Venture capital, startups and investing, on tape.

Every prediction, opinion and bold claim from Lenny's Podcast: extracted from the transcript, verified against the tape, checked against cited public sources, playable at the exact moment it was said.

4,541 insights1,995 assertions882 disclosures706 opinions444 predictions40 what-ifs

Recently on the ledger full ledger →

Opinion
MacInnis: Hopes competitor Deel goes to zero due to its 'criminal behavior'
“I was one of the first investors in Deal, if you've heard of them. I, you know, I was able to exit, I was able to exit that position, and then, you know, hopefully that company's going to zero with their criminal behavior, but whatever.”
Matt McGinnis Dec 28, 2025 ▶ 58:35 “I deliberately understaff every project” | Leadership lessons from Rippling’s $16B journey
Opinion
Benioff calls Microsoft Copilot 'really a terrible product'
“And I'm running aggressive marketing against Microsoft because they have really a terrible product co-pilot that I'm have to position against and market against.”
Marc Benioff Dec 22, 2024 ▶ 20:45 Behind the founder: Marc Benioff
Opinion
Kalinowski: OpenAI lacked proper governance around its Department of Defense deal
“And I feel that what happened with the decision-making, the speed of the decision-making, the governance, and the lack of defined guardrails around the announcement of the Department of War deal is not how I thought it should have been done.”
Caitlin Kalinowski May 17, 2026 ▶ 1:16:16 Why the next AI boom is physical AI | Caitlin Kalinowski (ex-OpenAI, Meta, Apple)
Disclosure
Rabois: I refuse to let colleagues talk to consumer customers
“I refuse to allow colleagues of mine to talk to customers.”
Keith Rabois Apr 12, 2026 ▶ 52:19 Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)
Insight
Rabois: Criticizing employees publicly optimizes for the system over the individual
“When you give people feedback negative individually, you're optimizing for the atomic unit, not the system. The reason why to do it in public is it's more important for all the colleagues to understand that there's an issue it's being addressed.”
Keith Rabois Apr 12, 2026 ▶ 1:13:10 Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)
Insight
Rabois: High-performance teams do not have psychological safety
“No, no, I don't believe in that at all. Like high performance machines don't have psychological safety. They're about winning.”
Keith Rabois Apr 12, 2026 ▶ 1:14:38 Hard truths about building in the AI era | Keith Rabois (Khosla Ventures)

How the calls resolved the full record →

Assertion Supported
Mullenweg notes WordPress started as a fork of abandoned project b2
“WordPress was actually a fork of abandoned open source project called B two.”
Matt Mullenweg Mar 2, 2025 ▶ 21:12 Matt Mullenweg on the future of open source and why he’s taking a stand
Assertion Contradicted
Pincus: Every member of Andy Jassy's C-suite was Bezos's technical assistant
“And in fact, Andy Jassy at Amazon, everyone on the C staff used to be someone who'd been the tech assistant to Bezos.”
Mark Pincus Jun 14, 2026 ▶ 1:24:49 The hidden pattern behind successful products | Mark Pincus (FarmVille, Words with Friends, & more)
Assertion Supported
Berkowitz: Deel was founded before the COVID-19 pandemic
“A lot of people think Deal was started as a response to the pandemic. We actually got started before the pandemic and then the pandemic happened.”
Meltem Kuran Berkowitz Aug 27, 2023 ▶ 44:40 An inside look at Deel’s unprecedented growth | Meltem Kuran Berkowitz (Head of Growth)
Assertion Contradicted
Shah: Many Indian and Asian languages lack a word for efficiency
“Many Indian languages do not have a word for efficiency. And that's true for many Asian languages. The word for efficiency does not exist.”
Kunal Shah Mar 24, 2024 ▶ 27:36 Kunal Shah on winning in India, second-order thinking, the philosophy of startups, and more

Open predictions the full timeline →

195days Misra: Indistinguishable photorealistic AI video is a couple of years away Gaurav Misra · prediction date: 2027-03-27 253days Shipper: Near-term enterprise AI will center around company super agents Dan Shipper · prediction date: 2027-05-24 253days Shipper: Workplace AI agent interactions will happen mostly in Slack Dan Shipper · prediction date: 2027-05-24 253days Shipper: Coding models won't independently rewrite broken codebases within a year Dan Shipper · prediction date: 2027-05-24

Track records all people →

Ordered by full support rate, then by supported count. Minimum three resolved. Partly supported claims count as resolved but not as fully supported, same as everywhere on the ledger.

PersonEpsStatementsSupportedPartly supportedContradictedFull support rate
Nick Turley 1 41 10 0 0 100%
Claire Butler 1 20 8 0 0 100%
Melanie Perkins 1 28 6 0 0 100%
Robby Stein 1 28 6 0 0 100%
Dylan Field 2 43 6 0 0 100%
Nesrine Changuel 1 10 6 0 0 100%
Ben Mann 1 37 6 0 0 100%
Sebastian Barrios 1 17 6 0 0 100%

From the Wisdom Wall all quotes →

“how could we pull that stuff to today? Even if it requires a little bit of, of engineering on top to make it work or a lot of engineering on top. To make it work. Even it requires changing the product…”

“I think that we believe that people want to be more productive, but they don't. I think more people want to spend time than save time.”

“chat makes sense if you're the highest agency person in the world, which is Elon and Sam. But for the average consumer, like their ideal interface is TikTok. So we need to find something between chat…”

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