Surrender in order to master (Ricky weekly #21)

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

Announcement: I wrote a new essay called Single-serving friends to highlight the benefit of “single-serving” relationships and safe spaces in general. It seems to have struck a chord (~600 views in just a few days, which is more momentum than average). If you like it, share it with a few friends.

A picture from my life:

Here’s blurry me at my friend Ben’s compound in East Palo Alto performing standup this past weekend. Ben’s made maximum use of the land he got. Not only is there the performance space pictured here but also an aquaponic greenhouse growing lettuce fertilized by fish poo, former kombucha brewing stations now turning into an operation to make cheap insulin, a workshop space for van upgrades, etc. I’m a city dweller with no survial skills who can’t (and don’t really want to) make anything with my hands but it was awesome to see what Ben’s been able to do. The best part was the community he brought together for the open mic. There were kids, parents, and grandparents. Immigrants and current students. People who came up from San Jose, down from the city, and neighbors in EPA. I loved it!

Thing on my mind:

The last few days I’ve been doing some quarterly planning following Taylor Pearson’s Antifragile Planning technique (I started doing this in the middle of February that’s why Q4 for me is right now…). By the end of my Q4 I would be at the one-year mark of my time off. The plans I set for myself have to be even more deliberate and results-oriented as I transition back into startup founder mode.

I’m thinking about how to set up a system to make sure that I’m operate at my best as a startup founder. Having seen the benefits of writing this newsletter in clarifying my thinking, I definitely will change how I send company updates to my investors. I feel like I have always underutilized my investors’ enthusiasm for what I’m building. Having reflected on the importance of “seeing clearly” while in the startup trenches, I need to figure out how to forge a relationship with a few individuals who I really, really trust, enough to let them help me see what I need to see. Kind of like a personal board of advisors whose vested interest are in me and me only. I know I need to be better about surrendering and allowing people to help me. I got the idea of “surrendering” from a book my friend Michael recommended called Mastery by George Leonard. the author breaks down the process of mastery to five components: Instruction, Practice, Surrender, Intentionality, and The Edge. A useful frameworks and a quick read.

Piece of content I recommend:

I fell down the YouTube rabbit hole of re-watching a bunch of Billy On The Street clips and found this video of Billy and Keegan Michael-Key making fun of our gun control policies. It’s brilliantly done and has 150k views so you likely haven’t seen it!

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

Dabblin' (Ricky Weekly #20)

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

A picture from my life:

This is Ryan, a great man. Yesterday was his birthday. Happy birthday bro!

Thing on my mind:

I have a productivity system where I track my time in 25-min (Pomodoro) chunks, and at the end of each day I audit it to see how many chunks were productive chunks. If I get to 12, I’m happy. I fail all the time.

In the last few weeks during my daily audit I’ve also started asking myself to write down what “output” I was able to generate for the day because my brain is extremely sensitive to the input-to-output ratio getting too high, especially because these days we’re all drinking straight from the firehose.

So I define “input” as just whatever information or communication I consume. “Output” is whatever I put out there into the world and begins some sort of feedback loop. Ideally that feedback loop consists of more than just me, but depending on what it is sometimes just putting something out for myself is enough. This newsletter has become important to me because it’s output I can generate on a regular basis and my thinking gets refined from your feedback.

Pivoting this into a discussion on how I’m finding my next thing. Someone told me that I’m the busiest unemployed person she knows and that was funny to hear. I don’t think I’m that busy, but I just need to be generating output. But because I’m unemployed with a vague goal of finding my next thing, it’s hard to know what is the right output to work towards. So there were days where my desired output was “a framework for people to find their next thing,” which is kind of what this is 😂.

What I’ve found to be helpful is that I naturally don’t get too caught up in not knowing exactly what to do. Maybe it’s all the years of being startup founder. Instead, I dabble in a bunch of things. This newsletter is just me dabbling. Writing blog posts based on deep dives into my interests is dabbling. So is organizing events, advising companies, joining an accountability group, etc. Those are just the ones I feel okay saying because there were also some dabbling where I lost interest. Oh, standup comedy is not dabblin’ I’m so serious about that 🙃.

