Why This Amazon Director Walked Away From Everything at 42 | Dave Anderson

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Sep 15, 2025

Dave Anderson, a former Amazon director turned newsletter writer, shares his unconventional journey from failing high school theater to leading at Amazon. He reveals the surprising reasons behind Amazon's cultural decline and contrasts its rigorous promotion processes with Facebook's informal approach. Dave discusses his unique management style involving absurd ideas to spark creativity and reflects on the true cost of ambition in demanding corporate environments. He also shares his secrets to financial independence, having saved 85% of his income to retire early.

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ANECDOTE

Chickenpox, A D, And A Career Pivot

Dave wanted to be a doctor but a single D in high school theater closed that path and redirected him to computer science.
That early pivot led him into a tech career that eventually landed at Amazon and shaped his life trajectory.

INSIGHT

Bezos Stepped Back Before He Left

Dave felt Bezos began stepping back years before officially leaving, which changed Amazon's decisiveness.
He observed slower stopping of questionable projects and increasing bureaucracy as groups scaled beyond the 'two pizza' mentality.

ANECDOTE

Burnout From 14 Direct Reports

At one point Dave had 14 direct reports and missed hiring a manager in time, forcing him into weeks of 8am–midnight work.
The crash nearly made him quit and illustrates the human cost of unchecked workload during growth spurts.

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Dave Anderson went from getting a D in high school theater (which derailed his medical career dreams) to becoming a director at Amazon, where he helped change the company's transfer policy that affects hundreds of thousands of employees. In this candid conversation, Dave reveals how a recruiter told him his resume was "terrible," why he believes managers don't need to be great coders, and how he saved 85% of his income to retire in his 40s. He shares unfiltered insights about Amazon's culture, including why he thinks the company started declining before Jeff Bezos even left, and offers a surprising take on why Facebook's chaotic promotion process might actually be better than Amazon's rigorous documentation requirements.

The conversation takes unexpected turns as Dave explains why he tests his team by proposing "absurd" ideas, admits he was never actually a senior engineer despite writing guides about it, and reveals what number would bring him back to corporate life (spoiler: it's in the millions). He challenges conventional wisdom about AI replacing engineers, arguing that current layoffs are finance-driven rather than efficiency-driven, while also warning that we're essentially using capitalism to destroy capitalism itself. Whether discussing his move from the Midwest where he could "spend weeks doing almost nothing" to Amazon's pressure-cooker environment, or predicting a future where AI makes most human jobs obsolete, Dave brings a refreshingly honest perspective to career growth, money, and what's really happening in big tech.