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Opinion
Allred: Lambda School Erred by Adopting Uber's Decentralized Operational Model
“But I think we picked the wrong one. We went with the Uber model. And the educational model is so sensitive to changes and so sensitive to experience that you can't Really get away with that.”
Austen Allred Sep 18, 2020 ▶ 17:37 20VC: Lambda School Founder, Austen Allred on How To Assess Your Relationship To Risk and Money, Why San Francisco Is A Case Study For The Greatest Squandering of Wealth in History & Why Complexity Increases Exponentially with Scale
Insight
Helmer: Uber's scale density power is local and non-transferable globally
“So for example, if you look at Uber's source of power that they might have versus, for example, an upstart, it would be the scale density, physical scale, regional scale density. In a particular region like the Bay Area, if they have enough riders and enough c…”
Hamilton Helmer May 18, 2020 ▶ 34:17 20VC: 7 Powers: The Foundations of Business Strategy: Deconstructing Economies of Scale, How To Assess True Market Size, Assessing Risk vs Uncertainty, What "Brand As Power" Really Means with Hamilton Helmer, Managing Partner and Chief Investment Offi
What-if
Maples: Lyft and Uber could not exist before the iPhone 3GS
“So before the iPhone three GS, you could have had the idea for Lyft and Uber. It wouldn't have mattered because you wouldn't have been able to connect drivers and riders accurately on a map.”
Mike Maples May 11, 2020 ▶ 11:49 20VC: Floodgate's Mike Maples on 3 Key Breakthroughs Startups Experience in Success, The Rise of Angel and Operator Funds, Multi-Stage Funds Re-Entering Seed Investing and The Insight Development Framework
Disclosure
Suster passed on Uber and Box due to personal biases
“The obvious example, Harry, is Uber, where having lived in London and seen the taxi lobby and how strong the taxi lobby was in London, that clouded my vision for what was possible. Having lived in Los Angeles and seeing how few people ever use taxis, that clou…”
Mark Suster Apr 20, 2020 ▶ 34:13 20VC: Upfront's Mark Suster on COVID Redefining What A Great Company Looks Like and What Valuations Look Like, Why Pay-To-Play Is Back On The Table & Why We Will See The Death of Party Rounds
Assertion Contradicted
Gurley: Uber in San Francisco was already 10x the local taxi market
“And at the moment he wrote it, the size of Uber in San Francisco was already 10 X the taxi and black car market.”
Bill Gurley Jun 24, 2019 ▶ 12:51 20VC: Benchmark's Bill Gurley on 5 Traits Benchmark Look For When Adding To The Partnership, Why The Abundance of Capital Is Today's Biggest Challenge in VC & The Right Way To Think About Market Size When Assessing Opportunities
Disclosure
Lime deliberately rejected Uber's playbook of launching without prior city approval
“When we started a company that the proven formula, which is a uncommon common practice, That idea to get into a city. Well, you know Uber established it, right? You just go to the city, you launch the service, and talk about it with the city after that. And we…”
Brad Bao Jun 14, 2019 ▶ 26:40 20VC: Lime CEO Brad Bao on How Lime Assess The Micro-Mobility Landscape and Competition Today, What It Takes To Launch and Win A New City & Why Lime Have Spent $0 on Marketing To Date
Insight
Eggers: Maintaining 15% ownership in capital-intensive startups is nearly impossible
“Yeah, I think that it depends on some of these projects that require a ton of capital. It's really hard to get 15 or 20% of them over time. You look at the Ubers of the world, and some of the guys who are, you know, the electric bike companies and scooter comp…”
Barry Eggers Sep 4, 2018 ▶ 10:48 20VC: What It Takes To Found and Scale A Global Venture Firm Like Lightspeed, 3 Ways Firms Do Not Succeed in Generational Transition & What Makes The Truly Special Board Members Like Jim Goetz with Barry Eggers, Founding Partner @ Lightspeed Venture Partn
Assertion Partly supported
Motschwiller: Series A rounds for top consumer decacorns occurred pre-2012
“You look at the series A Funding times of the consumer decacorns that are out there, the Ubers, the Lyfts, the Airbnbs, the Snaps, the Pinterest, the Spotifys, those series A's were all done pre-二零 12.”
