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Omar commented on College Bound Toolbox

Thanks for inviting feedback, Cynthia Blair Tognotti -- this is really great stuff. A few quick reactions (and hope we can sync up via phone or in-person later in March): 
1) I can definitely appreciate the need for this intervention, and think you're on to something, as someone who's done a bit of work with this population. The transition from high school to college in particular is something that yearns to be demystified, both for students and for parents. To have a Chief Demystifier and Curator of Great Knowledge Already Out There would be a huge value-add! This is especially true for low-income students, who commonly lack the 'college advisor' sort of role that parents of more affluent children tend to play at the breakfast table. I used to work for a great organization called College Summit -- you should check out their curriculum and peer leader programs for helping manage the minutia of this process. Where they really shine is creating a college-going culture in schools, and helping students write truly compelling personal statements (as well as applications, FAFSA etc). For 20 years they've been running very successful summer programs for rising HS seniors on college campuses, somewhat similar to your summer enrichment approach. 
2) Re my pt above about low-income students, can you clarify your target audience a bit? Students across socioeconomic strata? Those who have the willingness to pay? Regardless of whether this is a for-profit or nonprofit endeavor, I wonder if there might be an opportunity to 'sell' into school districts or charters, who suffer from awfully unsustainable guidance counselor:student ratios (I think it's on the order of 1:500 or worse in CA alone). Districts may even be able to use Title 1 money for this kind of thing, not sure.
3) In terms of format for delivery -- it sounds like you have some experience running these actual 'bootcamps' so this is more than a theoretical early-stage idea, right? I wonder if the intensive in-person model is the only option -- could this curriculum/you and other experts who present as part of it be leveraged as a Coursera type of course? Maybe this is the eventual scale play once the program is more refined...
4) It seems like self-guided interviews are a part of this process, or at least for intake / diagnosis. Other players like Zinch (who I believe were acquired by Chegg), and LinkedIn, have attempted to do some of this. There may be best practices you can leverage, or gut-checking of the questions you've been using.
5) I'd love to hear more about your learnings to date running this 'class.' In particular, are there any pieces of this wide-ranging curriculum that are--or are not--especially well-received? My thought is perhaps you should take on one discrete component and really nail that first instead of trying to tackle the entire process sorta soup-to-nuts (or at least before thinking about digital opportunities to really scale), such as creating a college portfolio. Just seems like a lot, and a lot of work. But kudos to you if you're able to do so -- you're the expert! 
6) Not totally sure what you mean by a 'Digital Planning Kit' and Google Forms -- but if it's for scheduling purposes/a desire to hold students accountable to specific dates, etc. -- Google allows you to create a shared calendar that you can invite multiple people to. Not sure if that's what you're looking to do.
7) I used to work at LinkedIn in its higher ed/student group, and heard that universities were increasingly doing online searches for prospective students. You should consider including a 'LinkedIn profile optimization' component to the curriculum -- maybe even in place of the resume workshop -- and also discussion of how important it is to have a legit and professional online presence (no silly tweets, inappropriate FB pics, etc!). Here's a post I made with some tips for students in case it's of interest at all (meant for college students but can apply for high schoolers as well, who can now legally be on the site):

Sorry if any of this is obvious, inapplicable, or not useful. I don't know a whole lot beyond your description above just yet! Look forward to future collaborations if you want to!  Good luck!