Thanks for posting and sharing all that info! You're quite right, that's a pretty unconventional path. So I'll provide my thoughts on each of the main sections and then we'll go from there, sound good?
Academics: Great GMAT and a decent GPA. While your undergrad institution isn't exactly pedigree that isn't the end of the world. Your Finance major will be a plus because it requires a bit more quant than other concentrations so that'll be good. Overall, however, your academics are kind of a wash. The GMAT and GPA against your undergrad institution and the drop out component, etc.
Professional Experience: Well, now this is an interesting path. Your pre-2008 experience is going to have to be carefully portrayed. It's sufficiently in the past such that you won't have to necessarily use it as a source of stories, but it'll be a big part of your resume and history. Especially given the issues with some businesses failing, you'll have to make sure it supports your story. Your experiences post graduation are really strong. There are a lot of key themes that folks in innovation/product development can tap into that others can't as easily. Also, like the fact that you lead the team and, more importantly, that your team's ideas have actually been implemented (which means NUMBERS!). Sorry, I get excited when it comes to impact
EC: This is the first time I have ever read these types of EC activities. Not a lot of folks work with inmates. Even fewer enact successful programs for them. That's pretty impressive! Your involvement in undergrad is noticeable as well and I like that you're a martial artist. It seems to be something you're passionate about and probably fairly good at! It adds a "cooler" dimension to your personality and that's important.
Personal & Goal: Ok, you're a little bit on the older side. Nothing disastrous, but the top tier programs, especially Stanford, value youth. However, having recs from Stanford alum is KEY. As for goals, I'd stick with product management. Consulting is a dime a dozen. You can pursue that when you get there, but for story purposes, product management/biz dev is stronger.
I think you have a pretty interesting and strong profile but you do have a few yellow flags. Nothing that will derail your application but it'll make some of the schools you think are "reaches" or "targets" harder than you believe. I don't say that because I don't think you should apply there - but I think your school list could use two things. One, it could use a little diversification. You've listed the top 5 programs and nothing outside of that. You should really consider looking outside of just the ranks to find the schools that fit your goals. For example, Ross is fantastic for Product Management. Secondly, I'd suggest you narrow the list based on what's important to you. The schools you've listed are really different from one another in a lot of ways.
I hope that helps and if you want to talk about any of this in more detail or want to ask more questions, we'd love to chat with you so just let us know!
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