Why Silicon Valley and thinking like a maker

On why Silicon Valley…

It seems like so many people are talking about leaving San Francisco / Silicon Valley, given how much I complain about the shoddy city infrastructure, I’ve had to answer why I’m still here many times. The short version is I that the same toxic groupthink is what pushes what’s considered “normal” to the edges, and that makes for extremely stimulating conversations and collaborations. But recently I found even better answers from Patrick McKenzie and Marc Andreessen:

Probably the single biggest change in belief I’ve had since joining is that ambition properly harnessed can be an enormously productive force in the world. This is largely informed by working with people who are extremely ambitious and yet well-grounded, both at Stripe and at our customers. There is a great, great difference between “Build a credit card processor? That’s impossible.” and “Build a credit card processor? That probably involves compliance with an enumerable set of regulations and writing a finite number of lines of code.” You want more people in your life who say the second version, probably at most margins.

Relatedly, I think I agree with Tyler Cowen that raising others’ aspirations is an effective way to increase productivity.

One way that Silicon Valley does this at scale is creating a space in the culture for being just a little bit wild-eyed when envisioning potential impact and then, this is important, actually shipping tractable engineering artifacts against the vision.

This is often poked fun of when it is deployed in the service of ends people view as unserious or when done by folks who confabulate. I have probably made jokes like that before. I think I have come to regret them, because they’re also heard by people with serious goals who are scrupulous. The jokes, and the broader culture, discourage those people from trying extraordinarily ambitious things.

Patrick McKenzie (@patio11) on “What Working At Stripe Has Been Like

Couple things notable. It is also my experience that the circle I have around me are both “extremely ambitious” and “well-grounded.” The magic of the valley has been the same this whole time which is that it is the only place in the world where it’s not only okay but encouraged to be “a bit wild-eyed” because “shipping” is also ingrained in the culture.

And then there’s Marc Andreessen.

Marc: And part of it is you should get into a scene. So this is part of it. By the way, this also goes to another kind of view of unfairness right now which is like, okay, why do all the great movies and TV shows get made… why do the vast majority get made in LA.? Like, that’s so unfair to people. There are people who, like, try to make movies in San Francisco, and they’ll tell you like, “It’s so unfair. Like, it’s just so much easier to do this in LA. Like, it should be easy to do this…” We get this in the startup world, like, why are a disproportionate number of startups built in Silicon Valley? Isn’t it unfair that you don’t have equal odds of doing this if you’re in Topeka?

Well, that’s one way of looking at it. The other way of looking at it is, if I’m the indiv– you know, I grew up in rural Wisconsin — like, if the job is to get enmeshed into the system, right, into the network, then basically, what you wanna do as an individual is you wanna get yourself into the scene.

Brian: Yah Tony Hsieh calls them “collision spaces”.

Marc: Yeah. You gotta get in the mix, right. And if you’re not willing to get in the mix, it’s not their fault. It’s your fault, right? Again, as an individual, that’s the

Brian: Because we’re talking about is people who… what did… other than Van Gogh get to paint those paintings and feel that feeling, but his inability to talk to people — the work ultimately, it did him some good, but not nearly the good it could have done him, right? …Emily Dickinson, the same thing.

Marc: Yeah. Look, I’m completely open to the idea that there’s an alternate-universe Brian Koppelman, let’s call him “Krian Boppelman” <Yes!>, who’s a machinist in Albany, New York, who’s got a whole bunch of genius screenplays on the shelf. And, you know, someday he’s gonna die and his kids are goona discover and publish them and we’ll be like, “Oh my god. Look at all these great TV shows that never got made.” Because the world wasn’t enlightened enough to be able to go seek him out. I’m open to the possibility that that person exists… [but] I don’t know what to do with that?

Marc Andreesen on The Moment with Brian Koppelman podcast (transcript)

The point here is that it is unfair that these ecosystems are concentrated and exclusionary, but as an individual, the basic understanding should be that the great work you create has no value if people can’t find out about it. Because people are busy, they’re not going to go out of their way, so it is imperative for the individual to do everything in their power to inject themselves and their work into the mix, and that’s why you have to be in Silicon Valley.

On thinking like a maker…

The media has been calling out tech, which is warranted. Power should be checked and tech is powerful. However, I find that there’s a lack of empathy for the makers of tech and how they are grappling with these complicated issues. Recent long-form interviews with Jack Dorsey and Mark Zuckerberg show that these two CEOs are thinking deeply about very difficult problems and I think it’s important to notice that and help move the more productive conversations forward instead. If we could see this level of deep thinking from powerful people regardless of industry, the world would be a better place. But we are not directing the attention to these discussions.

Jack Dorsey on introducing Edit Tweet:

you could build it such that you know maybe we introduced a 5-second to 30 second delay in the sending and within that window you can edit…

But the issue with going longer than that is that it takes the real-time nature out of it. Then we’re delaying these tweets like when you’re watching UFC or Warriors basketball a lot of a lot of the great Twitter is in the moment just like, you know, it’s the roar of the crowd…

if you’re if you’re in the context of an NBA game you want to be fast and you just want to be in the moment, you want to be raw, but if you’re in the context of considering what the president just did or making a particular statement that you probably need some more time and and we can be dynamic there.

Jack Dorsey on The Joe Rogan Experience

On fighting harassment:

What we are seeing with harassment is I don’t know this person and they’re just coming at me. What they’re doing is that they’re just gaming the system or that we haven’t provided enough tools to ward that off. We’re looking at product fixes like what if you could, being a host, have more control over the replies, who replies, or hide it from your conversation. What does that do for you and what does that do for the experience? It has positives for the author, but it also has negatives in that you’re likely creating more of a filter bubble. We see a lot of the power of Twitter is speaking truth to power. You can imagine some folks you disagree with heavily moderating or having teams of people heavily moderating their own reply space which takes out some of the conversation that might have been enlightening or emboldening to you.

…with the thesis being you tweeted something and you are effectively host of a conversation. Should we give you more controls to curate the conversation to the degree that you want to take it. If we were to do something like that we can only do so by saying, ‘Sam moderated this reply, it’s still here you can see it if you tap this button but you have to do some work to get to it because he has chosen to go in this direction.’

We ultimately believe that we need to measure our success here and I don’t know of another tangible metaphor than health. I know it sounds a little bit abstract and weird right now but we intend to study conversational health and understand what it means in the digital space and what it means specifically for Twitter and share all of our findings.

Jack Dorsey on Sam Harris’ Making Sense podcast

Mark Zuckerberg on decentralizing authentication on Facebook:

So, the question is if you have a fully distributed system, it dramatically empowers individuals on the one hand, but it really raises the stakes and it gets to your questions around, well, what are the boundaries on consent and how people can really actually effectively know that they’re giving consent to an institution? In some ways it’s a lot easier to regulate and hold accountable large companies like Facebook or Google, because they’re more visible, they’re more transparent than the long tail of services that people would chose to then go interact with directly. So, I think that this is a really interesting social question. To some degree I think this idea of going in the direction of block chain authentication is less gated on the technology and capacity to do that. I think if you were doing fully decentralized Facebook, that would take massive computation, but I’m sure we could do fully decentralized authentication if we wanted to. I think the real question is do you really want that?

Mark Zuckerberg’s discussion with Jonathan Zittrain at Harvard Law School

Zuckerberg on encrypting messages:

Yeah, so, this is a really interesting point, right? So, when people talk about how encryption will darken some of the signals that we’ll be able to use, you know, both for potentially providing better services and for preventing harm. One of the— I guess, somewhat surprising to me, findings of the last couple of years of working on content governance and enforcement is that it often is much more effective to identify fake accounts and bad actors upstream of them doing something bad by patterns of activity rather than looking at the content.

