Imagine that you’re an executive at a huge company. How much would you pay to undo a mistake? How much to avoid one in the first place?

Let’s use the example of Elon Musk’s purchase of Twitter. Was it a bad idea? We know one person who thought it was a terrible idea:

Elon Musk.

Here’s the sequence of events:

1. Elon Musk jokes about buying twitter
2. He buys a bunch of shares
3. He enters into an agreement to buy the entire company
4. He gets cold feet and tries to back out, eventually suing Twitter to cancel the deal
   • It is at this point that we can safely say Musk felt buying Twitter was a bad idea
5. It becomes obvious he’s going to lose so he settles, going forward with the purchase basically unchanged

Musk tried to back out by claiming that Twitter overstated the number of human users on the platform, and that there were a lot more bots which fundamentally changes the economics of the deal. That would be a decent point to make, but it didn’t matter because musk had waived due diligence.

What this means is that he decided to skip the process of confirming that what Twitter said was true. So even if it turned out that Twitter users were 50% bots and they had claimed 5%, it wouldn’t matter. He had a chance to look at the books and decided he didn’t want to.

Whether or not the entire deal was a good idea, we can safely say that waiving due diligence was an awful, terrible decision — one that Musk himself came to regret.

I imagine Musk’s lawyers told him it was a bad idea, but he uh … doesn’t listen to them much. Did any of his friends or advisors tell him it was a bad idea? Probably not. Texts made public in court are full of other billionaires, millionaires and executives cheering him on. Only one person pushes back against Musk: Parag Agrawal, Twitter’s then-CEO, who told him that Musk constantly bashing Twitter ON Twitter wasn’t “helping [him] make Twitter better in the current context…” This relatively mild pushback soured the relationship, which Jack Dorsey tried to patch up but eventually gave up, saying: “At least it became clear that you can’t work together … That was clarifying.”

The scourge of Yes-Men

Musk, like many powerful and/or wealthy people, is surrounded by “yes-men” —

(I was going to say “yes-people” to indicate a yes-man doesn’t have to be a man, but the phrase is so well-known I don’t think it makes sense to try and de-genderize is at this point, though I could be convinced. You know what, I may be convincing myself right now. Naw, not yet)

— Yes-men are those that basically say what someone wants to hear. They create echo chambers around the powerful that lead them to believe that their bad ideas are good ones. Some people surround themselves with yes-men by ejecting anyone who challenges them (Musk seems to be this type, but I don’t know him personally), while others are surrounded by yes-men almost by accident.

However it happens, it’s bad news. It means if you have an idea to do something crazy (like buy Twitter) and it keeps getting crazier (let’s do this! Who needs due diligence!?!?) there’s no one in the room to pump the breaks and introduce some rationality.

Enter the No-Men

That’s when you need a no-man. Someone who is a professional devil’s advocate, there solely to be a lone voice of dissent amidst a sea of enthusiasm.

That’s not to say they should be a downer or a constant source of negative energy. Instead they provide constructive criticism.

Think of the example of Musk buying Twitter. A No-man in the room would’ve likely said almost immediately “Hey, is this the best way to spend your time and money? Think of all the good you’re doing with your other businesses? Shouldn’t you stay focused on them? Think of the good you could do with almost …. $50 Billion Dollars. Is buying Twitter really the most valuable thing you can do with that money?”

If Elon said “It IS the most valuable thing I could do with that money! And I’ve got plenty of time to manage Twitter along with everything else” (which he almost certainly would) the No-Man might then say “OK, I understand this is important to you, but there’s no rush to get this done tomorrow. And there’s certainly no need to waive due diligence. Twitter’s value isn’t going to skyrocket over the next month and become unaffordable for you. Let’s take some time and run the numbers. Let’s not waive due diligence. Let’s meet with the people at Twitter and get to know the product intimately before we invest the GDP of New Zealand into a it.”

Could a no-man have stopped Elon Musk from buying twitter? No. But could a no-man have given Elon Musk the ability to stop himself from buying twitter once he realized it wasn’t the great idea he thought it was? Maybe! And how much is that worth? In fractions of “The GDP of New Zealand?”

So what’s the business?

A no-man is an expert at understanding and evaluating ideas. They are incredible communicators who can build a rapport with almost any one, empathize extremely well, and can challenge without offending.

These people are out there, but they’re rare and, probably, very expensive to hire. So we would, unfortunately, only offer very expensive services:

• A dedicated no-man for one individual, to basically either serve as their shadow, or to have the same access as an executive assistant and meet regularly with the individual to discuss ideas and plans that are coming up.
  • This person would be contracted for at least a year so that, if the client hates them, they’ll be incentivized to stick with it because they already paid, say, a million dollars for a year of services up-front
• A fractional no-man, who meets regularly with clients but discusses things they bring up — they aren’t proactively inserting themselves into conversations to know what the client is up to and head off potential mistakes. This would be significantly less expensive.
• A single idea evaluation — send us your proposal and we’ll poke it full of holes in the kindest way possible. This would be very expensive to discourage people from just using that service over and over again instead of hiring a fractional or dedicated no-man.

This would more or less be a think-tank that is focused solely on critical thinking, research and evaluation. It would be a very cool place to work!

It would also be very difficult. Powerful people typically don’t like to be told “no” and paying lots of money to have someone do that continuously … seems like a hard sell. You could go about it in other ways (my wife recommended targeting boards to encourage them to hire a no-man for their CEO if they’re worried about risky behavior), but that first hurdle still may be too difficult to overcome.

On the other hand … who can resist that pitch? What would you pay to avoid mistakes?

If only there were some service that would poke holes in this idea for me so that I can perfect it.

Appendix: Other names

Obviously I don’t love the term “No-man.” It’s both negative and exclusionary. So here’s some ideas for other names, as a little bonus:

• Professional Devil’s Advocates
• Diligence Doers (Due-ers????? — my dad gave me this one but he had poor reception and I may have misheard him)
• OTTH (On the other hand, and we’d call the people … OTHER HANDERS? That’s terrible)

Never mind, this bonus is making me feel terrible about my creativity. This appendix is OVER.