Mar 27, 2023 · 48m · news
Dara Khosrowshahi: How I Became CEO of Uber; Uber Eats vs DoorDash; The Postmates Acquisition | E994 · 20VC with Harry Stebbings
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In this candid 20VC interview, Uber CEO Dara Khosrowshahi shares how his immigrant background shaped his drive for impact, outlining his philosophy on capital allocation, learning from mistakes, and guiding Uber's strategic transformation.
How this conversation actually went
Every chapter scored 0–10 on four independent dynamics. Hover any point for the reasoning behind the score. Harry holds 19% of the talking time here. How this is scored →
Harry as informed peer 2.9 Guest teaching 3.3 Guest disagreement 2.4 Harry pushing back 3.1
speaking balance: gold is Harry, purple is the guest (3 minute bins)
Sharpest disagreement ▶ 17:31 Rejecting DoorDash Loss Premise
Dara immediately rejects Harry's anonymous insider question about losing to DoorDash, arguing Uber Eats is globally equivalent in scale and pointing out the flawed US-centric view.
Hardest push from Harry ▶ 29:04 Pushing Back on One-Way DoorsHarry directly challenges Dara's decision-making framework by quoting Alex Schultz to argue that true one-way doors are exceptionally rare in business.
Biggest teaching moment ▶ 18:30 Speed vs Selection Trade-OffDara educates Harry on platform marketplace trade-offs, explaining how optimizing for tight 5-minute ETAs inherently sacrifices restaurant selection density relative to suburban delivery models.
Harry holds his own ▶ 19:33 Synthesizing Marketplace Trade-offsHarry demonstrates sharp domain knowledge by immediately capturing and restating Dara's marketplace theory into a clear rule regarding selection size versus delivery times.
the scores for every segment, with the reasoning behind each
| Chapter | Topic | Harry as informed peer | Guest teaching | Guest disagreement | Harry pushing back | Why |
|---|---|---|---|---|---|---|
| Family Background and the Pursuit of Excellence | 2 | 4 | 2 | 3 | Harry asks what Dara is running from regarding his family's refugee history and later asks if rebuilding equals worthiness. Dara gently reframes both prompts, clarifying that his family is running toward rebuilding and that worthiness comes from daily effort rather than an end state. | |
| Joining Uber & Defining Impact | 2 | 4 | 3 | 2 | When Harry asks what Dara learned about himself as a leader transitioning to Uber, Dara openly rejects the question's introspective premise. He explains he does not spend time being introspective because the job is too demanding and fast-paced. | |
| Leadership Philosophy and Sustained Performance | 2 | 3 | 2 | 2 | Dara outlines his philosophy on high performance as sustained results and willingness to go against groupthink, quoting Barry Diller. Harry prompts with questions on wartime leadership, which Dara validates through Expedia and Uber turnarounds. | |
| Managing Constraints and Capital Allocation | 3 | 2 | 1 | 2 | Harry quotes Tobi Lutke on business constraints and asks Dara about capital allocation successes and failures. Dara candidly acknowledges that ATG self-driving tech and Jump hardware bikes were capital allocation errors outside Uber's core software network. | |
| Core Expansion and Global Competition with DoorDash | 5 | 6 | 5 | 5 | Harry delivers an anonymous insider question asking why Uber Eats lost the lead to DoorDash. Dara strongly rejects the premise by highlighting global parity, while educating Harry on the structural trade-off between delivery speed radii and restaurant selection in suburban markets. | |
| Strategic Acquisitions and Learning from Failure | 3 | 3 | 2 | 2 | Harry questions Dara on strategic acquisitions including Kareem, Postmates, and Jump. Dara freely admits Jump was a mistake because software executives fundamentally underestimated the complexity of hardware operations. | |
| The Philosophy of Mistakes and Executive Advisory | 4 | 3 | 2 | 5 | Harry pushes back on Dara's decision framework by quoting Facebook CMO Alex Schultz to argue that almost no executive decisions are truly one-way doors. Dara responds by clarifying that high blast radius decisions affecting earner livelihoods carry irreversible friction. | |
| Trust, Personal Life, and Generational Resilience | 2 | 2 | 3 | 4 | Harry launches into an impassioned rant about modern workplace entitlement and generational softness. Dara chuckles and agrees that society has gotten softer, while playfully reminding Harry that he himself belongs to that younger generation. | |
| Governance, Cultural Transition, and the Pandemic | 3 | 3 | 2 | 3 | Harry probes Dara on taking over Uber's fractured board, managing the transition from Travis Kalanick, and lessons from the pandemic. Dara reflects candidly on inheriting high talent alongside public brand damage, and how pandemic cuts honed company discipline. |
Statements from this episode (22)
Khosrowshahi: A CEO's job is to make mistakes and learn
“If I didn't want to make mistakes, I'd be a treasury bond manager, right? Like, my job is to make mistakes and learn from them.”