Dabbling somewhat aimlessly is useful because it still means generating output and feedback loops, which helps me get more precise about what it is I’m looking for. Dabbling also helps me get more out of all the input. You know how sometimes you read something and you’re like “omg, this is exactly what I’ve been trying to figure out” — that’s because a piece of information happened to meet your “prepared mind.” Dabbling prepares your mind and really helps you filter for signal.

David and I when we were building startups liked to call ourselves “heat-seeking missiles” because honestly doing a startup feels exactly like dabbling. You know your goal is “product-market fit” or “hyper growth” but you don’t actually know which output will get you there. You have some ideas but you don’t really know, so you just dabble, generate output, feedback loops, and try to identify the heat.

Piece of content I recommend:

The Peter Attia Drive: #68 - Marty Makary, M.D.: The US healthcare system—why it’s broken, steps to fix it, and how to protect yourself

One of my best friends Sid is a general surgery resident at UCSF so we talk about the healthcare system all the time. Talking to Sid is fun (and frustrating) because he is able to go through all that medical training while maintaining an “outsider” perspective, enough to clearly see and analyze the system for all of its flaws. This podcast is basically two famous “outsider” MDs talking to each other for two hours and I found it to be extremely fun (and frustrating) to listening to.

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

"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

Searching (Ricky Weekly #18)

No, not the movie with John Cho / Harold.

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

A picture from my life:

I discovered Kanhfections. It’s an awesome bakery in the Mission. They have great breakfast biscuits. Here’s a picture of me taking a picture of their nutella croissant. I love croissants and I love nutella. The combo is just perfect. 🤤 The place across the street from my house sells spam croissants, but it’s not good even though I love spam.

Thing on my mind:

I’ve been thinking about social products because I spend a lot of time in them. I wrote about it a month ago but it’s kind of like a mind virus so I just keep thinking about it. Specifically I’m doing some thinking around groups. As a YC/StartX founder I have access to Bookface/Founder Center. Both are “forum” type tools that are extremely useful, but only because both the YC and StartX communities have strong vested interest in each other and a culture of paying it forward. I’m also in a habit / accountability group, but there is a very strong leader who is making this group a great experience for me. I have a “virtual house” on a Discord server with friends, and I’m trying to not moderate too hard and force activity (btw, reply if you want to come check it out). I don’t know what I’ll come up with, but if this is a topic you’ve thought about in the past, let’s chat more.

I’ve also been thinking about how to make better progress as a founder searching for an opportunity. We’re not talking about ideas. I’ve got plenty of ideas and I think most entrepreneurial people do. Rather than starting with ideas, I’d like to start with a problem or a customer in mind. The easiest one is to focus on my own problems. However, I’d love to have a better framework on determining which problem spaces beyond my own problems are interesting to me—something that’s more than just “big market” or “platform shift” or “crack in existing market” or “emergent behavior” etc. I think for an idea to be interesting to me there needs to be a piece of insight or a nuanced approach or something. I’m not sure yet.


Piece of content I recommend:

Two videos of awesome YouTubers explaining things to me.

One answer from last week, one question for this week:

In my last newsletter and I asked:

Where do you practice vulnerability? How do you experiment and work out messy feelings and unclear thoughts?

You told me that you do your incoherent rambling with close friends and significant others, or you just work it out in your own head or write out thoughts in your journal. A few of you mentioned being vulnerable with new friends, which I thought was interesting because it tells me that existing relationships can have fixed context, and if that context is not conducive to being vulnerable, then it might be easier to be vulnerable with a new relationship.

Some of you go to therapy to practice vulnerability. A few of you are like me and feel relatively more comfortable being vulnerable in general.