Max Motschwiller Jun 25, 2018 ▶ 26:28 20VC: The 4 Key Skills All VCs Need To Be Successful, How To Build, Maintain and Scale Your Network in VC and What is The Process Through Which VCs Build Conviction in Opportunities with Max Motschwiller, General Partner @ Meritech Capital
Insight
The biggest sin in venture investing is missing outlier winners
“The biggest sin is missing that 10% deal that's the huge winner, right? Because no amount of mediocre kind of deals can make up for missing Uber or whatever, Zoom or Arista or whatever you want to say. No amount of things can make up for missing something that…”
Dan Scheinman May 21, 2018 ▶ 21:20 20VC: Why The Days of Spray and Pray at Seed Are Over, How To Compete In A World of Sequoia Seed Funds & Why Price Doesn't Matter with Dan Scheinman, Angel Investor @ Zoom & Arista Networks
Assertion Supported
Uber's growth team drove Indian expansion by introducing cash payments
“There's a very good example in Uber where, you know, the whole premise was it's a cashless transaction app. And they went to India, which has no credit cards. And the growth team actually ran an experiment by turning on cash to figure out how much it helped wi…”
Anu Hariharan Mar 5, 2018 ▶ 22:36 20VC: Why, How and When To Think About Growth Teams, The Right Way To Think About Network Effects & Scaling from Phase 1 To Phase 2 of Startup Life with Anu Hariharan, Partner @ YC Continuity Fund
Assertion Supported
Tung: Uber turned $1B–$2B investment in China into $7B Didi stake
“They put in about a billion to two in, and they have a stake that's worth seven billion.”
Hans Tung Jan 8, 2018 ▶ 7:16 20VC: Why This Is Just The Start for Consumer Mobile, 3 Lessons China Taught About How To Invest Better In The US & How To Think About The Opportunity Cost of Capital Deployment with Hans Tung, Managing Partner @ GGV Capital
Prediction Partly held up
Belsky: Uber and Lyft's data and route optimization will be their moat
“Because I think that the data that is being collected and the optimization of the routes based on the data is a moat, so to speak. And I think a lot of the technology for managing these dispatch systems and autonomous vehicles will be created by those companie…”
Scott Belsky Feb 27, 2017 ▶ 18:40 20VC: Benchmark's Scott Belsky on What Makes Truly The Best VCs? Why Entrepreneurs Must Focus on 'The First Mile' & The Key Ingredients To The Perfect Onboarding Process
Disclosure
Lynn: Passed on early Uber investment pitch from Travis Kalanick
“The biggest miss was Uber and Travis Kalanick was actually in my office with Talking about his angel portfolio years ago, we both had a healthcare IT company. He was in Cario and I was in practice fusion. And I brought him in to talk about, you know, how we ca…”
Rebecca Lynn Dec 19, 2016 ▶ 25:29 20VC: Learnings From Mary Meeker & Larry Summers, Missing Out On Uber & The Changing World of VC with Canvas Partner, Rebecca Lynn
Assertion Not checkable as stated
Srinivasan: Uber is a more closely regulated marketplace than taxi medallion systems
“Uber is a more closely regulated marketplace than the taxi medallion system. It's harder to abuse it. Right. It's actually better at achieving the aims of the early twint century progressives than this antiquated system. Right. So it's not deregulated. It's re…”
Balaji Srinivasan Nov 25, 2016 ▶ 20:49 20VC: a16z's Balaji Srinivasan on Why There Is A Financial Incentive For Truth In VC & Why The Best VCs Invest In Founder To Make Them Richer Than Themselves
Disclosure
Caldbeck: Passing on Uber at 10 employees was my biggest miss
“My biggest miss far and away was Uber. Far and away. I mean, I met Ryan when the company was 10 people, and I just, I didn't get how people could afford to be paying 50 dollars for rides that were, you know, eight, 10 blocks, and at that point, there was no no…”
Justin Caldbeck Nov 7, 2016 ▶ 21:42 20VC: Binary's Justin Caldbeck on Specialisation Being Key To Success In VC, The Biggest Problem In VC Today and Why The Future Is A Moneyless Barter Economy
Disclosure
McClure passed on investing in Uber multiple times, starting at seed
“Clearly Uber was the deal that I totally fucked up. Travis gave me the opportunity to invest in June of... The reality is I didn't invest multiple times, not just in the seed realm, so it's probably my mistake multiple times over.”
