Entrepreneurship and Banking

I'm currently a consultant in strategy & economics, working exclusively with F500 (and global equivalent) CFOs and Corp Dev VPs. It's mentally stimulating, but as a decently successful entrepreneur, I realized I can't stand being arms-length from creating value and need to be IN the market to be happy. I also came to despise, at a deep philosophical level, the stable, salaried job that lacks worthwhile production-based incentives.

Despite this being a fairly elite firm, I was somewhat ostracized when people realized that I, the analyst, had earned several million dollars through the sale of a business I built in college. I didn't put this on my resume for fear of being unjustly treated in a corporate environment, but alas word gets around. Now that I'm setting my sights on the buy-side, I'm wondering how my early success should be addressed, and who would value this experience.

The Story: I boot-strapped an internet media company (EBITDA $2m, high growth) with a partner and exited in 2007 before valuations plummeted, personally taking in sizable piece of the $10-20M sale minus taxes.

It's all invested and I don't intend to live off of anything I don't make at work. Some will say I'm masochistic, I should quit working, but I love the game that much. I want to work with and learn from the best in IBD or a global macro hf (very different, but my exposure and interests are pretty broad).

College highlights include top-20, research with the Atlanta Fed, and articles published in a couple of well-respected journals. GPA won't do me any favors but I'm one of those who valued learning for learning's sake, less about the residual measurement. Still, I was highly-respected by professors and invited to participate in departmental honors for econ despite not making GPA cutoff.

I'm applying and having some success with interviews, but still feel as though the typical HR generalist doesn't know how to handle a candidate like me. Any guidance would be much appreciated.

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