…You can identify a lot of that without necessarily even looking at the content itself. And if you have to look at a piece of content, then in some cases, you’re already late, because the content exists and the activity has already happened. So, that’s one of the things that makes me feel like encryption for these messaging services is really the right direction to go, because you’re— it’s a very pro privacy and pro security move to give people that control and assurance and I’m relatively confident that even though you are losing some tools to— on the finding harmful content side of the ledger, I don’t think at the end of the day that those are going to end up being the most important tools—

Mark Zuckerberg’s discussion with Jonathan Zittrain at Harvard Law School

On curbing misinformation:

So but then you get the question of what’s the cost benefit of allowing that. And obviously, where you can accurately separate what’s good and bad which you, like in the case of misinformation I’m not sure you could do it fully accurately, but you can try to build systems that approximate that, there’s certainly the issue, which is that, I mean, there is misinformation which leads to massive public harm, right. So if it’s misinformation that is also spreading hate and leading to genocide or public attacks or, it’s like, okay, we’re not going to allow that. Right. That’s coming down. But then generally if you say something that’s wrong, we’re not going to try to block that.

We’re just going to try to not show it to people widely because people don’t want content that is wrong. So then the question is as something is approaching the line, how do you assess that? This is a general theme in a lot of the content governance and enforcement work that we’re doing, which is there’s one piece of this which is just making sure that we can as effectively as possible enforce the policies that exist. Then there’s a whole other stream of work, which I called borderline content, which is basically this issue of as content approaches the line of being against the policies, how do you make sure that that isn’t the content that is somehow getting the most distribution?

Mark Zuckerberg’s discussion with Jonathan Zittrain at Harvard Law School

If we were to listen closely and try to answer some of the questions pose by Dorsey and Zuckerberg ourselves, we can gain more appreciation for the difficult job these people have at designing meaningful systems for the rest of us. Maybe some of us can then contribute perspectives to help shape their thinking.

The future is Asian American

In Silicon Valley parlance, we are witnessing a “zero-to-one” opportunity in Asian American cultural construction. I’ve been thinking about this since my reaction to Crazy Rich Asians got more attention than I expected. 

Still, saying that Asian Americans are doing anything new might come as a surprise to a lot of people. After all, there are sixth and seventh generation Asian Americans, and you can easily find Asian restaurants, Chinatowns, and even Asian-themed museums. However, these artifacts are vestiges from a different generation. They are closer to representing the few sentences that mentioned Chinese railroad workers and the Chinese Exclusion Act in our history books than anything we can relate to today. As an Asian American, visiting an old Chinatown or an Asian museum makes me feel just as foreign as when I visit Asia. The idea of the model minority has stripped us of any discernible character.

Wesley Yang’s been writing about this for a while.

Wesley Yang on the New York Magazine cover

Here is what I sometimes suspect my face signifies to other Americans: an invisible person, barely distinguishable from a mass of faces that resemble it. A conspicuous person standing apart from the crowd and yet devoid of any individuality. An icon of so much that the culture pretends to honor but that it in fact patronizes and exploits. Not just people “who are good at math” and play the violin, but a mass of stifled, repressed, abused, conformist quasi-robots who simply do not matter, socially or culturally. — “Paper Tigers” by Wesley Yang in New York Magazine. May 8, 2011.

That is what zero feels like.

But what does one feel like?

These Tweets from famous Asian American athletes look quite ordinary because…they are. But these were also the rare moments where an Asian American got to display her or his full personhood, in all of its simplicity (like feeling hangry and having a celebrity crush) and complexity (like talking about cultural appropriation). Something that most ordinary Americans are not used to seeing from Asian Americans so publicly. 

Since Yang’s article in 2011, Asian Americans have experienced an unprecedented number of opportunities to publicly renegotiate with the rest of America about what it means to be Asian in this country. At the Oscars, Chris Rock inadvertently ticked off Asians, fueling #OscarsSoWhite and the ensuing attempts at reconciliation, which helped set the stage for the success of Crazy Rich Asians. Harvard, the most sought-after Asian brand, is currently contending with its biggest boosters about how to fairly evaluate their children. The progression from zero to one will require more cultural representation and public discourse about what it means to be Asian American. In Taiwan where I grew up, people can’t tell white people apart. Racism and stereotypes strike me as problematic largely because compelling alternatives are not readily available. I feel like we are at the cusp of this rise in the American cultural consciousness as I read these names — Michelle Phan, Steven Yeun, Amy Chua, Mindy Kaling, Aziz Ansari, Ryan Higa, Tim de la Ghetto, Hasan Minhaj, Eddie Huang, David Chang, Shib Sibs, Fung Bros, Bobby Hundreds, Akwafina, John Cho, Ken Jeong, Ali Wong, Daniel Dae Kim, Grace Park, Shim Lim, Lana Condor, Randall Park, Kamala Harris, Andrew Yang, Harry Shum Jr., Ted Chiang.

This rise is not an accident. We are seeing the rise today because Asian Americans have built up hard power (i.e. economic means) and we are beginning to demand soft power (i.e. cultural influence) in the United States.

Asian American Hard Power (the market)

It must first be noted that the simplicity of the “Asian American” grouping ignores the important differences among the 40+ subcultures that fall in this bucket.

Population: The Asian American population is projected to grow to 25.7 million by 2019 (7% of the U.S. population), more than doubled from 10.9 million in 1999 just twenty years ago (and the year when I moved to the United States). Asian Americans are the fastest growing population group, faster than the Hispanic-American population. 

Purchasing power: According to Nielsen, Asian American buying power increased 257% between 2000 and 2017 (compared to 203% from the second-fastest growing group of Hispanic Americans). They are projected to have a combined purchasing power of $1.3 trillion by 2022. Asian American household income of $110,523 is the highest among all population groups including non-Hispanic White households (Asian Americans are also the highest in individual mean income of $44,887).

Young and educated: Because the most recent immigration wave started in 1965, Asian Americans skew younger than the general population (34 as opposed to 38). If you only consider the second-generation, the median age is only 30. Asian Americans are more likely to enroll in college at 87% compared to 72% for the average American. 

Greater Asian Diaspora: It would be remiss to not mention a similar rise in the Greater Asian Diaspora. In terms of population, there are 1.7 million Chinese in Canada and 1.2 million in Australia. There are 1.8 million Indian-British, 1.5 million Indian-Canadian and 1.3 million Indian-South African. Unsurprisingly, Crazy Rich Asians, the movie that spoke specifically to Asian Americans, also dominated the box office in Canada and Australia.

The rise of Asian American Soft Power (the opportunity)

A few months ago, I started noticing my Asian American friends started to share memes from a Facebook group called “Subtle Asian Traits.” The group now has more than one million members and it seems like almost every Asian American I know is in there. If you’ve read this far, it shouldn’t surprise you to find out that the group was started by students in Australia. As one of the founders told the New York Times:

She said she doesn’t mind that her friends ask her about her heritage, although answering questions can be “a bit tedious.”

The endless stream of memes in the “Subtle Asian Traits” group provides relief — it’s a chance to belong for once without having to try.

“We don’t have to explain stuff,” she said.

A New Yorker article describes the impact of this random Facebook group has had on an Asian Canadian:

Jin Angeles, who is twenty-six and lives in Toronto, told me that he has become much less apprehensive in opening conversations about his own Asian upbringing — topics that, before Subtle Asian Traits, would only come up if some event occurred to break a silence that he had never quite noticed before.

Specifically the way Subtle Asian Traits (“SAT”, lol) helps create feelings of belonging is through the sharing of memes that only those in the in-group would understand. Here’s an example:

A meme from “Subtle Asian Traits”

According to Pew Research, second-generation children of immigrants are more likely to identify with the Asian American or American label than the label associated with their heritage country (i.e. “Korean-American”). There is a tremendous opportunity in being part of this secular movement, and entrepreneurs are starting to pay attention.

Opportunity: Asian American-first businesses

What does it mean to build a business to specifically cater to Asian Americans? With an exploding population and spending power, it pays to explore this idea more. 


The first 99 Ranch Market opened in 1984 in Westminster, CA and has since expanded to 50 locations, making roughly $350M a year. Alex Zhou started Yamibuy in 2013 as the online equivalent of 99 Ranch Market to target the younger generation of Asian Americans. In just five years, Yamibuy has grown to $100M in annual revenue and has received $10M in venture funding to fuel its growth. Yamibuy has expanded to beauty and home/kitchen appliances, which maps perfectly to the categories Asian American consumers over-index on according to Nielsen.

