At Uber, If You Don't Perform, You're Out

Herbert Allen's investment-banking lesson: companies come and go, but great people stay great. The right unit of investment is the operator, not the cap table.

“[{"text": "Always bet on people. Companies go, there are good companies, bad companies, but great people stay great all the time.", "speaker": "Herbert Allen (via Dara)"}]”Dara Khosrowshahi · quote

In technology transitions, every deal that compounded was expensive at the time. You overpay against today's market assessment and win because reality exceeds it — because you identified the hockey stick before it was visible.

“[{"text": "We never completed a successful deal because we got the company cheap. We actually overpaid for every single great company that we bought, but we overpaid based on what the market thought at the time, not what the reality turned out to be.", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote

Growth curves up are exponential. Decay curves down are too. A year into a slipping tech company things don't look bad — but they are bad, and the ten-year terminal state is a disaster. Act on the pattern, not the current number.

“[{"text": "Just like the curves up are exponential, curves down are exponential as well. The first couple of years look bad, but they''re not that bad. But you know in your mind that 10 years from now, it''s going to be a fucking disaster.", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote

When two modes of error are both likely, the leader's job is to choose which direction to err in — explicitly. Dara's choice: err on blunt over soft; err on celebrating too little over too much. The wrong-people self-select out.

“[{"text": "If I make a mistake, where do I want to make the mistake? I''m gonna err in telling the truth and potentially scaring someone away.", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote

Uber's original 'toe stepping' value got weaponised — people used it as permission to be jerks. The reset value Dara wrote himself: 'Do the Right Thing period.' No elaboration. Judgement is the job.

“[{"text": "Toe stepping, whose spirit came from a place of, we want to speak the truth, became an excuse to be a jerk.", "speaker": "Dara Khosrowshahi"}, {"text": "It was, Do the Right Thing, period. It wasn''t crowdsourced. It was just that. You have to figure it out.", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote

Barry Diller's release after losing Paramount: 'They won, we lost, next.' Dara's operator discipline: recognise the loss, analyse once, move on. Neither ignore it nor obsess over it.

“[{"text": "They won, we lost, next.", "speaker": "Barry Diller (via Dara)"}, {"text": "Recognise why you lost, recognise that you lost. Say it. Analyse it, but then move on.", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote

The most important skill in life is the skill of working hard — a specific, teachable habit (focus, resilience to failure, relentless effort) that you either learned early or mostly don't later. Dara has never seen a non-hard-worker become a hard worker.

“[{"text": "The most important skill in life is the skill of working hard. And it''s not a skill you can just decide to do.", "speaker": "Dara Khosrowshahi"}, {"text": "The thing that''s different about them is they work their asses off, and that''s a learned skill.", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote

If a competitor takes one shot, you take two. Each shot is a data point AND a probability increase. Speed of change + opportunity identification are the two variables CEOs must nail.

“[{"text": "The speed of change, you know, if you can work fast, you''re kind of accelerating time. Every one shot that you take, I can take 2 shots. I''ve got more time than you do.", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote

A team mirrors its CEO. Bullshit them and they learn to bullshit back — leaving the CEO with filtered, sanitised data. Radical honesty is not a value statement; it's a data-extraction mechanism.

“[{"text": "The failures I see with CEOs aren''t because they made the wrong decisions, it''s because they were getting the wrong data that led to the wrong decisions.", "speaker": "Dara Khosrowshahi"}, {"text": "If their boss isn''t telling them the good stuff, why should they give the good stuff back to the boss?", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote

Your staff's incentive is to control information upward because you can be overwhelmed. Counter it with random direct channels — especially engineers four levels down, who have a healthy disrespect for authority and will just tell you.

“[{"text": "I''ll meet with engineers 4 levels down consistently because usually they''ve got the kind of personality where they don''t give a shit. They''ll tell me anything and everything and they like putting the CEO down. That''s great.", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote

People with too-clear career plans filter out signals that don't fit the plan, lose curiosity, and miss the bigger turns. Dara wound up CEO without planning to; every major job came from being open.

“[{"text": "Before you go out and try to change your world, let the world change you first. You know, take input.", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote

Dara's retrospective self-critique of Expedia: we were selling vacations, so I softened the hard-work message — and that was wrong for a tech company. At Uber he names it explicitly: 'You come to Uber, you're gonna work your ass off.'

“[{"text": "At Expedia, we worked intensely, but not as hard as I like because Expedia, we were selling vacations. So we did talk about work-life balance, and in hindsight, at Uber, I don''t.", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote

Most successful companies become risk-averse from loss aversion. Dara's antidote: the $9.8B cash-flow cushion is exactly why Uber should take more risks, not fewer — and he'd rather celebrate too little than let momentum soften.

“[{"text": "I''d rather make the mistake of celebrating a little bit too little and kind of being a little pissed off about life in general and pushing.", "speaker": "Dara Khosrowshahi"}]”Dara Khosrowshahi · quote