Ex-Amazon VP tells us what it’s really like working with Jeff Bezos

The episode opens with Ethan Evans joining Sam Parr and Shaan Puri to discuss his long Amazon career—about 15 years—and his time as a senior executive at Amazon Prime. Shaan explains that when his company was acquired by Twitch, he joined Twitch’s executive team alongside Ethan. Because Ethan had been assigned by Amazon after its roughly $970 million acquisition of Twitch, the Twitch executives jokingly viewed him as Amazon’s “parental guardian” or “adult in the room.” Ethan says the suspicion went further: people worried he was an Amazon spy who would shadow Twitch CEO Emmett Shear and eventually replace him. He says that was never the plan, but denying a conspiracy only made people more convinced it existed. They also discuss the acquisition’s economics. Amazon stock rose roughly fivefold during the earn-out period, causing some Twitch employees’ compensation to rise from a market salary of roughly $200,000–$250,000 to about $2 million annually. When the earn-out ended, Twitch could not pay them at that level, creating a salary cliff and prompting many employees to leave even though they did not dislike Twitch.

Asked to give Jeff Bezos a 360-degree review, Ethan identifies his first major weakness as giving almost exclusively corrective feedback. Bezos would examine a proposal, quickly identify several things that needed fixing, and move on without saying what was good. Ethan recalls a meeting where Bezos spent about an hour explaining everything the team had missed, began to leave, then turned around and added, “Oh yeah, but good job. You’re doing great,” as if remembering a coaching instruction to praise people. Ethan says Bezos’s taste and judgment were generally excellent, citing Kindle, Prime, and the shift from two-day to one-day shipping, although Bezos also made major mistakes such as the Fire Phone, which generated a $170 million hardware write-off alone. Ethan’s deeper criticism is that repeated success convinced Bezos his vision was nearly infallible. That confidence contributed to the Fire Phone: many people warned that it was a bad product, but it was difficult to challenge Bezos after several earlier products had succeeded despite similar objections. Ethan also describes Bezos ridiculing a team by asking whether “the A team” was available because the presentation seemed like it came from the B team.

The hosts ask whether Bezos’s ability to identify the key weakness in a plan after only a few minutes came from exceptional intelligence, pattern recognition, or learned behavior. Ethan says Bezos was clearly unusually sharp, but he believes repetition was crucial. Bezos reviewed three, four, or five businesses and documents every day for years—effectively accumulating the equivalent of 10,000 hours of turning unfamiliar business information into useful questions and insights. Ethan contrasts this with less intellectually spectacular but highly dependable Amazon leaders. One person became wealthy because Bezos trusted him to take any difficult assignment, “run through any wall,” and turn a D or F into a B. Ethan says that at Amazon’s scale, a B can be exactly what is needed: an A-level product elsewhere may carry the business, so the company may prefer a reliable operator who consistently improves a troubled area rather than a high-beta leader who attempts an A and might fail. He illustrates this with a Twitch “trust equation” exercise involving intimacy, credibility, and integrity. Most people, including Ethan, chose integrity, while Emmett Shear chose credibility: if an employee says, “I got this,” the important question is whether the employee truly has it. Ethan says Bezos rewarded people who reliably delivered on that promise, even when they were not the company’s most brilliant thinkers.

Ethan says Bezos viewed every customer as his own customer and used direct complaints to stay close to Amazon’s problems. Anyone could email Bezos, and he personally read many customer complaints before a team eventually helped filter them. Bezos told executives to trust anecdotes over aggregate data because even a 99% success rate at Amazon’s scale could still mean roughly 25 million failed or incorrect deliveries in a day. The most famous mechanism was the “question mark email.” When Bezos received a complaint about an executive’s area, he forwarded it with only a question mark at the top. Everyone understood that they had roughly 24 hours to explain what happened. The best response showed that the incident was an unusual exception; the next-best response showed that it was a real problem with a solution already implemented or underway. The worst response was effectively, “Yes, this is a serious problem, and it will take a long time.” Ethan recalls an even harsher message when he ran Amazon’s app store: Bezos wrote, “Please tell me we’re not doing this.” When Ethan’s team had to admit that Amazon was doing it, Bezos replied, “Just euthanize me.” Ethan says the standardized process allowed Bezos to scale customer focus across hundreds of leaders: customers complained to Bezos, Bezos sent the question mark, and the responsible team had to investigate and fix the issue.

