Key Moments
Ex-Amazon VP tells us what it’s really like working with Jeff Bezos
My First MillionKey Moments
Jeff Bezos's intense focus on customer feedback, even in his criticism, was a double-edged sword that drove Amazon's success but also led to costly failures like the Fire Phone.
Key Insights
Jeff Bezos's management style was characterized by relentless criticism, often delivering feedback without initial praise, which he later learned to balance with encouragement.
The Fire Phone, a $170 million write-off, is cited as a prime example of Bezos's tendency to over-rely on his own vision, even when market consensus suggested otherwise.
Amazon stock experienced a 9,082% increase from Ethan Evans's first day to his last, significantly enriching employees.
Bezos's 'strategically patient, tactically impatient' approach meant holding a long-term vision while pushing for daily progress, exemplified by the evolution of Prime shipping.
A core Amazon principle was prioritizing speed and sales over aesthetics; page load time was considered more critical than pixel-perfect design.
Bezos believed in trusting anecdotes over data, especially when a small percentage of issues at Amazon's scale still represented a significant number of customer problems.
The 'adult in the room' and early Amazon acquisition dynamics
Ethan Evans, a former VP at Amazon Prime, spent 15 years at the company. He initially joined Twitch after its acquisition by Amazon, not as a regular team member, but as an 'adult in the room,' essentially an overseer assigned by Amazon. There was an early perception among Twitch employees that Evans was a spy sent to eventually replace Emmett Shear, the CEO of Twitch. This 'conspiracy theory' was never true but proved difficult to dispel. The acquisition itself, for $970 million, was significant, and employees who joined Amazon saw their stock options multiply exponentially, with Amazon's stock increasing by 9,082% during Evans's tenure. This led to some employees vesting out at $2 million a year, making it difficult for them to return to previous salary levels.
Bezos's feedback style: Criticism as a driver
Bezos's management style was notably demanding and primarily focused on critique. Evans observed that Bezos would often present a team's work, identify three key areas for improvement, and then expect immediate action, rarely offering initial praise. For those without thick skin, this constant corrective feedback could be demoralizing, regardless of their achievements. However, Bezos's taste and judgment were generally excellent, leading to successful ventures like Kindle and Prime. Evans recalled a meeting where Bezos spent an hour detailing everything the team had missed, only to deliver a brief, almost an afterthought, 'good job' before leaving, indicating an intentional effort to incorporate praise due to coaching. This intense, critical approach, while effective in driving results, could also be perceived as harsh.
The 'every great man' flaw and the Fire Phone debacle
A significant weakness attributed to Bezos, and common to many highly successful leaders, was the belief that his vision was infallible after numerous successes. This conviction, combined with immense courage, ultimately contributed to the Fire Phone disaster. Despite considerable internal and external skepticism, the project, which resulted in a $170 million write-off for hardware alone, serves as a stark example of how even brilliant leaders can misjudge market demand when they become too insulated from dissenting opinions. It highlights the challenge of delivering negative feedback to a visionary leader who has a track record of being right, making it difficult for the team to effectively convey market realities that contradict the leader's vision.
Attack mode and the emotional leader
When frustrated, Bezos would sometimes enter 'attack mode.' Evans explained that this wasn't just frustration with a team's mistakes but also with himself for allowing the situation to occur. This relentless approach could be incredibly tough on individuals. An example involved a customer-facing feature where customers could photograph prices in stores to report lower prices found elsewhere. This initiative was perceived negatively in the media as Amazon using customers to spy and undercut small businesses. In a meeting discussing this, Bezos reportedly exclaimed, 'How could we be so stupid? How could anyone screw this up?' While this outburst was directed at the situation, the PR representative present initially felt it was aimed at her, illustrating how Bezos's emotions, both positive and negative, were palpable and expressed openly.
Pattern recognition and the '10,000 hours' of insight
The ability of leaders like Bezos and Emmett Shear to quickly identify key leverage points or flaws in business plans was attributed to extensive pattern recognition. Evans suggested this was akin to the '10,000 hours' of expertise, with Bezos, in particular, spending thousands of hours reviewing documents and providing feedback. This deep immersion in analyzing diverse business scenarios, even those he wasn't intimately familiar with, honed his ability to distill complex information into actionable insights rapidly. This skill set, developed over years of dedicated practice, allowed him to consistently make sharp, often prescient, strategic decisions.
The 'B' player and the value of loyalty and grind
Not all success at Amazon was dependent on brilliant, transformative ideas. Evans highlighted the value of individuals who could reliably turn a 'D' or 'F' situation into a 'B.' These 'B' players, often characterized by loyalty and a strong work ethic, were crucial for maintaining operations and supporting 'A' products. While not necessarily top leaders, their consistent effort ensured that less critical but necessary functions didn't falter. This demonstrated that in a massive organization, dependable execution and grinding through challenges were as vital as groundbreaking innovation. Bezos recognized and rewarded this type of steadfast commitment, understanding that a solid 'B' performance could be sufficient when supported by other high-performing initiatives.