Coffee Meets Bagel, EastMeetEast, 2RedBeans, Minder, Shaadi

In the competitive dating market, Coffee Meets Bagel has survived against better funded competitors by carving out a niche of Asian Americans and that niche pays at a much higher rate. Compared to CMB, EastMeetEast is more overtly focused on Asian Americans, from working with Asian YouTubers to creative billboards in LA K-Town to having “fobbiness” as a filter in your dating profile.

Filter for “age arrived” aka “fobbiness filter”

2RedBeans went directly after the overseas Chinese market (you can log in with WeChat), which has also enabled them to stay relevant. I haven’t checked these out but I hear there are Minder and Shaadi to tailor to Muslims and Indians specifically.

Michelle Phan / Ipsy

Asian Americans are the most digitally connected minority group in the U.S. Using the YouTube, Asian Americans have side-stepped being overlooked by the mainstream media and built their influence online. Amongst all the Asian beauty and food influencers, Michelle Phan has had the most success riding this wave. Her company, Ipsy, is doing north of $360M in ARR and has people talking about a $2B exit. Building on YouTube is a great way to target Asian Americans.

Instant Pot

When I first heard about Instant Pot, it was around 2016. My Asian American friend Esther Yu was spreading the good word about the Prime Day discount. Then in 2017, my other friend Wil Chung convinced me to buy one, but by then I’ve already seen Instant Pot infiltrate every Asian household I go to. The product was engineered to facilitate making immigrant comfort dishes like curry. It even has buttons specifically for “porridge” and “rice.” Typically, the young people are the first to discover new products, but in the case of Instant Pot, they started magically appearing in the homes of my older family and relatives at the same time because Asian Americans are the more likely to be connected with their families through messaging apps like Skype and Whatsapp (Young Asian Americans are twice as likely to be using those apps compared to the average population because of their families), and they made for convenient gifts for our immigrant parents who love to cook.

Crazy Rich Asians, GoldThreads and NextShark

Movies are like startups (with longer odds). The phenomenon that was Crazy Rich Asians grossed $238M worldwide on a $30M investment. The lesser-known movie Searching, #StarringJohnCho, did $78M worldwide with South Korea accounting for $22M of the box office on a shoestring budget.

South Morning China Post with their Goldthread and Abacus properties are bringing professional, high-quality media production to target Asian Americans and those with an interest in China. New media startups like Nextshark has also quickly carved out a niche celebrating Asian Americans in a relatively short time.

These are just the first of many businesses that are smart enough to take advantage of Asian Americans’ digital savvy and desire to identify with their culture.

Opportunity: Asian cultural import

It’s not rocket science to think that something that works in Asia might work in the Western world, especially with a growing and established Asian Diaspora. Many Asian Americans I know grew up without role models who look like them, beauty standards they can aspire to or products that speak to them, but when we visit Asia, we find them in abundance. 

Mari Kondo / KonMari Media, Inc.

What sparks joy for me is to tell people that Mari Kondo is VC-backed. She’s helping to export Japanese Shintoism and minimalist values to the rest of us. While she is clearly Japanese, the backlash she’s facing in the United States has many Asian Americans up in arms defending her because the other-ification is not dissimilar to how they’ve been treated and threatens to take away one of the few heroes they can look up to who looks like them.

K-Beauty and Yoga

K-Beauty, at least according to my female friends (and a few male friends), has been on the come-up for a while. South Korea exported $5B worth of cosmetics. While it’s unclear how much ended up in the U.S., Rakuten’s survey indicates that the category has grown by 300% between 2015 and 2017, and these products are disproportionately purchased by Asian Americans.

Yoga, which came from India, has also been growing rapidly in recent years. 36M people now practice yoga according to the 2016 Yoga in America Study, which is up from 20.4M in 2012. It’s a $16B industry that has grown 60% between 2012–2016. 


This past February, BLACKPINK went on Good Morning America to announce their US tour dates and quickly sold out. A week later, BTS presented an award at the Grammys. You can find many Asian Americans at the root of K-Pop. Jae Chong moved to Korea in 1992 to start the first K-Pop Hip-Hop boy band SOLID. Tablo from Epik High grew up in Canada and graduated from Stanford before moving to Korea for his music career. Jay Park was doing YouTube videos from Seattle before he became one of the biggest K-Pop stars to cross back over to the U.S.. You can trace many more K-Pop producers, songwriters and business executives back to their Asian American roots. The rise of K-Pop is really Asian American homecoming. 


There’s this guy, Sean Miyashiro, who’s been going around signing artists out of Indonesia (Rich Brian), Australia (Joji, who recently became the first Asian artist to debut #1 on Billboard‘s Top R&B/Hip-Hop Albums chart), Korea (Keith Ape), China (Higher Brothers) and making them superstars in the U.S. and worldwide. Only a few artists on the label are Asian Americans, but the formula is a hit with Asian American youth.

Rich Brian addresses the audience at the 88rising Double Happiness show at the Shrine Auditorium & Expo Hall in Los Angeles on February 10, 2018 (Forbes / 88 Rising)

Opportunity: American fast-follow

We’ve moved from the days of Chinese knock-offs and copycats to Americans “fast-following” Chinese startups and localizing their strategies for the U.S. consumers. Not only has venture capital started to flow more to China than to the U.S., the staggering number of urbanized consumers in China will inevitably produce ideas that Americans will only adopt later on as we become more urban over time. Connie Chan has been talking in much more depth and nuance than I can capture. If you follow her on Twitter, you will find great talks like this one on how Chinese startups have more diversified income streams than advertising. 


Lime is a clear fast-follow from the Chinese trend of dockless bikesharing, but they’ve adopted it for the American commute by electrifying its micromobility fleet and adding scooters to the mix. The startup is most recently valued at $2.4B. Asian Americans who have experienced these services first-hand in Asia and have strong ties there are most likely to be the ones to help bridge their cross-over to the United States. 


Wish is a shopping app that boasts 300M users with a valuation over $8B. Chinese consumers already benefit from being able to order from Chinese sellers on sites like Alibaba and JD.com, but American consumers has to go through various middlemen marking up low-priced Chinese products. Wish offered an alternative. 94% of the sellers on Wish are Chinese while 30% of its buyers are based in the U.S. (the rest are in Europe).

American Ninja Warrior, The Masked Singer

Americans will also continue to copy the best of Asian media. You probably could’ve guessed that American Ninja Warrior is based on a Japanese show Sasuke, but did you know that the latest show on FOX, The Masked Singer, is based on the South Korean show The King of Mask Singer (you will be really delighted to learn who won the first season)?

Betting on #AsianAmericanRising

Now is literally the defining moment in history for Asian Americans and I’m optimistic because betting on Asian America has always yielded high returns against all odds.

In the technology industry where Asian Americans historically have the most advantage because they represent 27.2% of the work force, only 18.8% become managers and 13.9% become executives. This is the classic “bamboo ceiling” and it highlights the struggle that Asian Americans face even when they are relatively privileged.

However, when I compiled a list of “unicorn” startups (i.e. companies with private valuations over $1B) and their founders, I found that out of 206 unicorns, almost one in four (23.8%) are led by an Asian American or Asian Diaspora founder. In other words, Asian Americans have created nearly $200B (29.4% of $659B) in aggregate value. Just like with Hollywood, Asian Americans are impacting Silicon Valley by side-stepping traditional corporate ladders and writing their own rules as entrepreneurs.

In a world where everyone is connected through the major tech platforms, focusing on niche populations and helping them fuse their identity makes for smart business. The restaurant review platform Yelp can attribute much of its success to finding product-market fit among Asian Americans. One study found that Asian American women are 201% more likely to use Yelp. The online publication BuzzFeed has also found success by identifying with Asian American users. Their staff of writers regularly create content about Asian American topics after discovering that people like to share content that help them express their identity.

I’m excited for the future of Asian America. There are a lot of exciting opportunities to create new products and services created for a population that is more likely to live in multi-generational homes, more likely to travel, more likely to purchase consumer electronics, home, kitchen and beauty products, and more connected digitally and globally.

Where can we share stories through food? Where can we buy glasses that fit our noses and falsies that fit our eyes? Where can we watch our version of BET, Univision and Telemundo? Where do we go to feel like we belong? Where is the next Uniqlo that’s made for our bodies? Where is the next Lime to bring innovations we enjoy in Asia to us?

I can’t wait to see what we do next.

