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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

Opinion
Pishevar: Bill Gurley was the wrong VC on Uber's board
“We had the wrong venture capitalists on the board. Unfortunately, in my opinion, it was Bill Gurley at Benchmark.”
Shervin Pishevar Jan 13, 2025 ▶ 0:17 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Assertion Contradicted
Pishevar: Bill Gurley hired PIs and met weekly to oust Travis Kalanick
“We found out in our investigation that he hired Some private investigators had weekly meetings about how do we get rid of Travis.”
Shervin Pishevar Jan 13, 2025 ▶ 0:24 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Opinion
Emil Michael: Benchmark Capital lost its nerve ousting Travis Kalanick from Uber
“I was taken out with Travis because benchmark capital lost their nerve.”
Emil Michael Oct 25, 2022 ▶ 38:57 Emil Michael: How I Negotiated the $4B Uber-China Deal, Why DoorDash Caught Up to Uber | 20VC #941 · 20VC with Harry Stebbings
Opinion
Asparouhov: Bill Gurley's firing of Travis Kalanick was morally depraved
“I wish that, you know, Bill Gurley's, you know, firing of Travis, you know, was, you know, sort of talked about more publicly about how morally depraved that entire basically situation was so that people can choose to opt into.”
Delian Asparouhov Jul 29, 2024 ▶ 42:16 Delian Asparouhov: Inside the Walls of Founders Fund: What the World Does Not See | E1183 · 20VC with Harry Stebbings
Assertion Supported
Didi and the Chinese Government Had Full Access to Uber's Data
“It became very clear that everyone had all our data. Didi knew everything we were doing whereas, like, Lyft and Uber always knew what each other were doing, because we were watching each other, we're friends, things like that, but, like, we never had each othe…”
Adam Grenier Mar 15, 2023 ▶ 0:00 Adam Grenier: The Inside Story to Uber’s Hypergrowth; How We Spent $1B/mo in China | E989 · 20VC with Harry Stebbings
Opinion
Emil Michael gives Uber CEO Dara Khosrowshahi an 'F' grade for performance
“He was a diplomat. He was able to get the company public, but in terms of hiring talent, innovating, and succeeding from a financial standpoint, you know, it's not, it hasn't happened. It's a, it's an F, you know.”
Emil Michael Oct 25, 2022 ▶ 46:32 Emil Michael: How I Negotiated the $4B Uber-China Deal, Why DoorDash Caught Up to Uber | 20VC #941 · 20VC with Harry Stebbings
Assertion Supported
Ed Baker: Uber secretly ran India test against CEO orders, doubling conversion
“We decided to run a test In Hyderabad, India, where we said, let's let riders request their first ride without putting a credit card number in. In fact, we were told by our CEO not to run that test because he felt so strongly against it, but we had so much con…”
Ed Baker Feb 16, 2022 ▶ 36:16 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 @
Prediction Open · timeframe Jun 2020
Altucher in 2015: Uber will become a trillion-dollar company
“They're ultimately a logistics company where on one side are people who want to do things for money, and on the other side are people who want to pay for services. So they're going to be an entire slice of kind of the world's, you know, GDP at some point. So, …”
James Altucher Jun 4, 2015 ▶ 15:45 James Altucher: Ideas, Investing and Entrepreneurs
Prediction Open · timeframe Aug 2031
Waymo and Tesla Will Eventually Have to Partner With Uber
“I think ultimately it's in both of their interests to put their vehicles on our network, even if they have their own robo taxi apps or their own one P apps, even if they work with our competitors on the rideshare side or on the delivery side. I think everyone …”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 27:01 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Insight
O'Driscoll: Major Startup Breakthroughs Rely on Boundary Pushing Legalized Upon Success
“So many breakthroughs rely on a little bit of pushing the boundaries. I mean, Uber did with taxi regulation. Airbnb did with regulation. You're right. Polymarket did in terms of how they're regulated. So I'm actually going to get off my high horse and say you …”
Rory O'Driscoll Jul 16, 2026 ▶ 59:52 Zuckerberg Back on X Challenging Codex & Claude Code | SK Hynix’s $26BN IPO · 20VC with Harry Stebbings
Opinion
Lemkin: Uber Leaders Are Justified in Hating Benchmark Capital
“I think the folks that hate benchmark from Uber, I think they deserve to hate benchmark.”
