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

Episode of My First Million · October 28, 2026 · 1 h 16 min

Former Amazon VP Ethan Evans tells Shaan Puri and Sam Parr about Jeff Bezos's management style, flaws, Amazon Prime's origins, and life after Amazon.

Summary

Ethan Evans, who spent about 15 years at Amazon and served as Amazon's executive overseer on Twitch's leadership team, joined Shaan Puri and Sam Parr to describe working with Jeff Bezos. Evans characterized Bezos as exceptionally smart and usually right, but said his flaws included giving only criticism, cutting remarks such as asking whether "the A team" was available, and an overconfidence in his own vision that Evans blamed for the Fire Phone write-off.

Evans explained Amazon practices including "question mark emails" forwarded from customer complaints, Bezos's preference for anecdotes over data, the principle of being strategically patient but tactically impatient, and a culture of long hours he described as euphemistically justified. He recounted the origins of Amazon Prime as "Project 100", tied to a weak quarter, its precursor in free-shipping thresholds, Amazon's speed-first web design driven by Weblab A/B testing, and Bezos's avoidance of heavily regulated industries. He also described Twitch burning over a billion dollars while perpetually forecasting profitability in three years.

The hosts discussed timing and project selection, with Puri praising Bezos for waiting for "fat pitches" such as AI. Evans said he is happier as a coach, earning roughly comparable money while working about 20 hours a week, described his Ukrainian refugee charity in Poland and plans for a coaching community, and explained how streaming career advice on Twitch gave him practice. He closed by recommending Leadership and Self-Deception as the source of his approach to delivering hard truths with care.

Chapters

  1. 0:16

    Evans at Twitch and the acquisition

    Puri recalls Evans as Amazon's 'adult in the room' at Twitch, and Evans explains how Amazon's rising stock created a retention cliff after the earn-out.

  2. 2:43

    Bezos's flaws

    Evans describes Bezos's criticism-only feedback, overconfidence behind the Fire Phone, and his attack mode in meetings.

  3. 8:28

    Pattern recognition and the 'I got this' leader

    Evans attributes Bezos's sharpness to thousands of hours of document reviews and explains why reliable B-grade operators were rewarded.

  4. 15:14

    Wealth, losing touch, and question mark emails

    Evans discusses Amazon stock gains, wealthy executives losing touch, and Bezos's use of customer complaints to scale accountability.

  5. Linked moment · 22:15Skip to 22:15 using a listen link in the info box.

    22:15

    Amazon's work culture

    Evans explains strategic patience with tactical impatience, 'work-life harmony', and Amazon as a place high performers feel bad about themselves.

  6. 28:49

    Evans evaluates Puri and Twitch's losses

    Evans critiques Puri as too entrepreneurial for a corporation and describes Twitch's years of 'profitable in three years' plans.

  7. 31:45

    Life after Amazon

    Evans compares corporate executive life with running his own coaching business and the loss of identity and platform.

  8. 34:39

    Timing, project selection, and fat pitches

    The group discusses luck and timing in Bezos's success, Project Prometheus, and the industries Bezos declined to enter.

  9. 44:00

    Security and isolation

    Evans recounts how Amazon executives became progressively isolated behind security as the company grew.

  10. 47:23

    Origins of Amazon Prime and website design

    Evans tells the story of Prime, free-shipping experiments, and Amazon's speed-and-price-driven design philosophy.

  11. 55:56

    Morality, influences, and the CFO

    Evans discusses Bezos's free-market view of consumer choice, his fondness for Benjamin Graham, and a sharp exchange with his CFO.

  12. 1:00:59

    Ten-year goals and Twitch streaming

    Evans describes his mission, charity work, and how streaming career advice on Twitch built his coaching practice.

  13. 1:11:50

    Delivering hard truths

    Evans shares his method for honest feedback rooted in caring for the person, drawn from Leadership and Self-Deception.

Key points

What was said, by whom, with the exact words. Timestamps jump to the moment.

