevitably standardize urban living
“I just like fun, again, like there's, this goes on my list of course, this is the way the world will work. I can't imagine a world in which, you know, everyone's living in these kind of low, these apartments where they don't know their neighbors and there's no…”
Sam Lessin May 25, 2016 ▶ 25:15 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Insight
Lessin: VCs take longer to master selling than buying
“As an early stage investor, you get hundreds of shots to buy. You get really good at buying. You have so fewer shots at learning to sell that it actually takes much longer to learn to sell well. Right. But it's still as important as learning to buy well.”
Sam Lessin Jun 5, 2025 ▶ 16:49 Is DPI The Only Thing That Matters? with Sam Lessin, Jason Lemkin & Rory O’Driscoll · 20VC with Harry Stebbings
Prediction Held up
Lessin: Exceptionally low startup mortality rates will inevitably rise
“We've looked at our portfolios recently and it's comical how low the mortality rates are. That's obviously shifting in real time, right? And will go up.”
Sam Lessin Aug 11, 2023 ▶ 7:46 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Disclosure
Lessin: I personally invest in deals Slow Ventures deems too expensive
“There are places like, you know, in history, there have been a few instances, my partners are like, we like the deal, it's too expensive. I'm like, ah, fuck it. I'll put in a few personal dollars because like, who cares? It's so little money, right?”
Sam Lessin Aug 11, 2023 ▶ 12:48 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Assertion Supported
Lessin: Muck Rack Raised Zero VC Money Until Late Private Equity Round
“By far, the most successful company come out of that is a company called Muckrack, right? Unbelievable success, right? And it was a team in the corner that actually took zero dollars of VC, Right? Until very, very late in the game when they did a private equit…”
Sam Lessin Aug 11, 2023 ▶ 15:15 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Disclosure
Lessin: TeamShares reached nearly $1B valuation after $4M post seed check
“I have a company called TeamShares, which we put in our first check at four posts that is now touching a billion and is a real company with hundreds of millions of revenue.”
Sam Lessin Aug 11, 2023 ▶ 21:22 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
Insight
A $5M exit is a failure for a $200M VC fund
“A five million dollar exit to a two hundred million dollar fund is basically irrelevant, right? That's actually a failure in a lot of cases.”
Sam Lessin Feb 4, 2019 ▶ 5:26 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Insight
Investors systematically underestimate the scale of global niche markets
“I think people systematically under appreciate how large the world is, and therefore, especially in a globalized environment, how big niche markets actually can be when you blow them up and scale them up.”
Sam Lessin Feb 4, 2019 ▶ 6:47 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Prediction Not checkable as stated
AI will make steady, repeatable, predictable jobs much harder to find
“I think the real thing that's going to be challenging is that I think it'll be harder to find steady, repeatable, trusted work.”
Sam Lessin Feb 4, 2019 ▶ 16:00 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Insight
Crypto fundamentally provides decentralized memory and identity
“What crypto really fundamentally is that when you really strip it all away, it is that secure ability to have secure, decentralized, private memory and secure decentralized private identity.”
Sam Lessin Feb 4, 2019 ▶ 18:03 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Disclosure
Slow Ventures avoids dApp investments to focus on crypto protocols
“First, we, I generally don't invest in dApps. Again, like we're much more focused on protocols. There are very few exceptions we would make to that.”
Sam Lessin Feb 4, 2019 ▶ 21:26 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Assertion Not checkable as stated
Crypto is the most globalized tech boom to date
“So crypto is by far the most globalized The tech revolution or boom we've seen in my mind to date”
Sam Lessin Feb 4, 2019 ▶ 23:11 20VC: Slow Ventures' Sam Lessin on How VC Forces Certain Companies To Exist and Makes It Difficult To Finance Others, Why Cities Won't Let Scooter Companies Be Profitable and Why Dapps Are A Concern and Where Emphasis Should Be Placed In Crypto
Disclosure
Lessin was the first investor in Birchbox and Venmo
“And so I was, you know, one of the first investors in MakerBot and the first investor in Birchbox and, you know, the first investor in Venmo and a bunch of awesome companies.”
Sam Lessin May 25, 2016 ▶ 2:51 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Opinion
Lessin: Augmenting memory is the most compelling bot use case
“I'll tell you the thing that I love the most is augmenting my memory. I don't have the world's greatest memory. I like to take lists. I try to keep lists together and things like that, but I find it really, really hard to keep track of all The ideas and people…”
Sam Lessin May 25, 2016 ▶ 8:56 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Opinion
Lessin: Conversational bots are not new and recur in cycles
“The bots thing is, you know, look, it's not new. It's the Asian bot ecosystem has been around for a while. There's a bunch of reasons why people are now excited about it, but these things come in cycles. Like, you know, I remember very distinctly the days of a…”
Sam Lessin May 25, 2016 ▶ 10:09 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Opinion
Lessin: Amazon Echo is the best glimpse of the tech future
“It's the future. I mean, it's a total taste of the future. I cannot tell you how excited I am about Echo. I have five in my house, literally. I've built applications for it myself. Finn has an incredible integration with it. It isn't there yet, but it's the be…”
Sam Lessin May 25, 2016 ▶ 21:52 20VC: Sam Lessin on Why Bots Will Change Business & The Internet Has Mostly Failed
Disclosure
Lessin: I never successfully hired sales talent during my founder career
“I would actually argue in my life as an entrepreneur, I've like never successfully hired sales.”
Sam Lessin Aug 11, 2023 ▶ 48:20 DEBATE: State of Seed Investing w/ Jason Lemkin, Sam Lessin, Frank Rotman & Harry Stebbings | E1047 · 20VC with Harry Stebbings
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