Starting own incubator / family of companies - advice on structure

The most important thing is to congratulate you for your success in this. Starting one thing without any external capital is impressive; doing it with multiple ventures even more so.

It's hard to give relevant tax advice without knowing more of the specifics. For that and legal, you should call around to college or family friends who pursued those fields and see if they'll give you 20 minutes of pointers.

From a capital raising perspective, there's one thing that immediately jumps out. There's an advantage to having all the businesses you've launched in the same legal umbrella. If you choose to pay for professional audit and accounting (of that umbrella entity), you have the option of positioning yourself as a sponsor to institutional investors.

Say sometime in the future you find a company you wanted to buy. Maybe it's a competitor to one of your own. Maybe it's somebody who offered to buy you, pitched you really hard on what the combined entity could do, and you like the logic but don't want to give up control. Maybe it's an unrelated business run by someone you know who wants to get out of it for some reason (family reasons, divorce, relocation, timing, whatever).

If you're able to point to clean third-party verification of your portfolio, it's pretty straightforward to put on the independent sponsor hat and explain that the opportunity at hand is larger than you're able to fund principally and you're looking for a partner. Family offices, other private equity funds, and an entire array of professional allocators in the pension, E&F, and fund-of-funds space will happily have the conversation.

Also, if you spend a couple years developing one or two really solid banking relationships, showing a portfolio-level entity can really offer benefits. When I say solid, I mean you either put all the business assets at the same place or make an account for each company at two different banks and divide the assets such that each bank can see meaningful deposits in each company's account.

You should pick regional banks that have strong private banking or commercial lending or sponsor finance practices. Those tend to really invest in the relationship, so there may be instances where you can fund an acquisition entirely with bank debt collateralized by a PG and some or the entirety of the other assets in your portfolio.

The most general recommendation would be to make a limited partnership that owns all the other businesses, then make all the businesses a C-corp. No one (serious) will acquire an LLC, it's a headache. If you choose to sell any of the individual companies, you just sell that particular corporation and there's no exposure to the other corporations owned by the partnership entity.

Long story short, the tax issue is easily solvable through a few thousand spent up-front on professional advice. Be really proactive to share how you think things will scale; that will change the advice you receive. This can get complicated.

The tax complications come from who is the limited partner in the Limited Partnership entity. You can make it yourself as an individual. You can make it another limited partnership (domiciled somewhere else). If you already or plan to have a family, you may want to create a number of different entities, some of which could be trusts, etc. This can also protect you in the event of divorce.

All of this structuring will impact how you're taxed, not only on cash flows you dividend out to yourself in the interim but also on proceeds from any liquidity event in the future.

Congrats on what you've done so far. The fact that you've got unsolicited investor interest speaks pretty strongly.