  • Ethan Evans

    Evans says Amazon's stock rise during the earn-out left Twitch engineers vesting about $2 million a year, causing many departures when it ended.

    “we had engineers whose market salary anywhere else was say 200, 250K back then, vesting out at 2 million a year”

    Listen from 2:11 · Twitch

  • Ethan Evans

    Evans says one of Bezos's flaws was giving only critical, corrective feedback.

    “And that only criticism, only corrective feedback, that was one of his flaws”

    Listen from 4:05 · Jeff Bezos leadership style

  • Ethan Evans

    Evans argues that Bezos came to believe his vision was perfect after being right often, which led to the Fire Phone failure.

    “having been right a lot, he started to believe his vision was perfect. And that's what led to the Fire Phone disaster”

    Listen from 5:30 · Fire Phone

  • Ethan Evans

    Evans attributes Bezos's ability to quickly find flaws in proposals to pattern recognition from years of document reviews.

    “He literally spent 10,000 hours reading those documents, and giving feedback”

    Listen from 10:32 · Jeff Bezos leadership style

  • Ethan Evans

    Evans argues that in a business as large as Amazon, a reliable leader who lifts a failing area to a B can be more valuable than a high-variance leader.

    “in a business as big as Amazon, sometimes all you need is a B because there's some other A product that's gonna drag through the revenue”

    Listen from 12:07 · Organizational culture

  • Ethan Evans

    Evans says Bezos instructed that anecdotes should be trusted over data because even a 1% failure rate at Amazon's scale affects millions.

    “Jeff said between data and anecdotes, trust the anecdotes”

    Listen from 19:23 · Jeff Bezos leadership style

  • Ethan Evans

    Evans explains that question mark emails meant leaders had 24 hours to explain and resolve a customer complaint Bezos forwarded.

    “we called these question mark emails and everybody knew what that meant, which is it meant you have 24 hours to get back and explain what's going on”

    Listen from 20:08 · Organizational culture

  • Ethan Evans

    Evans characterizes Amazon's work-culture phrases as euphemisms for demanding long hours.

    “a lot of euphemisms to say, yes, we're a sweatshop in a slightly more acceptable way”

    Listen from 24:48 · Organizational culture

  • Ethan Evans

    Evans says Twitch burned over a billion dollars in its first five years under Amazon while repeatedly forecasting profitability in three years.

    “over the first five years burned over a billion dollars of cash with no real sight to profitability”

    Listen from 30:53 · Twitch

  • Ethan Evans

    Evans says he expects to earn $700,000-800,000 this year coaching about 20 hours a week, versus low-million pay for 50-60 hour weeks at Amazon.

    “this year I'll end the year at like seven or $800,000, but as opposed to 50 to 60 hours a week plus travel”

    Listen from 33:22 · Executive coaching

  • Ethan Evans

    Evans believes Bezos's success depended partly on timing, arguing that being ten years older or younger would likely have changed his outcome.

    “And that's no insult to Jeff. I just think for anybody, there's something about timing”

    Listen from 35:17 · Project selection and timing

  • Shaan Puri

    Puri argues Bezos's most impressive trait is not swinging at wrong opportunities between big bets like Amazon, Blue Origin, and AI.

    “It's that for five years or six years or whatever in between, he didn't get itchy and swing at the wrong thing, right?”

    Listen from 41:16 · Project selection and timing

  • Ethan Evans

    Evans says Bezos repeatedly declined to enter finance, travel and other industries, generally avoiding heavily regulated or mature sectors.

    “he generally tried to avoid things with lots of regulation because that slowed down his ability to do whatever he wanted”

    Listen from 42:24 · Amazon (company)

  • Ethan Evans

    Evans says Prime began as 'Project 100', a fast-delivery program Bezos pushed to have good news for investors ahead of a weak quarter.