Fans at the 88 Degrees & Rising Tour show in New York. Harrison Jacobs/Business Insider

If you’d like to chat more about this essay, follow me on Twitter or shoot me an email at last name dot first name at gmail

How we take care of our mental health

I like to joke that startup founders eventually become interested in mental health because startups turn you into a nutcase. I got interested in this topic about six years ago during some of the toughest times of my startup journey, and I feel much stronger today mentally having worked on it. I wanted to go beyond my own experiences to talk to other “users” of mental health and write about it as part of a regular series where I explore various topics that interest me (check out my last article about my teenage nephews’ digital habits), so I posted this to Facebook.

People love an excuse to talk about their mental health

Based on the number of comments, my post definitely struck some kind of nerve. Over the past two weeks, I was able to talk to twelve of my friends about their experiences with mental health. Note that my friends are mostly in their late-twenties / early-thirties and relatively privileged in society, and I’m not a mental health professional but simply viewing their experiences from the perspective of a startup founder interested in building something useful in the space.

As the conversations got going, I quickly realized what I got myself into. I assumed people wanted to tell me about solutions like how they meditate and what kind of therapy they go to. Instead, almost everyone I spoke with wanted to give me a bigger picture of the journey they had to go through to get better. I really had to scramble to grasp the complexity of this problem enough to write about it.

How we become aware of our mental health challenges

The first question I asked my friends was how they became aware of their mental health problems enough to want to work on it. I wanted to find someone who was good at it so it doesn’t seem like it’s always too late and requires a lot of suffering before you realize you can help it. Unfortunately, everyone sucks at this.

For many of my friends, there’s typically a life trigger like the death of a loved one, a health scare or a career failure that hijacks their attention to really tune in to their feelings, but I also think some people are just naturally more in touch with feelings. The stereotype that women are better at this seems true to me. Talking to men about their mental health definitely felt like pulling teeth. A male friend described it as a “lag” — men are aware of their feelings, but they don’t address it until the condition is right (who knows when). Until then, you drown yourself in some other activity that helps get your mind off of it.

I have a friend who was very aware of his emotions starting when he was a small child, but was very inhibited because his immigrant parents called him “too sensitive.” Another friend of mine felt depressed growing up but didn’t really understand it. Her immigrant parents told her, “you don’t get to be unhappy, you have everything.” These children grew up depressed without anyone there to supply the labels and validate their feelings. In some ways it feels worse than simply being unaware because you have to repress the feelings and mistakenly think that something is wrong with you.

Imagine trying to address a problem that you don’t even know the name of. All you know is that you are experiencing pain, so you look for ways to soothe the pain. People come up with all kinds of solutions that aren’t real progress. In my friend group of ambitious young people, the answer is typically to overachieve. It never feels quite satisfying, but it’s the only societal prescription they know. Some people turn to substance abuse and alcoholism.

Sometimes, people get lucky. Maybe someone points them in the direction of counseling. Maybe they came across a book, a lecture, or a website that gave them the words to understand why they feel sad. Maybe the suffering is so great that a switch eventually flips in their brain to start actively defending against it. They go from being a passive victim to an active caretaker of themselves. They know the problem has to do with what’s in their head. As someone who has built startups and interviewed countless users, I’m very unsatisfied with how random this whole process seems to be.

We suck at this as a society. A friend quipped that there’s not a common understanding of what is good mental health versus bad mental health. How do you improve what you don’t know how to measure? As complex as our body is, we still have measurements like our weight, BMI, blood pressure that most people understand despite being imperfect proxies. When it comes to our mental health, we have basically nothing before the clinical definition of mental disorders, which is scary and not user-friendly. “Am I bad enough that I need therapy?” “If I call the suicide crisis line, does that make me suicidal?” “Am I just sad or do I suffer from depression?”

A lot of the commonly touted “solutions” are fraught with friction as well because different things work for different people. Multiple friends told me that “meditation didn’t work for me.” One friend said he basically tries to get into meditation every year and every year he fails. For friends that have sought out therapy, it took most of them multiple tries until they found the right therapist. It’s a miracle how anyone actually gets better.

What it feels like when you are suffering

Source: http://www.collegehumor.com/post/7043699/what-you-say-about-mental-illness-vs-what-you-actually-mean

I feel like it’s important to talk a little about what suffering feels like in the context of mental health. A common feeling is that there’s no one to talk to. Even if you have lots of friends, you feel like your friends don’t understand. Some people don’t have close enough friendships that are conducive to opening up and others simply don’t want to be a burden. This feeling can persist even if you go to therapy because therapists don’t have super powers. You may not connect with your therapist. You may find that they don’t have the context to really empathize with what you are dealing with. Some therapists don’t listen well and sometimes they say the wrong things.

When you try to help yourself and you fail over and over, you start to feel helpless. Learned helplessness can set in and you may retreat from people completely. You can get in a “funk” that lasts many months where you aren’t able to do anything. Getting out of bed becomes difficult. You become numb.

Almost everyone I talk to understands the idea of the downward spiral. When you feel depressed, everything reinforces the depression and it easily spirals out of control. You start to consider suicide or you see that you are only a few spirals away from doing it, but you can’t seem to get out. The downward spiral starts to surface in your relationships. When you are suffering, you attract negative people who make you spiral faster because you forget what normal, positive people look like (or you’ve never known). You don’t let yourself be better. You think you don’t deserve any better.

Getting better is ultimately about a perspective shift

Before going into specific methods people use to improve their mental health, it seems to me that the goal is always some sort of perspective shift. Unfortunately, there’s no easy answer on how people get there. One friend described it as knowing the inputs (your mental problems) and the output (perspective shift), but he has no idea how the function works.

In almost every conversation, I was reminded of how powerful the stories we tell ourselves are. However, I was also impressed by my friends’ abilities to eventually reinterpret the stories or make them less powerful. One friend felt that she grew up disadvantaged and that story led her to feel maligned by parents and an unfair society. Growing up for her was about doggedly fighting that disadvantage and never winning. Today, that story of disadvantage is still there and a source of strength, but it’s only a piece of her much greater story. She no longer feels it viscerally.

One friend felt like he was abandoned by his parents. “Why won’t they love me?” was the question that caused him a lot of grief. Today, he has learned to sit with that feeling of abandonment. One big thing he did was to live abroad by himself. He lets himself be sad when he feels alone instead of feeling bad about being sad, and after a while, his story began to lose its grip. One day he was told that his battles growing up made him who he is today, and he relishes in that new understanding.

A friend defined his life by being an overachiever, but today he focuses on the journey rather than the outcome. Another friend felt like she couldn’t fit in with the overachieving peers she met in college, but these days she has embraced her individuality and loves that she is pursuing a path that is unique to her.

All of these perspective shifts “make sense,” but they happen slowly over time. I asked a friend what would happen if he were to go back and tell his 24-year-old self exactly what he needed to do. He said the message would’ve simply fallen on deaf ears. Even if these new stories make perfect sense, you have to hear them over and over again until the time is right for the message to be received.

I tried to explain to myself why some people seem naturally happier than others. What I came up with is perhaps these people adopted positive versions of stories earlier in their life and they’ve experienced the positive version of the spiral. For example, I have a friend who has always cared mostly about family. I have another friend that loves his freedom above all else, and another who wants to live out his individualism to the fullest. They seem very confident in what they care about, which helps them focus on doing the things that make them happy.

What to do to get better

The “work” people do to get better really varies. Our mind is so complex, different things work for different people. Something that has worked for someone in the past may not work for that same person in the future.

A good place to start seems to be journaling. That’s what I’ve personally found the most useful. Journaling forces me to put the thoughts swirling around in my head down on (digital) paper, helping me sort out what I’m feeling, why I may be feeling it, and creating a healthy distance between me and my thoughts. My friends recommend different variations like Minimalist Journals, Gratitude Journals and Morning Pages, which can help achieve similar effects depending on what you’re looking for. I recently started tracking my mood throughout the day using Daylio, which has enabled to become aware of changes in mood throughout the day and better hone in the causes. I think there’s a lot more that can be done here to popularize tracking mental fitness just like how we track physical fitness.

Daylio (left) helps track your mood through out the day and Youper (middle/right) has incorporated some concepts from the emotional color wheel to help people better label their feelings.

