Even if AI is the best thing since sliced bread
Sending money from novice investors is just not a good idea. There is a reason that the big markets have rules about sales/expenses etc along with generally accepted accounting principles. So that a person investing 10 grand doesn't need a PhD in accounting to make a somewhat informed decision.
And even in the big boy markets, silly me, I got a lesson. I bought a stock that was public, that is called a PTP, Publicly Traded Partnership. Like always, I dipped my toes in as it was an area I wasn't too familiar with. The brokerage even popped a dialog indicating it was "risky". I looked over several years of their price and thought looks stable, they were a energy pipeline company, payed good dividends as "Return of Capital" which again, silly me, I had no idea the implications. What the brokerage should have popped was a dialog saying your taxes are going to be a nightmare. And they have been. The complexity added to my return as a result of this short lived purchase and fairly minimal return is nothing less than bewildering. I'd never expected a "K-1" from a stock I owned and all that goes with it. The 1099 from the brokerage was just the beginning of the tax journey, whereas for all the other stocks I've owned, it is the end and the beginning.
So my overall point is, I can't imagine the tax complexity added by owning a "private" company. And the complexity may not happen until the year you sell it. I doubt the small investor has access to the accountant they are going to need to decipher the tax forms they get.
