Substack...what's the hype? (Ricky Weekly #33)

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

A picture from my life:

Did you know the “Tres Comas” tequila from HBO’s Silicon Valley is now a real thing? 😂

Thing on my mind:

There’s a lot of hype about Substack (the service that powers this email) and the creative economy in general. I think the idea is that if you can make things people want, you now have an easier time making a living just doing that. But a friend who interviewed at Substack told me that they were only doing $400k in revenue and most of that revenue comes from their top two paid newsletters. I suspect services like Patreon, OpenCollective, Gumroad, etc have similar top-heavy dynamics. Of course, anything that makes the long tail more viable makes a dramatic difference for the creative class, so I’m all for it. I’m wondering if anything else has really changed to unlock the creative economy.

Attention and $$

Our attention and wallets are still limited. Sure we’ve found a little more time to consume content from our devices and we have a little bit more money to pay for content from the money we used to spend on cable, but the found time and money are incremental. That’s not even considering the overhead of subscribing to all these different things. The cable bundle was easy. Now that Peacock, HBO Max, Quibi, and Discovery streaming services are all slated to launch later this year, people are wondering how many we can reasonably sustain even if the aggregate price is still lower the cable.

Discovery infrastructure

Even if you can charge for a newsletter easily, you still need to tell people about it. Social media is more mature and more people have followers they can monetize right away, so maybe that’s what’s new. Because otherwise in terms of discovery, there’s way more competition. It’s much harder to get found on Google or stand out on social media compared to the early days. Big brands and celebrities have more power and closed systems like Spotify and Medium are more attractive today because they have the power to help the little guys get discovered, but they’re very limited in what they can do (eg if Spotify puts too many new artists in a playlist and you don’t get your Justin Bieber fix, you’d stop using it).

Supply and demand of quality

It’s possible that after being spoon-fed junk by Facebook and having lived long enough in the age of information abundance, we started to crave more quality content, but that doesn’t seem like a strong effect.

Charging for content has the effect of signaling quality, but as more people start charging money for content, money becomes a less useful signal. Social signals like “likes” and “shares” used to signal quality, but once people started to game it or realize that it only captures the lowest common denominator / popular vote kind of quality, the social signal became less useful. So basically I’m not sure if we are really demanding more quality, but we definitely have more supply.

With money directly coming from subscribers we are getting better quality content in two ways. Platforms like Netflix can spread out the cost of developing shows over millions of subscribers, giving them way more leeway to experiment and go for more niche content as long as it appeals to a segment of their subscriber base. The other way is that if you can make videos for your 100 Patreon supporters, you can make the best videos for those niche 100 people without feeling like you need to appeal to more people.

Am I missing anything important?

Piece of content I recommend:

Is Joker Cinema? by Now You See It

The “video essay” is one of the best things to emerge from YouTube in my opinion. This one’s special because it’s a video essay without a narrator!

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

How not to ask for help (Ricky Weekly #32)

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

A picture from my life:

Lots of restaurant and cafe restrooms have this extra lock, especially Asian restaurants. Why? Is it because the lock on the door handle breaks too easily? Do I really care to know? 🤷‍♂️

Thing on my mind:

I got “feedback” from a friend this week because I asked for an intro without asking if he wanted to catch up first, and he didn’t like that. We haven’t talked in about a year, but I’ve known him for a while so I didn’t think too much about it. He said that I should’ve known because he’s a relationships-first guy, and maybe it’s true I should’ve known especially because I think of myself as a “people person” so I should’ve been able to discern how to best approach each person.

These things are tricky though. Sometimes I’m on the receiving end of it. People have asked me to catch up, and then I find out they’re just trying to get me to send them to someone else. If I like the person and the reason is a good one I probably would’ve been happy to help over email or a quick call. That’d be way more efficient for both sides. Sometimes when I don’t think I know the person that well, I’d want to catch up first and remind myself why this person is awesome, and if they don’t offer to do that I get a little annoyed. It also depends on timing - sometimes I’m busy and I can’t get back to all the people asking me for help. Other times I feel like my head’s above water and I can take a few phone calls or coffees.

