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.

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.

Startup explorations #15 / The 7-day audience building challenge

This week we’re shaking things up a bit by actually implementing the project idea on a small, small scale as a way to validate it. Obviously nothing at all has been built yet—so I’ll be doing everything manually. I will personally walk a handful of real, live users through meeting daily Twitter goals over seven days. The goal is to help these users get a habit started of regularly engaging with people on Twitter, in the hope of growing their own personal communities.

Specifically, here’s what I’ll do for each user:

  1. Give them a daily goal to meet.
  2. Recommend people for them to follow.
  3. Recommend conversations for them to engage in.
  4. Give ideas about what to post.
  5. Send a reminder when they forget or miss a goal.
  6. Track their progress daily.

In addition to the above, I’ll be analyzing their profiles as carefully as I can to guide my recommendations. The main challenge here for me will be keeping track of everything (and in different time zones), and meticulously crafting a decent user experience, but I think by the end of seven days we’ll get a good idea about the validity of the project and how to move forward.

I’ve created a very simple form to collect basic user info, with a link to a Slack workspace from which I’ll be running everything. I’ve no idea what to expect, but this is an exciting next step in the project where I get to actually test the ideas I’ve been brewing and see how they fare against reality. Once again I refer to Derek Sivers for inspiration: you can get started right now by just helping one or a handful of people.

Startup explorations #14 / Restating the problem; validating solutions

At this nebulous stage of the work where things are taking more and more shape but could still veer off in one direction or another, it becomes a tough balancing act to solidify the ideas in my head while trying to validate them at every step of the way. It’s ever so tempting to just let the imagination run wild—which is why it’s necessary to make sure we’re on course by always going back to the problem we’re trying to solve, and finding different ways to state it if needed.

I stated the problem and my proposed solution a few posts back; I’ve even gotten as far as to create a simple wireframe to help visualize the solution, about which I also wrote earlier. But as I float this project idea in its current form to prospective users, I find it difficult to get substantial feedback—more than a simple, “Yeah! This looks cool,” or “Great, can’t wait to see more.” In truth, it’s not their fault; because the way I’ve stated the problem, I haven’t accounted what actually makes a user stick to using a particular product—not just thinking it sounds like a great idea but actually feeling no need to use it.

To reiterate, I previously summed up the problem as: 1) Building an audience from the ground up is too intimidating or discouraging; 2) Careful searching for like-minded people to follow is too time consuming; and 3) Difficult to engage with already established people.

Notice how, while these problems do point to a specific pain point, that is, the frustration of starting out to build an audience from nothing, it says nothing of the other, more human piece of the whole puzzle: that it takes steady, consistent effort over a long period of time. I would thus restate the problem as follows:

  1. Building an audience from the ground up is too intimidating or discouraging; difficult to engage with already established people.
  2. Careful searching for like-minded people to follow/engage is too time consuming.
  3. Audience building needs to be systematic and consistent to get results.

Therefore, it also leads us to a solution that enables our prospective users to make such a commitment:

  1. A platform on top of social network sites like Twitter that recommends the best people for you to engage with.
  2. No need to calibrate or manually enter a whole bunch of parameters; the platform would base its decisions on your follower count, frequency of engagement, keywords, etc. and would learn about you and your ideal audience over time.
  3. It would break down a large target into small goals, and walk you through a plan daily.

Because this problem-solution statement now takes into account the need for a prospective user to commit to a plan in order to get the value we’re offering, the project idea now requires a much more robust approach to validating it, which will hopefully give us quality feedback, whether positive or negative.

The third point of the solution is particularly an interesting area to investigate: what if we actually walked a prospective user through, say, a seven-day plan to build out their audience even a little bit? If it turns out to yield value, then we know there’s something in this project idea. At any rate, as I hope to have shown here, revisiting the problem and thinking through it a little more carefully each time can lead us to solutions that we might have otherwise missed—and the solutions themselves offer the clues as to how they can be validated.

Startup explorations #13 / A problem I hate

Lately, I have been reflecting on my relationship with this problem I’m working on—that of audience building—and the irony of finding myself working on it now as a builder and developer. It is a problem that haunted me throughout my years as a musician; now, it continues to be my problem. The difference is I no longer view it with the same set of eyes as I once did.

