Optimal structure for a HNW family investor

investor profile

October 26, 2022

by an investor from University of Pennsylvania - The Wharton School in Los Angeles, CA, USA

Hello SF Community,

I am speaking with an extended family member who is a HNW individual considering backing me in a future acquisition in a $3-10M EV range. He wants to provide terms that is somewhere in between a favor as a family member and a commercial investor so he receives a reasonable return. Optimizing for taxes is very important to him.

I am trying to figure out structural ideas that would satisfying the following, assuming no other equity capital:

1) Allow me to retain the majority of the economics and decision making (>70%) with a limited or no cash contribution on my part.
2) Not require the business to ever be sold should I want to keep running the business in perpetuity.
3) Ensure I am repaying him his "principal" or initial proceeds as quickly as the business can manage in a healthy manner.
4) Limit his exposure to ordinary / pass through income and maximize his capital gains.

I am probably being over simplistic here. But what about an LLC or S-Corp, taxed as a partnership, where he owns a small amount of the equity (5-20%), and the bulk of his investment is a promissory note with an agreed timetable and ability to prepay as business can manage. Then create some kind of "agreement" that I repurchase of his LLC shares in the future at a premium. This would allow me to repay his principal back through the promissory note, and provide upside generating capital gains tax treatment for repurchasing his shares over time.

Appreciate any feedback + considerations to my simple idea and other creative structures or ideas that would helpful here.

Thanks so much everyone!

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commentor profile
Reply by a professional
from Dartmouth College in Los Angeles, CA, USA
You can probably accomplish this using a more traditional preferred unit structure for LLC's, The problem with structuring as debt is that he gets no upside on increased value of the business (could be convertible debt but often not ideal for LLC's). I wouldn't try to plan his taxes for him though, as that can be tricky and there are lots of variables. I would propose a structure with the most upside for him and he likely has advisors that can let him know the tax implications and whether it needs tweaks.
commentor profile
Reply by a searcher
from Texas A&M University in Elizabethton, TN, USA
I like your Promissory Note approach. Check with your SBA lender to make sure they will avoid a PG with your proposed structure.

Check out Put and Call options. They will probably need assurance that they can liquidate the equity if needed.
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