Okay, as promised I'm back with a real analysis.
I'm going to assume that the reason you are planning to apply in two years is because you have a number of hot irons in the fire that you really can't (not want) to get away from. Otherwise, you would be a reasonably good candidate right now at a top 10 program. Along with a top percentile GMAT score, these next two years should get you closer to a top five program... So I get it.
With respect to how an entrepreneur will be viewed, they are going to pay particular attention to a three factors, vetting them with closer scrutiny than other traditional applicants. Of course these factors are closely related... Think Venn diagram.
The first is your demonstrated passion as an entrepreneur. So have you gone balls out and taken (smart) risk to achieve your goals, or take big steps towards them? Could you have been successful in other arenas, but elected to take the path less traveled. The answers appear to be yes, clearly.
The second is your demonstrated success in your current experiences. That is, while you have passion, is it enough? Put another way, "the road to hell is paved with good intention." So the legit but introductory banking experience appears to be a feather in your cap, so does D-I athletics. I am not sure how much significant traction you have gained with Borgen, but your edu startup appears to be another accomplishment - especially when I consider the sale of the business. Nice work.
The third is going to be the future you project to the adcom - that is, your goals. You could always say that you want to continue being an entrepreneur, but that is something hard for the adcom (and even the career center, who will probably view your app) to quantify. You are going to have to be really specific, especially if it is some type of greenfield initiative. At first glance, I would advise you to examine the possibility of joining an "entrepreneurial" firm, and one that recruits at the school to which you are applying. Let's take Stanford GSB for example. Google will recruit there. They definitely have an entrepreneurial culture. They would definitely love to have someone like you. The kicker - they would have some type of educationally oriented division/function/group that you could eventually work yourself into. With respect to function, you could leverage your product and business development skills, and enter a similar function at Google. These are all suggestions, but they should give you something to think about and investigate.
One last thing on goals - stay away from S/T goals such as "start an investment firm." I'm not sure if you are taking about a fund or some type of VC outfit, but it's going to scare the adcom. These jobs are like unicorns and Yeti. They exist, but do they really? That is, they are really hard to get especially for someone breaking into the industry. Long-term you can pull it off, but in the S/T get more experience in the industry and perhaps a few more gray hairs.
Besides GSB and HBS, I would also put MIT on your shortlist - its an excellent program with strong ties to Silicon Valley.
Let me know what questions you have about the above.
I'm considering applying to MBA programs in two years or so and wanted to get a sense for where I shake out and how I can improve my profile.
Academics: ~3.7/4.0 from Top 5 Public School (BS Business Administration, History minor); Strong upward trend after freshman year; Graduated in 2010
GMAT: Should be in the 750 - 800 range based on practice tests
Athletics: D-I varsity athlete (olympic sport); Team was typically ranked in the top 15 in the country but I didn't play much due to injuries; Academic team captain my final year
Work Experience: Investment banking analyst at highly-regarded group at Goldman/Morgan Stanley/JPM for 2 years; Left in summer of 2012 to launch an online education startup; Recently was "acquired" by another EdTech startup to serve as a de facto cofounder (with commensurate equity stake). The current startup has a significant international component and has an office in Latin America, although we're based in San Francisco/Silicon Valley. In addition to the three founders, we currently employ 4 people. I also started an e-commerce site selling CFA and FRM study materials on the side
Certifications: CFA (not offically a charterholder since I don't have 4 years of finance experience but I've passed the tests), FRM (similar to the CFA program)
Volunteer/service: Regional director at the Borgen Project, a national organization working to eliminate global poverty (5-10 hours weekly time commitment); Participated in tutoring outreach program at GS/MS/JPM; Middle school math tutor at local public school during college
Other: Taught myself to code while bootstrapping my first startup
Post-MBA I’d like to either continue on the entrepreneurship path or start an investment firm focused on high-impact but long-cycle/capital-intensive businesses/projects that don’t fit the typical VC model (e.g. companies like SpaceX, Tesla, Planetary Resources, etc. as opposed to the next social/local/mobile network for XYZ).
I'm curious as to how adcoms view entrepreneurs in general and how you think they will bucket me given that I'm a bit of a hybrid between the banking/private equity prototype and a less traditional applicant. I'm most interested in Stanford (ties to Silicon Valley) and HBS (new Innovation Lab, Rock Accelerator).
Thanks for your thoughts/feedback!
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