"Everybody could rap but not everybody could make a song" (Ricky Weekly #19)

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

A picture from my life:

Here’s a picture from hip hop class where four asian dudes wore black tees. Two crew necks and two v-necks. Can you even tell us apart?

Thing on my mind:

I’ll share fragments of my thoughts this week…

  • There is a lot of bitching about how the valley is changing. It’s fun to bitch sometimes and important to recognize the massive inflow of capital and increasing influence of tech. But honestly whenever I get asked for my take, I feel like most of the founders I meet today are still the same humble and focused idealists I met ten years ago, and I still love them to death. And really, it hasn’t gotten any easier to succeed, so I feel like the Man in the Arena quote is even more apropos these days.

  • In the last year since I started dabbling in writing, organizing dinners for founders and standup comedy, I’ve heard my label change from “startup founder” to “comedian,” “organizer” and “writer” when people introduce me or talk about me. It is interesting for me to hear that the activities I’m only dabbling in have now taken over as the thing people think of when they try to find a word to describe me.

  • I’m writing a blog post on “single-serving friends” because a friend of mine pointed out an interesting dynamic—sometimes you can’t be totally vulnerable with your closest friends or loved ones because they know too much or you care too much about what they think of you. That means the context of our relationships tend to become too rigid over time. I want to tease this out more.

  • I’m part of three group social experiments now: a “virtual house” for my friends, a habit accountability group, and a book club*, and I’ve learned quite a bit. For example, last week I created an ephemeral “secret room” in my virtual house so that my friends can share things closer to their chest, and I’ve been surprised by how vulnerable people have been willing to be in there. I feel the need to be even more intentional with the experiments so I can learn even more.

  • A quote from Planet Money talking about baseball players income pooling: “they are asking some of the most confident people on the planet, professional athletes who want the bat on their hands with the World Series on the line, to consider the idea. For this to work, there needs to be professional athletes who can live with this cognitive dissonance…to be able to believe in their hearts that they can make it big, and yet, somehow, also understand they probably will not.” I think this applies to founders and equity pooling as well.

*lmk if you want to join the book club to read Annie Duke’s Thinking in Bets, we’re starting soon.

Piece of content I recommend:

Rhythm & Flow on Netflix.

Why I love it so far five episodes in:

  • It’s honest. Cardi B: “Everybody could rap but not everybody could make a song. And it’s all about making a song that sells”

  • It’s a study in confidence. Snoop Dogg: “n***as sweating you and checking you and asking you where you from, trying to draw you back into that negative world…and you wouldn’t allow me to do that, which is strong.”

  • It’s tough love. Cardi B: “Every rapper got a sad story. I got a terrible story. He got a story. He got a story. We all got the struggling story, so we cannot be going for the struggling stories.”

  • It’s technical. Royce da 5’9”: “Maybe have the DJ cut the beat out on certain punchlines that you really want to come off.” Chance the Rapper: “You enunciate really clear but there’s a lack of intimacy there a little bit”

Oh and I love Cardi B.

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 The arc of social