A eulogy

There are two different angles from which I want to muse, however briefly and poorly, on the recent death of a friend.

First: social media has made the experience of friendship, loss, and mourning weird in ways that I don’t yet know how to articulate. I don’t go on Facebook much, but about two weeks ago while scrolling my feed I noticed a post from my old friend Ariel. The post was pretty unremarkable, but it made me think of him for a moment.

I wondered what he was up to, what he’d been working on lately – it had been a few years since we last communicated. But social media gives us a sense that people in our lives are just there, anytime, waiting to be reached whenever you feel like it. So I continued scrolling my feed and instantly forgot about him. Today, I learned that he died a few days ago.

Second: our relationship went back about a decade and a half, when I first got myself involved in a production of a musical he wrote. I remember many conversations about music: learning it, pursuing it as a career, doing it as a side hustle, etc. A few years after that, we reconnected when he needed someone to help him record his musical.

We met up many times over several weeks to arrange and record 20 or so songs – he was very glad to get me on board at that time because I was a couple of months away from flying off to Singapore to study music. We had many more conversations about composing, piano playing, musicals, etc. Even after I left, we stayed loosely connected, and occasionally he’d get my help on something he was working on. I gave him advice about notation software.

He was a self-taught musician, which always took a backseat to his real job, and he picked my brain at every opportunity because I was the “real” composer. But I think he loved music more than I ever did, and was so humbled by it in a way that I don’t often see in people, which showed in how gently he always acted and spoke. I admired him for these reasons, and regret not getting his own advice. May his memory be eternal.

Startup explorations #25 / Building, slowly

I’m very thrilled to say this project has entered the building phase. This process will be very slow at first, but it’s off to a meaningful start. Actually, barely anything has been built: I wrote down a series of steps as to how I was finding tweets to recommend to my users, and had a back-end developer turn it into a simple program, which sits on top of the Twitter API.

The program takes a Twitter username, a list of keywords, and a desired maximum number of results; then it returns a list of recommended tweets for that particular user. Each tweet returned has some kind of visible engagement (at least 1 like, reply, or retweet), some relevance based on predefined keywords, or an invitation to respond, i.e., a question.

There isn’t a user interface yet; I simply use Postman to make a request. Yet this is a significant step forward because what used to take me 20 or 30 minutes for each user (without taking various distractions into account) now only takes a few seconds. This will enable me to run the next experiment much more efficiently, leaving room for more users, not to mention more room to experiment with various aspects of the project (see one of my previous posts about ideas for future improvement).

From here, apart from getting more users into our community, the main development task is to figure out how to keep improving this automation tool. It will still take a human mind to look through the results of each request and determine whether they are actually appropriate. There are still many other areas too that can be automated, such as finding keywords, determining the challenges to give each day, etc.

I’ve enjoyed this essay from Paul Graham about doing “things that don’t scale” and have been keeping it mind at all times. While the building process at this stage is slow, gradual, and iterative, it’s actually a great opportunity to engage all the more intently with my early users, include them in the process, and focus on meaningfully making a difference toward meeting their needs. I’m looking forward to running a third experiment very soon.

ADDENDUM: I’ve decided to conclude this blog series with this post. I’ve greatly enjoyed “learning in public” and intend to continue and ramp it up in other ways. As for the project itself, the way forward is still long and unclear, with different possible directions to take, but I will look back to all I’ve learned and have written here as a guide.

Great Lent

The particular draw of the more ancient forms of Christianity, to me, lies in imagery. In Eastern Orthodoxy, this is most evident in the use of icons. Every icon, or holy image, points to something higher—the saints, stories from the Bible, God himself. But it’s not just pictures and paintings; the Bible is itself a verbal icon, for instance. The liturgical seasons too are images.

The one year so far that I’ve been prevented from moving by the pandemic, and cut off from religious community, is now bookended by two Lenten seasons. I can’t help but dwell on the imagery: the great and holy fast, as the Orthodox call it, points to Christ’s time in the desert immediately after his baptism in the Jordan. Out there, he fasts for forty days and resists the devil’s temptations.

