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 25 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 Partly held up
Emil Michael predicts Uber's Postmates and Careem acquisitions will be total write-downs
“I think we, instead of buying Kareem in the Middle East, Postmates, Jump Bike I think all of those will be a hundred percent write downs. Those are some of the worst acquisitions done in tech. Maybe Postmates may be the worst acquisition done tech in the last …”
Emil Michael Oct 25, 2022 ▶ 48:58 Emil Michael: How I Negotiated the $4B Uber-China Deal, Why DoorDash Caught Up to Uber | 20VC #941 · 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 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 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
Insight
Singlehurst: Founder zeal matters more in growth investing than competitive analysis
“The thing that I should have placed a much greater weight on. Was the founder of DoorDash and, you know, why he'd started the business and the level of commitment that he had to these small businesses that he was wanting to help and kind of bring online and he…”
Peter Singlehurst Jul 15, 2022 ▶ 46:24 Peter Singlehurst: The Most Powerful Investor You've Never Heard of | 20VC #907 · 20VC with Harry Stebbings
Insight
VanDevender: Digital platforms increase the economic value of physical proximity
“The lesson has been that actually those digital technologies have actually made proximity more valuable. If you think about like where, where a lot of that value to people has come from, it's from companies like Lyft, like Postmates, a Craigslist, Amazon Prime…”
Aaron VanDevender Oct 16, 2017 ▶ 23:56 20VC: Founders Fund's Chief Scientist on Why AI Is Mostly A Scam, Why The Value of Large Datasets Is Mostly Overplayed & The Societal Effects of 4m Truck Drivers Being Unemployed with Aaron Vandevender
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
Sequoia Passed on Grubhub, Caviar, Postmates, and TaskRabbit
“And actually, between 20 11 and 20 13, we evaluated opportunities to invest in Grubhub, in Caviar, in Postmates, in TaskRabbit, because I was fascinated with this space. We passed on each of those opportunities, not partly because we're somewhat concerned abou…”
Alfred Lin Jan 27, 2021 ▶ 4:42 20VC: The Memo: Sequoia's Alfred Lin on Why Chasing GMV Leads To Bad Behaviours, How To Approach Competition and Capital Efficiency & The Core Importance of Understanding the Difference Between Input and Output Metrics
Prediction Not checkable as stated
Kyle Hill: Homogeneous marketplace workers will eventually be replaced by robots
“I look at those and no offense to any of those companies, but you could probably replace those workers with robots.”
Kyle Hill Jul 15, 2016 ▶ 7:09 20VC: Why Every Employee Should Re-Apply For Their Job Every Year & The Strategies To Prepare For A Successful Fundraise with Kyle Hill, Founder & CEO @ HomeHero
Assertion Supported
G Squared generated a 3x return on Postmates in 18 months
“We made a three X on Postmates”
Larry Aschebrook Jun 16, 2025 ▶ 1:03:32 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
What-if
Lehmann: Postmates was preparing for an IPO prior to Uber acquisition
“As a matter of fact, we were planning to go public and would have probably been one of the last companies to do so before, ah, you know, the world ended.”
Bastian Lehmann Apr 8, 2024 ▶ 18:14 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Assertion Not publicly verifiable
Lehmann: Postmates had under $100M cash remaining before turning profitable
“We had just under a hundred million dollars left in cash, and our negative gross profit margin was, I think, single digits.”
Bastian Lehmann Apr 8, 2024 ▶ 17:56 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: Major food delivery competitors had sound unit economics and profitability paths
“The fundamentals of, I think, the companies, and I can, I know this for us, but I have some insight in the other players. They were all pretty sound, and by that I mean there was a clear path to profitability. There was a clear understanding of unit economics,…”
Bastian Lehmann Apr 8, 2024 ▶ 12:25 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
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
Assertion Partly supported
Postmates was market leader in California prior to Uber merger
“And with DoorDash being the, clearly the market leader in most of the U.S., but not in California and certain regions that That are very attractive. Where we were the number one.”
Bastian Lehmann Apr 8, 2024 ▶ 16:53 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Disclosure
Lehmann: Postmates operated standalone for 8-9 months post-Uber acquisition signing
“After we signed the paper, because we had to run the company as a standalone company for, I believe eight, eight, nine months. So we had to hit our quarterly goals. We did not want it to have a scenario where we lose market share because now we're thinking tha…”
Bastian Lehmann Apr 8, 2024 ▶ 38:13 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Disclosure
Lehmann: Uber and Postmates planned shared backend tech with distinct front-end brands
“When we discussed the merger, we sort of had this idea that you leave these brands, you start uniting the tech underneath, and then at some point it's the same product, but it sort of has a, basically a different name. And that's literally like the one differe…”
Bastian Lehmann Apr 8, 2024 ▶ 26:06 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Disclosure
Postmates raised approximately $900M in total venture funding
“And look, we raised quite a bit of money. I think we raised around nine hundred million.”
Bastian Lehmann Apr 8, 2024 ▶ 11:08 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Disclosure
Postmates and Uber held preliminary merger talks 18 months before deal
“A year and a half earlier, there were some preliminary discussions with the Uber team, so there was some familiarity.”
Bastian Lehmann Apr 8, 2024 ▶ 16:15 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
Assertion Supported
Khosrowshahi: Postmates backend integration enabled aggressive cost cuts for Uber
“While Postmates as an app is still in the app store, they've got millions of loyal customers, all of the backend is essentially being served by our infrastructure, which allowed us to save pretty aggressively as it related to the cost side.”
Dara Khosrowshahi Mar 27, 2023 ▶ 22:46 Dara Khosrowshahi: How I Became CEO of Uber; Uber Eats vs DoorDash; The Postmates Acquisition | E994 · 20VC with Harry Stebbings
Assertion Supported
Lemkin: Postmates sold for nearly $3B despite being the third-place player
“Postmates, like, you know, I used it, but in the US, I think it was number three or number four, and it still sold for almost three billion dollars.”
Jason Lemkin Jan 13, 2023 ▶ 2:32 Jason Lemkin: WTF is Going On in VC? Are LPs Investing in New Funds? | 20VC #965 · 20VC with Harry Stebbings
Disclosure
McLoughlin's first angel check was $10,000 into Postmates in 2011
“And so I invested 10,000 dollars into this entity that became a company that turned into Postmates. And so that was my first ever investment.”
Andy McLoughlin May 8, 2018 ▶ 4:44 20VC: Andy McLoughlin on The Benefits of Backing Unsexy Businesses with Non-Obvious Founders, How To Distinguish Between A Good Bridge Round and A Bridge To Nowhere & Whether VCs Really Do Add Value?
Disclosure
Charles Hudson Invested in Postmates Before It Had Meaningful Delivery Volume
“When I think back to when we first invested in Postmates, Postmates did not have meaningful delivery volume at all”
Charles Hudson May 9, 2016 ▶ 13:37 20VC: Raising A Solo GP Fund & Why They Are So Prominent Today with Charles Hudson, Managing Partner @ Precursor Ventures
Disclosure
Lehmann: Every single Postmates funding round was hard to raise
“Everyone, every single round.”
Bastian Lehmann Apr 8, 2024 ▶ 15:25 Bastian Lehmann: How the Uber Deal Went Down and How a $2.65BN Deal Turned into $5BN | E1137 · 20VC with Harry Stebbings
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