Therapy is very common, but finding the right therapist is so hard a friend described it to be similar to dating. Some go for the same reason why I journal, which is to talk out their feelings and understand them. For me, I was looking to talk to a therapist who has a different background and context than my friend circle, while others look for therapists who have coached successful startup CEOs or dealt with a specific life trauma so they can have the shared context. Some people really care about their therapists’ credentials because that helps them suspend disbelief and buy into a self-improvement program that they otherwise wouldn’t have considered. Others appreciate the therapists age and experience level so that they can feel like they’re not the only ones with the problem. Some friends specifically look to get mental frameworks and thinking exercises from their therapists while others use their therapists just for prescribing anti-depressants. A friend uses a therapist to keep himself accountable to a third party, kind of like a personal trainer. Three people I spoke to go to couple’s counseling, and they use their therapists to help articulate hard truths and moderate uncomfortable conversations. Sometimes the reason why a therapist works out is simply because there’s a connection that helps you feel open to be more vulnerable. This is a really hard matching problem.

This kid is really good at meditation

Meditation has become so popular recently I was surprised to learn that the leading app Headspace only celebrated 1M subscribers in June 2018. That’s such a small number! Most of my friends have tried meditating, but it’s hard for the habit to stick. The most successful friends take their practices very seriously, and one friend mentioned having been on weeklong silent retreats. A friend of mine meditates because he knows his default state is hot-headed, so he meditates twice a day to bring himself down. Another friend meditates so she can practice being okay with all of her thoughts, insecure as they are. A good number of friends like to practice yoga, which is a more physical manifestation of meditation that works for them.

Some of the most transformative effects can be attributed to mental frameworks people get from therapy, meditation or just reading. For example, “Unlearning ideas that don’t serve you anymore” is a popular framework that, when heard at the right moment in life, can help people get rid of the autonomous programming they grew up with. Another one is “Thought, emotion, and behavior,” which is the idea that whenever one of the elements like emotion gets out of control, you can mobilize the other two elements to bring the emotion back in control. A framework I like for measuring if you have achieved healthy mental state is, “your pain one day will just play like a movie” because that’s when you know you are no longer reacting viscerally to your past traumas.

People who get better practice being kind to themselves. It sounds simple but most people prefer to beat themselves up all the time instead. This starts with knowing what activities make you happy, and then proactively seek to do them with regularity. That could mean sleeping in, reading, playing basketball, sending updates to the family group chat, hiking, planning trips, visiting family, volunteering, working out, hanging out with friends, or simply being a potato. Whatever it is that makes you feel good, let yourself do it. Even the busiest people like my friends who are doctors and lawyers find ways to squeeze in an extra 15 minutes of sleep or an extra 30 minutes of alone time in the morning. It’s important to know that what it takes to be kind to yourself can be something really tiny. For example, a friend of mine said that if she has a bad day and she’s about to go to bed, she’ll drink a glass of water to be healthy and call that a win for the day.

You have to be a little lucky or just wait until you’re older

I couldn’t help but notice the role luck plays in all of this. Two people with equally traumatic upbringings can have such radically different interpretations that one person got really good at choosing to be happy and the other person had to struggle for much longer before becoming nicer to herself. Some people were exposed to meditation and mental health because of their parents or religion, while others grew up in families where that’s simply not a thing. This is especially true if their family is immigrant or low-income. Some people have personalities that afforded them close friendships while others had to learn to build relationships that truly served them. Some people had big life events that triggered deep self-reflection while others had to wait until the pent-up feelings finally tip them over in a long and painful process. Some people are lucky enough to reach their goals, even if they’re unsatisfying, false goals, while others don’t even get to achieve the false goals that they thought would give them meaning.

And then there’s just age. They say “time heals all wounds” but also you just give less of a f*ck about your wounds. Time wears out the power of your negative narratives. Some of the friends I talk to swear by their practice or therapist as the reason why they are better, but others hesitate to really attribute their improvement to anything other than just getting older and getting a better understanding of what actually matters. The ego becomes less of a thing as you get older and you begin to treasure relationships, health, family, and yourself much, much more.

To better appreciate the role luck and age plays, I recommend checking out the Oscar-nominated documentary Minding The Gap.

Thanks for reading! Are you working on your mental health? Please leave me your feedback in the comments section.

This is the second post in the series where I deep-dive into topics that I’m interested in by talking to users. Check out the first essay on teenagers and their digital habits:

View story at Medium.com

My teenage nephews’ digital habits

One of my favorite activities as a startup founder is talking to customers or potential customers to understand how I can create something to make their lives easier. Now that I’m not working on anything specific, I’d still like to have some of these conversations and force myself to think about them. I was home in Los Angeles for Lunar New Year celebration, so I decided to casually chat with my 16-year-old twin nephews about their digital habits because every consumer startup seems to be trying to get their attention. I’d love to hear how their experiences compare with the teenagers in your life!

How do my nephews talk with their friends?

They mostly talk to their friends on Snapchat and Instagram. Ever since Instagram copied the stories feature, some of their friends moved over to Instagram, but Snapchat still retained a good amount. “I used to use Snapchat more when I was doing streaks,” is what one of my nephews said. For the uninitiated, here’s a Tweet about Snap streaks.

They also use the default Android Messages (texting), Facebook Messenger, and Discord (but they don’t play games or use the voice chat), depending on whom they’re trying to reach. This doesn’t sound very different from what I do, but it is way less convenient compared to when everyone was on AIM and later, Gchat.

I saw on one of my nephews’ DMs that he takes advantage of groups. One that I saw was called “the Musketeers” and the other one was “key club.” I love that “key club” is being coordinated via group DMs because that’s definitely better than what we used to do without group messaging.

What surprised me was how much phone and FaceTime are being used. If they needed to get in touch with someone, they’d just call or FaceTime them. I assume calling would mean VoIP via any of the messaging apps or calling their actual phone number. My nephew told me that he uses his MacBook mostly to do homework and FaceTime because he doesn’t have an iPhone. This all sounds similar to what I did in high school, minus the FaceTime and VoIP calling, of course. Not having to save phone numbers and being able to FaceTime feels to me like a significant improvement, and from what I hear, talking to friends in-person is totally still a thing, despite the apocalyptic prognostications from the olds.

What about sharing more intimate thoughts?

I remember I had a Xanga and then a LiveJournal to broadcast my teenage angst. I didn’t really bother with limiting who could see my posts (they were public) since discoverability was relatively weak without a full-fledged social graph. I imagine that’s harder to do when you live in the Facebook world.

My nephews told me about “spam accounts” on Instagram (some called it “finstas”), but they professed that they didn’t have one 😏. Apparently some people would create “spam accounts” and only let their closest friends follow and that’s where the real feelings and interests are shared. There’s also a “close friends” feature on both Snap and Instagram that you can use. I knew about this phenomenon but I was skeptical about how much you can actually express on Instagram between feed posts, stories and DMs. Looking at my old LiveJournal posts, I shared a lot. A picture is worth a thousand words but sometimes I wrote more than a thousand. My nephews told me that you can make the texts really small, but still. They also said that sometimes you post something to hint that you’re feeling some kinda way, and the people who care will message you to talk more. Maybe that’s good enough.

How about self-expression?

I remember my Myspace had a music player playing my song of the moment complete with a custom theme and lots of pictures. That was how I tried to express myself. Instagram and Snapchat just seem infinitely better because they’re way more dynamic. Sure, Instagram filters make everyone’s life look awesome, but that’s exactly what we tried to do with Myspace. The only difference is that Instagram updates way more, making it a more realistic representation of the person. To that point, Snapchat’s stories feature was revolutionary because it made self-expression even faster and way more authentic than anything that had come before. I think teenagers today clearly have us beat in terms of their ability to express themselves.

How do they waste time?

The primary time-waster for my nephews is probably tapping through their friends’ stories. Outside of that, Instagram’s Explore tab is where my nephews get the basketball highlights and Internet memes to forward to their friends. They told me that they also watch the Discover content on Snapchat, which Instagram is trying to copy with IGTV but it’s not as good yet. They also waste time together with their friends posting stories with questions, polls, lenses, stickers, etc.

