How I went from finance → AI

How I went from dead-end financial consulting and no technical skills to machine learning engineering in 5 years, and then to AI research 3 years later.

My guiding principle was to maximize my usefulness - I never planned farther than 6 months ahead. If I'd seen this roadmap in 2012 I probably would've given up immediately and started that pub crawl business.

Tip: try zooming out until the columns line up.


2011 Q2

2011 Q3 - 2012 Q4

2013 Q1

2013 Q2 - 2013 Q4

2013 Q4

2014 - 2015 H1

2015 H2

2015 Q4 - 2017 Q4

2016 Q1

2016 Q2 - 2019 H1 (3 years)

2016 H2

2017 H1 - 2019 H1 (2 years)

2017 Q4

2017 Q4 - 2020 Q4

2019 H2 - 2020 H1

2020 Q1

2020 Q4-2021 Q2


Graduated with econ degree, 3.1 GPA

Job 1: financial consulting

Web Development curriculum (step 1)

Dev Bootcamp

Job 2: Web development


Dipping my toes in CS

Job 3: Fullstack Engineer

First attempt at CS Curriculum

CS Curriculum (step 2)

Dipping my toes in ML

ML Curriculum (step 3)

ML sabbatical

Job 4: ML Engineer

NLP Systems Curriculum

CS294 Deep Unsupervised Learning

Job 5: ML Researcher

















Do differently

Things don't just "work out"


Find mentors


Ignore unhelpful degrees

Project sequencing

Sabbatical sooner

Narrow scope

Better curriculum

Ask for help

Focus on other bottlenecks


I loved my job as an AI researcher. Research is simply learning the answers to questions that nobody has asked before, so the learning skills I’ve accumulated served me well. But I had no choice but to quit: the Archive had broken up during the pandemic, and I couldn’t stop thinking about starting a community that would last for 50 years instead of 5.

I usually encourage people to start programming if they love to build and could imagine themselves being a programmer for 5+ years.

I generally recommend the Bloom Institute of Technology, because it’s one of the longest bootcamps and because it briefly covers computer science fundamentals. Be advised: you get out of it what you put into it, so prepare yourself like it’s one of the hardest things you’ll ever do.

There are many folks with business skills that want to “learn how to talk to engineers”, learn how to build their own MVPs, or otherwise don’t plan to be a full-time programmer for the bulk of their career. I usually discourage these folks from going to a bootcamp or taking intro to programming courses. Instead, I’d bet on the no-code movement. Here’s a curriculum I prepared for a friend:

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