Without getting hung up too much on the presumptuous comparison, I’ve come to think of this whole time as my personal desert. It came after a year of spiritual abundance, despite thorny personal circumstances, as I prepared to join the Church. And then, almost immediately—this. My relationship to Orthodoxy has become tenuous as a result. I’m constantly noticing demons.

Many saints of old went long stretches of time without holy communion while living in the desert or in adverse conditions. Monastics have a calling, and, I suspect, a gift that empowers them to leave the world behind and do what they do.

Modern converts to Orthodoxy, especially those of a Western persuasion, tend to romanticize monastic life: there’s something about the combination of crosses, icons, beards, prayer ropes, and desert imagery—I’ve not been immune to the allure of these things. But there’s nothing romantic about this suburban desert.

The rest of us who are not monastics must be content to do our best in the world. Ironically my friendship with the world has improved significantly in the last year—materially, professionally, even psychologically. But I feel malnourished in the spirit and unable to do a thing about it but wait: forty days, four hundred, or more.

Startup explorations #24 / Reflection on audience building

Lately I have been reflecting a lot on the “journey” of audience building as it relates to this project I’ve been working on in the last couple of months. Now, the perspective I take on this subject is wholly my own, though I’m sure many people in my circle can relate—that is, that of a creator whose primary motivation is craft rather than making sure I’m noticed. In fact, much of the time, being noticed makes me uncomfortable.

I believe in the importance of listening to oneself carefully, no matter what one might find. There’s something about the words “audience,” “following,” etc. that still makes me recoil. Instead of dismissing this outright as a function of some undesirable quality that I have to snuff out—insecurity, unwillingness to get out of my comfort zone, or whatever—I’ve become very curious about it. And I find that much of it has to do with the images that these words conjure in the mind.

The images that come to my mind are celebrities, movie and pop stars, politicians, commentators, etc., all constantly under the prying eyes of their fans. On the internet, it’s blue-checks and high-follower accounts and their hordes of mostly pseudonymous followers constantly hanging on to their every word. There’s great power in having such an audience, but it’s also a liability—they have a cost to maintain, which is keeping them happy with lowest-common-denominator content that will keep them coming back.

In my first newsletter, I responded to an article that came out on Rolling Stone about how Juilliard, a classical music conservatory, must embrace pop artists in order to make itself relevant to the times. There is some truth to that, but I was critical of the article because while it made appeals to innovation, all it could offer as models were superstars who make millions in ticket and album sales and win big awards.

In fact, rather than innovative, I find such thinking old-fashioned—a vestige from an older time. This older time was full of gatekeepers and middlemen who defined what success was (usually related to money and fame), and decided who deserved it. The solidification of the creator economy at present has made all of that obsolete; creators of today no longer need permission to create and distribute. With the ability to define their own careers comes the space for more personal ideas of success.

By extension we are free to define what “audience” means. I don’t like getting hung up on precise definitions. I think I’m most inclined toward how Daniel Vassallo described it in his Twitter course (to paraphrase): having an audience means having people who are interested in what you have to say. This is difficult to quantify (unlike one’s follower count) but you know it when you see it.

This also implies the right kind of people, depending on who you are. Consider what value it brings you if have thousands of followers attracted by banal content designed only to appeal to the largest number of people possible. Maybe to some people, only numbers matter—this is all well and good. But I think a creator to whom their craft is the primary consideration would be more discerning.

The beauty of our current moment is that independent creators are free to maintain niche interests that are true to themselves; it is no longer necessary to appeal to “mass taste,” like that Rolling Stone article suggests, only to find a select group of people with whom you resonate strongly. Still I don’t mean to suggest that numbers don’t matter entirely, only that it matters much more what those numbers are made up of.