Jason Lemkin Jun 11, 2026 ▶ 33:25 SpaceX Launches Largest Ever IPO | OpenAI Files to Go Public | Uber Cuts 23% of HR · 20VC with Harry Stebbings
What-if
Lemkin: Uber would be worth $1 trillion today under Travis Kalanick
“I think Travis Uber would be a trillion dollar company today because it would be five years ahead of where it is today.”
Jason Lemkin Mar 19, 2026 ▶ 0:21 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Disclosure
G Squared lost 20% on Uber and made 3x on Lyft
“We lost I think we made, we lost like 20 cents on the dollar, and Lyft we made like a three X.”
Larry Aschebrook Jun 16, 2025 ▶ 31:32 Larry Aschebrook, Founder & MP @GSquared: How We Lost Money on Uber and Made Millions on Lyft · 20VC with Harry Stebbings
Opinion
Östberg: Large competitor balance sheets are not a threat in food delivery
“I don't think that the balance sheet matters. I don't know. In the end, that is not what limits any compared to spend money. It's going to be the return that is going to limit a compared to spend money. So it's going to be hard for a door dash or Uber or somew…”
Niklas Östberg Mar 12, 2025 ▶ 51:37 Niklas Östberg, Founder @ Delivery Hero: Competing with Uber and Doordash in a Capital Arms Race · 20VC with Harry Stebbings
What-if
Pishevar: Uber allies should have staged OpenAI-style employee revolt for Kalanick
“What I wish I had done or had the wisdom to know to do was what, you know, Sam and his allies did in getting the employees at OpenAI to back Sam and say, if he doesn't come back, we're gonna leave. . It was very powerful, and if we had done that at Uber, becau…”
Shervin Pishevar Jan 13, 2025 ▶ 1:20:52 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Opinion
Pishevar: Benchmark ousting Travis Kalanick was one of worst VC decisions ever
“I believe that it was, you know, one of the worst venture, ah, decisions ever.”
Shervin Pishevar Jan 13, 2025 ▶ 54:39 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Assertion Supported
Pishevar: Holder's investigation report found no personal wrongdoing by Kalanick
“And the report, by the way, didn't find anything wrong that, you know, Travis did, or I did, or there was nothing, nothing in there about, you know, him, you know, directly and the recommendation was like to go hire a Sheryl Sandberg, like a chief operating of…”
Shervin Pishevar Jan 13, 2025 ▶ 39:29 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Opinion
Pishevar: Firing Kalanick from Uber was tech's worst mistake since Jobs
“And so they got two, two of the greatest minds in Silicon Valley were taken out of the company. This is the greatest value destruction that's happened since firing Steve Jobs at Apple. And it was a massive mistake.”
Shervin Pishevar Jan 13, 2025 ▶ 48:12 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
What-if
Pishevar: Uber would be worth $1T if Travis Kalanick stayed
“I believe if Travis and Emil had stayed at Uber, Uber would be a trillion-dollar company by now.”
