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 7 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

Opinion
Lessin: Venmo is a great product but a terrible business
“I great fucking product. Terrible fucking business.”
Sam Lessin Jun 16, 2023 ▶ 34:18 #2: Reddit and the death of the public internet; the end of the VC "epoch" · More or Less Podcast
Prediction Open · timeframe Jul 2029
Lessin: Venmo Will Never Make Money Despite Being an Important Product
“It's like how Venmo is an important product, but never will make money and never has.”
Sam Lessin Jul 31, 2026 ▶ 45:18 The Lilian Weng Saga, Mental Health Essay Then OpenAI | Meta's AI Ad, China Cracks DUV
Opinion
Sam Lessin: Venmo has become a broken user experience under PayPal
“It is still big, but it's like, kind of shitty. The app's kind of broken now. It's been, you know, owned by PayPal for the last decade, and they've kind of like, I don't know, I wouldn't say it's not usable. I certainly use it, but it's like, pretty terrible e…”
Sam Lessin Jan 26, 2024 ▶ 32:55 #31: Fintech Struggles, Netflix Rises and 'Big' is Winning · More or Less Podcast
Disclosure
Sam Lessin discloses he is the largest investor in social app Jelly
“There is an app called Jelly started by Ikram, who is one of the two co-founders of Venmo. I am its largest investor. I think, you know, certainly, I think I'm the only institutional investor. I'm certainly the largest investor.”
Sam Lessin Nov 7, 2025 ▶ 37:08 Apple Chooses Gemini, Sequoia's Leadership Shake-up, and Meme Coins · More or Less Podcast
Disclosure
Lessin: Fin Exploration warned its investors upfront it would lose their money
“And so, years later, Cortina, who founded Venmo, and I went off, and we just said, look, we're going to start a company called the Fin Exploration Company. And we basically raised some money and told the investors we literally were going to lose all the money …”
Sam Lessin Dec 27, 2024 ▶ 1:01:50 #79: The More or Less Holiday Special Pt. 1 (AI Highlights) · More or Less Podcast
Disclosure
Sam Lessin says he was the first financier of Venmo
“As, you know, as the first financier of Venmo, let's just talk about this story.”
Sam Lessin Jul 19, 2024 ▶ 12:17 #56: Trump and the PayPal Mafia · More or Less Podcast
Disclosure
Sam Lessin: Facebook Forced Me to Sign Non-Compete Over Venmo
“When I went and worked at Facebook on the way in, one senior executive reviewed all my investments and told me which ones I had to divest from. Interestingly, path was fine at the time, but Venmo was a big problem. And then, yeah, believe it or not, I had to s…”
Sam Lessin Apr 26, 2024 ▶ 6:33 #44: The $1B AI Girlfriend Market, the Tech Hedge Fund Fallout and Why VCs Can’t Quit AI · More or Less Podcast
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