Bastian Lehmann

Founder & CEO, Tiptop · 1 appearance on the record.

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founderexecutiveinvestor@Basti ↗docs.tiptop.com ↗

Bastian Lehmann is the co-founder and former CEO of Postmates, which pioneered on-demand urban delivery before being acquired by Uber for $2.65 billion. Following the sale, he launched Tiptop, a fintech company enabling instant trade-ins at checkout.

40statements → 15claims → 6claims resolved → 50%fully supported → 3.75/5average certainty → 2.42/5average debate potential → 4.1/5argument clarity · the sources → 1said about them ↓

3 supported 2 partly supported 1 contradicted 3 not yet assessed 6 not checkable as stated how the 15 claims stand · each chip opens the sources

4 predictions · 11 assertions · 8 opinions · 8 insights · 8 disclosures · 1 what if · every statement was checked. The predictions and assertions are the 15 claims: statements the public record can support or contradict. 6 are resolved, 3 are not yet assessed, and 6 name no date, number or outcome precise enough to check. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how Bastian argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
Lehmann: Postmates acquisition has not been written off by Uber
“I see no signs of the Postmates acquisition being written off because I think the brand is very strong. It continues to be very strong in LA.”
Bastian Lehmann Apr 8, 2024 ▶ 25:39 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings

Their most notable contradicted claim

Assertion Contradicted
Peter Thiel and Brian Singerman were Postmates' only early backers
“When we started out, when Postmates started out, this thing sounded so crazy that the only people that wanted to give us money were Brian Singerman and Peter Thiel.”
Bastian Lehmann Apr 8, 2024 ▶ 14:06 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
100% certainty 3
83% certainty 4
25% certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

Argument clarity: do they answer the question? how? →

4.1 / 5 directness 4.4 · coherence 4.3 · precision 3.8 · compression 3.5

redirected or did not address 5 of 46 assessed questions (11%). Watch them ▸

This is a score against a rubric. It is not a rank. Every host question → answer exchange is scored with names hidden on directness, coherence, precision and compression, 1–5 each, on meaning alone: disfluencies are ignored, and only raw unedited episodes count. This is the score that measures thought. Every scored exchange, scores shown → · The rubric and its checks →

How they sound: speaking style how? →

259 words/min while actually speaking · 25.3 um and uh per 1k words · 60.8 false starts per 1k · 41.2% of pauses land inside a clause

English is their second language (first language: German). These numbers measure fluency in English. They do not measure thought; the argument clarity score above is read from substance alone.

Measured by listening to the audio itself: 10,415 words across 1 episode of raw-level tape, transcribed verbatim with every um and uh kept, each one attributed only where the alignment onto our timed stream is unambiguous. These are measurements of speaking style. We do not rank them: across this corpus, fluency and argument quality are nearly uncorrelated (ρ≈0.2), and smooth talking does not signal clear thinking. How it's measured →

Everything Bastian Lehmann said on 20VC that made the record, most notable first. Filter by type, assessment or year in the ledger →