A friend pointed out that it’s hard to be vulnerable sometimes even with your closest friends or significant others because:

I feel like that it doesn't matter how much respect, closeness, earned with someone, having a low point or being vulnerable in front of them does seem to incur a cost in how they think about you, even if its tiny or imperceivable.

That sucks, but I think therein lies the problem.

My question for you this week is: I’m sure you’re part of many groups and online communities? Which one is your favorite and why?

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

A newsletter about the newsletter (Ricky Weekly #17)

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

A picture from my life:

Went to the Coliseum to watch the A’s wild card game. I haven’t been following baseball for the last decade and during that time my Dodgers have become one of the best teams in baseball. That makes me sad because I used to tell people that baseball’s my favorite sport. Unfortunately, I never got to play baseball myself but I play a lot of basketball, so when life got busy and I had to make a choice of which sport to follow I ended up choosing basketball. Baseball is important to me for many reasons, one of which is that it’s the one thing my mom and I can bond over. She’s a huge baseball fan. I didn’t watch a lot of cartoons growing up, but I watched a lot of baseball so I can talk to her about it.

Go Dodgers!

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 our friends. He mentioned Tim Ferriss’ 5-Bullet Fridays and I thought “Five bullets every week, that sounds do-able!” So I decided to write a personal newsletter following a simple format that I can see myself sticking to indefinitely. 17 issues later and roughly 5 months later, I’m still sending these and I love it.

Open rates. In the beginning when the list was about 25 people, the open rate was >85% for the first few issues. Now the list is at 140 people and we’ve settled at around 65%. Not bad.

Click rates. Sometimes 30% of the openers would click at least one link. Sometimes <10%. Really depends on the content. I think people only like to click on articles, not podcasts or videos.

Openers. I can see how many times you open the email. I find that if you’re working on a response to me, you tend to open and re-open the email a lot.

Responses. I get at least 1 or 2 every week. Out of 16 issues I’ve had 2-3 that really resonated and those would get 5 or 6 responses. The responses are great and it’s one of the best things that’s happened with this experiment.

Who seems more engaged? My strongest ties definitely pay attention and once in a while reply or reference it when we hang out in-person, to my surprise. The people who seem to get the most out of my newsletters though are weaker ties that I don’t get to interact with as much for whatever reason (family, location, career, etc). I’m surprised that a few people I only recently met have subscribed to my newsletter because I put it in my email signature. They seem to enjoy it and when they respond to me it feels like our relationship is developing faster. I’ve inspired at least two people to write newsletters. That’s so cool!

How do I write it?

I track my time and it takes me anywhere between 30 minutes to 2 hours to write an issue. How long it takes depend on 1) if I already jotted down my thoughts during the week so I can just take the notes on Sunday and churn it out and 2) how complex is the thought I’m expressing. Pictures and link recommendations take no time. If I don’t feel inspired to write the newsletter on Sunday, I don’t stress about it. I’ve skipped a week a few times and I’ve sent the newsletter late on Monday or Tuesday a few times too. I’ve learned from your feedback that this exercise is first and foremost for me, and that you only want to read if I feel inspired enough to share, so forcing it serves no one.

Other thoughts

I find that most of our social media sharing today has to do with milestones or manicured thoughts. Otherwise it’s photos which mostly express where we are and what we’re doing. What’s missing for me is what is inside people’s heads. What are you thinking about? The newsletter is an attempt to get what’s in my head out there, and it’s been great because when people respond they are responding directly to a thought in my head, which cuts through the noise and I feel like we are connecting on a very meaningful level.

Having a weekly cadence is good practice to just force me to practice publishing my thoughts. It also has the added bonus of creating availability bias to my benefit because I show up in your inbox every week, you think about me more and engage with me more.

In the beginning I started with 25 people who I knew wouldn’t mind me just subscribing them to a newsletter, then I announced it on my Facebook and added it to my email signature. Before I announced it on Facebook I wondered if what I write would change with a bigger audience, but I still did it because I’m more comfortable than the average person to appear vulnerable so I might as well lean into that. I can also just stop if I don’t feel like writing anymore. Over the last 17 issues there were two instances where I had to censor myself or obscure the facts a bit because I knew I didn’t want certain subscribers to know some things, but those were pretty extreme examples. In general, I’m sharing way more than I would anywhere else online, and that’s a good feeling.

