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.

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.

Startup explorations #18 / A reflection: Discomfort zones, and dealing with them

Talk of comfort zones is nearly always ridden with clichés but I’ll do my best. I’m a person who by now usually knows what I like and tries to only do things that I like. To quote Derek Sivers once again, “The real point of doing anything is to be happy.” At the same time, life offers better payoffs—not to mention it’s far more interesting—when boundaries are pushed and seemingly crazy things attempted.

I’m used to being outside of my comfort zone. When I was pursuing a music career I constantly had to “put myself out there” amidst fierce competition and try to get people interested in my work—by far the worst part of the music profession, and even worse for attention-hating introverts like me. Yet at the same time it was comfortable in a way because I was very confident in my abilities and had the experience and credentials to prove it.

When I moved back to the Philippines at the start of the pandemic and taught myself to build apps, and later started looking for software development work, I was yet again very far outside of my comfort zone. I had little programming experience and no related credentials to speak of. But simultaneously, I was in a comfortable position because I was back in my childhood home with no rent to pay, and I could keep up the job search for as long as I needed to. There’s also much less competition in the local job market than back in New York.

Disgruntled by my past failures, I had been wanting logical and “comfortable” work, and software development seemed to fit the bill (whether or not it’s true). Yet, after joining my current company, I found myself once again back in old discomfort zones: the chance to start my own project, which means going out into the wild and potentially making a fool of myself as I try to validate project ideas all before a single line of code can be written.

This latest example lies at the heart of a lot of reflection I have been doing lately as someone who has embarked on personal reinvention during this time of worldwide upheaval, when questions about the nature of work and what matters most are at the forefront. Lately, I have been asking myself: should a person really only do the things that they find comfortable or enjoyable? How does one discern between true discomfort as a measure of going the wrong way, as opposed to the good kind that leads to growth?

As I see it, it is a good clue that one is not going the wrong way when discomfort coexists with some comfort or another that serves as a stabilizer. People need stability. In the case of my recent work, which has been anything so far but comfortable, I’m comfortable at the same time because no matter the outcome, I get a paycheck at the end of the month. And no matter how far I have to go outside my comfort zone, all the work is on the internet—all from the comfort of my desk. I can even be anonymous if I wanted to. What’s there to get hung up on?

From here I’d like to offer a few more ways, though by no means the only ones known to people smarter than me, that I deal with discomfort.

The first one is a little naiveté—just a little of it can help one power through seemingly impossible situations. The naiveté that made me think I could pull off a music career is the of the same stuff that led me to believe I could teach myself a new skill and make a career change within months. And if I were not just a little naive about this project, I would never find it in me to get started, knowing all the difficulty in store.

The second is to not take oneself too seriously; what a miserable person who does so, whose sense of self collapses at the thought of any kind of failure, and who can’t have a laugh sometimes at the silliness of things.

The third is to decouple one’s sense of self from pure work. Work that fails is still all too human. I’m not sure that I believe in an “authentic self,” but I notice in myself and others that there are multiple selves, more than one of which can be just as authentic as another. There’s a large and genuine part of myself that values comfort, stability, and familiarity; and there’s no reason it should be threatened by the part of myself that wants to be much more adventurous.

Startup explorations #17 / Wrapping up the first 7-day audience building challenge

I’ve gotten a lot out of doing this experiment over the past week. To reiterate: I set up a Slack workspace and over 7 days, told a few creators what to do each day to encourage them to keep up their Twitter engagement. I recommended accounts to follow and conversations to respond to.

I’m not a Twitter expert by any stretch of the imagination; I just looked at their profiles individually, got a quick sense of what they were about, and gave them daily targets based on what they were already doing or what they were obviously not doing.

Anyway, doing this experiment as a way to test my product idea on a very small scale allowed me to confirm a few of my assumptions early on:

  • That creators indeed go on Twitter specifically for audience/community building.
  • Creators who don’t have high engagement yet but are motivated enough would appreciate being told just what to do everyday.
  • The need for habit-building, target-setting, and consistency over a period of time.

To the third point above, the results speak for themselves. In just seven days, one of my “users,” an app developer, reported significant improvement in tweet impressions, profile visits, mentions, and follows. I was happy to know as well that by the final challenge, he had built enough momentum to write a post on Reddit about the app he’s building.

