Decisions, Decisions

Wow! Thanks everyone for signing up before we’ve even hit the first issue(!) Fall is busy season for everyone, so decisions are on my mind this week—

"What do I sound like if I say yes?" he asked. 

"I'm sorry, what?" I wasn't sure what this CEO was asking me. 

"What do I sound like if I say yes, and then what do I sound like if I say no? Can you just write one announcement for each so I can look at them and decide?"

This was a first. 

Here was a founder making decisions based on how he thought it made him look, and he wanted me to hold the mirror.

The most shocking part is this decision was about taking $ from a certain investor.

Slightly related: one of the better nuggos of advice I've heard is, "you can fix every mistake you make in a business, except one: your cap table."  

It's true. And here was a guy with the biggest line in a $X00,000,000 cap table, making decisions like it was a Tinder profile. Boys will be boys?? 

(The cool thing about working for tech founders is I keep getting happier, and they stay the same age...)

No surprise, his high-flying company hit a wall. They made dumb acquisitions, allowed bad ideas to thrive, and squandered their shine. 

They tried everything to fix it. One of those coaches with overly nice pants convinced the founder he needed a 2-week silence retreat. The board tried a new CFO. We did a big thought leadership campaign to make the CEO popular again.

Nothing worked. Yet today, his company is wildly successful by at least 10x and cash flowing so much that even the VC's don't seem to care whether he IPO's.  

What changed?  

The answer is someone convinced him that decision-making is not an innate skill, no matter how great you think you are at it. 

Instead, you have to learn it, and practice. So he did.

But HOW do you make better decisions?? 

Thinking you are born with strong decision-making is the leadership equivalent of a casual jogger who runs every day versus an olympic medalist. You probably both won meets in high school, but one of you has a desk job now.

Here are the three best models that I've seen work in many situations. I'll be quick on these since this isn’t a lecture and we all have Google.

After these, I'll share one you can do—yourself, right now—and put it to work, called MY LIST. (Yours will have the same name) And after that, I want to blow past my own word-limit to share a hilarious one. 

Model One

I call this the "Dalio Method," but it's been around longer than the $15B he’s made from it. Think of it like "expected value probability." Method: with every choice, you have a probability of being right, and of being wrong. Write what % chance you have for each. Try your best. Then, write the cost of being wrong, and the reward of being right. Multiply those numbers by their respective probability, and repeat for each choice.

It's amazing how often the right answer is not what you thought it would be, and how well this works. I recommend it more for investors and founders than for managers or organizations. 

Model Two:

SPADE. This method is famously designed by the great Gokul Rajaram, who I've never seen or heard discuss it and you should be following on LinkedIn. But like a lot of Gokul's advice, hundreds of strong founders and teams WIN with it. You can dive into the details here, but I think SPADE is most appropriate for managers, teams, and organizations. 

Model Three

is called Regret Minimization, courtesy of Jeff Bezos. All you do is imagine you’re 80 and want to have as few regrets as possible. Now think about the decision in front of you. Mark Zuckerberg’s version was, "What would you do if you weren't afraid?" I recommend this mindset only in more personal decisions, such as whether to bid ole Zuck adieu and start your small business, or whether to ask a lovely Greek girl from Idaho to marry you. (10/10 on both.) 

But what if you don’t have time for frameworks?

Or, even worse, what if you can’t find any consultants with post-it notes and whiteboards to help you adopt them??! Enter, MY LIST.

Here's the easiest, best, and fastest method to make better decisions as a better version of yourself. 

I call it MY LIST. Not because I invented it (I once thought I did), but because mine has always lived in a doc on my desktop titled “MY LIST,” for the simple reason it's about me. 

Method: All you do is start and regularly update a list of your most common mistakes and flaws. Then look at it when you're deciding something. That's it. No gimmicks, no whiteboard. No nice pants. (A little self-loathing does help).

I like MY LIST because it started as a writing tool. As a mild dyslexic, my 2 most common misspellings are "just" and "milk." I literally retyped those 3 times just now. So for 25+ years, whenever I finish any draft, I ctrl+F to search the doc for "jsut," then "mlik." And then onward down my list of usual errors. 

Eventually, MY LIST has expanded. Yours should too.

In particular, it covers the flaws of my character (many), it has why I f**ed up when I've gotten things wrong, and it includes the powerful tendencies of my very ADHD (before it was cool) autist's brain to say the absolute worst possible thing with the best possible timing. (At least a few of you reading this have experienced the other side of that..)

For you: just start your list. Right now. Start with one line, and add on whenever you think of something. Keep it under 50 lines.

This will do more than change your life and relationships. It will financially enrich you and personally fulfill you. I promise. Make my list YOUR LIST. 

And finally, a high-fun decision tool I recommend for every home: 

My little brother is an award-winning winemaker married to an even more successful surgeon. Aka, they don't cook. And they really like Chinese food. Thus is born THE DECISION BOWL.

Method: save the fortunes from your cookies in a centrally located bowl armed with chopsticks. Then, on decisions big or small, consult the bowl by picking any fortune you find with the chopsticks. There you go!  Marital bliss awaits.

The funny thing? It'll surprise you how well it works, for one simple reason: all you really need to do to make better decisions is rethink your own first instinct. Then decide!

You’ll do great, and I want to hear how it goes.

Sorry for the long one this week—I'm humbled so many of you have signed up!  

Write me any time,
Jesse

PS- like all newsletters, below starts the weekly poll.  Keep me honest: was this even remotely helpful? 

PSS - I am BLOWN AWAY by how many thoughts, ideas, and questions I got from my announcement post. Thank you! I've got them all written down and will keep responding 1:1, while I probe my network for better advice than mine. Thank you! And, while this newsletter is still mostly friends and friends-of-friends (please share?), I have to mention the luckiest thing in my whole life is the people I've met. Aka, you. Any other thoughts, obstacles, or ideas you have, I would love to hear them.