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Simple answer:

A successful founder will sell 1 (maybe 2) companies in their lifetime, while PE/VC firms do these deals every day of the week.

It's like entering the ring with a pro MMA fighter and expecting to have a fair fight. You have a massive disadvantage that can't be overcome. The best you can do is take precautions and "do your best" but "your best" and "precautions" still isn't good enough if your opponent really wants to screw you over. Unfortunately this happens all the time in VC, and especially in PE.

As an example, when you sign a term sheet to sell a company, most founders assume the deal will go through at the price that was agreed. In reality, deals almost never close at the originally agreed upon price. The buyer usually waits until the very last minute, then drops the bomb on the seller "Btw, we can't do the deal anymore at this price, but we can sign tomorrow for 30% less". The sad part is it's such a common tactic and PE firms will do things like encourage founders to get their whole team excited about the transaction -before- dropping the bomb / new deal terms. At which point the founder is basically trapped with their whole team excited about an exit, which PE then exploits.

All of the lawyers in the world won't help if the PE/VC firm has the ability to spread the word "Don't do business with John Appleseed" effectively shadow-banning you from future funding from anyone. PE/VC world is very small and they have a lot of political leverage, which almost always trumps any legal leverage a founder might have.

The best defense is to have another VC/PE on your side.

That also puts bootsrapped companies at a severe disadvantage (no VC fighting on their side for the best outcome). There literally are PE firms who specialize in buying "family run bootstrapped businesses". Why? Because they're the easiest to screw over and exploit.



> The buyer usually waits until the very last minute, then drops the bomb on the seller "Btw, we can't do the deal anymore at this price, but we can sign tomorrow for 30% less". The sad part is it's such a common tactic and PE firms will do things like encourage founders to get their whole team excited about the transaction -before- dropping the bomb / new deal terms. At which point the founder is basically trapped with their whole team excited about an exit, which PE then exploits.

Eh, this was tried on a friend of mine selling his company. He simply said "the deal's off" and walked away. A couple weeks later, he got another call which said "ok" and he got the full price.

> That also puts bootsrapped companies at a severe disadvantage

It's very simple. Just say "no". It's an incredibly powerful tool. It's crucial to getting a proper deal on anything from selling/buying your house, your car, to your company. Be ready to walk away. Sometimes by the time you started your car and are backing out of the parking spot, they'll come running out and say "ok".

But you gotta mean it when you say "no" or you'll fail. They can smell weakness.


“You have to be prepared to walk away.”


At a first approximation, negotiating power in most things is proportional to your credibility to abandon a deal.

As soon as a counterparty knows you can't / won't, you're negotiating from a much worse position.


One other advantage of buying family run bootstrapped businesses is that they're too small to trip antitrust scrutiny. There are entire industries whose driving consolidation force is a handful of PE firms buying up old family businesses and running them into the ground. Things like funeral homes, dental offices, and the like.

Yes, I did learn about this from Cory Doctorow, why do you ask?


Links? I’d love to read more.



> while PE/VC firms do these deals every day of the week

That's why you hire a lawyer that also does this stuff everyday of the week.


This sounds so easy but plenty lawyers sound great but have no clue either, or will believe that bad ideas aren’t, etc. And they’ll deal with the same VC much sooner than with you, so they’re not particularly incentivized to play super hardball.

If I were a first time founder I wouldn’t know where to find the right lawyer. In all honesty I still don’t and I’ve been at it for 8 years now.


I was tangentially involved in a deal where a Big Tech company acquired a VC-funded startup. The startup hired an investment bank as an advisor. The same investment bank that routinely underwrites debt offerings for the Big Tech company. Somehow they advised the startup to take the deal and not play hardball, even though there were public company comps at twice the valuation offered.


>effectively shadow-banning you from future funding from anyone.

"You had better sell your business to us for a pittance, otherwise we'll lock you out of future deals."

"Ok, here you go. Now can you fund my new thing?"

"Ha! After we screwed you so hard last time? No way, you'll just set our money on fire out of spite. Way too risky."


> "Btw, we can't do the deal anymore at this price, but we can sign tomorrow for 30% less".

Is this bad-faith stunt pulled after the company spent months focusing energy on the deal (rather than on the business)?


> You have a massive disadvantage that can't be overcome

If somebody can't understand that they need to retain a majority of the voting rights to retain control of a company, then you're certainly right about them being at a massive disadvantage.


> You have a massive disadvantage that can't be overcome.

You hire a law firm to advise you on the deal.


I wonder how one would select a competent law firm that won't charge exorbitant fees, knows what they're doing and actually has your best interests at heart. It seems like a similar problem to the one you're trying to solve by finding a law firm, namely not having any experience in the area to make a good decision.




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