I noticed similar improvements in two other users, though only about as much as you can expect from the very short timeframe. I plan to continue following their accounts over the next several days to see how they’re doing. A fourth user dropped out of the experiment after the third day, as he decided he wanted to take a more organic approach to Twitter—fair enough, and all part of the process.

Still, to me there’s enough of a green light to try the experiment again with a few tweaks and specific areas that I might want to play around with. In no particular order:

1. Recommending accounts to follow
I learned early on in the experiment that recommending accounts to follow didn’t seem to make that much of an impact, as my users would pretty much just follow whoever they want anyway. Besides, one of my users was more deliberate than usual about curating his timeline, with which I sympathize, and was very selective about his follows. Still, it might be useful to suggest them occasionally when a user doesn’t seem to be growing their network, or getting much engagement from the usual options.

2. Recommending conversations
Corollary to the above, there seems to be a lot more value in curated lists conversations that a particular user might find easy to respond to, based on their interests, recent activity, and so on. Usually these conversations have some kind of prompt or invitation to respond, and are often made by larger accounts. I’ve found this to be an effective way to get exposure, especially with consistency, as lots of other people looking to make connections hang around these big accounts.

Similarly, I’ve also found it easy to get people to just respond to thoughtful questions in general, even from smaller accounts. This doesn’t result in a lot of exposure, but does increase the likelihood of a connection that can become more meaningful over time.

Naturally, I have a long way to go to streamlining this whole process so that the recommendations are more likely to be good fits than not—one can only do so much manually!

3. Progressive difficulty and retaining users
A sharp and linear progression makes sense over a short period of time like 7 days, but what if we were to extend this over months? A whole year? It would probably make more sense for it to have ebbs and flows. In the future I’m thinking of giving the option to opt out on certain days.

4. What if a user misses a target?
Initially, when this happened, I just restarted with the previous day’s challenge, with a new set of recommendations. Again, this makes sense over a 7-day timeline, but if this is built out and extended, there would have to be a much greater incentive for a user not to miss any daily target.

5. Recommendations or strict orders?
I’m continuing to think of ways to make this experiment more challenging and engaging. Perhaps a fun challenge might be to make users, either on all or some days, follow my directions strictly in order to meet a day’s goals—for example, follow so-and-so users, respond to this or that conversation specifically. But I don’t believe this would be necessary if the recommendations were always as good fits as possible.

6. Finding the right users
I like to think of this whole thing as an audition to find the right users who will benefit the most from what I’m offering, rather than a race to make everybody happy. I noticed the most positive results from my users the more open they were to following my recommendations, and of course, the more they had to offer in the first place—for example, having one main, visible project that they’re working on or trying to promote. As I work with more people I hope to get a much more refined sense of our ideal customers.

7. Will anybody pay for this?
Pretty self-explanatory.

Naturally, all of this is just the tip of the iceberg, and I may have many more thoughts in the coming days. We have a very long way to go from here to actually building anything. But my hope is that by sustaining this experiment and allowing it to evolve, we create a feedback loop that will serve us in the long run and lead us toward a product that will actually achieve our stated goals.

Startup explorations #16 / The 7-day audience building challenge: How I’m making recommendations

In my last post I wrote about testing this ever-evolving idea I’ve been writing about here by actually running a few people through a weeklong Twitter challenge. I’m running all of it in a Slack workspace, which is all running smoothly so far with four participants of various stripes. Naturally, promising actual “audience-building” is a tall order, so we focus instead on things we can actually control: I like to think of it as helping people build a habit of regular community engagement. It is meant for creator types who need an audience but would rather not have to think about it.

The heart of the project, if it turns out to be viable, is a personalized recommendation system that gives you a daily goal or challenge, along with recommending other users and conversations that a user might be into. I’m doing this manually right now by looking at each profile in advance and trying to get a sense of what each one is about as quickly as I can. I look at who they’ve recently followed, what they’ve recently responded to, etc., and adjust my recommendations accordingly. For example, if you already tweet regularly but don’t reply much, I’ll handpick a few ongoing conversations and make you respond to one or another. Otherwise I stick to a default plan.

I’m trying to recommend profiles that have been active recently, are engaging with other users, and especially those who ask questions in public or invite feedback. I’m also trying to get a good mix of profiles that have roughly a similar follower count, and some larger accounts as well who engage with smaller accounts (this is not all that common). To make things more interesting, I also include a little randomness. Obviously, as a human, I can’t do all of the above very efficiently, but there might be something in a system that can respond to what you’re doing and make very good suggestions.