As a musician, or anybody adjacent to the broadly elusive thing known as “the arts,” I’ve noticed in myself and others that it can be very difficult to accept that one’s industry is a business as much as it is an art. And that means, whether one likes it or not, that one needs to adopt the language of business to some extent if they hope to make a meaningful living out of their craft. This means having to do things that you wish you didn’t have to, like having to build an online following, and using the tools available with some consistency and discipline.

A useful thing I’ve encountered repeatedly by learning everything I can about product discovery is the importance of passion for problems rather than solutions. In other words, it is better to be committed to whatever problem you’re working than any one solution. Indeed, a product may go through many different forms, and at the end of it you may find that in reality, it’s not much use at all—but a problem that remains to be solved is a wellspring of endless possible solutions. 

And personally, this is a problem I hate—not one that I hate trying to solve, but one that follows me wherever I go, no matter how much I try to ignore it—because of my history with it, and because of the stakes involved. Like it or not, as a creator working in the present day in whatever industry, when there are no middlemen anymore, and traditional institutions have largely failed, an audience is the most useful asset one can have next to actual skill.

As a fun little side note, I’ve also been thinking of all of this in terms of Derek Siver’s approach to business, which I wrote about earlier. A business, just as a work of art, can be an extension of its creator’s personality. How fun to think about: an audience building solution for people who hate audience building.

Startup explorations #12 / Starting wireframing

It has been a month since I began this exploration—I had no idea where it would go, or where I even wanted it to go, but now it looks like something is just beginning to take shape. I have been finding myself with less and less to write here as my work shifts away from thinking, daydreaming, and thinking some more, and I actually begin to get my hands dirty and create a wireframe. The idea remains that which I described a few posts ago: a tool to help creators build an audience or community.

I’ve drawn it as a mobile app for now, as a small screen proves to be a useful constraint. To my mind, the heart of the application consists of two main screens: a list of people to check out, drawn from some API based on some yet-to-be-designed algorithm, and a list of conversations to participate in. From here, you might check out any of these people, follow them, comment on their posts, and with luck you’ll get a follow-back. Here’s a rough idea of what these two screens might look like:

This is a no-brainer, if the product is ultimately about bringing you people with whom you might likely form good connections. But it’s no magic bullet: building a community or following takes actual work that not even the best app can do for anybody. No doubt approaching the whole enterprise with some kind of deliberate plan or strategy appeals not to everybody—certainly only a number of the initial ten artistic types I talked to. But a good app would make it just a little easier for anyone to get started, and continually encourage its users to keep at it until they see results.

Fitness apps prove to be a good source of inspiration as I work on this problem. These apps might give notifications and reminders; they might have ways to let users keep track of their progress—charts, calendars, etc. I’m working on incorporating such a system of progress reports, reminders, and notifications into the app’s flow so as to make it all just a bit more of a pleasant experience. Hopefully at the end of it we’ll have something helpful, nice to look at, and fun to use.

Weekly Notes #3 / Digital gardening

Some stirrings here and there lately, for anyone paying attention. As I mentioned two weeks ago I’ve been keeping a separate blog of “startup explorations,” which I’ve now decided to merge with this site, so that it might benefit somehow from proximity to everything else that interests me. This is an experiment.

I’ve been thinking more of this space as a “digital garden,” a space in which to pursue multiple streams of thought (“blogchains”), and discover points at which they might intersect. A digital garden might take the form of a personal wiki, or a loose collection of networked pages, folders, and files, which may or may not be organized by publication date. For my current purposes, the reverse-chronological blog stream works well enough—a particular disadvantage of it is that older posts are necessarily left to decay in favor of newer ones, although this is exactly what I want, until I change my mind.

I rather detest the idea of specializing in any one thing, and have always looked up to polymaths, multi-hyphenates, and many-hat-wearers. But surely even these people must be able to synthesize all their competencies into a a singular purpose or other, if only out of convenience? My aim here is to discover if I can—if nothing else, a great excuse to write.