As the creator economy grows, I wish to see it be more inclusive; many creators are not businesspeople, marketers, nor social media experts. On the other hand, a creator, by virtue of the nature of their work, is an agent of human connection. They have the power to touch, move, illuminate, charm, and entertain. This need not always happen at scale; on the contrary, when it happens on a personal level it’s much more powerful.

I say all these things as a matter of intuition rather than scientific fact. I’m an obscure person on this earth, going on the journey myself of building my audience and growing my personal community, both on and off the internet, and from very little. This project therefore is a quest of betting on the ideas I have.

One important caveat, based on observation: audience building as such cannot be used as a proxy for something else. If there is a hole in someone’s heart to which they think having an audience is the answer, well, it’s probably not. This is slow and long work, and if one’s sense of self is coupled tightly with the size of their audience, it can be the cause of some great dissatisfaction.

The most successful people in this area would attest to the importance of giving rather than taking. This means that one ought to have something to give in the first place—and cultivating that must take precedence. When that foundation is in place, one can feel secure, and the rest is play.

Startup explorations #23 / Game plan – Starting a newsletter

Obviously this blog series has begun to transition away from poking around for ideas and “startup explorations” per se to the early stages of actually building a product! This means I’m no longer working alone: now I have developers on hand working with me on 1) automating my tweet recommendation process, and 2) creating a landing page. I’m hoping that by the end of the month we’ll have something more tangible to share.

Not that the exploration is over—this will be a long process, involving building the software gradually and continually finding new users and going back to them for feedback. When this initial, early building phase is done I’ll be in a position to run a third experiment with more participants and over a longer time span.

I’m intrigued by the ethos of building in public and plan to continue documenting this project in its own dedicated site. Hence, I will conclude “startup explorations” here at the end of the month.

It also occurs to me that if I’m going to be in this problem space, I need to participate in it much more than I already do. So the time has come to graduate this blog series into something more public-facing: a newsletter. This will be my attempt at understanding the creator economy space, drawing on things I already know well (creation, the arts) and things I want to learn more about (technology, the startup ecosystem). Read it here.

Startup explorations #22 / Ideas for future improvements

This is a continuation of my last post about my thoughts after wrapping up my second Twitter experiment. Here are some things to consider in the future, based on feedback I’ve gotten:

More difficult challenges. So far, each day’s challenges are really only a combination of posting and/or commenting (at first I also asked my users to follow recommended accounts, but it didn’t seem that meaningful); I have never asked for more than 3 posts and 3 comments at any one time. With a longer timeframe than one week, I’d be able to include much more difficult challenges to keep things interesting.

Allowing users to set their own targets. For example, aiming for a longer-term target, such as +x% profile views or tweet impressions after y days, and adjusting daily challenges progressively toward said target.

A time limit for each day’s challenge. I have been hearing from some of my users that this experiment has pushed them to engage with content they wouldn’t have on their own, and that they’re spending more time being thoughtful about what to post. This is good, especially if we want meaningful engagement, rather than just empty metrics. At the same time, I also don’t want them spending too much time. Work fills up whatever time you allow for it; perhaps a time limit would solve this.

Ebbs and flows. I have mentioned this before. A straight, progressive series of challenges works well over a short time frame like 7 days. Over a longer period, it would make more sense to lighten up on some days, such as weekends. Perhaps users could be given the option of setting the number of days a week they want to be active.

Getting to know other participants. I thought this was an interesting suggestion; since this is about community building, why not include a way of letting participants interact with each other through the challenge? They would be able to compare progress, see what others are doing that works or doesn’t work, etc. The added element of competition may be encouraging to some, but probably not everyone.

More recommendations from outside a user’s network. I have been focusing on getting recommendations based entirely on a user’s past activity; introducing an element of randomness might make the experience more interesting and unpredictable.

Startup explorations #21 / Wrapping up Experiment No. 2, and looking ahead

I had even more fun doing this experiment a second time; the feedback continues to be encouraging, and now I think I have enough information to keep going with the project and move on the next step.