Khosrowshahi: Family ambition stems from rebuilding after Iranian Revolution
“God, it's I do think that the events of Iran and our family losing everything, and we had a huge family, big family business, etc., I don't know if it's something that we're running from, but I think the whole family to some extent is running to rebuild essent…”
Khosrowshahi: A great CEO's legacy is defined by post-departure performance
“The hallmark of a great CEO is isn't necessarily how the company did while the CEO was there, but also how the company performed after the CEO left.”
Khosrowshahi: Agreeing with your team on obvious choices yields average performance
“If you're agreeing with your team, and you're doing what is obvious, then essentially you're going to perform a in an average way, your output will be average. As a leader, you have to be willing to kind of bust out of the obvious, do something non-obvious, di…”
Khosrowshahi: Uber completed two billion trips in the previous quarter
“Now in this last quarter, two billion times a quarter.”
Khosrowshahi: Uber provides income to over five million earners globally
“You know, we are an incredibly important entity in terms of Transportation and cities in terms of earning power for over five million earners.”
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…”
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.”
Khosrowshahi: Uber Eats is as big as DoorDash globally
“Uber Eats is actually as big as DoorDash on a global basis, and so when we think about Uber, we think globally, right? And we are the global leader along with DoorDash.”
Khosrowshahi: Uber Eats initially bet on the wrong delivery strategy
“So I think the biases that we had Which is coming from an urban rides business that was all about the five minute ETA, made us early on bet on the wrong thing.”
Khosrowshahi: Predictable delivery ETAs beat fast delivery with fewer choices
“As long as you're accurate in the prediction of the delivery time, as long as you let the person know, Harry, that your delivery is going to come in 35 minutes, if it gets you in 35 or 40 minutes, most people are fine with that, because then they can plan acco…”
Khosrowshahi: Australia is overall Uber's best geographic market
“Overall for Uber, I'd say Australia is, is the best market.”
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.”
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…”
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.”
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 …”
Khosrowshahi: Technical candidates who explain complex issues simply possess superior clarity
“If they are able to simply explain a deep technical problem, then they've got clarity of thought, and they're generous in terms of their information sharing, which is something that I'm looking for.”
Khosrowshahi: Society has gone soft by protecting kids from adversity
“If you're protecting your kids from adversity, is not doing them any favors, because the real world, you know, is, can be really difficult. And I think the same applies with our generation, which is have we gone too soft? Yeah, of course we've gone too soft. I…”
Khosrowshahi: Best Travis legacy was talent; worst was brand damage
“Best thing I'd say is is a bar for talent. Travis went after incredibly talented people, and I got to keep some of them, which is great. Worst thing, I think it was just the brand damage as it related to Uber, the enterprise.”
Khosrowshahi: Travis Kalanick will lead dark kitchen success if anyone does
“He has a, he's built a dark kitchen company that we do work with, and I think it's the biggest dark kitchen company out there, so if anyone succeeds in that area, I think it'll be Travis.”
Shorts cut from this episode
▶ Why Dara Joined Uber · 20VC with Harry Stebbings (@3:58)
▶ Uber Lost $200M On This Acquistion · 20VC with Harry Stebbin (@24:01)
▶ The Mistake Uber Made That Let DoorDash Catch Up 🤦♂️ · 20V (@18:06)
▶ Uber CEO: Why I Left Expedia for Uber 🚗 · 20VC with Harry S (@3:58)
▶ Uber CEO: What I Look for in Job Interviews 👩💻 · 20VC wit (@32:43)
▶ Uber's $200M Mistake 🙈 · 20VC with Harry Stebbings (@24:01)
▶ Who is Uber CEO Dara Khosrowshahi? · 20VC with Harry Stebbin (@1:12)
▶ What do Elon Musk and Jeff Bezos have in common? Uber CEO ex (@6:44)