    “Prime was originally called Project 100 because they had to figure out how to announce it and start doing it in 100 days”

    Listen from 48:40 · Amazon Prime

  • Ethan Evans

    Evans explains the $25 free-shipping threshold worked because it required buying two items, generating enough profit to cover shipping.

    “$25 was this magic number that meant you had to buy two. you had to put two things in the box”

    Listen from 50:27 · Amazon Prime

  • Ethan Evans

    Evans says Amazon's key design principle was page load speed rather than visual appeal.

    “the overall design principle, I guess I'm telling you that was hidden behind the scenes was speed equals sales”

    Listen from 53:32 · A/B testing and web design

  • Ethan Evans

    Evans believes Bezos holds free-market views that customers should be given choice in what they buy.

    “he's also very much a libertarian and a free market guy. And his viewpoint is give customers the choice”

    Listen from 56:33 · Amazon (company)

  • Ethan Evans

    Evans says his Twitch career-advice streams gave him practice that now makes him hard to throw with questions.

    “why can't I be thrown by most questions, right? And it's because I've answered 10,000 questions live”

    Listen from 1:11:22 · Executive coaching

  • Ethan Evans

    Evans recommends delivering hard truths by first caring about the person, an approach he draws from Leadership and Self-Deception.

    “you have to see the person as a human, not as a machine to fix. So I have to care about the person first”

    Listen from 1:12:43 · Leadership and Self-Deception

People

In the conversation

  • Shaan PuriEntrepreneur and investor, co-host of My First Million, former Twitch executive
  • Sam ParrEntrepreneur, founder of The Hustle and Hampton, co-host of My First Million
  • Ethan EvansFormer Amazon vice president (Prime Video, Appstore, Twitch oversight) turned executive coach

Discussed

Topics

More from My First Million

From the publisher

Sam's database on how long it takes to become a millionaire: https://clickhubspot.com/tewg Episode 877: Shaan Puri ( https://x.com/ShaanVP ) and Sam Parr ( https://x.com/theSamParr ) talk to Ethan Evans about what it’s really like to work with Jeff Bezos. — Show Notes: (0:00) Intro (3:15) Criticism without praise (5:15) The every-great-man flaw (7:05) Attack mode (11:45) “Sometimes all you need is a B” (19:35) Question mark emails (22:25) Strategically patient, but tactically impatient (24:10) Work hard, long, and smart (25:15) Where high-performers go to feel bad about themselves (28:05) Ethan evaluates Shaan (35:55) Project selection (39:50) Waiting for fat pitches (42:30) Jeff’s security detail (45:50) The story of Amazon Prime (47:55) Amazon's idea tool (50:55) Good design vs. bad design (54:15) The morality of Amazon (56:15) Who Jeff studied (31:35) Post-Amazon (1:04:10) Streaming career advice on Twitch — Links: • https://www.ethanevans.com/about — Check Out Sam's Stuff: • Hampton (joinhampton.com): My community for founders. Average member does $25m/year. Many of the guests are members. Get after it...apply: http://joinhampton.com/mfm — Check Out Shaan's Stuff: • Shaan's weekly email - https://www.shaanpuri.com • Visit https://www.somewhere.com/mfm to hire worldwide talent like Shaan and get $500 off for being an MFM listener. Hire developers, assistants, marketing pros, sales teams and more for 80% less than US equivalents. • Mercury - Shaan uses Mercury across all of his companies. you can too: http://mercury.com/ Mercury is a fintech company, not an FDIC-insured bank. Banking services provided by Choice Financial Group, Column, N.A., Members FDIC • I run all my newsletters on Beehiiv and you should too + we're giving away $10k to our favorite newsletter, check it out: beehiiv.com/mfm-challenge My First Million is a HubSpot Original Podcast // Brought to you by HubSpot Media // Production by Arie Desormeaux // Editing by Ezra Bakker Trupiano /

Summary, chapters and key points were generated from the episode transcript on November 8, 2026. Quotes are checked word for word against the transcript.

Categories: Management·Business·Careers