Shervin Pishevar Jan 13, 2025 ▶ 48:33 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Opinion
Replacing Travis Kalanick with Dara Khosrowshahi was a mistake for Uber
“I don't think so. I'm a big fan of founder led businesses, and I think Travis is an incredible founder who, you know, should have been given the opportunity to lead Uber into the next generation. It's really unfortunate how things happened and played out. And …”
Scott Gorlick Aug 30, 2024 ▶ 31:55 Scott Gorlick: How Uber Acquired 1M Drivers & The Uber’s Expansion Playbook | E1196 · 20VC with Harry Stebbings
What-if
Asparouhov: Uber would be a $1T company if Travis Kalanick remained CEO
“But perhaps those benchmark LPs would have made even more money if Travis was still CEO, And the future of self-driving cars lived within Uber rather than living within Google. And maybe Uber becomes a one trillion dollar company over the course of the 20 twen…”
Delian Asparouhov Jul 29, 2024 ▶ 44:28 Delian Asparouhov: Inside the Walls of Founders Fund: What the World Does Not See | E1183 · 20VC with Harry Stebbings
Disclosure
Khosrowshahi: Uber's investment in self-driving division ATG was a mistake
“Where we got it wrong was when we went outside of our core. So for example, we had a very large self-driving business, ATG, trying to develop autonomous tech, and that wasn't what we were passionate about every day, and it was outside of the core, and ultimate…”
Dara Khosrowshahi Mar 27, 2023 ▶ 14:35 Dara Khosrowshahi: How I Became CEO of Uber; Uber Eats vs DoorDash; The Postmates Acquisition | E994 · 20VC with Harry Stebbings
Prediction Didn’t hold up
Stebbings: 97% of Capital Invested in Uber Will Not Return 1x
“97% of the money that's gone into Uber will not return one X, just given the quantum of money.”
Harry Stebbings Jan 24, 2023 ▶ 12:00 The Ultimate Guide for Building a Two-Sided Marketplace | a16z's Jeff Jordan · 20VC with Harry Stebbings
Opinion
Stebbings: 97% of capital invested in Uber will not return 1x
“Point being though, Jeff, like if we're just being blunt, I think I sort of start like seven, 97% of the money that's gone into Uber will not return one X, just given the quantum of money.”
Harry Stebbings Jan 16, 2023 ▶ 17:58 a16z GP Jeff Jordan: The Ultimate Guide to Two-Sided Marketplaces | 20VC #966 · 20VC with Harry Stebbings
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 Contradicted
Sacca: Travis Kalanick was ousted by 13 Uber managers, not VCs
“In the end, what pushed Travis out was when his team held him accountable. It was when the, you know, his 13 senior managers all wrote a letter and said, dude, you gotta stay out of the company. You know, that's really the only force that Silicon Valley leader…”
Chris Sacca May 4, 2022 ▶ 11:12 20VC: The Memo: Chris Sacca on Why We Are Breeding a Generation of Entitled Assholes, Harley Finkelstein on What Great Fatherhood Really Means, Deena Shakir on How Kids Make You a Better Investor and Anne Wojcicki on How Children Change Your Approach to R
Opinion
Claure: SoftBank disrupted venture capital just like Uber disrupted taxi drivers
“The same way Uber disrupted the taxi drivers, we disrupted the venture capital industry. While people used to write these small checks, we suddenly showed up with a hundred billion dollars, and we disrupted the way venture capital works today, and therefore, w…”
Marcelo Claure Aug 30, 2021 ▶ 21:30 20VC: Marcelo Claure, CEO of Softbank Group International on Lessons From Investing $1BN Per Week with Masa Son, How Softbank Could Have Up To 8 Companies Go Public in LATAM Alone Next Year & How Softbank Analyse Both Deal Pricing and Competition Today
Insight
Cyan Banister: Uber could not build a world-changing company by being nice
“They pushed people to move fast, break things, and challenge all regulations, etc., but in order to be Literally a world-changing company, they had to do that, and they had to have those behaviors. They weren't going to be able to do it by being nice all the t…”
Cyan Banister Oct 19, 2020 ▶ 17:05 20VC: Cyan Banister on Her Relationship To Money, Risk, Her Investment Decision-Making Process, Why We Will See A Reckoning in the Early Stage Market, Her Biggest Takeaways from HQ Trivia & The Future of Silicon Valley
What-if
Cuban claims Uber and Twitter would be more successful outside Silicon Valley
“I think if you take some of the companies, Twitter, or almost any of them, Uber in particular, Lyft, and you move those to Kansas City, Dallas, Pittsburgh, Buffalo, New York, they would have been so much more successful, so much more quickly.”