Dave McClure Aug 15, 2016 ▶ 23:30 20VC: 500 Startups' Dave McClure on Whether Unicorns Are Necessary For Venture Returns & Why Ownership Is Not The Math To Think About When Investing
Opinion
Flynn: Messaging platforms suit peer communication over single-player utility tasks
“The one use case that I find more compelling, at least in the near term, is around these applications that are really native to the communication experience, right? It's not booking a taxi or booking an Uber that I think is native to that experience, but it's …”
Sean Flynn Jul 27, 2016 ▶ 18:21 20VC: Mythbuster: Is Mobile Dying? Is AR/VR Overhyped? Is The Excitement Around Bots Justified with Sean Flynn, Partner @ Shasta Ventures
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
Insight
Mycroft: Copying successful business models into new verticals leads to failure
“I think that any entrepreneur, any starting company that is trying to simply apply what was a successful business model in a different space to their new vertical is setting themselves up for failure.”
Frank Mycroft Jul 8, 2016 ▶ 7:02 20VC: When To Transition From Growth to Profitability & The KPI's of The On Demand Economy with Frank Mycroft @ Booster Fuels
Opinion
Biyani: Uber expanded more responsibly than Lyft in the early days
“I would say that Uber was a little bit more responsible in their growth than Lyft was, frankly.”
Gagan Biyani Apr 8, 2016 ▶ 9:13 20VC: Sprig's Gagan Biyani on The 3 Principles Of Fundraising and Building The World's Largest Restaurant
Disclosure
Uber's 2010 seed funding round was not overly competitive
“It wasn't, no, it wasn't a terribly competitive round. I don't think, I mean, it was a real negotiation around it, and there were a few other people around the table. You know, I don't think that, you know, it wasn't one of these crazy, I mean, this was You kn…”
Rob Hayes Mar 21, 2016 ▶ 11:51 Uber's First Investor, First Round Capital's Rob Hayes on How The Deal Of The Decade Originated and Why Product Orientated VC Is The Future
Assertion Partly supported
Ryan Graves built Uber's operational core and expansion playbook
“In Ryan's case, it turned out to be true. I mean, he, he's an amazing guy. And, you know, if you look at You know, the impact that he's had on Uber and the culture there and, you know, how they, you know, kind of started, you know, going from city to city and …”
Rob Hayes Mar 21, 2016 ▶ 7:40 Uber's First Investor, First Round Capital's Rob Hayes on How The Deal Of The Decade Originated and Why Product Orientated VC Is The Future
Insight
Standard VC market size analysis failed to predict Uber's potential
“The market analysis that, that a lot of people were using was the wrong market analysis, because even though there was an actual car and it was black and it pulled up and it picked you up, this was not the black car market. This was something very, very differ…”
Rob Hayes Mar 21, 2016 ▶ 8:45 Uber's First Investor, First Round Capital's Rob Hayes on How The Deal Of The Decade Originated and Why Product Orientated VC Is The Future
Insight
VCs passed on Uber due to a small market and unknown CEO
“A lot of the reasons that people didn't invest were one, at the time it was an unknown guy, Ryan Graves running the company and two, It was seen as not a very big market.”