Having never thought much about consumer apps, the basic product strategy from these companies seems quite straightforward and similar to Facebook and the consumer web portals from the early web days. You aggregate different types of content (ephemeral, permanent, short-form, long-form, professional, semi-professional, social) to keep users in your ecosystem as long as you can, and you build out communication utility like text, voice, and video-calling to keep them there even longer. Open DMs are like email. Different lenses and stickers are like Yahoo! and Facebook Games and Quizzes. A Snapchat-commissioned show is like Yahoo! paying to livestream NFL games.

I had to ask about YouTube because I spend so much time on there and I was surprised it was never brought up. My nephews said that sometimes creators they follow would do a preview on Instagram and then send them to YouTube to watch the full clip, and that’s when they would go. They rarely go to YouTube otherwise and they don’t really follow any creators on YouTube. Gaming-wise, they told me Fortnite is for kids. Instead, they play Brawl Stars and Clash Royale (both Supercell games). They don’t use TikTok and neither does anyone else in their school, but they get a lot of TikTok content on Instagram. They have never heard of tbh or Houseparty.

Given that Fortnite is all the rage with kids and I for sure have seen another crop of teenagers in Taiwan obsessed with YouTube and TikTok, my nephews’ answers made me think that I’m stupid for expecting all teenagers to be roughly the same. Now I wonder if the Fortnite-playing population correlates with playing Minecraft when they were younger since it’s a First-Person Shooter. As far as YouTube and TikTok go, maybe because they’re not social, there’s no real reason to visit them if the best content are already getting ripped and shared to Instagram. This is why Facebook’s moat is extremely formidable.

What else?

When I asked my nephews what gifts they’d want me to buy them they said the iPhone, and the primary reasons are Facetime and…GamePigeon. On Android phones when their friends send them GamePigeon games it just looks like a link and it doesn’t work.

My sister has parental controls over their phones and that’s why they have a VPN, which sometimes lets them get around it. The device differences and parental involvement probably underscore the “not all teens are created equal” realization.

Finally, here’s a picture with my nephews!

Have you talked to teenagers about their digital habits? How do they compare to my nephews? Let me know!

The “Full-Stack Startup” and Jiro’s Dreams of Sushi

Five years ago, Chris Dixon coined the “Full-Stack Startup” to describe the new wave of companies like Uber looking to upend entire industries through building a new, vertically-integrated stack.

The basic idea is this. Traditionally, as startup founders we see ourselves as toolmakers because we build software and that’s what software is best suited for. If we thought the experience of hailing taxis were broken, we’d build a better taxi dispatch software and sell that to taxi companies. Software can solve the dispatch problem elegantly because it’s relatively close-ended. Running a taxi company, on the other hand, seemed extremely under-leveraged in terms of technology and a terrible business.

However, Uber not only built dispatch software but also hired drivers to offer rides, allowing them to control the entire production function and eat the taxi industry altogether. That’s a much more expansive role for software, but a truly exciting one because the experiences are much more magical when it works.

Since then, venture capital has poured into all kinds of full-stack startups. Opendoor, Compass, WeWork, Shift, Triplebyte, Gigster, Pilot, Honor, Forward, Atrium, just to name few. At the same time, we’ve seen spectacular failures like Homejoy, Sprig, Munchery, Luxe, HomeHero, and to a lesser extent, Zenefits and Altschool. What explains the differences in outcome?

I think the two most important questions to ask are 1) how variable are the customers expectations and 2) to what extent can software help deliver on those expectations.

A lesson from Jiro

Jiro Ono, the software of sushi-making

Jiro Ono is a three-Michelin sushi chef in Japan and the subject of the documentary, Jiro Dreams of Sushi. At 85, Jiro has mastered every facet of his craft. From knowing the perfect length of time to massage an octopus (40 minutes) to developing a technique to preserve sushi rice at its optimal temperature (body temperature) to only serving each ingredient at “its ideal moment of deliciousness,” Jiro has explored, refined and practiced every painstaking detail to perfection. In a way, Jiro has done to sushi-making what software has done to many human tasks — eliminated variability and refined the quality of the output.

However, here’s the kicker. Three-Michelin Sukiyabashi Jiro has only 4 out of 5 stars after 71 reviews on Yelp. The problem? Even though Jiro has the best sushi-making software, he’s in the full-stack restaurant business where software does not provide enough leverage in providing a consistently positive customer experience.

Some of the two-star reviews on Yelp

First, Jiro’s customers come with a wide variety of expectations beyond great sushi. Some expect a certain level of service for the price while others care more about comfort and ambience. Some may even be looking for the meaning of life in Jiro’s sushi. Obviously, Jiro promises none of these things, but customers expect them nonetheless.

Second, even if Jiro has the most refined process for making sushi, customers are eating the sushi, not the process, and sushi tastes are highly subjective[1]. So in a way, Jiro’s software failed to deliver against even the singular goal of great sushi.

Traditional startups sell sushi-making software. Full-stack startups operate restaurants. Operating a full-stack startup, you live and die by your ability to manage your customer’s expectations while consistently delivering against the expectations leveraging software. Sounds basic but anyone in the service industry would tell you that it’s hard to execute on let alone having to do it at scale.

The bane of variable customer expectations and why services offer “Free Consultation”

When I built Crowdbooster, a social marketing software-as-a-service startup, we would often talk about “landing pages” because our customers knew roughly what they wanted and the landing pages together with a free trial were mostly sufficient in helping them figure out if Crowdbooster was right for them.

Crowdbooster’s landing page. That screenshot of the product was worth a thousand words.

My second startup, Upbeat, was a full-stack, tech-enabled public relations agency. Our product was not something you used, but a service to help you garner media coverage. Our customers did not know how public relations worked nor did they care to. All they knew was that they desired media coverage, and they paid us to help achieve that outcome. However, even when we delivered great media coverage, some of our customers were still dissatisfied.

The problem is that full-stack customers don’t really know what they want beyond the fact that they have a problem, and when the outcome is delivered, that’s when they begin to realize what they were looking for. This is why consultants have offered “free consultation” for ages — it’s the service industry equivalent of a free trial. The free consultation is an opportunity to explore the nature of the customers’ problem, educate them on what to look for, and set expectations on what they can and cannot expect from an engagement. Many full-stack startups like Honor, Atrium, and Pilot take this approach and force you to talk with an expert agent during the sign-up process.

However, a free consultation, like any human conversation, is a lossy process at best. To avoid dealing with the fickleness of humans, you can instead choose a more bounded problem by constraining the customer segment to only customers you know you can deliver for (as long as it doesn’t constrain your market long-term). This is the like running a fast food chain as opposed to Jiro’s restaurant. For example, OpenDoor targets only customers who want to sell their home fast (and fit their many other criteria). If the customer is not in a rush or they prefer to be serviced by a real estate agent for the experience or to feel like they got the best price, then they are not for OpenDoor.

If you qualify for an OpenDoor offer on your house, they still require a “review” with a human because it helps align expectations

How much leverage can you get from software?

Assuming you figured out how to manage your customers’ expectations and filter for the right segment, full-stack startups still have to consistently deliver a great customer experience with a production function that they don’t fully control. Uber, for example, went as far as calling human drivers their existential dependency and the final barrier to a perfectly-controlled customer experience. This is despite having built one of the most successful marketplaces in the history of startups. Traditional marketplace tactics like user ratings, apps to manage workers, offering different levels of service to different customer segments, insurance, etc. will eventually be insufficient for Uber because when you sell the outcome of a ride, any problems caused by drivers along the way is your fault, so you’d want to ultimately subsume that variable.

For a better framework on how to properly leverage software to tackle full-stack opportunities, I’d send you to Andrew Chen’s brilliant essay, “What’s next for marketplace startups? Reinventing the $10 trillion service economy, that’s what.” Notice in his essay that as we move fuller-stack, the leverage you gain from software begin to diminish. This is something to watch out for and you can use the strategies in his essay to mitigate.

From Andrew Chen’s essay

As Arthur C. Clarke once said, “any sufficiently advanced technology is indistinguishable from magic.” To me, full-stack startups are the ultimate magical feat, especially when you can appreciate the complexity of their production functions. As software continues to “eat the world,” full-stack startups will become more of the norm. I’d love to see more discussion from operators about how full-stack startups can better improve their odds of success. Let’s continue the discussion in the comments below or with me on Twitter @rickyyean.