Mark Cuban May 4, 2020 ▶ 17:18 20VC: Mark Cuban on His Relationship To Wealth and Risk, Why Coming Out of The Pandemic Will Be The Best Time In The History of Mankind To Start A Business & Why Silicon Valley Investors Are Like Old Hollywood
Insight
Carlson-Wee: Companies launching tokens must stop extracting direct network revenue
“The second thing is that if you are launching a token and you're a private company, you should be ready to stop extracting any revenue from your network. So however you were extracting revenue from the network, whether this was advertising or paid subscription…”
Olaf Carlson Wee Dec 11, 2017 ▶ 15:51 20VC: Inside The World's Leading Crypto Fund, The Future Exit Environment for Crypto Assets & The Beauty Of Benevolent Dictatorship with Olaf Carlson-Wee, Founder @ Polychain Capital
Assertion Supported
Kevin Rose: GV deployed its entire $254M annual fund into Uber
“I definitely know that largest GVs ever done is Uber, where it was two hundred and fifty four million, I believe. So it was our entire fund into one of their rounds.”
Kevin Rose Jun 12, 2017 ▶ 6:55 20VC: Kevin Rose on Putting The Entire Fund Into Uber, The Future For Mobile & Whether Angels Should Have Super Pro-Rata Rights?
Assertion Not checkable as stated
Uber's Human-Driven Rides Grow Faster in Top AV Markets Than Nationally
“Even in the largest AV markets, where today we don't have AVs, like San Francisco and LA, our human-driven business is growing faster than the rest of the US.”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 23:47 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
What-if
Mac: Uber Could Run Today's Scope in Five Years with Fewer People
“If you took everything Uber does today and held it static and said, you know, in five years you're going to need more or less people, I'd say, well, we could do everything we do today with less people in five years because of the power of AI, but we're going t…”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 45:27 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Prediction Not checkable as stated
Autonomy Will Take Decades to Match Human Labor Costs in Brazil
“Two of our large, three largest countries by volume are India and Brazil. You know, the average fare in Brazil is like, Three 54 bucks USD and India it's two 53 bucks or something like that. It's going to be decades until the cost of autonomy compresses to the…”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 24:09 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Disclosure
Mac: Uber refuses API access to third-party price-comparison aggregators
“We've not participated historically in the aggregation apps where some, you know, somebody will come to us and pitch and say, hey, you know, give us APIs that give us real-time info on Every car, every Uber car in the network what the price of that ride is, wh…”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 48:58 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Insight
Enterprise AI ROI Requires Top-Down Headcount Constraints, Not Bottom-Up Cuts
“I think the way companies ultimately have to extract AI efficiency, at least from like a pure OPEX perspective, is just in your target setting, hold the constraints tighter. Like, if we really believe that AI is making our employees 10% or 20% or 30% more effi…”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 39:12 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Prediction Not checkable as stated
Macdonald: Waymo, Tesla, and Multiple Other AV Players Will Win Globally
“I think there's going to be more than two winners. Do I think Waymo and Tesla will ultimately be winners? Yes, I do. I don't know who, who's going to bet against either of those, but I think there will be more winners.”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 25:25 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Opinion
Macdonald: A US Tech Company Winning Chinese Mobility Was Geopolitically Implausible
“I don't think it was plausible that we were ultimately going to be the market winner. I mean, even for geopolitical reasons alone, like the notion that a U S tech company would ultimately be the largest mobility service in China. I just don't think it's someth…”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 32:25 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Prediction Not checkable as stated
Mac: Autonomy will eventually be superior to human rides in all use cases
“It's existential because at the end of the day, it's a better product than our core product in many use cases, and I think those use cases grow over time, and eventually it's better in all use cases.”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 17:46 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Assertion Supported
Uber Burned $52 Million Weekly on Subsidies Before Exiting China
“I remember the last few weeks in the negotiation, we were burning fifty two million a week in China, just on price subsidies, because there was this heated behind the scenes battle happening To get to the best economics and the ultimate sort of surrender or u…”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 30:26 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Insight
Macdonald: In the End, Distribution Wins Over Autonomous Technology
“I think in the end, distribution wins.”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 27:28 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Assertion Open
Uber president's biggest fear is ChatGPT routing rides purely by price
“I just interviewed the president of Uber. What is his single biggest fear? It's actually the disaggregation of UI or the removal of UI where you say, I want a car, and ChatGPT automatically routes you to Lyft, Uber or another provider based on price.”
