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Silicon Valley is obsessed with “mafias” — the idea that a particular company at just the right moment can find lightning in a bottle. The employees that go through that gauntlet move on to do great things. PayPal is the company by which all other mafias are judged. That small cabal still dominates Silicon Valley. It didn’t matter that PayPal itself didn’t become a Silicon Valley juggernaut. Its members leveraged their shared network to win deals, build technology companies, and make lots of money.
No company has come close to PayPal, though others have tried. Facebook and Google engineers have saturated Silicon Valley, but that mostly reflects the vast numbers of talented employees who have spent time at those two companies.
We’re at a point where former Uber employees are similarly ubiquitous. Ex-Uber employees work at many of the top venture capital firms. They’re founding companies. The media has planted the seeds that this might be the next mafia. The New York Times wrote ‘We Know Them. We Trust Them.’ Uber and Airbnb Alumni Fuel Tech’s Next Wave. Inc wrote, The Rise of the Uber Mafia and its Search for the Next Big Thing.
But I don’t think the Uber diaspora will ever be anything like the PayPal mafia. It’s too sprawling and riven with old wounds. The ouster of Travis Kalanick — which was supported by investors and some senior Uber executives — split the network into loyalists and reformers. And even when Uber alumni can put old battles behind them, there is a lot of disagreement about when the “real” Uber golden age was exactly. Was it during those early days when they were building from scratch with Kalanick? (The group of people Kalanick would call the “OGs.”) Was it when the company weathered the crisis of Kalanick’s ouster? Or was it during Dara Khosrowshahi’s leadership when those that remained salvaged Uber’s brand and reputation? Even if its alumni network were unified in their view of what made Uber great, it’s still too big of a pool of people for it to function anything like the PayPal mafia.
Still, the Uber network is already a powerful force in Silicon Valley and I think it will be for years to come. There are a couple reasons.
Uber’s bet that the future of technology would go from moving bits to moving atoms seems to be playing out. Yes, a lot of Uber alumni dove in head first to scooters and that seems like a mistake, but many others headed to Opendoor and DoorDash. And like PayPal it feels like there’s a lot of unfinished work here. Khosrowshahi is shedding Uber’s side projects. So there’s plenty of interesting areas for Uber alumni to chase after that their old employer abandoned.
Whatever you might say about him, Kalanick hired a lot of talented operators and gave them room to run their own businesses. General managers and regional general managers got to run their own P&L. How many other employees can say they got to do that? To his credit, Kalanick cut through the organization, working with promising individual contributors and raising their stature within the alumni network. So it’s not just higher ups who have Kalanick cred.
The dark times at Uber solidified everyone’s Uber identity. Even though people don’t necessarily agree on heroes and villains, there’s a sense that they all made it through hell. They saw the company savaged in the press and saw their friends and family wonder why they ever went to work there. And while Uber alumni hold different views about Kalanick, many think the critique of Uber’s corporate culture was overblown. Khosrowshahi’s leadership has made it easier to brag about working at Uber and now it’s a group of people whose self-conception is shaped by their time at Uber.
But navigating the world of Uber alumni can be hard for an outsider. That’s part of what makes it powerful for members of the club. Insiders can easily reference check their former colleagues and get a read on how they were seen within the organization.
To me, there are a handful of the people who sit at the core of the Uber network.
THE OPERATORS. Rachel Holt, Andrew Macdonald, Pierre-Dimitri Gore-Coty, and Jason Droege led Uber through the crisis. Those four played a big role in Uber’s operations during the Kalanick era, saw it through the period without a CEO, and then maintained continuity when Khosrowshahi took over. Holt and Droege have left Uber, while Gore-Coty and Macdonald remain key executives today. Holt co-founded her own venture capital firm called Construct Capital with Dayna Grayson from NEA. If Holt is as good at investing as she is at operating, she will do well. She’s a brass tacks type of person who is well-respected among Uber alumni. I would expect Droege, who led Uber’s food delivery business, to land somewhere interesting if he wants to. Macdonald is doing some angel investing in Uber alumni from his perch at Uber. Meghan Verena Joyce, who long ran Uber’s U.S. ride sharing business, also deserves a mention here. Not that she needs the press, she’s already the COO at insurer Oscar Health.
