Taking money off the table

I believe the complete opposite. If someone is willing to buy your business, no matter the amount, it’s because it’s worth MUCH more than what they’re paying. It’s illogical for them to pay less than its real value. It’s even illogical to think they’d pay exactly what it’s worth. Why would somebody bother buying a company if they were only going to break even?

You are ignoring the risk aspect. There is a chance that it is worth more than they are paying, but there is also a chance it will be worth less.

Selling a part of your business can help spread risk to a new investor reducing your own personal risk.

This assumes risk appetite is the same. For instance, insurance works this way - in expectation you’d pay less yourself, but a 3 sigma event can bankrupt you. You willingly pass on this risk for a price.

Almost all startups go to zero, meaning every cent what VCs paid for stock, at any price, did not end up being worth more than they paid.

Everything you said is true. It doesn't refute that you should sell the 10% though. You're describing commerce.

not getting it.

what I'm saying is the buyers are subject to the same risks, I'm not ignoring them

But obviously an investor with $XYZ under management that can make N bets is better equipped to handle that risk than you, an individual with 1 bet.

Sure, what I'm getting at is that in your hands, or in the buyer's, the value can go to zero or multiply. If they buy, it's because they assess that the chances of it multiplying are greater than it going to zero. Why sell in that case?

The reason anybody is willing to buy and sell anything is because there's no single "real value" of anything. Value is contextual. When the grocery store gives me a cake in exchange for $20, it's because the value of the cake, to them, is less than $20. Conversely, the value of the cake to me is more than $20, otherwise I wouldn't be buying it.

If you sell your business, it's because the value of the business to you is less than the purchase price. Likewise, the value to the buyer is greater than the purchase price.

fair point :)

great example, thanks

what if the buyer has something that can add value to the business?

The buyer is not assessing that way. The buyer has a diverse portfolio where they only need 10-20% of their bets to succeed. The math is not in your favor as an employee.

I worked for a company that had a buyout offer for 8 or 9 figures that they turned down. After I left the company ended up collapsing with no exit. It happens frequently.

No, it means they buyer thinks it is worth more than what they are paying. It doesn't mean they are right. It also means that this is the only buyer who thinks the company is worth that much, because if someone was willing to pay more, the company would be selling to them instead.

Ideally startups are about creating value, and making a return on that value, but more and more they look like they are instead selling hype to a series of investors who are trying not to get stuck with the hot potato.

You're selling only 10%, you still get to see the other 90% go up in value, but that 10% you sold protects you from a wipe-out.

Your intuition is wrong here. Check out the Kelly criterion and do a little math - by my math, when you have modest personal assets <$1m, if you expect a 200x return from today, and you think there's a 1% chance that'll happen, you should sell 99% of your current stock and only hold the 1%. This maximizes the preservation of your net wealth.

VCs have MUCH larger bankrolls and so their Kelly bet is proportionately larger, but not percentage larger.