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Churchill, Optimism, & ‘F*ck You” Money

By: Michael Blankenship |

“We will either find a way, or make one.” 

~Anibal Barca.

Greetings from LA and Oahu!

This week we’re discussing Churchill’s legendary saga, why “F*ck you” money is the pinnacle of true wealth, and the difference between beneficial optimism and unbeneficial optimism


Churchill’s Saga

“Churchill’s great trick—one he had demonstrated before, and would demonstrate again,” Erik Larson writes, “was his ability to deliver dire news and yet leave his audience feeling encouraged and uplifted.”

The history of WWII and of Churchill’s part in it has been documented by experts ad nauseam, but Erik Larson’s recounting of Churchill’s leadership and defiance during the blitz in The Splendid and The Vile offers a refreshing and highly personal account of what occurred during those dark years in Britain. 

For example, here are some anecdotes you might not find elsewhere…

“Churchill believed marriage to be a simple thing and sought to dispel its mysteries through a series of aphorisms. ‘All you need to be married are champagne, a box of cigars, and a double bed,’ he said. Or this: ‘One of the secrets of a happy marriage is never to speak to or see the loved one before noon.’ Churchill had a formula for family size as well. Four children was the ideal number: ‘One to reproduce your wife, one to reproduce yourself, one for the increase in population, and one in case of accident.’”

Here’s another…

“Churchill stayed at the White House, as did secretary Martin and several others, and got a close-up look at Roosevelt’s own secret circle. Roosevelt, in turn, got a close-up look at Churchill. The first night Churchill and members of his party spent in the White House, Inspector Thompson—also one of the houseguests—was with Churchill in his room, scouting various points of danger, when someone knocked at the door. At Churchill’s direction, Thompson answered and found the president outside in his wheelchair, alone in the hall. Thompson opened the door wide, then saw an odd expression come over the president’s face as he looked into the room behind the detective. ‘I turned,’ Thompson wrote. ‘Winston Churchill was stark naked, a drink in one hand, a cigar in the other.’ The president prepared to wheel himself out. ‘Come on in, Franklin,’ Churchill said. ‘We’re quite alone.’ The president offered what Thompson called an ‘odd shrug,’ then wheeled himself in. ‘You see, Mr. President,’ Churchill said, ‘I have nothing to hide.’”

In many ways, it has the entertainment value of a fiction book but with the accuracy of a history book. We highly recommend it if you want to learn more about the WWII time-period… without reading the same old retelling of events. 

“F*ck You” Money

What is the optimal amount of wealth? 

One common way to answer this question is through the idea of “f*ck you money” — an amount of wealth that gives you the ability to say “f*ck you” to people who would like to control you. 

This is usually thought of as a minimum threshold which, once surpassed, provides freedom forevermore. 

But Jack Raines over at Young Money suggests that the correlation between wealth and freedom is more of a bell curve. 

Being poor means less freedom. But also being too wealthy means less freedom — true wealth and happiness lies somewhere in the middle. 

“Would you,” he writes, “switch places with Elon Musk? $229B net worth. Known for creating the world’s first reusable rocket ships, taking electric vehicles from pipe dream to reality, and posting dank memes on Twitter. You could live anywhere you wanted. Date anyone you wanted. The world would know your name, and you would go down in history as one of the greatest minds of the 21st century. If you said yes, I want you to really think about it for a minute. Read these quotes from a 2018 New York Times article about Tesla’s CEO:”

He then provides strong evidence of Elon Musk’s personal challenges, concluding, “And Musk isn’t an exception. I would say for the ultra rich, he is the norm.”

It’s important for each of us to ask how much wealth is enough — we don’t need to be billionaires to have maximal freedom and happiness. We just need to be wealthy enough. Then, we need to have the wherewithal to actually embrace and enjoy the wealth we’ve created. 

So… how much is “enough”?

“Ironically, the best indicator of having ‘f*ck you’ money is the absence of having to think about money at all. The billionaire hedge fund manager trying to outperform last year’s returns doesn’t have ‘f*ck you’ money. Neither does the minimum wage worker struggling to survive.

While these individuals reside on opposite ends of the income spectrum, their minds are consumed by thoughts of needing more.

The guy with ‘f*ck you’ money? He doesn’t think much about money at all.”

Beneficial Optimism

It’s no secret that optimism is critical for success.

Daniel Kahneman wrote, “When action is needed, optimism, even of the mildly delusional variety, may be a good thing.”


Something we’re learning is that there are different modes of optimism. Some are beneficial and some aren’t.

There’s the optimism someone has at the outset of a pursuit — the belief that this thing they’re doing is going to work.

That’s critical.

Because without that they’d never get started.

Then there’s the optimism someone has before they show the thing they created to the world.

Here’s where optimism gets dicey.

Being overly optimistic about how your thing is going to be received by the world often leads to discouragement… and quitting.

Because there’s a very real chance that it’s not going to be a huge success.

This is where a person’s optimism needs to be kept in check — it’s far better, in fact, to expect poor results and to be surprised by excellent results.

Or better yet, throw expectations out the window and embrace the journey.

Remain curious.

Think of it like you’re trying to solve a puzzle.

The best mode of optimism endures in the face of failure — it’s the belief that you’ll figure it out EVENTUALLY. 

Maybe not this time around… but by trying, failing, and above all, learning, you’re going to succeed at some point.

THAT is the mode of optimism we’ve seen in our most successful friends.

They are unphased by failure, always curious, and they have an unrelenting belief that they’ll succeed eventually with enough hard work. 

Extra Stuff

Here is some other random stuff we found interesting this last week!

This Week’s Photo

Pedro Pardo / AFP / Getty

“People run from fireworks before the traditional “torito” (little bull) made of paper, wood, and fireworks during celebrations of San Juan de Dios in Tultepec, on the outskirts of Mexico City, on March 8, 2022.” via The Atlantic

This Week’s Riddle

Here’s this week’s riddle — the answer is at the bottom of the email!

Two men are in a desert. They both have backpacks on. One of the guys is dead. The guy who is alive has his backpack open and the guy who is dead has his backpack closed. What is in the dead man’s backpack?

This Week’s Question

Answer this question — either privately or by replying to this email. If your answer inspires us, then we’ll ask for permission to include it in a future email!

Where do you think the line between beneficial optimism and un-beneficial optimism lies? 

This Week’s Challenge

Choose a point in history that you’re interested in learning about and purchase a book to learn about it. History is full of fascinating stories and lessons, and, fortunately, many great writers have taken it upon themselves to document those events in an entertaining and easily-consumable manner. Take advantage of that!

Until next week, 

Mike & Alec

Riddle Answer: A parachute.

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