Opinion
Bastian Lehmann: 99% of VCs are sheep who lack independent thinking
“I would probably today say that 99% are sheep.”
Bastian Lehmann Apr 8, 2024 ▶ 39:52 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2029
Lehmann: Screenless dedicated AI inference computers will be in every home
“I think when it comes to AI and personal AI, we may be at a moment in time where there is an opportunity for a new computer, a new type of computer that we may see in every home. A computer that runs your own personal AI on a chip that does not have to be as p…”
Bastian Lehmann Apr 8, 2024 ▶ 49:51 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Prediction Open · timeframe Apr 2029
Lehmann: AI startups created today will grow larger than tech incumbents
“There will be companies born today that will be larger in the field of AI. Then the companies that are the largest companies that we have today, and they will start as toys and they will start as something that is probably overlooked and something that is not …”
Bastian Lehmann Apr 8, 2024 ▶ 55:42 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Opinion
Lehmann: Google went from most respected company to laughingstock over AI
“This is Google that you're talking about, and they shed the bed so hard. They literally just went from like the most respected company in the world to laughing stock in a matter of month.”
Bastian Lehmann Apr 8, 2024 ▶ 58:01 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lehmann: Apple Vision Pro will have record high returns and fail
“This will be the first product for Apple where they have more returns than they have on any other metric You. You can plot the graph, and it's since Steve Jobs came back, this is probably the first thing that is a turd.”
Bastian Lehmann Apr 8, 2024 ▶ 58:38 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Opinion
Bastian Lehmann: Failing to develop AI rapidly poses humanity's greatest existential risk
“The risk is not that there will be an evil AI that will kill us. I think the risk will be that by not becoming more intelligent and using these intelligent tools will become extinct.”
Bastian Lehmann Apr 8, 2024 ▶ 1:03:40 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lehmann: Every scaled market was profitable for Postmates and DoorDash
“No, I think Tony and I knew from the start that, that this is a tremendous business. If you can scale it and every market that you had at scale was profitable for us, and I know that the same thing was also true for DoorDash.”
Bastian Lehmann Apr 8, 2024 ▶ 13:14 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Assertion Partly supported
Lehmann: Postmates-Uber acquisition returned nearly $5B to shareholders
“We negotiated the deal so well, there was no color on the deal. By the time the deal closed, it was almost five billion dollars.”
Bastian Lehmann Apr 8, 2024 ▶ 19:45 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Assertion Supported
Lehmann: Postmates acquisition has not been written off by Uber
“I see no signs of the Postmates acquisition being written off because I think the brand is very strong. It continues to be very strong in LA.”
Bastian Lehmann Apr 8, 2024 ▶ 25:39 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lehmann: Founders Fund believes board seats offer all downside, no upside
“So at Founders Fund, they obviously believe in this very deeply. We just saw this obviously with Keys leaving there and being somewhere else, they, the belief is that there is very little you can do to actually move the needle, other than writing the check. An…”
Bastian Lehmann Apr 8, 2024 ▶ 42:43 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Insight
Lehmann: Founders should walk away from VCs requiring deep convincing
“I do believe that there's unlimited amount of capital out there, and I believe that it is easier and it's better worth your time by focusing on the people that initially believe in that than trying to ride two or three rounds with the same VC firm and spend tw…”
Bastian Lehmann Apr 8, 2024 ▶ 44:23 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Insight
Lehmann: Local home inference is the only cost-effective way for personal AI
“Inference is very powerful the closer it is to the source of data. I mean, given that you, if you think about a personal assistant, the personal assistant needs a lot of information about you and inputs, That's why you would see that at home. It also is the on…”
Bastian Lehmann Apr 8, 2024 ▶ 51:31 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Lehmann: Smartphones have reached the peak of their societal importance
“So when I call it dead I don't call it dead in the sense of we won't use it anymore, but I think it has reached the peak of its importance in people's lives.”
Bastian Lehmann Apr 8, 2024 ▶ 54:04 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Opinion
Lehmann: Apple Vision Pro is a product in search of a market
“On the Vision, as it is, how it is today? I, short. I think it's a product in search of a market.”
Bastian Lehmann Apr 8, 2024 ▶ 54:19 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Opinion
Bastian Lehmann: OpenAI may struggle to build successful products beyond ChatGPT
“It's a fantastic research company is how I would describe OpenAI. I think it remains to be seen if they can launch extremely successful products other than a chat based a chat GPT.”
Bastian Lehmann Apr 8, 2024 ▶ 1:00:12 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Insight
Lehmann: Most companies fail because founders give up
“Most companies fail because the founders give up, and we refuse to give up.”
Bastian Lehmann Apr 8, 2024 ▶ 0:19 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Insight
Lehmann rejects luck, attributing success to grit and hard work
“I don't really believe in luck much. But I also don't have a definite answer. I think I believe in determination and grit and hard work.”
Bastian Lehmann Apr 8, 2024 ▶ 1:48 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Insight
Lehmann: Top VCs and hype cannot change startup outcomes
“A lot of times even the great VCs and a lot of hype can't really change the outcome of a company.”
Bastian Lehmann Apr 8, 2024 ▶ 15:16 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Lehmann: Postmates prioritized deal structure over headline price in Uber merger
“And I think he came out with a number that was around 2.2 or something, and we negotiated it up a little bit, but I didn't want it to push too hard, because the two things that we negotiated for are no breakup, Absolutely no way out and no color on the deal be…”
Bastian Lehmann Apr 8, 2024 ▶ 21:00 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Assertion Supported
Andreessen Horowitz passed on Postmates four or five times
“I pitched him four times or five times the entire firm with Postmates. They were smart enough to say no”
Bastian Lehmann Apr 8, 2024 ▶ 29:20 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Disclosure
Marc Andreessen committed to funding Bastian Lehmann over a single phone call
“He pinged me actually, because a friend told him that I was working on something and he called me and I said, I don't even know if that idea is good. And he said he said, okay, like, you, Are you, do you want to do it again? And I said, yes. It's like, well, t…”
Bastian Lehmann Apr 8, 2024 ▶ 29:46 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Assertion Supported
Lehmann: High LLM compute costs prevent killer apps beyond chatbots
“I believe that one of the overlooked areas of the current state of AI and the large language models that we're using is that they're still very expensive. And as a result of that, they're dramatically more expensive than a Google search. And as a result of tha…”
Bastian Lehmann Apr 8, 2024 ▶ 49:08 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Opinion
Lehmann: Apple is caught in the inventor's dilemma over AI
“I believe that AI happened too fast and Apple is caught in sort of the inventor's dilemma here.”
Bastian Lehmann Apr 8, 2024 ▶ 52:56 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Opinion
Lehmann: 'First X revenue is hardest' is common BS startup advice
“Oh, the first X dollar in revenue is always the hardest, or something like that. There is a version of that in, in, in, in, in sort of coming out of everybody I've ever met”
Bastian Lehmann Apr 8, 2024 ▶ 1:05:27 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings

Show 16statements(16 left)

The other half of the tape: Bastian Lehmann's own voice is left out of every number here. Other people bring the name up 1 time in 1 episode on 20VC. every mention, with the transcript →

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Appearances (1)

EpisodeDateSpeaking time
Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E11 Apr 8, 2024 51m
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