I haven’t done a deep reflection here but off the top some variables are: 1) how well you know the person 2) how fresh is the relationship 3) do you have a personal interest 4) what’s the objective of the meeting (eg quick intro, catch-up or a deep-dive on strategy) 5) what method of connecting is best for the objective (eg two friends catching up is probably best done in-person) 6) how well you can communicate the objective without warming up the relationship 7) what the person prefers 8) what you prefer 9) how well you can communicate your preferences, etc. There are probably a lot more variables and that makes this a pretty complicated problem. Some people have strict policies like only email or only calls, but if you want to do that you’d need to get comfortable making, say, a big investment decision over email without ever meeting the person. Some people like Mark Cuban can do that, but it requires work and probably lots of trial and error.

Piece of content I recommend:

I coached 101 CEOs, founders, VCs and other executives in 2019: These are the biggest takeaways by Leo Widrich

Helping founders is mostly playing therapist (or “coach” if you’re too alpha for therapy), but not everyone does it well because they haven’t been in the shoes of a founder or they just don’t have the right kind of empathic powers. Based on this essay I think Leo Widrich has found his calling. Some quotes I loved:

What I’ve learned is that most of our problems occur when we don’t see our own power anymore.

The question I often like to ask then is: What do you have to accept to step back into your power in this moment/relationship? Frequent answer: That the answer might be “no”.

Whether it’s fear, anger or hurt, what I started to practice with my clients is to let these things come and as they come, notice how they don’t want to stick around if we really agree to them:

  • The sadness wants to become tears and flow and become tender thereafter

  • The anger wants to punch, ball hands into fists and then fizzle out through the arms and legs

  • The loneliness wants attention, to be held, embraced and just sat with.

  • The fear wants to be felt, receive attention and permission to flow through the body, only to leave a trail of energy and aliveness behind.

Enduring gets us far, but I don’t think that’s what life is for. To let go of that belief and to allow a new one to emerge, often one rooted in love and joy, is scary and takes courage. Especially when endurance has helped you build a massive company or another successful thing.

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

"Kobe, Kobe, Kobe..." (Ricky Weekly #31)

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

A picture from my life:

I performed a standup set in SF earlier this week but also caught the flu. Not the corona kind, just the good ol’ bud light.

Thing on my mind:

Since I’m been in bed recovering from the flu, I spent the afternoon watching people cry on ESPN and revisiting vintage Kobe clips.

I moved to LA in the beginning of the Kobe-Shaq 3-peat era so Kobe was probably one the biggest things to me growing up. I watched so much Kobe from middle school all the way to the start of my career that I’m pretty sure I’ve spent more time watching him than any other athlete. So it was pretty crazy today when I heard someone screamed “KOBE DIED,” my heart almost stopped.

Reminds me of the time against the Warriors when Kobe drove and his left Achilles gave out. That moment felt crazy because here’s someone you’ve watched growing up who’s been just consistently amazing. In middle school, whenever he’d have a good game, I’d pick up the ball and run to the park to try to do the same thing. That means I went to the park almost every day. When I got older, Kobe also got older but his game stayed great. He went from afro Kobe to bald Kobe. He went from Shaq’s Robin to Mamba, and then Vino. He went from 8 to 24. From being told to pass more to everyone wanting the ball to be in his hands. I remember the TV graphic showing how Kobe had sustained a bunch of injuries and was still playing. And then poof, his Achilles gave out. We thought that was the end because we all knew the end was near, but he came back and then retired with a 60-burger just to remind us that he will go out on his own terms. Kobe is willpower personified.

And now he's gone. I was looking forward to watching him translate that willpower to things outside of basketball. It felt good to have a person that you feel like you grew up with continue to set the bar for what excellence looks like. Thanks Kobe. RIP.

Piece of content I recommend:

Women and Black Dudes by Neal Brennan

I just discovered Neal Brennan from his tribute to Dave Chappelle at the Mark Twain Award. He co-created the Chappelle’s Show and his comedy is fire. You can totally see that the Chappelle’s Show is half-him half-Chappelle.

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

"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

Stepping into your most formidable self (Ricky Weekly #29)

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

Announcement: David and I are building again. For now, we want to help you improve your relationships. If that’s a goal of yours this new year, take our Stronger Relationships 2020 Pledge to make it official. We’ll keep you accountable and share with you something we built that could help when we’re ready.

A picture from my life:

Happy new year 🎉! I celebrated with some friends I haven’t seen in a while. Here’s us doing the Asian squat together.

Thing on my mind:

Two week ago, I went on a train ride with Wefunder to visit entrepreneurs in various cities across America. On the trip, I noticed that there were lots of city-based, themed accelerators, fellowships, competitions and diversity-oriented entrepreneurship programs. This feels like a good development for the world. Just ten years ago when I was in school, the only game in town was Y Combinator.

