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why aren't all 296 resolved? a statement only gets an assessment when the public record can support or contradict it. opinions and what-ifs never can, and 8 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

Assertion Supported
Calacanis: Uber and Thumbtack had a combined $9M valuation at first round
“Thumbtack and Uber, You know, they were nine million dollars, and they're like, well, we only want one million dollars more. I was like, no, no, combined. Their valuation was nine million combined when I invested in their first rounds”
Jason Calacanis Jun 1, 2015 ▶ 45:55 Jason Calacanis: The World's Greatest Angel Investor
Prediction Open · timeframe May 2020
Tran King-Yens predicts Uber will become a trillion-dollar company
“Yes. They're changing the way in which people move from A to B, and that, and democratizing that in a way that it's not owned by companies, but by individuals.”
Angela Tran Kingyens May 21, 2015 ▶ 19:48 20 VC 038: How Make Connections with VCs and Maximise Employability with Angela Tran Kingyens @ Version One Ventures
Assertion Partly supported
Teare: Series A and B Face Severe Capital Shortage
“There's about five billion dollars available at the seed stage for all the companies every three to five years. There's about one to two billion available at the A and B stage. And then at the growth stage, at the other end, there's more than a hundred billion…”
Keith Teare Apr 16, 2015 ▶ 21:15 20 VC 028: Co-Founding TechCrunch and The Benefits of Not Raising Venture Funding with Keith Teare
Prediction Not checkable as stated
Ghoorah: Uber will grow into and exceed its $40B valuation
“Uber certainly is a company that can grow into that valuation and frankly exceed it.”
Bob Ghoorah Jan 13, 2015 ▶ 19:04 20 VC 003: Bob Ghoorah on Startups, The Pitch and Uber
Prediction Open · timeframe Aug 2029
Food Delivery Will Soon Be Significantly Larger Than Uber's Mobility Business
“And for us, like when this deal, you know, we have to go through the sort of requisite regulatory and shareholder processes, but delivery will be a much bigger business for mobility.”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 56:38 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Opinion
Macdonald: Missing Out on Autonomy Would Be Existential for Uber
“If Uber doesn't have autonomy on our platform, and we will we will, we are investing actively and aggressively to bring it to market, but if we didn't, then it certainly would be existential for our core business.”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 18:52 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Assertion Supported
Macdonald: Uber's delivery business is nearly mobility's size and growing faster
“Because, I mean, even this sort of like the existential questions we get about AV tend to ignore the fact that we have basically an equally sized food delivery business that's in market leading positions in most of our markets around the world. We get almost z…”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 54:44 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
What-if
Frankel: Following On in Every Round Boosts Absolute Returns, Not Multiples
“If we follow, our view would be we'd had, we would have had to have followed on in everything, and I think that the absolute return would be better. I don't think that the multiple would necessarily be better on the fund.”
David Frankel Aug 7, 2026 ▶ 33:32 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Disclosure
Grinberg: Dozens of Factory clients privately capped employee AI spend
“What's happened with Uber publicly has happened privately with a lot of customers of ours.”
Matan Grinberg Jun 13, 2026 ▶ 19:19 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Assertion Supported
Stebbings: Uber placed a $1,500 individual budget cap on employee AI spending
“Uber announced last night, I think it was, or yesterday, that they were having like a 1500 dollar budget. Per individual.”