Ethan explains Bezos’s principle that companies should be “strategically patient but tactically impatient.” Large strategic projects take years: putting people into space requires rockets, facilities, and software, while Prime took decades to evolve from two-day delivery toward one-day and same-day delivery. However, Bezos did not want teams to use the long time horizon as an excuse for slow execution. Every quarter, and effectively every day, teams had to ask what additional progress they could force out of the five- or ten-year project. The hosts summarize the approach as a ten-year view governed by a 24-hour clock. Ethan says Bezos pushed Amazon to work “long, hard and smart,” arguing that two out of three was insufficient. Amazon’s euphemism “work-life harmony” also reflected this intensity: if employees enjoyed the work, Bezos argued, working long hours could still be harmonious. Another Amazon idea was that careers have seasons; people with children could either leave, work less, or work after putting their children to bed, but the company did not pretend the job was low-demand. Ethan repeats another Amazon saying: it was a place where “high performers go to feel bad about themselves,” because every achievement led to a higher bar. He says he evaluated himself against roughly 300 Amazon vice presidents and concluded he was a middle-ranking VP—better than some, but clearly not operating at the level of the best.

Asked to evaluate Shaan, Ethan says Shaan taught him the value of ten-year plans and ten-year lists. Ethan had written a plan but done little with it; his conversations with Shaan prompted him to use it more deliberately. Ethan’s criticism is that Shaan never really fit Twitch, much less a conventional corporation. He was entrepreneurial and “kept it too real,” making him a round peg in a square hole rather than someone likely to become corporate. Ethan also says Shaan recognized that Twitch could “mail it in” after being acquired. He recalls a Twitch leader sincerely asking why the company had to worry about money or profit when Amazon owned it. Twitch repeatedly produced plans promising profitability in three years while burning roughly $200 million annually and, over its first five years, more than $1 billion in cash. Andy Jassy tolerated this for about five years before Emmett left and layoffs followed. The conversation broadens into project selection. Ethan says success depends not only on a capable person but on an equally strong opportunity and good timing. He describes joining Amazon and choosing a video team over a shared ingestion platform simply because he arrived a week before another executive who had expected the video role. Their later careers diverged, but Ethan cannot know how much came from ability versus getting the desired chair first. He compares Bezos’s later return to work on AI with a baseball player who can wait for a “fat pitch,” emphasizing that avoiding bad opportunities can matter as much as pursuing the obvious good ones.

Ethan describes Bezos becoming progressively less accessible as Amazon grew. Early on, a single retired minor-league baseball pitcher served as a receptionist-security guard; after a reporter reached Bezos’s office, Amazon installed tighter security. Later, Ethan discovered that a person sitting in an awful cubicle beside an elevator bank was actually guarding Bezos and had a panic button linked to a response team. Newer Amazon buildings reportedly had a dedicated Andy Jassy elevator and executive floors resembling Fort Knox. Bezos once played the dangerous company picnic game broomball, but stopped attending once events involved stadiums and roughly 10,000 employees. Ethan joined just after Amazon Prime began, and he says both Bezos and principal engineer Charlie Ward claim credit for the idea. The original program, called Project 100, had to be launched in 100 days and initially promised two-day delivery rather than a broad bundle of perks. It emerged partly because Bezos expected a poor quarter and wanted positive news for investors. Prime also built on Amazon’s earlier experiments with free shipping: the minimum order fell from $100 to $75, $50, and eventually $25. Amazon learned that two books, DVDs, or CDs in one box generated enough profit to cover shipping. On website design, Ethan says Amazon used its WebLab system to run thousands of simultaneous A/B tests and kept whatever increased sales, regardless of whether it looked attractive. The hidden design principle was “speed equals sales.” Page-load time mattered more than visual polish, because slow pages caused abandonment. Amazon prioritized a consistent buy box, clear pricing, discounts, and delivery information; Bezos believed low prices were a stronger driver than beautiful pixels.

Ethan says he is happier running his own work than he was at Amazon, although he did not know that was possible beforehand. His final Amazon target compensation was about $900,000, and he often earned slightly more than $1 million because the stock outperformed expectations. Today he expects to earn roughly $700,000–$800,000 while working about 20 hours per week with substantial vacation, compared with 50–60 hours per week plus travel at Amazon. The tradeoff is losing the identity and platform of being an Amazon VP; Amazon’s name made almost any external party take his call. He now works as an executive coach and wants to help people reach financial security and then use that freedom for meaningful work. He also runs a charity in Poland that helps people displaced by the war in Ukraine find housing. His planned coaching community will use small groups and masterminds to scale his advice. He describes the ten-year vision as creating more people with enough money and confidence to do the good they have always said they would do. Ethan says he used Twitch strategically after Amazon. Although Amazon executives were not supposed to speak publicly without PR approval, he obtained approval to stream career advice on Twitch as a way to use the product and practice. He started with roughly 30–40 viewers, endured skepticism and trolls, and gained thousands of repetitions answering questions live. His advice for delivering uncomfortable truths comes from *Leadership and Self-Deception*: see the person as a human rather than a machine to fix, and let genuine care shape the tone. For coaches, he adds that explicitly telling a client they are paying for difficult truth establishes permission to be direct.