The Exit Plan
Dave Anderson is the person your manager is secretly reading before your next performance review. His newsletter, Scarlet Ink, has become the most trusted insider guide to big-tech careers - not because he softens the edges, but because he refuses to. He spent 12 years inside Amazon's machine, reached the level of Technology Director and General Manager, became a Bar Raiser, helped build Bezos Academy from scratch as its first CTO, and then - in May 2021 - walked out. Not burned out. Not pushed out. He planned the exit down to the spreadsheet cell.
This is not a "tech bro writes motivational content" story. Anderson grew up in the Midwest, graduated from Michigan Technological University with a computer science degree in 1999, and spent years grinding in heartland tech before landing in Seattle. Amazon changed everything: his bank account, his physique (he lost 50 pounds - not from a diet, just from stopping the deep-dish pizza and starting CrossFit), and his worldview. He met his wife there. His career accelerated beyond anything he'd mapped out. And somewhere along the way he discovered the concept of FIRE - Financial Independence, Retire Early - and quietly began building his exit strategy.
The red pen is the detail that makes Dave Anderson human in a way that LinkedIn profiles cannot contain. At Amazon, he always carried a red pen in his shirt pocket. The company has a document-obsessed culture - every meeting begins with six pages of narrative prose, read in silence. Anderson annotated everything in scarlet. When he started his newsletter, he wanted the domain "redink" - taken. He settled for "scarletink," which he admits felt more literary anyway. The newsletter name is not a brand decision. It's a personality tic made permanent.
"I needed to remove the power others had over me."
- Dave Anderson on why he pursued financial independence
That quote is doing more work than it appears to. Anderson is careful with his words - the newsletter proves it - and this sentence isn't about hating his job. He loved parts of it. He was good at it. But there is a particular freedom that comes from being genuinely indifferent to whether your employer needs you to stay, and Anderson spent 15 years building toward that indifference. He hit his conservative FIRE number in late 2019. He kept working anyway - because retiring *to* something matters more than retiring *from* something. Two years later, he was ready to retire to Scarlet Ink, to chickens, to trail running in the Pacific Northwest, and to a scuba certification that would take him further than any Amazon badge ever did.
The thing about Scarlet Ink is that it works because Anderson has nothing to sell you except clarity. He's not recruiting for Amazon. He's not running a coaching business. He explicitly stopped offering paid coaching when he realized it didn't fit his post-FIRE life. He writes a weekly newsletter, he shoots landscape photos on hikes with his wife, and he occasionally volunteers at local high schools teaching teenagers how to ace job interviews. That last detail reveals something important: Anderson believes in radical information access. The insider knowledge that gets people promoted in big tech - the kind that circulates privately through the networks of those already inside - should not be a secret. Scarlet Ink is his argument that it doesn't have to be.
Inside the Machine
01
The Bar Raiser
At Amazon, a Bar Raiser is a trained interviewer independent of the hiring team - their job is to ensure every new hire raises the overall standard of the company. Anderson wasn't just a Bar Raiser; he became part of the Bar Raiser core leadership group. He coached, mentored, and promoted dozens of leaders during 12+ years. Three of those promotions were his own, climbing from the lowest management rung straight to Tech Director and GM.
02
The First CTO
When the pandemic started, Dave Anderson was tapped to help build something brand new: Bezos Academy, Jeff Bezos's tuition-free school initiative. As its first CTO, he had to construct the entire technology foundation - infrastructure, culture, leadership team - from zero. He spent approximately a year doing it. It is, by any measure, one of the more unusual items on any tech executive's resume.
03
The FIRE Number
Around 2006, Anderson discovered the FIRE community and reframed his entire financial life - not around a retirement age, but a retirement number. His final year's compensation exceeded his starting salary by more than 20 times. He hit his target in late 2019 and kept working for two more years, deliberately. His investment philosophy is Boglehead straightforward: three-fund portfolio (VTSAX, VTIAX, VBTLX), rebalanced semi-annually, 9+ months of expenses in money market as float.
04
The Newsletter That Works
Scarlet Ink is not content marketing. There's no product being sold on the back end. Anderson built it because he had spent 12 years watching talented engineers miss promotions, fumble interviews, and get passed over for reasons that had nothing to do with their skill - and everything to do with not knowing the rules. His article "How to Interview at Amazon" became the most widely recognized piece on the topic. Readers routinely email him to report promotions and salary increases.
05
The Red Pen
Every Amazon meeting starts with a memo, read in silence. Six pages of narrative prose, no bullet points, before any discussion begins. Anderson took notes with a red pen tucked in his pocket - easier to spot against the black-and-white documents. When he started writing online, he wanted "redink" as his domain. It was taken. He chose "scarletink" instead, because it felt more literary. The newsletter name is an accident that became a brand.
06
The Midwest Origin
Anderson grew up and started his career in the Midwest. He speaks openly about the financial gap between heartland tech workers and those on the coasts. Moving to Seattle for Amazon was transformative: he saved ten times more per year, lost 50 pounds (not from dieting - just from proximity to CrossFit and distance from deep-dish pizza), and met his wife. He still carries the Midwest cadence: direct, skeptical of hype, uncomfortable with self-promotion.