Harry Stebbings Jun 13, 2026 ▶ 18:12 OpenAI vs Anthropic vs Open-Source | Token Maxing, AI Hangovers & The Coming ROI Reckoning · 20VC with Harry Stebbings
Assertion Supported
Geoffrey Woo: Uber Burned Tens of Billions on Paid Marketing
“I just saw that Bill Gurley was tweeting that you know, paid marketing is, like, the worst form of marketing, and I'm just like, hey, Uber, like, he's most well known for kicking out Travis from Uber, and Uber burnt, like, tens of billions of dollars on straig…”
Jeffrey Wu Apr 18, 2026 ▶ 12:00 Jake Paul: Traditional VC is Toast & Attention is More Valuable than Cash · 20VC with Harry Stebbings
Assertion Supported
Rajaram: Uber expanded margins continuously by altering driver pay economics
“Uber, I have to say, I don't know how, if they have raised price or not, but I know that they have basically changed the economics of how much they pay drivers over time so that their margins have just expanded continuously. And they've also raised prices in d…”
Gokul Rajaram Mar 16, 2026 ▶ 40:44 Gokul Rajaram: How to Analyse for Durability and Defensibility in a World of AI · 20VC with Harry Stebbings
Insight
Acharya: AI foundation and app markets resemble AWS and GCP, not Uber
“I think the foundation model companies look a little bit like that. And I think in the apps layer, you're just going to have people that want to Consume the code they generate through a rich IDE and those that want to be closer to the metal, and that's probabl…”
Anish Acharya Feb 9, 2026 ▶ 13:01 a16z, Anish Acharya: Is SaaS Dead? Do Margins Still Matter? Why We Are Not in an AI Bubble? · 20VC with Harry Stebbings
Insight
Using massive capital as a weapon rarely succeeds in consumer tech
“Capital as a weapon in consumer, most of the time it's, it doesn't really work. Like I would say TikTok is maybe the exception, maybe Uber.”
David George Dec 15, 2025 ▶ 36:56 a16z's David George on the Most Controversial Bet at a16z & Do Margins and Revenue Matter in AI? · 20VC with Harry Stebbings
What-if
Lime Would Not Have Survived the Pandemic Without Acquiring Jump
“Line wouldn't have survived if we did not do that deal.”
Wayne Ting Jan 27, 2025 ▶ 43:50 Wayne Ting, CEO @Lime: From Losing $3 on Every $1 to $90M in EBITDA | E1252 · 20VC with Harry Stebbings
Assertion Supported
Pishevar: Menlo's $26.5M Uber investment grew to nearly $6.7B
“For twenty million at the time, later I got another six and a half million through secondary for Menlo. So that investment at today's prices is worth almost seven billion dollars.”
Shervin Pishevar Jan 13, 2025 ▶ 12:01 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Disclosure
Pishevar sold all Facebook shares to bet everything on Uber secondary stock
“He allowed me to buy secondary shares from another early person, so I sold all my Facebook shares that had gone public at like, 53 bucks, 58 bucks a share, and I put it all I bet it all, everything I had, I put it all into Uber.”
Shervin Pishevar Jan 13, 2025 ▶ 13:25 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Assertion Supported
Villig: Bolt raised $1.5B while competitors raised up to $30B
“There's about seven companies left. What they've been doing better than us is raising money. They've just all raised multitudes of how much we have raised. Many of them have raised five billion. Some of them have raised 15, even thirty billion. Well, we have r…”
Markus Villig Nov 13, 2024 ▶ 1:15:40 Markus Villig, Founder @Bolt: The Most Insane Story in Startups & The Future of Self-Driving| E1225 · 20VC with Harry Stebbings
Disclosure
Frankel: Founder Collective regrets selling any secondary shares in Trade Desk and Uber
“Well, Trade Desk, I regret every single share I sold. Uber, I regret every single share I sold.”
David Frankel Oct 14, 2024 ▶ 1:02:13 David Frankel, MP @Founder Collective: Investing Lessons from Seeding Coupang, Pillpack & Suno|E1214 · 20VC with Harry Stebbings
Disclosure
Frankel: Trade Desk was a bigger outcome for Founder Collective than Uber
“Trade Desk was a bigger outcome for us. Coupang returned the fund, right? Like if, and multiple times.”
