Both too old and too young - Can't break into finance

Hope I can get some advice cause my job search has gone on for far longer than I had expected. Have still been actively searching for the better part of the year to no avail. My background is as follows:

  • Recently graduated from one of the top quantitative finance masters programs
  • Did undergrad in finance/MIS at a top 25 US school, 3.5+ gpa
  • Recent internship at a major IB on an equity derivatives sales/structuring desk
  • Completed 2 levels of CFA exam
  • Worked in IT consulting for 2 years
  • Created my own startup business for 3 years (non finance related)

I have gotten some interviews, but many of them have been very skeptical or outright hostile of my profile from the get go (lots of "justify your existence" questions). I think the fact that I started my own business is turning away interviewers that I'd be untrainable even though I'd be more than willing to do the dirty work to get the appropriate experience. I get rejected by associate+ level roles for being "too inexperienced" and rejected for analyst level roles cause "this might be too boring for you".

I'm considering to remove the fact that I started my own business and just say I was a sales guy or something, but I'm not sure what else to do to make my resume fit what they're looking for. I may not be an interviewing wizard, but I have my story down, speak coherently, and prepare thoroughly for every interview just to be shot down at every turn. Original target job was sales/trading at a major IB, but I'm open for nearly anything finance at this point. Any thoughts or advice?

 

Kill the startup from the resume unless you have recognizable clients. I feel you. Exact same situations. I just tell them my story, shut them down, and make them feel bad for asking in the first place.

 

So how old are you? Are you willing to take an analyst level position?

Have you tried going through on-campus recruiting of your grad school? If it's a top program, I'm sure you can get placed somewhere through the school

Born in hell, forged from suffering, hardened by pain.
 

You can get a rough sense of my age by adding up the years of experience + time for grad school. As said above, I've been aiming for analyst roles, but those have been just as difficult if not more so to get in the door despite my willingness to do busy work.

Naturally, the first place I went through was through my school career office, but that was working, I wouldn't be here.

 

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