"Stepping stone roles" for experienced hires

I had a weird recent career history that is making it hard for me to get a job in quant trading. I have 4 or so years of relevant experience but I took a couple years to start a company in an unrelated field which is making it now difficult to break back in. I did something super niche in trading and people aren't really hiring for that right now (and/or the roles that exist are super limited). I still am really keen to continue to pursue a career in quant trading over the long term, but I think its reasonably likely that I will fail to score a role in a reasonable amount of time. What are "stepping stone" roles that are similar that I could apply to, ideally at relevant startups or tech companies? One option I considered was going back to grad school but I don't know what else I could really do.  

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