David Frankel Oct 14, 2024 ▶ 30:10 David Frankel, MP @Founder Collective: Investing Lessons from Seeding Coupang, Pillpack & Suno|E1214 · 20VC with Harry Stebbings
Assertion Partly supported
Uber initially let Lyft launch first to absorb local regulatory risk
“And what a lot of people don't know about Lyft is when we started launching UberX, we let Lyft go first, and we had a policy that said, hey, if Lyft launches in a city, we are going to wait 30 days to see if the law enforcement comes after them, and then we're…”
Scott Gorlick Aug 30, 2024 ▶ 17:44 Scott Gorlick: How Uber Acquired 1M Drivers & The Uber’s Expansion Playbook | E1196 · 20VC with Harry Stebbings
Assertion Supported
Uber's advertising business has reached a $1 billion run rate
“I think the ads business is a monster. I think ads is really interesting because it's, I think, in a billion dollar run rate now, and what's really interesting is if you think about Uber as a platform, It's the app where you go from, like, point A to point B. …”
Scott Gorlick Aug 30, 2024 ▶ 38:06 Scott Gorlick: How Uber Acquired 1M Drivers & The Uber’s Expansion Playbook | E1196 · 20VC with Harry Stebbings
Insight
Ride-hailing market share swings were driven by pure price, not product
“On early demand, not really much, right? We were in a market and we had wild product market fit. Once competition came in, you could start to see market share swings based on the specific rider promo that Uber was offering in a city In a given week, and then w…”
Scott Gorlick Aug 30, 2024 ▶ 27:14 Scott Gorlick: How Uber Acquired 1M Drivers & The Uber’s Expansion Playbook | E1196 · 20VC with Harry Stebbings
Assertion Supported
Uber manually onboarded its first million drivers without major digital ad spend
“For probably the first million drivers that we onboarded, a lot of our processes were manual, right? So we weren't doing a lot of like paid spend on Facebook. We were doing a little bit on Craigslist. We weren't doing a ton on Google, but it was really the ope…”
Scott Gorlick Aug 30, 2024 ▶ 7:19 Scott Gorlick: How Uber Acquired 1M Drivers & The Uber’s Expansion Playbook | E1196 · 20VC with Harry Stebbings
Assertion Partly supported
Good annual driver retention for early Uber was 25% to 30%
“I would say, if you started the year with a hundred drivers, I think you would probably have 25 or 30 of them left at the end of the year. That would be good, right?”
Scott Gorlick Aug 30, 2024 ▶ 14:37 Scott Gorlick: How Uber Acquired 1M Drivers & The Uber’s Expansion Playbook | E1196 · 20VC with Harry Stebbings
Opinion
Uber's 2021 acquisition of Drizly made little strategic sense
“There were some deals we did in 20, 20, 21 that didn't make a lot of sense. I know Emil talked about Postmates. I think the Drizzly acquisition probably didn't make much sense either.”
Scott Gorlick Aug 30, 2024 ▶ 32:53 Scott Gorlick: How Uber Acquired 1M Drivers & The Uber’s Expansion Playbook | E1196 · 20VC with Harry Stebbings
Assertion Partly supported
Uber is the top global food platform but lost US to DoorDash
“Uber's the number one food delivery platform in the world, but I think we really fumbled the bag in the US with DoorDash. I think we missed out on a huge opportunity.”
Scott Gorlick Aug 30, 2024 ▶ 37:35 Scott Gorlick: How Uber Acquired 1M Drivers & The Uber’s Expansion Playbook | E1196 · 20VC with Harry Stebbings
Assertion Supported
Uber built its initial Atlanta driver supply by cold-calling Yelp listings
“When we went into the initial market, we got a Yelp list of all the drivers in the city and sort of like called through and trying to get them to sign up with Uber and, you know, got our initial list of drivers that way and launched a few weeks later with some…”
Scott Gorlick Aug 30, 2024 ▶ 3:40 Scott Gorlick: How Uber Acquired 1M Drivers & The Uber’s Expansion Playbook | E1196 · 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
Insight
Barnes: Analyzing Initial Market Size Causes Investors to Miss Market-Expanding Founders
“When you get stuck thinking through that and working through the hundred reasons why owning the black car market isn't worth it, then you miss That Travis would figure out UberX.”
Phin Barnes Oct 2, 2023 ▶ 44:18 Phin Barnes: The Services Model of Venture Capital is Broken, The Best Founders Do Need Help | E1067 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Dara Khosrowshahi Promised Careem Autonomy to Finalize $3.1B Uber Acquisition
“The thing that really made it happen at the end was Dara saying that you guys can continue, continue pushing your purpose, keep your culture, keep your org. I'm just going to replace your shareholders and become a better shareholder.”