[1] The documentary probably did more to align customer expectations and their subject taste to Jiro’s favor than anything else he’s done.

What startups get wrong about public relations

This article was originally written for MarTech Series in April 2018. I changed the title and I’m re-posting it here. Hope you like it!

If you are looking for media coverage, you’ve come to the right place. Successful PR is simple. Here are the steps.

  1. Generate interesting stories consistently.
  2. Pitch your stories to writers who create content for an audience you’re interested in.
  3. Analyze results, rinse and repeat.

It’s a simple process to follow, like keeping the count when you’re dancing. 1–2–3, 1–2–3, 1–2–3. However, in our experience, this might not be what you’re thinking about when you think about PR. You’re racing to the desired outcome — the gleaming article on a top industry news site trumpeting the latest and greatest about your company. It feels attainable (and it is) because we all consume a ton of content everyday. We read about companies, sometimes in our industry, having seemingly accomplished much less than us, yet they are receiving a glowing profile. Surely you can get the same treatment. PR doesn’t seem like it requires a process. No one expects to make a sale on the first call, rank on Google after a few days of SEO, or publish a few posts to immediately find an audience for your blog, but most people think of PR as an easy transaction — I have a story, it’s the reporters’ job to write it. This is wrong. Yes, if you just raised $50M in venture funding from Bill Gates, you can send an email to any reporter at a business publication and the story will get written. Outside of must-cover stories like that, successful PR requires a process because what is worth covering is, at the end of the day, subjective.

Let’s break down three common misconceptions about PR compared to reality.

Misconception #1: I have news (e.g. launch, milestone reached, etc) that is really significant to us. With the right PR help, we can get someone to write about it.

How it actually works. Journalists are choosing from hundreds of stories to cover everyday for maybe 1–3 slots. First, the sheer volume means that even if your story is perfectly targeted, they may simply miss it or lack the bandwidth to work on it, especially if Trump hijacks the media agenda. They are reading their inbox just like everyone else, without any more sophisticated triage processes. That’s assuming your story is a perfect A+. In reality, most stories we pitch for companies are “B+” stories. They’re interesting, hard news, targeted at reporters who would have a personal or professional interest. However, there are almost always other “A” stories being pitched to the same reporters from other sources who may be bigger and more credible than you, and in the case where we are being evaluated against 50 other “B+” stories, it takes some luck to be selected.

We like to think of PR as closer to playing baseball. A good hitter in baseball succeeds only 30% of the time. The important part is approaching every at-bat with discipline and look for the rare opportunity to really put the bat on the ball.

Misconception #2: I just read a non-news story (e.g. a feature profile, a trend story about the industry, contributed opinion piece, etc) about my competitor. With the right PR help, we can get an article like that about me.

How it actually works. News takes precedent at most publications because they are urgent and sometimes important, yet many reporters spend time (often at nights and weekends) working on non-news stories because of personal interest and potential for impact. However, reporters still have to justify it to their editor, so pegging it to a hard news pitch is still preferred. For example, if your company just raised $200M and became a unicorn, you can pitch a personal profile at the same time so the reporter can better justify doing a profile on you because you just accomplished a rare feat.

But what about the industry trend pieces? You never know when reporters are working on them, and sometimes they get shelved for months and even years because they’re not timely. There isn’t a public database of what reporters are working on (they don’t like to have their ideas stolen). However, you can influence the agenda by 1) pitching a trend piece anchored to some unique data and insight that you can bring to the table. For example, you can pitch a trend piece about how companies are increasingly ditching office spaces for completely remote setups, but you should bring supporting evidence to the table to help the journalist with research and offer help connecting journalists with companies without offices and their remote employees. Alternatively, to score inclusion in these trend pieces, you can 2) pitch frequently high-quality stories so you are constantly top-of-mind. Reporters, like the rest of us, suffer from availability bias. If they have to talk to three sources in your industry, you want to be one of those three sources.

Finally, how do you get a contributed opinion piece? Today, publications are starved for content — especially good, timely content. You have to pitch it to the editors and get them to consider letting you publish. Usually you want your piece to be finished, but not published anywhere else. Alternatively, it could be a piece that you have published already and seen a lot of traction on your own blog, which would help demonstrate that it’s “good” content that should be re-published and shared more widely. You also want it to be timely and insightful. You are competing with hundreds of people who want to write for a brand name publication, in addition to reporters on staff that have been hired, vetted, and has a track record. Why would the editor risk the publication brand to let you publish?

Misconception #3: I need a PR professional with strong relationships to the media in my industry. With strong relationships, we can get any media coverage we want.

How it actually works. Relationships are useful, but they tend to be overvalued and difficult to assess the veracity behind anyone claiming to have strong relationships. Because of that we think it should be discounted most of the time.

However, that’s not giving relationships its proper due. PR-Journalist relationships are like any business relationship: they exist to help everyone do business more effectively. Journalists trade in stories and they want access to high-quality stories. The way PR wins over a journalist in a relationship is by regularly bringing high-quality stories, and once in a while offer something exclusive. Essentially, for a journalist to see a PR pro’s name in the inbox and want to click on it more than any other email, the journalist has to trust that the story contained in this particular email will be high-quality and potentially lead to rare, unique access. PR pros can communicate that by establishing a record of consistently high-quality stories over time. However, PR is a business, and PR firms inevitably start working with less credible companies who are willing to pay. In order to keep existing credible clients, they inevitably start pitching “B+” or lower stories to journalists. From this perspective, the PR agencies that can plausibly have strong relationships are typically agencies that most businesses cannot afford or bully as a client. They’re priced high enough to filter for more credible companies, and even then, they are selective about who they choose to take on as clients and what stories they would pitch for them. It’s no surprise that the agency you paid $20k a month for did not appear to have strong relationships.


Obsessing about your competitors’ coverage is obsessing over the outcome, not the process. Worrying about PR agencies’ relationships is placing lopsided attention to a tiny (and typically unattainable) lever in the process.

Again, here are the steps to successful PR.

  1. Generate interesting stories consistently.
  2. Pitch your stories to writers who create content for an audience you’re interested in.
  3. Analyze results, rinse and repeat.

This process does not depend on you having to pay to retain a top-tier PR agency and it’s guaranteed to work. Of course, generating interesting stories is hard work, especially if you work on (relatively) boring enterprise procurement software. It’s also hard to find the story that is both interesting to you and the reporter. It pays to understand what drives reporters and their readers, especially when they may be different. Here’s a version of the Eisenhower Matrix from before that also includes a perspective from the average consumer of media. I hope this gives you more tools to think about your public relations efforts.

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Asian-Americans Are Cultural Orphans (aka I hope Crazy Rich Asians isn’t a flop)

The most anxiety-inducing movie poster ever

I just found out that there’s a movie coming out this summer with an all-Asian cast called Crazy Rich Asians and it’s making me very nervous. Is this supposed to be our Black Panther moment for stereotype-shattering Asian-American representation in mainstream media? Ok, that’s probably an exaggeration. I’m happy we are even represented in the first place. But what if no one watches it? Does it prove once and for all that Asian-Americans are not bankable stars? What about the fact that studios have largely given up on romantic comedies because they don’t sell as well as superhero movies. Would anyone care for our excuse? What about this male lead from Malaysia, Henry Golding. He’s not technically Asian-American and I don’t want to put it all on him, but he might be the only Asian-looking romantic male lead we will ever get. If he’s not a big enough thirst trap, can Asian-Americans men ever be found physically attractive by American standards? I’m asking, uh, for my friends…

How I became Asian-American

The media has given more attention to the lack of Asian-American representation in recent years thanks to movements like #HollywoodSoWhite and leaders like Aziz Ansari, Alan Yang and Constance Wu speaking out about the issue. However, I can’t help but feel like not much is going to change because “Asian-American” as an identity is not really a meaningful one.