Strategically patient, tactically impatient: The Bezos approach
Bezos's philosophy of being 'strategically patient, but tactically impatient' underscored Amazon's long-term vision. For grand initiatives like Prime or space exploration, patience was essential, recognizing that these endeavors would take years, even decades, to fully realize. However, daily execution demanded urgency and a relentless drive to make incremental progress. This meant maximizing every quarter's potential by pushing for more achievements, understanding that long-term success was an accumulation of countless small, consistent efforts. This approach translated into a culture of intense work, framed by euphemisms like 'work-life harmony' rather than 'balance,' emphasizing dedication and hard work as central to achieving ambitious goals.
The 'question mark' emails and customer-centric accountability
A powerful mechanism Bezos used to maintain customer focus was the 'question mark' email. When a customer complaint arrived, Bezos would forward it to the relevant leader with a single question mark. This signaled an urgent demand for an explanation and a plan of action within 24 hours. The response needed to demonstrate either that the issue was an anomaly, that a solution was in progress, or, at worst, that it was a known problem with a long-term fix. This system ensured that customer feedback, even at Amazon's immense scale, was directly addressed by top leadership, fostering a culture where every customer issue was treated with critical importance. Bezos's own 'euthanize me' response to a problematic Appstore initiative underscored the severity with which he viewed such failures.
The 'voting machine' versus the 'weighing machine' and avoiding regulation
Bezos frequently cited Benjamin Graham's analogy of the market as a 'voting machine' in the short term and a 'weighing machine' in the long term. He used this to manage expectations around Amazon's stock price, emphasizing that short-term fluctuations didn't reflect fundamental company strength. The real measure was increasing the company's 'weight' or intrinsic value over time. This philosophy aligned with prioritizing free cash flow over short-term accounting profits, even once leading to a 'terrible mistake' of becoming profitable for a single quarter, which set a precedent for future comparisons. Furthermore, Bezos consciously avoided industries that were heavily regulated, like finance or travel, preferring to operate in areas where Amazon could move quickly and dictate its own terms, unhindered by bureaucratic constraints.
Escalating security and the loss of 'normal' for top leaders
As Amazon grew, the physical security surrounding its top executives, including Bezos, became progressively more elaborate. Initially, security was minimal, with a retired baseball player serving as a guard. However, after reporters gained direct access to Bezos's office, security measures escalated dramatically. Gates, badges, and dedicated security personnel became standard. Later, the executive suites and even elevators became highly restricted, resembling 'Fort Knox.' This increasing isolation meant that attempts to maintain normalcy, like Bezos attending company picnics, became impractical. The sheer scale of events, with thousands of employees, made genuine connection difficult, leading to a gradual separation from the 'man of the people' image. This progressive insulation highlights a common challenge for leaders of massive corporations: maintaining relatable connections as their influence and responsibilities expand.
The genesis of Amazon Prime and the 'free shipping' experiment
The origin of Amazon Prime is attributed either to engineer Charlie Ward or Jeff Bezos himself, with Ward claiming to have invented the concept of rapid shipping. Initially conceived as 'Project 100' with a 100-day launch target, the core idea was fast shipping, not a perk-based membership. Bezos saw it as a strategic move to generate positive news for investors during a challenging post-dot-com bubble period. The evolution to free shipping involved significant experimentation. A precursor trial required a $100 minimum purchase, which was gradually reduced to $25. The key insight was that for certain product categories like books, music, and DVDs, purchasing two items made free shipping economically viable. Prime itself was an outgrowth of this experimental success in making free shipping feasible.
Data-driven design and the primacy of speed and price
Amazon's website design was rigorously A/B tested, with 'Web Lab' running thousands of experiments simultaneously. The ultimate arbiter of design success was not aesthetics but profitability. Features were only implemented if they maintained or improved page load times, which were identified as a critical driver of customer abandonment. Even when design VPs pushed for prettier interfaces, the underlying principle remained 'speed equals sales.' Key design elements focused on clarity, such as the consistent placement of the 'buy box' button, and attractive offers, primarily low prices, discounts, and clear delivery information. During the 2007-2008 recession, Amazon's focus on low prices proved advantageous as more consumers shifted to online shopping due to budget constraints.
The 'dumb stuff' debate: Customer choice and market economics
Addressing concerns about selling inexpensive, disposable items, Evans reflected Bezos's libertarian, free-market perspective. The belief was that customers should have the choice to buy what they want, and Amazon's role was to make it easy. While acknowledging potential downsides and personal concerns about environmental impact, Bezos's stance was that if Amazon didn't sell these items, competitors like Walmart would. This led to the principle of selling 'dumb stuff' fastest and cheapest. The focus remained on offering customers a wide selection and competitive pricing, trusting that the market and individual choices would lead to the desired outcomes, even if those outcomes involved perceived waste or lower quality products.