THE PRODUCT VISIONARIES. Okay the thing you have to know is that Andrew Chen — perhaps the most high profile ex-Uber VC with investments in Substack and Clubhouse — wasn’t a star product manager at Uber. He was seen as kind of an ideas guy but wasn’t particularly senior or seen as the most promising PM. Regardless, Chen’s prolific writing and forward-thinking clearly set him up to be an excellent VC and his deals speak for themselves. He’s already beyond sniping from the cheap seats. But I find the chasm between his profile at Uber and as a venture capitalist amusing nonetheless. Daniel Graf and Aaron Schildkrout were the real product leaders and they always seemed like frenemies. Graf had a knack for organization and Schildkrout had good taste and charisma. Post-Uber, Graf made a mistake and took the CEO job at the mental health company Mindstrong. He recruited some Uber alumni to come with him. But after looking under the hood once he got there, things seem to have been a mess. Graf and his deputy (also ex-Uber) have since left. A lot of people are leaving. I’ve heard that Mindstrong’s core product wasn’t as promising as it was pitched to Graf when he took the job. Mindstrong did not return a request for comment. Meanwhile, Schildkrout, always the cool guy, joined ex-Tiger Global investor Lee Fixel at Addition. That firm doesn’t chase press coverage, but Schildkrout is becoming a big behind the scenes player. A couple product honorable mentions here: Yuhki Yamashita spearheaded Uber’s big redesign. He won favor with Kalanick while staying out of the drama. Now he’s a leading product at Figma. Similarly, with Peter Deng running product at Airtable, Uber’s product sensibility is defining modern Silicon Valley software. More recently, I was surprised to see Daniel Danker leave Uber for Instacart. Khosrowshahi hasn’t hired an overarching product leader (and told me in my interview with him that he wasn’t going to). Danker seemed core to Uber’s product effort even if he ruffled some feathers internally from what I hear. Instacart’s gain.
THE DEALS PEOPLE. Raising money and cutting deals was always core to Uber’s success. Emil Michael — Uber’s former top dealmaker and Kalanick’s chief confidant during the Uber saga — has been working behind the scenes with a number of startups. I get the sense that he’s playing an important role at GoPuff, where he is an adviser. His old underling, Jonathan DiOrio, is chief business officer there. He’s also advising Brex and Revolut. And he sits on the boards of Homebound and Loft. Besides advising a couple companies, Michael is running a SPAC. That will be a good barometer of Michael’s pull these days. He still has a lot of friends in Silicon Valley. David Richter, another top ex-Uber dealmaker, made the mistake of going to Lime. A bunch of Uber employees went there hoping to strike gold again — but alas. Richter has left Lime and sits on the board of Polestar. I wouldn’t be surprised to see him back in a promising operating role. He’s a very thoughtful and principled guy. Meanwhile, Uber’s ex-financial executives have taken top jobs: Prabir Adarkar is the second-ranking executive at DoorDash and his old boss, Gautam Gupta, left Opendoor last year after serving a number of top roles at the home flipping company.
THE RICH GUYS. Garrett Camp, Ryan Graves, and Kalanick made a bunch of money from Uber. Camp has been trying to recreate the magic of coming up with Uber at Expa. He brought on Uber fixer Dave Clark. Expa is mostly playing in early stage startups and lightning hasn’t struck twice. Graves is running his own buyout firm called Saltwater. He recently made a $50 million investment in Metromile and took a board seat. Kalanick has infamously taken a secretive approach. He formed an investment vehicle called the 10100 Fund and founded CloudKitchens. He recruited a number of ex-Uber people but some of them have already left.
THE EARLY SENIOR EXECS.Ed Baker and Jeff Holden will always have a claim to the Uber spirit. Baker is making investments and Holden has a new wonky futuristic company called Atomic Machines. Salle Yoo, who spearheaded Uber’s dubious legal strategy over the years, is back in the chief legal officer role at IonQ. To Yoo’s credit, I hear she’s been a big booster of talented women out of Uber. Meanwhile, Thuan Pham, Uber’s long-time engineering leader, sure knows how to pick them. Pham is burning the candle at both ends at Coupang. The Korean e-commerce company just went public and has a roughly $80 billion market cap.
THE COMMUNICATORS. You learn a lot when you have to sell the world on a company the world is determined to hate. Uber communications and policy executives have a higher metabolism for work than most other places. They’re used to getting flogged in the press and then getting up the next day and doing it again. So I’m not surprised that Nairi Tashjian Hourdajian got back into the startup world at Figma after the sleepy work of venture capital communications at Canaan. She just hired Michael Amodeo, another ex-Uber communications person who took a detour at the New York Times. I’ve already written about Lane Kasselman taking the Chief Business Officer role at Blockchain.com. Chelsea Kohler just landed at Pill Club with some other Uber alumni. Rachel Whetstone is the Chief Communications Officer at Netflix.
THE UP-AND-COMERS. Many of the next generation of startups will be formed by less senior Uber employees. They’re turning to their old bosses for money and connections. I know Amy Sun at Daylight Labs has raised money from Uber alumni. I expect her to share more about her company next month. Allison Barr Allen has built a high profile as COO of the buzzy startup Fast.
UBER CHINA. Uber’s quixotic effort in China built a deep alumni network there. Zhen Liu, Uber’s China head, went on to become a senior executive at Bytedance. Now she’s working at Genki Forrest, which wants to be China’s Coca Cola. And Kate Wang may be the richest person you’ve never heard of. She’s the co-founder of the Chinese e-cigarette company Relx. I can’t verify this figure but the Chinese media pegged her net worth at $24.8 billion. That would make her richer than anyone else in the Uber network, including Kalanick.