Harry Stebbings Aug 12, 2026 ▶ 13:56 Canva Slashes Growth | Talent Exodus at Google | Revolut's $50B CEO Package | Musk's $55B Terrafab
Prediction Not checkable as stated
Arora: Consumer applications will be rewritten for AI agents within a decade
“I think every consumer app will get rewritten in the next five to 10 years. You know, why would I not have my agent talk to my DoorDash app or Uber app?”
Nikesh Arora Aug 5, 2026 ▶ 1:00:25 Leo Aschenbrenner's Situational Awareness Blows Up | Moonshot AI Raises $3.5B at $35B
What-if
O'Driscoll: Uber should have re-hired Travis Kalanick in 2022 for autonomy
“Actually, it turns out, in retrospect, they should have done the Steve Jobs thing. They should have swapped them out, got it public, got a cash flow like crazy, and sometime in 22 should have gotten back and said, now, Now is the time to do autonomy”
Rory O'Driscoll Mar 19, 2026 ▶ 58:05 NVIDIA Predicts $1TRN in Revenue: Everything You Need to Know From GTC & Anduril Lands $20B Contract · 20VC with Harry Stebbings
Disclosure
Siemiatkowski: Klarna built an Uber-style gig model hiring customers for support
“Is we actually built like our own Uber model, which means that we encourage today, we recruit our own customers, the most passionate customers that live in rural areas and so forth. And we say, Hey, do you want to work extra? Would you want to work part-time i…”
Sebastian Siemiatkowski Feb 16, 2026 ▶ 17:28 Klarna CEO: SaaS is Dead: Why Systems of Record Will Die in an Agentic World · 20VC with Harry Stebbings
Insight
Hacker: Opening an SF satellite office creates a talent drain to local giants
“It creates this internal funnel of your best employees moving from your HQ to Silicon Valley. Which by itself is not a problem. The problem is then they get recruited away by the whatever the hot Silicon Valley company is at the time. You know, like it could b…”
Severin Hacker May 19, 2025 ▶ 1:11:24 Duolingo Co-Founder, Severin Hacker: How AI Impacts the Future of Work and Education · 20VC with Harry Stebbings
Assertion Contradicted
Green: Only three $100B+ companies were created post-iPhone
“You know, since the iPhone came out in 2007, 2006, whatever it was, there's only been three companies built that did not exist before. That were a hundred billion dollar companies. ByteDance, Pindo Doe, and Uber.”
Mitchell Green Mar 26, 2025 ▶ 7:49 Mitchell Green, Founder @ Lead Edge Capital: Why Traditional VC is Broken · 20VC with Harry Stebbings
Insight
Delivery Giants Can Crush Local Rivals With a €20M to €30M Investment
“Because they have so much scale that they can just go into your home market and destroy your business with maybe like 20, thirty million investment.”
Oscar Pierre Feb 26, 2025 ▶ 33:59 Oscar Pierre, Glovo CEO & Founder: Selling 30% for €100K |The McDonald's Deal That Saved Them |E1263 · 20VC with Harry Stebbings
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