When Facebook ushered in the era of social media, the core insight was that by creating a space for us and our friends online, we would be motivated to share more. What we shared in the beginning was predominantly text because our phone cameras produced low-quality photos. Instagram changed all of that when they introduced filters that dramatically improved the quality of everyone’s photos [1]. After Instagram won the war for photos, the next natural front of sharing was videos.

Going from sharing photos to videos was a giant step because composing an interesting story in video was significantly harder…

This is an excerpt from my newsletter titled A newsletter about the newsletter (Ricky Weekly #17). If you want more of my newsletters, I recommend Ideas matter, but clear-seeing matters more (Ricky Weekly #4), “Strong opinions, weakly held” (Ricky Weekly #12), and Dabblin’ (Ricky Weekly #20). Or just subscribe.

Thing on my mind:

A few of you have asked me to write about this newsletter experiment, so here it is. It’s a little long so brace yourself.

This newsletter started because my friend Yoshio and I were talking about how much we both want to be better about connecting with…

Whenever people talk about the loneliness epidemic, I can’t help but nod my head in agreement. For people who know me, that may seem odd because I’m constantly surrounded by friends and loved ones. But loneliness is felt in the soul rather than in physical space. I guess that’s why there’s the idea of soulmates. In fact, sometimes I feel even more lonely when I have friends but no one I feel like I can really talk to.

I’ve been exploring ways to build safe spaces online where we can be vulnerable when a friend shared this:

I’ve been looking…

The era of social media feels like it’s coming to an end, but it shouldn’t because I’m not done with it yet. Recently Eugene Wei’s Invisible Asymptotes and Kevin Kwok’s The Arc of Collaboration gave me the language to decipher why I feel like there’s still a ton of white space. This essay is my attempt to break down that feeling and articulate what I think is missing.

Graphs

Social products are powered by a web of connections that you construct via following, adding or connecting with other accounts. In Silicon Valley, we call the result of these connections graphs and…

This post will be continuously updated on my website. Last updated June 19, 2019

“I GOT NEXT!” is what you say when you walk up to a pick-up basketball game that’s in session to declare that you’re next-up. You gotta do it loudly so people know. I’m at the phase of my startup career where I’m picking my next game to play and I’m doing it loudly.

How I am thinking about my next project

Strong leverage from technology: Leverage can come in many forms (e.g. finance, brand, patents, scale) but the best is still technology leverage. 100% of the decks I’ve seen positions tech as the secret…

For me, college was the best time to build startups. Living and working in the Silicon Valley has been the second best. Nowhere else in the world comes close, but will it stay that way? No. The next Silicon Valley is already online.

Why do all the best startups come out of Silicon Valley?

Life is just a game. We can understand the magic of American colleges and Silicon Valley by seeing how they are successful games.

American colleges are unique because the time we spend in college is time devoted to playing. The mission of the college game is personal growth. In the name of personal growth, we condone all…

The most important atomic unit of Silicon Valley is a team of two or three building something together out of nothing. I’ve been watching the team formation process over the last ten years and even though it’s more popular than ever to do startups today, finding teammates to work on a startup with doesn’t seem to have gotten any easier. Many people call this process “founder dating,” which is odd because I don’t think we actually treat it like dating. …

I remember the sense of wonder when I first signed up for Facebook and Twitter. Facebook helped me feel more connected to my friends, especially as I was graduating high school and going away to college. Twitter helped me find like-minded people who were also obsessed about technology and encouraged me to pursue my career. Today, it feels like these services are pitting us against each other rather than helping us feel more connected. What changed?

As technology products grow and their user bases expand, the nature of our agreement with them subtly changes. I call these technological context shifts…