Mudassir Sheikha Sep 4, 2023 ▶ 32:06 Mudassir Sheikha: The Meeting that Led to $3.1BN Buyout: The Battle Between Uber and Careem | E1056 · 20VC with Harry Stebbings
Disclosure
Careem Outcompeted Uber in Saudi Arabia by Enabling Cash Payments
“Early in Saudi Saudi Arabia, which is of course the largest market in the region not many people at that time had credit cards, or even if they had credit cards, they were not able to use credit cards, and people just preferred paying in cash. So this was some…”
Mudassir Sheikha Sep 4, 2023 ▶ 22:25 Mudassir Sheikha: The Meeting that Led to $3.1BN Buyout: The Battle Between Uber and Careem | E1056 · 20VC with Harry Stebbings
Opinion
Braun: Travis Kalanick Is One of the Best Founders Ever
“Travis is one of the best founders I've ever met my entire life.”
Scooter Braun Apr 17, 2023 ▶ 41:05 Scooter Braun on Being Enough, Insecurity, Wealth, Investing, Fame, Marriage and Much More | E1002 · 20VC with Harry Stebbings
Disclosure
Khosrowshahi: Uber slowed feature updates for drivers to avoid payment errors
“We've actually slowed down in terms of some of the velocity of features that we ship for our earners, right? So it's, we're iterating constantly as it relates to eaters, riders, et cetera trying X out or trying Y out. But as it relates to earners, this is how …”
Dara Khosrowshahi Mar 27, 2023 ▶ 29:54 Dara Khosrowshahi: How I Became CEO of Uber; Uber Eats vs DoorDash; The Postmates Acquisition | E994 · 20VC with Harry Stebbings
Prediction Not checkable as stated
Khosrowshahi: Kareem and Transplace acquisitions are or will be major hits
“I would say probably Kareem or there's a, we're pretty early on in terms of development, but a, an acquisition that we made in with Uber Freight Transplace, which really runs the logistics outsource logistics function of a lot of companies out there. Both of t…”
Dara Khosrowshahi Mar 27, 2023 ▶ 23:28 Dara Khosrowshahi: How I Became CEO of Uber; Uber Eats vs DoorDash; The Postmates Acquisition | E994 · 20VC with Harry Stebbings
Disclosure
Khosrowshahi: Uber's past allocations into hardware products were a mistake
“We're not particularly good in hardware, and I think our investment or the capital that we allocated in hardware in the past was a mistake.”
Dara Khosrowshahi Mar 27, 2023 ▶ 15:13 Dara Khosrowshahi: How I Became CEO of Uber; Uber Eats vs DoorDash; The Postmates Acquisition | E994 · 20VC with Harry Stebbings
Prediction Held up
Khosrowshahi: Uber will focus exclusively on software moving forward
“I will tell you right now, based on everything I see, we're going to stay squarely in software, because we're really, really good at it.”
Dara Khosrowshahi Mar 27, 2023 ▶ 27:21 Dara Khosrowshahi: How I Became CEO of Uber; Uber Eats vs DoorDash; The Postmates Acquisition | E994 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Uber Burned Budget Shifting Driver Ads From Earnings to Flexibility
“We're like, great, we need to, like, shift all of our messaging away from dollars to flexibility, and we spent a ton of money on that type of messaging, and then it just burnt, right? Like, it was just, like, no one clicked, right?”
Adam Grenier Mar 15, 2023 ▶ 36:20 Adam Grenier: The Inside Story to Uber’s Hypergrowth; How We Spent $1B/mo in China | E989 · 20VC with Harry Stebbings
Assertion Supported
Uber Built Its Growth Team by Hiring Cross-Functional Leaders Simultaneously
“When we built growth at Uber, like we infused an entire team In one fell swoop, right? Like, and Ed was hired, and he hired myself, a head of product, a head of engineering, a head of design head of analytics.”
Adam Grenier Mar 15, 2023 ▶ 17:46 Adam Grenier: The Inside Story to Uber’s Hypergrowth; How We Spent $1B/mo in China | E989 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Paid Acquisition Drove 40% to 50% of Uber's Global Growth
“When we were doing a billion dollars, that included China, and that was more than 50%, like paid drove a ton of our growth in China. And so, and it was like, it was nonsense. It was just wild. And so, like, let's say six, seven hundred million dollars on, like…”
Adam Grenier Mar 15, 2023 ▶ 52:04 Adam Grenier: The Inside Story to Uber’s Hypergrowth; How We Spent $1B/mo in China | E989 · 20VC with Harry Stebbings
Assertion Not checkable as stated
Uber Never Solved How to Allocate LTV Between Drivers and Riders
“And there's like, this is one of those challenges that like we've had, we had like dozens of data scientists working with it and we never got a great answer to it.”
