Which Opportunity?

5 to 10 YOE, don't want to be specific. All of which have been in IBD / PE - I'm in a region where PE opportunities were scarce until the past few years (MFs weren't even really present here until recently), so lots of people, myself included, only jumped to the buyside after Yr 5 or even Yr 6.

I made a couple of bad career decisions, so based on market feedback, I'm probably at a Snr Aso level for MF / UMM / MM, or VP at an LMM.

I might soon have to choose between 2 opportunities:

  1. Snr Aso at a top team in a MF 
  2. Working directly with a billionaire who has had multiple unicorn exits (and they've made at least 1000x on every one)

Option 1 seems more "safe" and typical, but I find #2 so much more exciting. I do have a history of making really bad career choices based on what is more exciting, so I'm second guessing myself.

Option 2:

  • I will be working directly with the Principal, they're explicit that they want me to shadow them
  • They are incredibly nice (vouched for by multiple people) and we clicked really well. They said that I have a similar thought process and temperament to them (I'm a bit quirky though generally I've been well liked in most of my past jobs), which tbh is not that suited to IBD / PE, though I've survived so far
  • cash comp will obviously be lower, but they may be open to me doing co-invest / having a bit of equity in each investment made. And since they are looking for unicorns, the upside could be really great. Also, I gather that getting carry at MFs is really, really hard

Option 1:

  • The team head is not only a rockstar but is a really good dude (vouched for by multiple people)
  • The sector has good tailwinds

What would you choose and have you seen any similar situations play out?


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