What Makes Scarlet Ink Different
Most tech career advice exists in one of two modes: optimistic coaching that avoids anything that might sound negative, or cynical venting from people who got pushed out. Anderson operates in neither mode. He was good at his job. He liked being good at his job. He left voluntarily, at a time of his choosing, for reasons entirely his own. That context matters enormously when reading his work.
The newsletter covers Amazon's Leadership Principles in a way that treats them as actual operating software, not slogans to memorize for an interview. He decodes "Are Right, A Lot" as one of the most misunderstood principles in the set. He explains why big-tech career incentives are structurally designed to produce cycles of overhiring followed by layoffs. He writes about frugality not as an accounting preference but as the reason Amazon actually ships products faster than companies with bigger budgets.
The practical value is why 72,000 people subscribe. The voice is why they stay. Anderson writes with the specific self-deprecating authority of someone who has been inside the machine long enough to know where the gears are, and funny enough to describe them without pretension. He makes fun of the Midwest. He openly discusses getting fat and then getting fit. He references his chickens. He uses random name generators in his article examples to avoid unconscious bias. These are not branding choices. This is just who he is.
"Retire to something, not from something."
- Dave Anderson, on the right reason to achieve financial independence
The scuba certification deserves its own paragraph. Anderson is certified to the OWSI level - Open Water Scuba Instructor - which is several rungs above recreational diving. He has swum with dolphins. He trail runs and hikes the Pacific Northwest, taking the photographs that appear in his newsletter (often alongside his wife, who also appears in the essays, though never named). This is a person who left one of the most demanding professional environments in the world and chose to fill the space with as much physical experience of the actual world as possible.
He also volunteers teaching interview skills at local high schools. The career access he writes about in his newsletter - the insider knowledge that helps engineers get past Amazon's notoriously structured hiring process - he gives away for free to teenagers who have no network, no former colleagues to coach them, no concept of what a bar raiser even is. This is the real editorial position of Scarlet Ink: the information isn't secret because it should be. It's secret because nobody bothered to write it down.
Career Timeline
1999
Graduates from Michigan Technological University with a Bachelor of Science in Computer Science. Enters the tech workforce in the Midwest.
2006
Discovers the FIRE community. Reframes retirement as a number, not an age. Begins building deliberately toward financial independence while still seven years from Amazon.
~2007
Joins Amazon as an SDM (Software Development Manager) - the entry-level management role. Moves to Seattle. Loses 50 lbs. Meets his wife. Saves ten times more than before. Life changes in every direction simultaneously.
2007-2020
Builds his career at Amazon over 12+ years. Promoted three times: SDM to Tech Director, eventually reaching General Manager. Becomes a Bar Raiser, then joins the Bar Raiser core leadership group. Coaches and promotes dozens of Amazon leaders.
~2020
Named the first CTO of Bezos Academy at the start of the pandemic. Spends roughly a year building the technology foundation for the school system and hiring the IT leadership team from zero.
Late 2019
Hits his conservative FIRE number after approximately 15 years of focused saving. Keeps working anyway - by choice.
2021
Completes a stint as Tech Leader at Meta. In May 2021, executes his planned exit from corporate life. Final year compensation: more than 20x his starting salary.
2021
Launches Scarlet Ink - a weekly newsletter on tech careers and leadership. The name comes from the red pen he carried to every Amazon meeting.
Late 2023
Moves Scarlet Ink from its standalone Ghost site to Substack, drawn by Substack's features. Notes it required less effort than expected.
2024+
Surpasses 72,000 subscribers and 186 published articles. Still raising chickens. Still carries a red pen.
Achievements & Impact
01
Built Scarlet Ink from zero to 72,000+ subscribers - one of the most-read big-tech career newsletters on Substack.
02
Promoted three times at Amazon across 12+ years, from entry-level SDM to Technology Director and General Manager.
03
Served as the first CTO of Bezos Academy, building its entire technology infrastructure during the pandemic.
04
Bar Raiser and core leadership group member at Amazon - trained to hold the interview standard for one of the world's most selective hiring processes.
05
Authored "How to Interview at Amazon" - the most widely recognized article on the subject, credited with countless promotions and offers.
06
Achieved FIRE in his early 40s after ~15 years of focused saving, with final-year compensation exceeding starting salary by 20x.
07
186+ published articles across tech, leadership, and career topics - with readers consistently reporting real-world salary and promotion results.
08
Volunteers teaching interview skills at local high schools - taking big-tech hiring knowledge out of insider networks and giving it to teenagers who have no access to it otherwise.
Fun Facts
✏️
The domain "redink" was taken when he started his newsletter - so he chose "scarletink" instead. He admits it sounds more literary. An accident that became a brand.
🍤
He raises backyard chickens. This was not a metaphor. It was a stated retirement goal. He did it.
🌊
Certified SCUBA diving instructor at the OWSI level - well beyond recreational. He has swum with dolphins.
🏃️
He lost 50 pounds after moving to Seattle - not from any diet, but from replacing deep-dish pizza with CrossFit and indoor climbing.
📷
Every photo in Scarlet Ink is one he took himself - landscapes and nature from hikes, often with his wife.
🏯
He uses random name generators when writing article examples, to make sure the characters don't carry unconscious demographic bias.
Find Dave
SCARLET INK FOUNDER