From VP to Coach: Redefining success and finding meaning
After leaving Amazon, Evans shifted his focus to helping others achieve career success and satisfaction. He contrasts his Amazon experience, where he was happy but not fully fulfilled, with his current life, where he finds greater joy and purpose, working fewer hours for comparable compensation. His target compensation at Amazon was $900,000, with stock options pushing it into the low millions, while his current coaching work averages 20 hours a week with significant vacation, yielding $700,000-$800,000 annually. A significant loss was identity; the 'former Amazon VP' title carries less weight than the platform Amazon provided. Despite this, he prefers his current autonomy, especially the ability to work on projects he loves. He also dedicates time to helping displaced Ukrainians through a charity in Poland.
Building a 10-year vision for impactful living
Evans advocates for clear, long-term planning, inspired by Bill Gates's observation that people overestimate what they can do in a year but underestimate what they can achieve in a decade. His personal 10-year vision is to cultivate individuals who, having achieved financial security and success, are empowered to contribute positively to the world. He emphasizes the danger of having only vague, undefined future goals ('someday') and aims to help people transition from dreaming about doing good to actively doing it. This involves building a foundation of financial stability and confidence, enabling them to act on their desire to make a difference, much like his own journey from envisioning impact to actively creating it through coaching and charitable work.
Leveraging current roles to build future aspirations
Evans champions the idea of using present opportunities to prepare for future aspirations. He recounts his experience streaming on Twitch while still at Amazon, an activity that initially required navigating company policy and gaining approval. By engaging in regular public speaking and career advice sessions, he honed his communication skills and message, preparing for his eventual coaching career. This proactive approach, akin to Tony Robbins's early days of seeking 'reps' through public demonstrations, is applicable to anyone. The key is to identify transferable skills and opportunities within one's current role that can serve as building blocks for future goals, whether it's public speaking, networking, or developing expertise.
The art of truthful, empathetic communication
Evans attributes his ability to deliver difficult truths without alienating people to a core principle of viewing others as human beings first, not just problems to be solved. This empathy, demonstrated through tone and body language, ensures the message of care and support comes through, even when the feedback is critical. He also uses a positional strategy as a coach: setting the expectation that he is being paid to deliver tough news, which makes the recipient more receptive. By framing feedback as a necessary part of their development journey, he can maintain honesty without causing undue offense. This approach, rooted in genuine care and strategic communication, allows for constructive criticism that fosters growth rather than resentment.
Mentioned in This Episode
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Common Questions
Jeff Bezos's primary weaknesses included being overly critical, not praising enough, and his strong conviction in his own vision, which, while often right, led to failures like the Fire Phone. He could also be very cutting and attack-minded when frustrated.
Topics
Mentioned in this video
Former VP at Amazon Prime, author of a database on successful people, and now an executive coach. He shares insights into working with Jeff Bezos and his experiences at Amazon and Twitch.
Founder of Amazon, discussed extensively for his leadership style, strengths, weaknesses, and business philosophies. His approach to criticism, innovation (Kindle, Fire Phone), customer service, and strategic patience is detailed.
An entrepreneur and investor whose writings on wealth creation and parallel lives are referenced in the discussion about Jeff Bezos's success and the role of timing.
An influential investor whose investment philosophy, particularly the distinction between the market as a 'voting machine' and a 'weighing machine', is referenced by Jeff Bezos.
Co-founder of Microsoft, whose quote about people overestimating what they can do in a year but underestimating what they can do in ten years is cited by Ethan Evans.
An investor and educator whose quote about the market being a 'voting machine' in the short term and a 'weighing machine' in the long term was frequently quoted by Jeff Bezos.
Former CFO of Amazon, mentioned in an anecdote where he tried to temper Jeff Bezos's investment plans, leading to a sharp rebuke from Bezos.
A motivational speaker and author whose early career tactics of cold-calling radio stations and performing at malls to gain experience are used as an analogy for Ethan Evans's early Twitch streaming.
A service from Amazon offering fast shipping and other perks to members. Its origin and evolution are discussed, including its initial 'Project 100' and the strategy behind its pricing.
A smartphone launched by Amazon that resulted in a significant financial write-off, cited as an example of Jeff Bezos's vision becoming detached from market reality.
Amazon's e-reader, highlighted as a successful product where Jeff Bezos fought the right battle, despite initial internal skepticism.
Mentioned as a technological shift that Jeff Bezos might have been too late to capitalize on if he had started Amazon a decade later, highlighting the importance of timing in innovation.
A software company that resurfaced Ethan Evans's early database on successful people, which he created at age 24.
A quantitative trading firm where Jeff Bezos worked as a trader before founding Amazon. He discussed his 'everything store' idea with colleagues there.
An earlier name for Amazon's video streaming service, mentioned as an example of Jeff Bezos's tendency to name products based on their function.
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