I think a lot of why I like it has also to do with email as the medium. “The medium is the message,” and email creates an expectation of something more thoughtful and personal. There’s no way to give me feedback other than replying, which leads to a 1-1 conversation. Technically my newsletter is public and anyone can subscribe, but it still feels semi-private because it’s not that easy to find and it gets delivered straight to your inbox. I think privacy by relative obscurity is important in getting me more comfortable at sharing.

Again I can’t recommend Yancey Strickland’s The Dark Forest Theory of the Internet enough, here’s a quote from him that really resonates:

In "real life" I'm a reasonably self-confident, 40-year-old human. If we sat next to each other on a plane we'd have a good-to-memorable conversation.

But on the Internet, I feel like a teenager struggling to find their identity. I'm all awkward exclamation points and weird over-explanations. I'm often too self-conscious to be interesting or real.

When I used the Internet as an actual adolescent in the 1990s and as a young adult in the 2000s, this wasn't the case. I blogged every day. Message boards were how I learned to test theories and debate ideas.

These communities were small enough that people knew each other but big enough that there was a diversity of opinion and conversation.

You could vehemently disagree with someone about politics in one thread while agreeing just as passionately with that same person in a debate about movie sequels in another.

I had no problem being myself online then. But now it feels different.

A lot of this difference is on me. I'm older. I have more at stake. But it's not just me that changed. The Internet did too. The Internet went from a venue for low stakes experimentation to the place with some of the highest stakes of all.

What resonates is the ability to be vulnerable. A Internet that is big enough yet safe enough. The idea of being able to test theories and having lower stakes. That leads me to the piece of content I am recommending to you this week…

Piece of content I recommend:

How to Design Social Systems (Without Causing Depression and War) by Joe Edelman

I like it because he calls out the need for “practice spaces” that support our need to work out our feelings, identities, thoughts, etc. Here’s a quote from the article.

So, imagine a teenager. She is sorting out how she wants to be, socially. She is exploring ideas about how people ought to act (intelligent, feminine, polite, etc) and questioning them. In different situations, she tries out different ways of being intelligent, feminine, or polite, and sees what happens. She may at first imagine she wants to be infinitely feminine or infinitely polite, but in the context of real choices, these values no longer seem right. She reflects on who she wants to be, and how she wants to live.

We all make small choices, everyday, using the same process the teenager used for these big choices. When we approach a conversation or meeting, for instance, we may need to decide how to balance honesty and tact. Even with these small choices, we need to experiment and reflect.

This newsletter is a “practice space” for me - and I’d like to create more spaces like it. I don’t think writing a personal newsletter is ever going to be a mainstream activity, but I believe we can all use something like it.

One answer from last week, one question for this week:

In my last newsletter and I said:

There seems to be no good rational reasons to startup. But there are millions of valid reasons why founders continue to choose to be founders.

I thought Gregory Rose’s response was interesting:

Something I've been thinking lately: This is only irrational at the individual level, but completely rational at the population level (as Taleb argues in Antifragile). Society's benefitted immensely from every single founder who made this irrational decision and was successful.

A message I keep personally thinking about, and that I'm increasingly seeing in a number of successful or happy people is this: "It's not about you. It was never about you."

I'm increasingly convinced that many things we think are irrational do make sense in some way we miss either on a broader timeline or broader group of people.  e.g. The prisoner's dilemma was the wrong experiment - it should've been the repeated prisoners dilemma. Or, irrational individual behavior might benefit the group, and therefore still be preferred by evolution. I'm sure there are still  exceptions, but I wonder how many there really are.

My question for you this week is: Where do you practice vulnerability? How do you experiment and work out messy feelings and unclear thoughts?

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

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