But coming from Silicon Valley, it’s hard not to see these programs as trying too hard to replicate the magic of Silicon Valley. For entrepreneurs participating in these programs, it’s hard not to notice the gap in quality or see that the good ones are being taken advantage of because the only game in their towns want an arm and a leg in return. It begs the question, “Wouldn’t the best entrepreneurs simply find a way to get to the valley?” or “Why would the best entrepreneurs bucket themselves as only a diversity or a local candidate or participate in any program at all?”

The answer is probably that even if you’re the Lebron James of whatever you’re doing, it takes time to develop the confidence to step fully into yourself.

What do these local accelerators, fellowships, competitions, diversity programs provide?

1) The right kind of community. Even though on the internet you can find almost all the knowledge you need and even people to talk to, a community of peers in the real-world is better. The programs are self-selecting mechanisms to make the same kind of people come together. “Kind” could mean whatever is meaningful to that entrepreneur: shared city, school, ethnic background, socioeconomic class, company stage, industry, etc. Being able to see someone who looks like you or sounds like you or share the same values as you on the same journey builds camaraderie and helps you draw strength from them. When someone who shares your attributes succeeds beyond your wildest dreams, it makes you think you can do it too. This is why it’s easier for Stanford kids like me to think they can be the next Instagram or Snapchat because it seems like they were just getting drunk on campus with Evan Spiegel or Kevin Systrom like, yesterday.

2) Validation. While you need to pass a certain confidence threshold or have a certain disposition to start up, once you’ve started, your confidence continues to swing up and down almost by the hour and that feeling is unbearable. Having seemingly credible people put a stamp on you to tell you they believe in you helps smooth out the ups and downs for a while, and once you buy into the credibility of the group you’re now in, your baseline confidence increases. The bigger the brand, the stronger the effect, but smaller programs looking for founders like you also means you have a higher shot at getting in, and that’s useful because often times the best programs in the Silicon Valley seems too unattainable.

3) Resources. Even though there’s money in Silicon Valley, it feels daunting to go and get it because it’s far and it requires resources and time to break into the network. “Paying a visit” to the valley is not nearly enough because it takes many more visits, and that’s untenable for most. So yes, if you need resources, even if you know what you get from investors locally is a bad deal, you take it and you’d count that as a win.

The most important thing here is probably still confidence because confidence gives people a chance to grow into their most formidable selves, and from there they can figure out the other stuff.

I led an entrepreneurship club when I was a student at Stanford. It was one of the biggest clubs on campus with the most resources so we did a lot of things. Too many things, I thought. But I understood the role every program played. To bring it all together, I used to talk about how our job was to nudge every student along the entrepreneurial journey, regardless of where they are on the journey. We had programs targeting students who have never heard of startups (I was one of them), programs teaching them the ins-and-outs of venture, programs to get students to hack on something over a weekend, programs to give funding to people who need a final nudge to go get it, etc. Virtually any student at Stanford would’ve been able to find a program that spoke to them, and when they participate in it, they’d be nudged forward a bit with a little more inspiration, knowledge, confidence, community, funding, etc. We even visualized it like a progression.

Imagine an arrow pointing down from Inspire —> Create —> Fund.

So to sum it up, “programs” help increase baseline confidence and tamp down the self-doubt that you feel on a daily basis as an entrepreneur. Something like this.

Fortunately for me, I was able to get into two of the “programs” in the world that create the biggest delta in terms of confidence: Stanford and Y Combinator. My confidence level still swings up and down, but my baseline is much higher, and with experience I feel much closer to my most formidable self.

Piece of content I recommend:

Terrace House: Tokyo 2019-2020 on Netflix

I’ve been a fan of the entire Terrace House franchise and have watched every single episode ever. I’ve even been watching the latest episodes from Japan that are not available on Netflix USA yet.

If you haven’t seen it before, the latest season is “Tokyo 2019-2020” and it’s very good, but it’s still going so you’d be left with a cliff hanger. If you want to watch seasons that have ended, I recommend “Opening New Doors” and “Boys and Girls in The City.”

The reason why I love it is because it’s the most wholesome reality show. Imagine a group of people living in a house, but the drama is that the guy who wants to be a chef isn’t working hard enough towards becoming a chef and the housemates stage an intervention. Yeah, I know right. It’s also hilarious because there are commentators who watch it with you and they always say exactly what you’re thinking.

Here’s a trailer I found for Opening New Doors that has English subs

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

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