It will remain important to keep running and iterating on this experiment, but now it seems appropriate to think about scaling up. Doing it manually, I have only been able to accommodate 3 – 4 users at a time so far. I’d like to be able to do the experiment with more people than that, and with a longer timeframe than 7 days; this means working to automate the recommendation/curation process somehow, which will save me a lot of time.

Over the last week, I settled on a precise series of steps that I followed as much as possible to find conversations to recommend to my users. Given that I observed that my users mostly followed the recommendations, I would say it’s a decent start. Contingent on access to Twitter data, a more experienced developer at our company should be able to translate it into an algorithm that takes any Twitter user as an input and returns a list of conversations relevant to that user.

The other side to all of this is marketing: who are our customers, what do they want, and why should they even care about what we’re trying to offer? The second experiment has given me a chance to get to know more users, from which to make a few generalizations, but this continues to be something for me to work on carefully. Hopefully, being able to iterate on the experiment while including a larger number of participants will help us further along this goal.

It has been highly enjoyable seeing this project sprout from nothing to what it is at the moment—still little more than a seed of an idea, but continually growing week by week. It can be difficult at any given moment to feel like I’m making any real progress, but with each new milestone reached the path becomes a little clearer.

Startup explorations #20 / Why am I doing this?

Two months and twenty posts into this project is as good a time as any to ask, why am I doing this? This is no project that will change the world or advance human civilization in any way. I can’t help thinking of the phrase, “stupid problems require stupid solutions”—and yet, that doesn’t mean it can’t be driven by a vision I have that speaks to things that I (and many others, I’m sure) truly care about.

This vision occurred to me today on the third day of our current experiment, as I was scrolling yet again through Twitter looking for conversations that my users might enjoy. I have been spending more time on Twitter than I’d like to admit doing this for my users, falling into rabbit holes here and there, as well as putting my own money where my mouth is by trying to step up my own engagement.

Twitter and social media in general offer great opportunities to any creator wishing to build an audience and willing to put in the time and energy to find their community. I’ve met many interesting people online who have made my life a little richer in these times of isolation. But all the same, I don’t really want a world where people are just scrolling their phones all day; I don’t want people spending a second longer than they have to to keep up with their communities. I want to save people (and myself) time to do far more interesting and important things: to create, and live their offline lives. This is what I want to accomplish.

Startup explorations #19 / Experiment No. 2: Kickoff

I’m kicking off the new month by repeating the same experiment as last time with a different set of users (more indie developers and founders). The objectives are to 1) see if we can achieve similar results as the first group, 2) get to know our prospective customers more, and 3) get a feedback loop going and hopefully generate continued interest in the project.

In addition, I’m paying special attention to a few more things this time around:

  1. More adaptability and responsiveness in each day’s challenges, taking into an account what a particular user has done the day prior and adjusting accordingly, hopefully making the experience much more personalized.
  2. Community instead of following: this means emphasizing thoughtful engagement over merely trying to get more followers.
  3. Defining one or more customer personas.
  4. Noting with as much precision as possible how I’m finding conversations to recommend (see my previous post about how I’m making recommendations).

Regarding the fourth point: recommending conversations is by far the hardest and most time-consuming part of the exercise on my end because I have to look at each user’s profile everyday to handpick good opportunities for engagement. If this second experiment yields good results, we’d be at a point where starts to make sense to think about ways to scale up this operation little by little. I think it could be a very fun engineering challenge down the road.

About this blog

At the start of this year I decided to have more of a public writing habit. I like it. I have no high literary ambitions here or anything; I see this site as a place for conversation with myself, fleeting thoughts, seeds for future enterprises, and most of all, Learning in Public. Check out the archive for a complete list of posts.

On the other hand, my very new newsletter Cranked Organ is meant for more intentional (though no less exploratory) writing. I don’t completely know yet what it should be about. Some of what I write in this blog might find its way there.