Rob Hayes Mar 21, 2016 ▶ 7:15 Uber's First Investor, First Round Capital's Rob Hayes on How The Deal Of The Decade Originated and Why Product Orientated VC Is The Future
Insight
Mehta: Messaging is the best transactional interface for infrequently used services
“Our thesis on that is that for infrequently used services, messaging is the best interface. So what I mean by that is that if you use Uber every day, you would take the pain to download an app, learn an interface, and use it. You know, the other services for t…”
Puneet Mehta Mar 18, 2016 ▶ 14:28 Pre-YC Demo Day: Msg.ai's Puneet Mehta on The Rise of AI, The Potential For Messaging and Life As A Current YC Startup
Insight
Breakout consumer tech success is 80% luck and timing
“Number 10, which unfortunately you and I have very little control over, is luck and timing. And that's about 80%, right? You have to do all these amazing things, have the right vision, have the right team, have the right culture, have the right marketing, you …”
Jim Scheinman Mar 2, 2016 ▶ 16:18 20VC: Building a Game Changing Consumer Startup and Hunting His 4th Unicorn with Jim Scheinman @ Maven Ventures
Opinion
Wertz: On-demand 'Uber for X' startup business models are overhyped
“As much as we're excited about on demand I think it's also a little bit overhyped. At some stage, you know, kind of people said kind of, I'm going to create the Uber for X, for vertical X. So there was a lot of this on demand for here, Uber for X et cetera. I …”
Boris Wertz Dec 28, 2015 ▶ 25:08 20 VC: The Ultimate Guide To Marketplaces with Boris Wertz, Founding Partner @ Version One Ventures
Assertion Supported
Polling Shows Most Uber Drivers Prefer Independent Status Over Employee Status
“If you actually look at some of the polls, it's actually not the case. I mean, if you even talk to a lot of Uber drivers, they're not even aware of it, and if you ask them if they prefer to be W-II or T-Nine-I mean, not necessarily in those terms, they say tha…”
Jonathan Libov Jul 13, 2015 ▶ 24:56 20 VC 053: Inside Union Square Ventures with Jonathan Libov @ Union Square Ventures
Assertion Not checkable as stated
Stebbings: Uber and the freelance economy cannot be significantly regulated
“I'm really bullish on Uber in particular, I think, and the freelance economy. It's now too large a section of the economy for significant regulatory changes to occur.”
Harry Stebbings Jul 3, 2015 ▶ 11:46 Founders Friday 002: Balderton's James Wise interviews 20VC Founder, Harry Stebbings
Prediction Held up
Calacanis pledges to invest in Travis Kalanick's next company if Uber fails
“Travis and I are very good friends, you know, from Uber and have been for a long time. And we, I would be good friends with him if his company failed, and I would invest in his next company”
Jason Calacanis Jun 1, 2015 ▶ 36:32 Jason Calacanis: The World's Greatest Angel Investor
Opinion
Menashy: Uber expands the transport market rather than replacing black cabs
“I don't think it's replacing black cabs. I mean, there may be a little bit of replacement in the short term, but I think it's enabling totally new journeys.”
Simon Menashy May 25, 2015 ▶ 9:19 How to Pitch a Top VC with Simon Menashy @ MMC Ventures
Opinion
McCall: Uber was evolutionary mobile-meets-taxis rather than revolutionary
“Uber is not revolutionary. It's evolutionary, right? It's mobile meets, you know, taxis at the end of the day, but it's how it was done.”
Matthew McCall Mar 26, 2015 ▶ 12:57 20 VC 022: Letting go of the life we planned and the Power of the Female Narrative with Matthew McCall
Opinion
Kris Jones argues 2015's high tech valuations reflect disruption, not a bubble
“I think the valuations right now are very, very high. But I don't believe so, and the reason I don't believe there's a tech bubble is because I believe that the period of time we're in right now is a period where you're going to see a lot of disruption, meanin…”
Kris Jones Jan 13, 2015 ▶ 21:03 20 VC 002: How to become a VC with Kris Jones
Disclosure
Mac: Autonomy is Uber's largest single standalone investment area
“It's the largest single sort of standalone investment we make. Now don't be, you know, don't get me wrong with at a PNL our size, we're moving billions of dollars around every month, but yes, it's the largest single area of investment.”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 19:12 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Disclosure
Macdonald: New Uber products must show a multi-billion dollar GMV path
“For that to even be interesting, I have to see a path within a few years to multiple billions of dollars of GMV, and it just actually constrains your thinking a little bit.”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 10:52 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Insight
Variable-Cost Model Makes Uber's Loyalty Perks Uniquely Difficult to Build
“The beauty of our model is we're primarily a variable cost model, right? It means when demand drops, great, our costs scale down with it, but it also means that we just don't have a fixed capacity to give away, and so it just makes the challenges for building …”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 9:54 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Insight
Macdonald: Corporate incubation is slower because teams get fat on resources
“The other challenge of standing up a new business with a big company with a big P&L and a big balance sheet is people just get fat on the resources, right? And so you don't build it the way you would build it if you were a startup because you just have more re…”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 13:10 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Assertion Supported
Mac: Uber is doing about 300 million trips weekly on core platforms
“We're doing like three hundred million trips a week on our core platforms.”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 23:16 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Assertion Supported
Uber Mobility Revenue Dropped 84% in Three Weeks During COVID
“Our mobility business had lost 84% of our top line in three weeks. The company was burning billions annually. We didn't have a core business producing cash.”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 21:48 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Opinion
Macdonald: Membership is Uber's most efficient long-term consumer lever
“I think membership is the most efficient long-term consumer lever that we've got.”
