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Back in the day, I liked a particular one by a guy named Steve Pavlina who wrote a rather excellent series on how he ended up coming to his senses while spending 24 hours in jail, finishing 3 years of college in 3 semesters, running a minor software company, and eventually earning a good living from his blog. For instance, if one day you woke up with 2 hookers sleeping on the floor of your hotel room and leftovers of cocaine on the coffee table, 30 text messages and 9 voice mails on your phone, all the while realizing that the model you were working on before the party started has to be done in 2 hours, and saw that as a day of reckoning for your IB lifestyle, we’d love to know.” So I’m not going to spare any of the juicy stuff.And you can take a shot every time I mention 2 hookers and leftovers of cocaine – the 30 text messages and 9 voicemails are optional.WARNING: Read This First This is an “off topic” post, and if you’re looking to read more about interviews, what it’s like on the job, hedge fund case studies, or financial modeling, well, you’ll have to wait until next week for more of that. When it came to business skills and “real world success,” though, they came up short.Also, if you’re easily offended or you want sugar-coated nonsense rather than my “no B. So I came from a very middle-class background – I don’t think my family ever earned more than -70K per year, combined – and I had a fairly unremarkable youth, where I never traveled far outside of my home state for 15-16 years.I was creating websites back when most people were using 28.8K modems on AOL, and I even started a web design and development business back then.It turns out that getting your local mayor and other small businesses and organizations as clients is easy when you radically undercharge for your services (not recommended).Over time, though, the work started to pile on and on and on, and deals started to look the same after a while (Jonathan Knee shares a similar story in , though he was at a senior level when this happened to him).

My other “passion” growing up was writing, and my proudest accomplishment was pulling one of my first all-nighters to write a version of The Pearl (John Steinbeck) set in the Middle Ages.I thought about all of those, and I interviewed extensively with tech PE and VC firms. This was before the credit crunch, so at one point I was actually working on multiple leveraged buyout deals at once.By the middle of 2007, I had progressed far into interviews with several of these firms. On May 17th, 2007, I was certain I was going to pull an all-nighter and I gave a status update to that effect to an MD as he was leaving the office that day.From middle school through university and beyond, I was set on following the usual “path” toward some elusive but vaguely defined “greatness.” Following that logic, I ended up at Stanford and bounced around between different possibilities both while I was there and after graduating: engineering, consulting, project management, and yes, ultimately finance. I had nothing even remotely finance-related in my background: I had completed a technical degree (Computer Science), I saw myself as an artist / creative type rather than a businessperson, and I wasn’t even a drug addict or serial killer.The only correct decision I made at this point was crossing “law school” off the list fairly early on (phew). Plus, I knew almost nothing about accounting or finance back then.In contrast to my immediate family members was my Grandfather, who had run his own small business – a chain of auto repair stores – for over 30 years.

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