Wedding. Party. (Ricky Weekly #14)

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

I wrote a new thing!

I published an essay this week called “The arc of social” to sum up how I’ve been thinking about “the next Facebook.” Unlike most VCs I think there are still big opportunities in consumer social, so I tried to flesh out the case. Since publishing I’ve been sent relevant articles and entrepreneurs / investors who have similar takes. The accelerated learning from feedback is my favorite part about writing essays.

A picture from my life:

I hosted a founder dating end-of-summer party. It was super fun! I hope the quality of people stays high.

I also went to a wedding and we stayed in a lodge that’s kind of like a dorm.

Thing on my mind:

I had a great time at a wedding this weekend up in Auburn, CA not only because I love the couple but also that they made the wedding about their community. There was a “hugs, not handshakes” rule and you can feel the earnestness in the couple’s desire to see their community come together to love each other. Typically all the love arrows are pointing in the direction of the couple at weddings, but at this one the arrows were pointing in all directions! Kudos to the couple.

I love weddings because there’s so much pure joy, but I always feel a little bit sad at the same time. I look at families come together and I wonder if I’d invite my family to my wedding. I hear fun stories about the bride and groom growing up, and I try to think about my growing up and all I remember are bad memories.

I also wonder about the idea of marriage. We don’t need it as an economic necessity anymore. If you think about the number of people stuck in unhappy marriages, you’d probably consider that an epidemic. The kids…I think they’ll be fine especially if we remove the stigma from single-parent or divorced households. We shouldn’t think of these households as “broken.” I’d prefer it if we dial back wedding celebrations and dial up divorce celebrations. I think figuring out that you don’t want to spend the rest of your life with someone is just as significant as figuring out that you do.

Sorry, I love weddings. I’d love to have one to host a big, loving party for my community. I didn’t mean for this to be a bummer. But this is about what’s on my mind…so there you go.

Piece of content I recommend:

When They See Us

h/t to Nik Baron and Oprah Winfrey for recommending this. I cried my eyes out and was really moved by the acting especially from the young actors. There are four parts followed by an interview with the real-life Exonerated Five. Make sure you watch.

American Factory

h/t to Barack and Michelle for recommending this. I thought this was a pretty unbiased look at manufacturing and the tension between America vs China, labor vs capital, and humans vs machines.

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

The telling and retelling of my story (Ricky Weekly #13)

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

A picture from my life:

This is the patent for the toilet paper roll (found in a bathroom of a Chinese restaurant). Clearly this means the roll should be “over” not “under.” Case closed?

Thing on my mind:

I was sick this week and got so bad Thursday I was in bed all day (I’m fine now!). Fortunately that gave me a chance to crack open Ocean Vuong’s On Earth We’re Briefly Gorgeous and it’s been hard to put down. The book is having an effect on me similar to the movie Boyhood. I’m transfixed because every single word seems to be taking me back to my childhood and giving me new language and perspective to understand what I experienced. I’m seeing memories flash before my eyes as I’m reading while trying to not cry too much. Sometimes my memories are very similar to what the author is describing, sometimes they’re different but feel the same. I find myself taking the author words and overlaying them on my memories to see if they fit, and if they don’t fit, I’d use the author’s voice to try to give my old self a fresh understanding especially because this guy is a great writer. It’s been forcing me to think about family more than I want to.

I still feel uneasy when people ask me about my family because if I were to answer the basics honestly, it’d still take a while to explain and change the tone of the conversation. So I have an official version that I tell people that’s more sanitized, and depending on who it is / what we’re doing I might share more while slipping in jokes to lighten the mood. There’s a version of the story that I tell myself that’s self-serving, but I know necessarily creates a “bad guy” character. Kind of like how rappers talk about the haters as the fuel for their drive. You have to have the haters if you want to keep that useful narrative. Over time as I received new information or perspectives, the self-serving version of the story has started to lose its power. Like realizing you don’t really hate the haters. What I fear sometimes is that I don’t have an equally powerful story to replace it. Reading this book and watching Boyhood are exercises in continually challenging my story and maybe searching for a better replacement, if I can find one.

Piece of content I recommend:

I Think it’s Important to Tell You How I Feel” by my friend Jessica.

My brain that picks up the happiness that is in the air during puppy golden hour at Alamo Square, equally picks up the sadness in small interactions, missed opportunities, setbacks, sometimes even situations that are not mine. If you don't know me, you really only see me happy or doing well - when I'm asking for something on Facebook for a new thing I'm thinking about, posting things that seem like there's lots going on, on insta stories watching my caterpillar friend on the lettuce plant on my sweet SF patio. And I don't really want to be that to you. Because it's also hard AF, and I'm confused, and uncertain, and feeling inadequate after browsing the LinkedIn feed. And I hope I never make you feel like I just have it going on.

I love Jess and I found myself nodding as I read it because I feel the same way. Other than my Resting Bitch/Tired Face (I’ve been told), people tend to remember my enthusiastic laughs because I’m easily entertained. But that’s only what you see, so important to remember that!