Andrew Macdonald (Mac) Aug 17, 2026 ▶ 6:33 Uber President on Travis, China & Self-Driving | Why Autonomy Is Existential | How to Beat DoorDash
Disclosure
Frankel: Founder Collective sold some Uber early near $10B valuation
“You know, in retrospect, we probably sold a little too early, so this was early on, you know, this is a business that's getting close to ten billion dollars in valuation, and there's an opportunity to take some off the table, and you're very new.”
David Frankel Aug 7, 2026 ▶ 52:22 The AI Boom Will Create Enormous Roadkill: Who Wins & Loses? | David Frankel
Assertion Supported
Stebbings: Benchmark returned roughly 640x on Uber versus 25x on WeWork
“Uber made benchmark roughly 640 X versus around 25 X with WeWork.”
Harry Stebbings Jul 29, 2026 ▶ 52:47 Jensen's Open-Weights Letter | Google Cloud Grows 82% But The Market Tanks
Disclosure
Ferriss was one of the first three advisors to Uber
“We're trading emails and that becomes Uber cab LLC. And I become one of the first three advisors.”
Tim Ferriss Oct 31, 2025 ▶ 47:18 20VC: Tim Ferriss: Why I Walked Away From Angel Investing After Uber | How I Accidentally Lost $150 Million | Money Fixed My Problems—Then Made Me Miserable
Insight
Östberg: Uber proved food delivery companies can succeed as late entrants
“Uber and others entered the market and proved that you can start this business way later than we did”
Niklas Östberg Mar 12, 2025 ▶ 35:19 Niklas Östberg, Founder @ Delivery Hero: Competing with Uber and Doordash in a Capital Arms Race · 20VC with Harry Stebbings
Opinion
Tolkin: Defaulting the Uber app to UberPool was a poor product decision
“And for a little bit the default was Uber pool. And I think that was a poor product decision. Because even if you had chosen Uber X on your last ride, it defaulted back to Uber pool. And so the UI wasn't clear enough what was happening. And so people were acci…”
Brian Tolkin Feb 7, 2025 ▶ 4:51 Brian Tolkin, Head of Product @Opendoor: How to Hire the Best Product Teams | E1257 · 20VC with Harry Stebbings
Disclosure
Uber Provided Under Half of Lime's $140M Emergency COVID Funding Round
“I think the total round was a hundred and forty million dollars. Not all of it was from Uber. In fact, I think less than half is from Uber.”
Wayne Ting Jan 27, 2025 ▶ 32:42 Wayne Ting, CEO @Lime: From Losing $3 on Every $1 to $90M in EBITDA | E1252 · 20VC with Harry Stebbings
Assertion Open
Pishevar: Closed Uber, Warby Parker, Tumblr, and Machine Zone in 90 days
“In my first 90 days, I closed Uber, Warby Parker Tumblr, and Machine Zone.”
Shervin Pishevar Jan 13, 2025 ▶ 6:26 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
Assertion Partly supported
Pishevar: TPG generated nearly $2B return on $83M Uber investment
“I think TPG on that eighty-three million made close to two billion.”
Shervin Pishevar Jan 13, 2025 ▶ 29:38 Shervin Pishevar: What Really Happened in the Firing of Travis Kalanick | E1245 · 20VC with Harry Stebbings
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