When confidence becomes delusion (Ricky Weekly #22)

This is where I share 3 things every week with my friends and anyone else interested.

A picture from my life:

This picture is special because these two guys are special. They fight me a lot. Intellectually, of course. Out of love, of course. They challenge me on everything and they don’t feel bad making me feel bad because they demand more out of me. That’s the ultimate vote of confidence in me and I cherish them for it.

Oh we ate at Daeho which is a very unique Korean restaurant. Never had anything like it. The line is nuts though I recommend putting your name down 45 minutes before and go sit at YakiniQ Cafe next door.

Thing on my mind:

I was talking to someone about what we can do to help more people start businesses. Some of you may know it’s something I’ve been thinking about since college. Of course, not everyone should start businesses, but outside of the Silicon Valley, the rate of new business formation has been declining for decades, so it is worth asking what is the difference between someone who starts businesses and someone who stops just short of starting.

It’s definitely not a matter of talent or skill. I know a lot of people who suck at most things and still start businesses (and succeed). The biggest factor is probably confidence. Confidence can come from a lot of places like how you were raised and your self-perception (or self-delusion). I’m guilty of sometimes poking fun at founders who seem way over their heads, but delusion is just when confidence crosses over to the point of being easy to ridicule, and where that line gets drawn depends a lot on the environment. I remember back at Stanford I thought my peers were extremely confident. Today looking back, a lot of them were simply delusional. But at Stanford, I was in an environment where I was encouraged to dream big, so I didn’t think of what I saw as delusion, but just confidence and ambition. It’s actually really hard to be considered delusional at a place like Stanford. Silicon Valley is not as encouraging as Stanford, but it is probably the only other place in the world where the line is much closer to the side of delusion. That line for America as a whole is closer to delusion than it is compared to the rest of the world. That’s why even though American students have terrible academic rankings, we almost always rank number one in self-esteem.

What’s also interesting is what happens after you start a business. There’s a certain threshold of confidence you have to have in order to start, but what follows is an onslaught of an infinite number of moments when you are require to muster up courage. When I help founders, a lot of what I help with boils down to helping them overcome these moments. As a founder you constantly have to tackle problems you’ve never seen before that you are not equipped to take on and that you are solely responsible for if you fail, and you fail most of the time. You might have to hire an exec, but you’ve never hired an exec before, and a bad hire could kill the company, and that’d be your fault. You might need to use the rest of the company runway to take the product in a new direction, and if you’re wrong, you’re SOL and everyone will need to find jobs. There are an infinite number of these moments big and small that require leaps of faith. Not as big of a leap as starting a business in the first place, but feels big enough especially if you’re constantly required to leap. You can’t run from it. You better have more than a healthy dose of confidence and know how to generate more when required.

I started a list of the techniques I use to increase my confidence because I was thinking about sharing them in the newsletter, but I ended up with too many so I’ll just recommend two of my favorites: David Goggins’ Cookie Jar and Tim Ferriss’ Fear Setting.

Piece of content I recommend:

Dolly Parton’s America by Jad Abumrad of Radiolab (h/t Charles Naut).

Just…WOW! The podcast series is not finished yet but it might be one of the best ever. I knew almost nothing about Dolly Parton. What struck me was the question, “can a celebrity be apolitical these days?” Her songs are feminist anthems, yet Dolly Parton says she’s not a feminist. She refuses to speak against Trump, even though her songs celebrate refugees and are embraced by immigrants. She is loved by both sides of the political spectrum but the contradiction is also more than blatant. I tend to not like it when people are forced to declare positions and risk losing the nuance in their views, so listening to Jad Abumrad question Dolly Parton, and hearing Dolly Parton parry with her charm, humor and music is fascinating. I don’t have a complete thought here yet, but I hope you get a chance to listen to it.

Question for you:

What do you do to generate confidence or reduce fear?

As always, you can find out what I’m thinking in more real-time on Twitter and my essays are on my website. My latest essay is called Single-serving friends