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I definitely had advantages in that I knew tools like Khan Academy existed, was not battling depression, and also had talked to people who I admired and saw they were not so different than me. I also had a mother who loved me and a step-father who came into my life a bit later who cared, but they were dealing with some pretty big challenges of their own, including mental health, bad relationships, debt, children who were in and out of jail, and everything that comes with that. I do not like to spend too much time focused on race, but I am a white male, which was also an advantage.

At the time I was leveraging Khan Academy I was around 24, had distanced myself from the people I had grown up with who were not on a positive track. I also don't know how, but somehow I got it in my head that finance was the universal language and that learning more about finance was the key to understanding more about the world. So I was very focused on that. I had no clue what economics was at the time, but once I learned about that, I was addicted. Finding topics like that deeply interesting is a HUGE advantage.

At that time, I was living on my own and had a stable job managing a department at Home Depot. I slept on an air mattress and didn't have any money to speak of, but I had enough time on my hands that I could spend time at a coffee shop after work and on my days off working my way through the knowledge map on KA, starting with long division (which was humiliating) and learning how to do everything by hand, and then progressing from topic to topic. My goal was to not have to take a remedial math class at the local junior college (2 year colleges in the US). I spent months mastering basic math and worked my way to more advanced topics (1 million energy points on KA, not sure if that's a lot but I'm still proud of it).

One last advantage I had was that I genuinely enjoyed learning and talking to people, and it showed. And I was young. So people were willing to take the risk. Many people were willing to give me a chance, encouragement, and their time as I was making my way through school. If I had a question or was interested in a career or topic, I would just ask someone if I could call them or shadow them, and most the time they would say yes. I had nothing to lose by asking, and was always amazed how often it worked.

I try to share this with others who were in my position so they know it is possible.

Thank you for asking.




Wow, this is a personal Top 100 post on this board for me. What a great story. This part was really touching: <<starting with long division (which was humiliating)>>

Keep it up. We are cheering for you.


Thank you! I would literally make sure my back was to a corner so no one could see what was on my screen haha.

Needless to say, I spend a lot of time on math with my oldest (who just turned four!). She does not need to be great, she just needs to not be intimidated and understand she can learn anything.


Thanks for all the detail, it’s inspiring! How did the learning lead to your first job in tech/AI?


I got into a job in corporate IT at a good company and then moved through a bunch of roles, including putting together one of our first data science/ML teams. A couple years later when I was doing product work, gpt 2 came out, so I had started working with it for fun and writing Points of View for our company about how we could leverage these technologies and what the market dynamics would looks like and implications, etc. (I am basically a dollar store version of Ben Thompson.)

It was mostly dismissed at the time, because Alexa and Siri were what people thought of, but when ChatGPT got released I was in a great position and was able to quickly ship. Now I lead that capability for one of our relatively large subsidiaries.

For me, what lead me here was mostly a fascination with the decreasing marginal cost of knowledge work. There is something about building these types of products that is just very fun and feels like cheating, I love it.


Was the lack of formal education a big problem getting started with that good company? I'm pleasantly surprised your resume made it past the first line of throwing-it-out


No, but I work for a company with a very unique perspective on education and merit. They are a large privately held firm that does not care about degrees (for 95% of things).

When I was a year in to my career I sat down with one of our senior execs and asked if I should get an MBA, and he said “don’t waste your time, you are already in a university and we will teach you everything you need to know”. And that has been true.

Make no mistake, it is definitely a disadvantage but I got lucky.


Thanks for the detailed reply, great story.




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