Hi there,
We can definitely leave room for Paul to reply to this one, but he was a workhorse this week taking home the Kellogg and Haas deadlines, among others. More of my clients finished up earlier, so I'm a bit more rested, if you will:)
I also happen to have a unique take on your situation, which stems from having been in admissions (three years as an undergrad associate director), making hiring and retention decisions (several firms, including this one), and even the "double agent" routine you are describing (while working at one of the world's largest law firms and later at a smaller company, I pursued - hard - a career in television writing that paid off with a manager, agent, and multiple recent sales). I can relate to what you went through, but see it from all sides. I am sure you are going to post this to a lot of forums and you will get a lot of "don't worry, you are great, make the story work for you!" answers, which is all well and good, but how exactly? Not only that, but if that's the advice you get, it's glossing over the most important thing, which is how something like this is interpreted.
Look, we all know how the world works. You have to take jobs because you need employment (to pay the bills, get insurance, and build your resume forward), even when your passion lies elsewhere. Every company that was bootstrapped either came in a fever pitch of desperation, bubbled up out of nowhere (like this did for Paul and later for me), or was done off the clock while working somewhere else. The last option is the most common, surely. So we can establish that you starting a company and getting fired for it is totally within the realm of how the world works and is nothing for which you could be blamed.
However, the world of perception differs from that of reality. I can promise you - and I'm being blunt here - that if I am an admissions officer reading your file, my immediate thought is whether you have maturity issues. Now, I fully and readily admit that THIS IS NOT FAIR, for all the reasons detailed above. You probably worked your ass off (just as I did when I was trying to write TV pilots on the side) and fulfilled all of your fiduciary duties, but a reader is still going to wonder. It's just human nature. So JOB #1 for you in any application is to address the underlying question of maturity. You do this with content selection, going deep on setbacks/mistakes (truly "going there" on HBS 2, for instance, is make-or-break on that app because it shows who has the self-possessed maturity to be real with the reader and who doesn't), and showcasing, when necessary, your capacity to handle difficult situations in a mature fashion. The way you handle this is really not that different from someone who had spotty grades in college, gaps on the resume, or anything other thing that showcase a *possible* lack of focus or discipline.
Okay, so where does that leave you? In good shape. The reason is that even the most distilled set of essay (HBS) allows you to showcase maturity in the app. GSB surely does with Essay 1, Columbia does with Essay 2, and Wharton does with it's entire set of essays (especially in what you choose to answer). Further, interviews are a great check on maturity. So unlike when someone's issue might be intellectual horsepower or something else that is hard to bring to the surface in essays/interviews, you should be able to get well out in front of any questions.
One other thing that I would add here, although it's unsolicited advice, is that you should definitely consider Booth. It's certainly the equal of Columbia and probably Wharton (both as an overall program and also in any individual area, including social life, believe it or not) and more importantly, it's a school built on the idea of taking risks. Your entire story really does become an asset rather than a problem at Chicago Booth because you can talk about not just your willingness to take a risk, but about the way you grow and thrive when you are "out there" engaged in something with a high risk element. MIT is another school you should strongly consider because it is a school that prizes the ability to navigate ambiguity. These are cases where you can take a natural character trait and resulting experience and make it work for you by feeding directly into the DNA of a school.
Anyway, good luck and hope this helps. Paul can certainly still weigh in with any thoughts, but I felt compelled to share mine with you.
Best,
-Adam/
Amerasia 
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11 Oct 2012, 16:44