Adam Grenier Mar 15, 2023 ▶ 22:42 Adam Grenier: The Inside Story to Uber’s Hypergrowth; How We Spent $1B/mo in China | E989 · 20VC with Harry Stebbings
Disclosure
Uber Dissolved Its Centralized Growth Team Prior to Grenier's Departure
“So like we actually, all of those functions within the growth team eventually actually merged back into the core business to where by the time I left, we actually didn't have a centralized growth team anymore.”
Adam Grenier Mar 15, 2023 ▶ 13:10 Adam Grenier: The Inside Story to Uber’s Hypergrowth; How We Spent $1B/mo in China | E989 · 20VC with Harry Stebbings
Disclosure
Escobari: General Atlantic passed on Uber's $2B round over market size limits
“So, one of my mistakes as an investor is Anton, my friend Anton Levy, co-president of the farm, invited me to look at Uber, the two billion dollar round, because of the international opportunity, and we went, and we met Travis, The entire black market industry…”
Martin Escobari Nov 11, 2022 ▶ 11:29 Martin Escobari: How to Invest During a Recession; Negotiation Tips; Developing Markets | 20VC #948 · 20VC with Harry Stebbings
Assertion Supported
Emil Michael: Uber burned $100M monthly competing against Didi in China
“And we were spending A hundred million dollars a month competing there.”
Emil Michael Oct 25, 2022 ▶ 26:01 Emil Michael: How I Negotiated the $4B Uber-China Deal, Why DoorDash Caught Up to Uber | 20VC #941 · 20VC with Harry Stebbings
Assertion Contradicted
Benchmark turned a $33M Uber investment into $10B in four years
“Bill Gurley was on our board, lost her nerve. And the reality is there's another economic principle called loss aversion, right? If you invest thirty three million dollars in Uber and it looks like ten billion four years later, ten billion on a thirty three mi…”
Emil Michael Oct 25, 2022 ▶ 39:04 Emil Michael: How I Negotiated the $4B Uber-China Deal, Why DoorDash Caught Up to Uber | 20VC #941 · 20VC with Harry Stebbings
Insight
Major initiatives drive more growth than hundreds of A/B tests combined
“When I look back at my time at Uber, every year we maybe had one or two things like that that accounted for more growth than everything else combined.”
Ed Baker Feb 16, 2022 ▶ 8:55 20Growth: Five Key Functions of a Growth Team, The Biggest Lessons Starting Uber's Growth Team and Scaling Facebook's, How To Structure The Hiring Process for Growth and What Separates Good From Great in Growth Leaders with Ed Baker, Former VP of Growth @
Insight
Hans Tung: Venture scale requires replacing fundamental behavior, not just incumbents
“If you believe that is a substitution of gym membership and enlarging the pie, and you can argue for those that miss Uber or anything that drive sharing, it's a car ownership substitution, not just a substitution of taxi services, then the pie becomes a lot bi…”
Hans Tung Sep 20, 2021 ▶ 12:56 20VC: Investing Lessons From Rounds In Peloton and Square, Why Great Investing is Stock-Picking and Sector Penetration & The Next Decade in Venture, Is Tiger's The Right Model with Hans Tung, Managing Partner @ GGV Capital
Disclosure
Chris Fralic: First Round took secondary liquidity in Uber and Roblox early
“If you look at our investments in our two most notable returns with Uber and with Roblox, we had taken some capital off the table along the way at various points, Which made sense and drove great returns relative to that investment, and yet what was left was s…”
Chris Fralic Apr 29, 2021 ▶ 22:28 20VC: The Roblox Memo: First Round's Chris Fralic on The 17 Year Journey to Build a $41BN Market Cap Company, Why It Is Way Harder To Increase Ownership Across Rounds Today & What Happens Post SPACMania
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