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 “I got next!” — a personal #RequestForStartups.

"Strong opinions, weakly held" (Ricky Weekly #12)

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

A picture from my life:

I was in Hayes Valley so I went to check out the new basketball court that Kevin Durant and Joe Gebbia (of AirBnB) renovated to the tune of $99,500. There are plenty of terrible courts in SF. I don’t think basketball courts need fancy art—they just need to be leveled and have no cracks. However, it seems like SF is particularly bad at pavement because we also can’t get leveled, crack-free sidewalks, roads and highways. Apparently Oakland is terrible too because Steph Curry had to do the same thing at Concordia Park.

Growing up I spent a gargantuan amount of time on the basketball court. It’s where I went to escape whenever shit happened. It’s one of the cheapest sports to play and cities really ought to keep the courts in good shape.

Thing on my mind:

It’s a cliche in Silicon Valley to have “strong opinions, weakly held.” A friend mentioned that her boss is really good at it because he’d pound the table all the time to get his way, but when given the right information, he’d also 180 and pound the table the other way. To an observer that feels erratic because he’d swing from one side to the other with the same enthusiasm as if nothing happened, but it’s actually quite effective.

To get better at this, it seems like you’d need to 1) know to pound the table and 2) be willing to change your mind completely.

What stops you from pounding the table?

  • afraid to be wrong / ego

  • don’t have a strong opinion

  • prefer consensus-building and other perspectives

  • don’t recognize that pounding the table is often the dominant strategy to get meaningful movement in order to gather more information

What stops you from changing your mind and 180?

  • afraid to be wrong / ego

  • don’t have the discipline to update your past decisions with new information

  • don’t know what info should change your mind

Six months ago I tried on a new way of planning my life to help me operate in a more strategic manner that’s closer to “pounding the table” yet have enough flexibility to “change my mind” completely. It’s a work-in-progress but if you’re interested, it’s called Antifragile Planning by Taylor Pearson.

Related. My friend Tom Currier mentioned on Facebook that a “time-boxed periods of suspended disbelief (intentional naivety) followed by a brief period of intense reflection/analysis” is advantageous. This essay by Nate Soares called “Deliberate Once” also describes this method of operating really well. They’re all different ways of saying the same thing.

Operating this way can make people feel uncomfortable because it feels too rational. The people I find who are the best at this tend to be slightly sociopathic. I think sociopaths are fascinating because unlike the rest of us, they don’t care about the rules or what you think, so their range of motion is much wider. I enjoy watching these people. There are a lot of successful people who sound like sociopaths, and I wonder if it could actually be a dominant strategy today. Nadia Eghbal makes an interesting case in “Shamelessness as a strategy” that it could be:

One explanation might be that it’s an expected effect of the blurring of social boundaries today. In the past, if the size of your community was finitely bounded (like a village, or an aristocratic social class), people didn’t enter or exit these communities as frequently. Under these conditions, sanctions are probably still effective, because members of the community want to be liked and accepted.

But the borders to online communities are much more fluid - perhaps even nonexistent. Under open borders, sanctions will backfire, because they just serve as a signaling boost for the transgressor, attracting outsiders who resonate with that person’s message. What’s meant to be punishment instead becomes a flare shot straight into the night sky.

Piece of content I recommend:

“Dissect” podcast from Spotify Studios.

I listened to Season 3 a few months ago because I’m a huge fan of Frank Ocean and Season 3 was all about Frank Ocean. I just listened to Season 2 this week about Kanye West and omg it’s even better than Season 3.

Note: this is one of the few podcasts that you should listen to on 1x (normal) speed because it’s music. Don’t ruin it.

Your answers from last week:

Last week I asked:

Excelling at knowledge work also requires deliberate practice, but it’s hard to think about how to deliberately practice knowledge work. Tyler Cowen wrote about how he practices what he does. I think writing this newsletter is practice, so is all my public writing. What do YOU do to deliberate practice intellectually?

Your responses:

Whenever I play a sport (ultimate frisbee, basketball, pickleball...), I think of one aspect that I want to focus on improving and write down a way to "practice" it on the field. During and after the game, I reflect on it. After the game, I grade myself on how well I practiced that particular aspect and how I can improve it.

I started codewars with [redacted] and [redacted]. I never used to liked studying algorithms, since I use them so rarely. Now, I think that can help me hit high notes when I need to. So that’s something I picked up on to deliberately practice.

The way I usually think about learning something new is I keep reading / talking to people about a subject until I feel like I’m not learning much that’s new. That’s the litmus test I use for fully understanding something. For example, when I was leaving [redacted], I talked to 20 founders, people who replaced founders, and board chairs who oversaw founder transitions - non profit and for profit in various types of companies - whichever is what it took for me to feel like I understood how to do a transition successfully. That investment of time helped immensely.

