Things I Learned From Tony

I was fortunate to work at DoorDash between 2019-2021. This was a fascinating experience that taught me more in 18 months than in any other period in my career. 

There were a few features of my experience that increased the rate of learning significantly. 

First, we were undertaking post-merger integration, a process that frequently reveals the inner workings of a company. 

Second, we were delivering food during the onset of COVID, a massive societal shift that had major effects on every side of the business, especially during the early months. And yet DoorDash through this period was profoundly anti-fragile. The people, processes, and culture at DoorDash had been built to withstand this level of chaos, and the company’s business performance accelerated dramatically as a result.

This outcome is a reflection of Tony Xu, DoorDash’s co-founder and CEO. I was lucky to spend a good amount of time with Tony during my time there, and learned many lessons from him that shape how I approach business building today.

Tony is an incredible leader, though his low-ego, low bullshit style has left him intentionally out of the spotlight of celebrity CEOs. Here are some of the things I learned from Tony.

  • Radical ambition. “If there’s a menu, it should be on DoorDash.” Tony’s ability to scale DoorDash to its current heights started with a very simple way of thinking about building a delivery business. The quote above is representative. At most companies, there are multi-segmented strategies and goals around different function-specific priorities. These typically all ladder up to company-wide goals. Most are phrased with carve-outs and exemptions. If the above sentences made you nauseous, you should consider working at DoorDash! There, goals were typically no more than a sentence long, and captured the type of absolute clarity this quote implies. “Move restaurant penetration from 10% to 20% nationwide.” No decimals, no caveats, no false precision. This way of thinking forced a couple things: it flushed out any ambiguity about how serious and how hard the work at hand would be, and the second was to provoke creativity and ingenuity to help make the goal a reality. Many companies have a completely disconnected sense of what output (work created by employees) leads to the outcomes they care about. At DoorDash, Tony put incredible emphasis on the outcomes that put points on the board versus those that were “work theater.” This is very difficult because identifying the inputs that lead to the outcomes are often hard to discover, but being radically ambitious about the right outcomes (e.g. going from a small food delivery startup to a massive global business) is the best place to start.
  • Cognitive overhead is the enemy. Tony’s emphasis on very clear, succinct communication is one of his greatest traits, and it permeated all of DoorDash. For any important meeting, a brief pre-read was required. There was a canon of internal notes on how to write these documents properly, including effective uses of graphs (such as waterfalls) that are adept at compressing large amounts of information into very simple, easy-to-digest visuals. While I won’t recount all the details of how we wrote internal docs, the effect of consistently crisp, succinct, actionable communication at every meeting was remarkable. Instead of the first 20 minutes of every meeting requiring a meandering discussion to establish a shared baseline of understanding, at DoorDash this was typically achieved within 2-3 minutes. The effect of this meant execution was often hours or days ahead of competitors, and the compound interest led DoorDash to outpace competitors consistently over time.
  • Recruiting is a superpower and the bar is way higher than most people think. DoorDash uncovered “superpowers” — significant competitive advantages — by hiring incredible talent in every function and pushing them further than they ever had been pushed to deliver tangible results. While recruiting in itself is a clear superpower of Tony’s, it wasn’t simply his ability to close great candidates that stood. Tony cared equally about ensuring that the bar for working at DoorDash remains incredibly high, and that bringing less than stellar talent into the company was its biggest existential threat. Up until the time I left, Tony reviewed and approved every single job offer that went out — this was while headcount exceeded 3,000 people. He frequently would reply to hiring managers directly with probing questions on a candidate’s experience, and was known to reject offers if he wasn’t satisfied with the quality of the screening process that led to the offer. I learned from Tony that 100x candidates exist not just in engineering, as Steve Jobs and others have established, but in every field. The bar for recruiting should be far higher than most companies are willing to accept.
  • Study history and test rigorously — the answers are there. At a simple level, DoorDash “won” the food delivery industry between 2013-2021 because it correctly identified the most important side of the marketplace to focus on, developed a very effective strategy for capturing this side of the marketplace, and built a world-class operational and sales machine to execute. This all sounds simple in retrospect. But during this time period, the strategy and tactics here were far from obvious. For example, GrubHub was by far the dominant food delivery company up until 2017, and then declined precipitously. Uber was deemed the inevitable leader from the immediate outset of UberEats circa 2015; market analysts and VCs were quick to crown them based on the strength of their driver network and consumer base. But DoorDash came out on top, against any prediction, because Tony had studied the market with more depth and rigor than anyone else out there, and created a strategy and organization to execute it. The major insight was that restaurant supply would be a powerful driver of customer acquisition and retention; that driver supply would lead to sublinear improvements in delivery times, but this would have much less impact on consumer activation and retention relative to having the best restaurant selection. Charts that show DoorDash’s rise to dominance are surreal; underlying the upward trend was a vast machine meant to maximize restaurant supply, and keep delivery times and fees as low as possible. Tony’s strategy for DoorDash was the result of deep understanding of other consumer marketplace businesses, starting with Amazon, to arrive at the hypothesis that restaurant selection would dominate above all else. This was tested rigorously for several quarters until it was proven with a level of certainty that led the whole company to shift towards restaurant sales.