Ask HN: How did you get to your current job/startup?

As for my resume, I have a PhD in computer science from Oxford. I also spent a year in Australia on a fellowship. Since I'm American, I came back to the US to work in quantitative finance, which is the field I've been in for almost nine years now---four at my current place.

So that sounds impressive. Now I'm going to explain how close all of this came to not happening...

I grew-up in the rural deep South. My parents were extremely well educated and well traveled, but they had careers that didn't make any money. So I basically put myself through school. I got some scholarships and I taught part-time, but I had to take-out a lot of loans in the end. By the time I returned to the US, I had over $100K in debt from students loans and credit cards.

I didn't manage to get a job when I first got back to the States. I moved to NYC anyway and couch-surfed with every friend I could think of. (I ran-out of people I know, so I ended-up in a hostel for a few weeks.) I'm a fencer, so I refereed college fencing tournaments for enough money to eat.

It took five months to get my first quant job. The job I have now is the fourth such role because the first three trading desks I worked for all ran into the ground one way or another.

Along the way I had a big healthcare issue that resulted in surgery. That took years to prepare for and to heal from.

And since you ask about failing a class, I never made below a B- in a course, but I did fail my thesis defense the first time around. I had to resubmit my dissertation with a ton of changes to pass. (By the way, I got rejected from every grad school I applied to except for Oxford.)

So when you think that your current path is difficult, just know that I have survived two recessions (dot-com and financial crisis) and been turned-down from most jobs I've applied to.

I have three pieces of advice for you. Firstly, always be frugal. Despite my heavy debt when I returned to the US, I actually have flawless credit since I've never paid a bill late. That kind of history comes in handy a lot.

Secondly, always keep learning. Especially in my field, I have to keep-up constantly, which means following Hacker News, reading ACM/IEEE, taking MOOCs, etc.

And third, make friends. Help-out other people as often as you can. You will need them in the future.

Throughout this time I kept playing with things I liked the look of, blogged a lot, generally spent a lot of time online. I picked up Ruby and Rails and a publisher who saw my blog wanted me to write a book. I did, launched a blog to promote the book, the blog became the most popular Ruby blog for several years and a business in its own right. I then branched it out into email and now run an email newsletter business with 5 employees. (Most of this last paragraph has taken 11 years - I first picked up Ruby in November 2004.)