Just came back from vegas and I would recommend texas-hold-em. It's a deep game and you practice more EQ than IQ. Try to consistently win/break even at 3/5 while playing low variance rather than GTO. Probably the best thing is how humbling it is, and also, as you get better, you realize it's less about luck and more like a trainable skill. Another thing for knowledge workers I found is to just be as relaxed and stress-free as possible. I find that my brain just soaks up every little detail in life and considers them in weird ways when I'm free. Or it might just be the coffee.

One last thing:

Sorry this newsletter got long. Ugh, so many thoughts.

I’m organizing a party in SF for everyone looking for co-founders to start a company with. I’ve been organizing smaller dinners but I’ve secured a venue for a bigger event now that I have a roster of 80 people. It’s going to be on Sep 5. If you know anyone in the bay who’d be a fit for the event, have them fill out this form and I’ll send them an invite. Fun times!

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 “I got next!” — a personal #RequestForStartups.

Communication fail (Ricky Weekly #11)

why we love talking about sports

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

A picture from my life:

I went to watch Team USA vs. Team Spain. It was basically watching the future all-stars and a ton of fun. Also was great to see what a NBA-level basketball game is like without all the timeouts and free throws to stop the clock.

Thing on my mind:

I was hosting people who have never been to the United States. I reminded them that it gets really hot and then really cold at night, but their understanding of “hot” and “cold” was limited by their context, so they were very unprepared. That’s how communication works most of time. Your existing context is what you use to interpret what you hear, and that’s why words are never enough.

It’s not like they didn’t know they were missing context. It’s sometimes painfully obvious. For example, when I’m with my family, I sound very alien sometimes because I’m more educated and I know more about certain things than they do. I code-switch, but I can’t hide it completely, and I know they don’t understand me completely.

The reason why so many people spend an inordinate amount of time consuming and talking about sports is because it’s a great leveler. Sports is easy to understand, and everyone can have an opinion and they’re all equally valid. When I was younger, someone asked me why my family was always talking about sports and nothing else of substance. I was offended because I didn’t know what to say but I knew it was important for my family to stay close to each other.

Piece of content I recommend:

SCMP’s China Internet Report 2019

If you like Mary Meeker’s Internet Trends report this is like that for China + better designed. Mary Meeker can really use some design help.

Your turn:

Excelling at knowledge work also requires deliberate practice, but it’s hard to think about how to deliberately practice knowledge work. Tyler Cowen wrote about how he practices what he does. I think writing this newsletter is practice, so is all my public writing. What do YOU do to deliberate practice intellectually? I’ll share some anonymized answers in the next newsletter.

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 “I got next!” — a personal #RequestForStartups.

The next Facebook (Ricky Weekly #10)

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

A picture from my life:

This is my friend Vik. He was my barber for three years and one day he told me he started making lemonade to sell at farmer’s markets. He wanted to test catering to companies so I invited him to come cater for my startup. We often talked business and when I was closing down my startup I told him about it and we had an emotional moment because he was about to pursue selling lemonade for real and that shooked him. Then he got a space in the Mission but because of the SF bureaucracy the opening was delayed and he had to get a loan on Kiva. Then he finally opened and the neighbors called the cops on him because he’s black, which turned out to be good for business. Now a year later he’s still there. Still positive and enthusiastic. The lemonade is still priced perfectly high for San Francisco. Did you know he was a dancer and he proposed to his wife while performing? What a dude. Shazaaammm.

Thing on my mind:

I’ve been tinkering with what the “next Facebook” could be because I think most people are now under-served by social networks. Internet companies have always tried to get people to share more online, but it wasn’t until social networking sites like Facebook figured out that people share way more when they can do it with/to their friends did sharing really take off. But then we stopped sharing, at least to Facebook, because over time you’ve connected with so many people you can’t easily share without fear of potentially saying the wrong things (which will eventually happen to this newsletter). The people I see today posting to Facebook are mainly doing it to look good (status) or for practical reasons like asking for travel recommendations (utility). If you don’t care much for status or need recommendations, then Facebook is just a glorified address book. Maybe you take your sharing to IG or Snap stories, which have less status pressure, but it still feels like you are performing life. Yeah you are connecting with friends, but it’s a lot of work (especially as you get older), and what are you really connecting on? Stories are mostly about where people are and what they’re doing. What about what’s in their head? We’re left with all the messaging tools like Messenger, WhatsApp, iMessage, etc…and uh, the rise of newsletters? Isn’t it weird in 2019 to be hyping up email?

I think there’s something in group chat like Slack and Discord. So I’ve been thinking about how that could be designed for the Facebook use case (casual, social). Yes, I know. Group chat is also old like email ie AOL chat rooms.

Piece of content I recommend:

Late Night Wars on YouTube.

I’ve loved creators who make “video essays” on YouTube but this is another level. This guy made basically super legit documentaries. I’ve come to love Conan O’Brien over the last few years so it was great watching these videos about him from when I wasn’t paying much attention to him.

Your turn:

Do you feel under-served by Facebook? Do you have a group chat with close friends? If someone were to take on Facebook, what do you wish they’d know about you?

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 “I got next!” — a personal #RequestForStartups.

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