"You should run your startup like you play basketball" (Ricky Weekly #30)

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

Announcement: I wrote a fun new essay called “From Socialcam to TikTok: How we figured out video social in a decade” to try to understand the TikTok phenomenon.

A picture from my life:

This is my friend Jessica’s ugly cry face. Her boyfriend and family planned an amazing surprise birthday for her.

Thing on my mind:

About six or seven years ago, I was playing basketball with one of my best buds and he told me, “You should run your startup like you play basketball.” It bothered me because I knew exactly what he meant and he was right.

On the basketball court, I’m a bit of an asshole, especially considering my mediocre skills. I always walk on to the court thinking that I’m the best player, even to the point of holding others in contempt. I tend not to defer especially when I’m the best option on my team. I get on my teammate’s case when they’re out of position. I’ve matured and mellowed out over the years for sure, but it’s probably still noticeable given that I’m normally a very jolly guy.

But I act like that because it’s the only way I feel like I stand a chance at winning. If I don’t execute every move with the confidence of the best player, I’m likely to mess it up. My shot might be slightly off balanced. My follow-through might not be perfect. My pass might be lazy.

Nowhere is the need for absolute confidence more obvious than free soloing a giant wall. Alex Honnold was interviewed at the Aspen Ideas Festival and here’s how he described that confidence:

Interviewer: I was struck by this, you write, “I was 100% certain I would not fall off and that certainty is what kept me from falling off.” Can you talk about that sense of certainty to climb like that?

Alex Honnold: There has to be a real confidence that you can do the thing you are setting out to do. The only way it works out is if you can maintain that confidence throughout. Basically if you get scared during free soloing, it all starts to crumble a little bit. You start to not trust your feet. You don’t weigh them as well. They’re much more likely to slip. Basically everything can kind of spiral negatively. Whereas if you are 100% confident you can do the thing and you go out and climb at your best, then you do actually do it.

It’s the same in startups. The winning conditions are so extreme that you have to execute perfectly, and to do that you have to assume you are the best. Find someone talented you could hire but you don’t have much of a runway? Hire her. Assume you can get the resources. Have an opportunity to raise more money at reasonable terms? Raise it. Assume you are equipped to find the best way to deploy that capital. Play offense. There are so many opportunities for self-doubt or over-thinking, especially with smart people. That’s why speed is the most important thing to optimize for. A fast-paced game means you only have time to be confident.

Piece of content I recommend:

The New York City Subway Map as You’ve Never Seen It Before by The New York Times

When public transit works, I really love it. I have a map of NYC on my wall at home with all the transit options. I’ve always found the NYC subway map to be very intuitive, but I’ve never looked closely enough to try to decipher why until this New York Times interactive masterpiece.

Related. If you understand Mandarin and you like the subway in Taipei, a new line just opened up after 20 years of planning, land purchasing, and construction in a very dense city. Here’s a 50-min video about it that I unfortunately couldn’t stop watching.

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 From Socialcam to TikTok: How we figured out video social in a decade