I really wanted to be Asian-American growing up. I immigrated to the United States when I was eleven from Taiwan. Since I didn’t speak English, I wanted to befriend the Korean-American kids in my school because they looked liked me. Kids being kids, they wasted no time to make fun of the new kid by pointing out that I was nothing like them — I was a FOB (Fresh Off the Boat) Asian, not Asian-American. At that age, being ostracized like that by what you thought was your people pretty much amounted to devastation. I stopped trying to talk for two years until I developed enough fluency to sound just like any ordinary Asian-American kid from Los Angeles. Eventually I joined the Asian-American kids in teasing the new FOB Asians in our school and feeling like I’ve succeeded in becoming one of them.

When I got older, I started to understand the complexities of being Asian in this country. I moved here at a young enough age that I had an easier time passing as Asian-American, but those who immigrated later often didn’t have a choice because it’s much harder to get rid of your foreign accent after a certain age. Not that identifying as Asian-American should be that important, but it does give you a shared identity to relate to other Asian-Americans as opposed to feeling like an alien all the time. For many of the older immigrants that can’t or don’t want to identify as Asian-American, they’re simply immigrants or “Overseas Asians.”

The Overseas Asians usually refer to themselves as “Chinese” or “Indian” living abroad. They have lived their formative years in their native Asian country, so they are culturally much more Asian than they are American. I’d speak to my Overseas Chinese friends in Mandarin because it’s preferred, and we’d talk about the latest Chinese shows and celebrity gossip. Where I live in the Bay Area, there are authentic Chinese restaurants that cater specifically to the Overseas Chinese. It’s a big enough market that there are even dating apps (2 Red Beans) and shopping services (YamiBuy) designed specifically for this population.

Sometimes I’m envious of the closeness of the Overseas Asian community. It feels like being “Asian-American” is simply what you end up with when you are not an Overseas Asian or a FOB Asian like myself who could swing both ways. In fact, it’s way more meaningful for an Asian-American person to identify as Vietnamese-American, Pakistani-American, Filipino-American, etc. since those labels point to much richer cultures. Asian-Americans do not have much of a shared history in the United States to unite us, which can be good because that history is mostly a history of struggle, but it does deprive us of the urgency to be authors of our own cultural narrative.

We don’t know what it means to be Asian-American, and so far we haven’t shown much interest in figuring it out. On top of that, our parents would remind us that Chinese and Koreans detest the Japanese. Indian and Pakistani people don’t get along. Generally the light-skinned Asians look down on the “jungle Asians” of South East Asia. Historically, we’re just not that interested in being lumped into the same group. However, the younger generation of Asian-American like me do not have this historical baggage. We’re simply interested in finding our identity, but when we look out to the world, all we can find is the lazy portrayal of the uni-dimensional, kung-fu fighting, smart, obedient, emasculated man or hyper-sexualized woman. The Model Minority. That sucks.

What being a cultural orphan feels like

Remember Linsanity?

Linsanity was the biggest media event of my Asian-American life. I remember my friends and I would leave work early to watch the Knicks play, not wanting to miss any precious second because deep down we knew this moment wouldn’t last, and we would never experience this powerful feeling again.

Jeremy Lin showed us that Asian-Americans are strong, masculine, and competitive at the highest level of our favorite sport. Of course, we’ve always wanted to believe that about ourselves, but few of us actually did because we’ve never seen that image reinforced in the media until we saw Jeremy Lin. Maybe cultural symbols and narratives were never that important to you to begin with, but for many of us, they are important because the media is like a mirror — we look to it to reflect the ideal image we want to believe about ourselves. If you’re Asian-American, you’re always left wanting more.

The term “Asian-American” wasn’t a thing until fifty years ago. Before that, we were simply Indian-American, Korean-American, Hmong-American, each group considered different from one another. In order to gain political power, activists at UC Berkeley took a page from the Afro-American playbook to create the Asian American Political Alliance, uniting Asian-Americans under one umbrella. This movement put pressure on the U.S. Office of Management and Budget to promote “Asian-American” from the “Other” category, with significant impact on how political resources are allocated — something we still benefit from today. But culturally, we never made much progress.

The Black Power political movement in the 60s had the associated Black is Beautiful cultural movement that rejected the racist perception of the country and helped define a more empowering narrative of what it means to be a black person. Even many of us non-blacks can recite speeches, poems, songs and identify influential black cultural figures. What about Asian-Americans? Our Model Minority status is sinister because it hides the significant cultural vacuum that we operate in. We have no aspirational images. No role models. Asian-Americans are cultural orphans.

Being a cultural orphan in America means that other groups of people don’t know how to interact with us. We are asked questions that you’d ask a foreign tourist from a culture you know little about. “Where are you from?” and “Do you know kung-fu?” Despite the fact that we grew up here in the United States. Our fellow Americans do not mean to belittle or relegate us to the stereotype, they’re simply under-exposed. Asian-Americans are still only 5.6% of the American population, so most people will be under-exposed to the Asian-American narrative. We need to leverage the media to help us scale that exposure.


Fortunately over the last decade, I believe we’re witnessing the beginning of the rise of Asian America. Every time Jeremy Lin attacks the rim and rocks a new hairstyle, he inflicts major damage on the stereotype. On Fresh Off the Boat, Constance Wu and Randall Park are showing off the eccentric Asian-American family and making it something endearing that we can all be proud of. Eddie Huang and David Chang are the irreverent chefs with untouchable swagger. Ali Wong, Aziz Ansari, Kumail Nanjiani, Ken Jeong, Mindy Kaling are the funny Asian-Americans that you wished you were friends with. Steve Yeun, John Cho and Harry Shum Jr. are sexy men ready to be your next male romantic lead (#StarringJohnCho). We even have an Asian-American running for president in Andrew Yang(!).

The biggest factor contributing to this rise is likely the maturation of second-generation Asian-Americans. The passage of the Immigration and Nationality Act of 1965 resulted in an unprecedented number of Asian immigrants coming to this country. Their now adult children are beginning to understand that culturally, they are not like their immigrant parents, but they have yet to define what it means to be Asian-American.

The Internet is also playing a big part in the rise of Asian America. For example, YouTube allowed Asian-Americans to sidestep Hollywood completely until they became too big to ignore. Pioneers like Ryan Higa, Wong Fu and Timothy DeLaGhetto paved the way for the ascendence of Michelle Phan, Fung Bros, Awkwafina and Eugene Lee.

The Internet also enabled a more global youth culture that is much more receptive to elements from outside of the United States. Asian-Americans like Maggie Q, Daniel Wu, Jay Park who moved to Asia to better build their careers abroad are now making their way back home because the American taste is becoming more multicultural. BTS, an Asian K-Pop import, just topped the American Billboard charts, and their songs are all in Korean. Music label 88Rising is seeing this opportunity and aggressively marketing Asian artists with American and Internet-friendly sounds like Rich Brian, Keith Ape, Joji and the Higher Brothers to the American audience. These Asian imports will also be part of the Asian-American narrative going forward.

88Rising artists: Rich Brian (Indonesia), Keith Ape (Korea), Higher Brothers (China), Joji (Japan)

Bruce Lee wanted to be so much more

I heard a great Bruce Lee interview recently on the NPR 1A podcast that made me think that if Bruce Lee was still alive, he would’ve already already pushed the Asian-American narrative significantly forward. In an interview from 1971, the man primarily responsible for the kung fu fighting stereotype talked about the importance of Asian-Americans like himself to be embraced more fully by our society.

Interviewer: are you going to stay in Hong Kong and be famous or are you going to go to the United States and be famous?

Bruce Lee: I’m gonna do both because you see I have already made up my mind that in the United States I think something about the Oriental…I mean the true oriental should be shown

Interviewer: Hollywood sure as heck hasn’t

Bruce Lee: you better believe it man it’s always that pigtail and bouncing around chop chop you know with the eyes slanted and all that and I think that’s very very out of date.

Perhaps my trepidation about Crazy Rich Asians isn’t actually warranted. Bruce Lee had all the confidence in the world that he was going to demonstrate all the different ways someone could be Asian-American. Fifty years after his tragic death, we are finally seeing the emergence of a new class of Asian-American role models who are doing exactly that. Crazy Rich Asians is simply the latest culminating event in the rise of Asian America, and the best is yet to come.


Thanks to David Tran, Sidney Le, Jennifer 8. Lee, Nancy Hua, Cory Bray and Ian Burgess for reading a draft of this essay.