Barriers to entry on middle market gig

Has anyone had any luck raising or advising capital on smaller scales after your BB stint, and turned it into an actual side hustle? True IB work is not necessarily difficult once you understand how the game works, so if you have a few relationships with a family office investor, or HNW, how feasible is it to make them a client and essentially run your own advisory shop? I'm referring to engagements that would look like private placements, equity raises, debt underwriting and managing the transaction with a bank, paper work, etc.

Anyone have experience doing this that can share their story about how they got it off the ground, or what the first step was?

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