Tweets That Made Me Think - 2023 March Edition

🤔 Random links that I spent time ruminating over and some of my commentary

No essay for this week, but I thought I would highlight a bunch of links that occupy my mind more than usual over the past few weeks

Balancing Experimenting and Assurance Needs

Dmytro Krasun @DmytroKrasun

I wanted to subscribe to an infrastructure product by an indie hacker. And to build on top of it. But they jumped on the AI-hype train and abandoned the product. It reminds me to stay consistent and predictable in my business. Can it be counted as a moat?

KimSia Sim (I tweet business & software stuff) @KimStacks

@DmytroKrasun Genuine question: how u feel abt small bets in this context? OOH, genuine need for experiment, b/c nobody knows what works OTOH, it's off-putting to customers who need more certainty How does one square the need for experimentation while assuring people you're not flybynight?

I have given a lot of thought about this whole “small bets” strategy. On the one hand, I am for it. This newsletter is a small bet for me, for example. Nobody really knows anything, so experimenting is the way out.

On the other, it’s hard to convince people to move to your small bet product if lives or livelihoods depend on it.

Killed By Google, a website that documents all the “small bets” that Google undertook over the years, is a great example of this strategy gone wild. Some of these products or services were much beloved and their demise irritated the hell out of users.

Other shutdowns have much worse impact. Imagine being a game developer spending months building games for Google Stadia, then having it get shutdown on you with no notice. How would you feel about it? Would you be comforted by Google telling you, “hey, no hard feelings. It’s just a small bet strategy.”

The Basecamp Exit Strategy: Maintain for existing customers but no new features or new customers

One way to square the circle is the Basecamp approach to phase out of past products. I like their approach.

Notice how they treat their existing customers in their past products. Here’s Highrise, Tada List, and Backpack. Just to name three. They all have the same exit strategy. It’s in the last line of every product description in their history.

Toys, Tools, And Trains Spectrum

The way I see it is there’s a spectrum across three categories of products. I call this the “toys, tools, and trains” spectrum. And by trains, I mean infrastructure.

The more that your product is depended upon, the more important you need to be reliable (and be seen as reliable). You can still be “small bets” and experiment, but you need a clear exit strategy like Basecamp where you take care of existing customers.

An exit strategy like that is admittedly more expensive than simply announcing the show’s over and chase everybody out. Don’t forget that infrastructure-like products usually command a greater premium and bargaining power over your customers when they’re successful.

Life, after all, is full of tradeoffs.

Do Hard Things Then Document in Detail

Arvid Kahl @arvidkahl

When you build in public, you have limited time and cognitive capacity. Sharing your progress, challenges, and learnings is great, but it should not come at the expense of your actual business adventures. When in doubt, prioritize the DOING over the TALKING.

I recall a very old Ahrefs article about blogging that basically cover the same point as Arvid here. Couldn’t find it via Google, I’ll be grateful if anyone finds it. The steps to a good blog post (I’m recalling on memory) are basically:

1. Do something hard

2. Document the steps in details

That’s it. All the SEO techniques in the world are just amplifiers of these pre-requisites.

Any failure patterns that arise from following these steps are just some version of avoiding Dirty Work such as:

1. Avoiding the Dirty Work of doing something hard and documenting the steps in detail. So you focus on all the SEO/build-in-public tips and techniques.

2. Avoiding the Dirty Work of doing something hard. So you focus on picking something trendy to talk about instead.

3. Instead of picking something you’re deeply interested in albeit with narrow appeal and try to “do something hard” in it, you pick something with wide appeal (sexy) and try to “do something hard” in it.

Useful and Yet Not Too Functional

My entire revenue currently comes from writing software for businesses with at least 100 million annual revenue. And even then as a service, not product.

The people I tend to follow on Twitter who are also running their own businesses solo, are either:

1. they are more like content creators

2. even the software creators who are solo, they tend to focus on prosumer space and sell products

I have not been able to convert my existing business into a more product-oriented business, though not for lack of trying.

When I looked at the people I follow on Twitter who are good at their solopreneur businesses, I asked myself, “what’s the main difference between me and them?”

Initially, I thought the biggest difference is that they are good at marketing themselves and I’m not. Starting this newsletter is my attempt to get better at it.

Then, I came across this tweet by

Gergely Orosz

which cited an experiment by Substack that made me rethink perhaps the real difference between me and such solopreneurs is something else.

Gergely Orosz @GergelyOrosz

Wow. @SubstackInc experimented with pricing, reducing it by 1 cent, so e.g. instead of $10/month, do $9.99/month. The result? A significant decrease for the pricing ending with .99. Which goes against conventional pricing wisdom!! Why it's worth running experiments!

I want to highlight this part in the tweet.

Notice how Substack took two separate observations:

1. that $X.99 pricing shows poorer conversion rate than round-number pricing (e.g. $10.00)

2. and that some of their largest publications by ARR don’t even paywall any content or offer extra benefits to paid subscribers.

And explained both phenomena with, “perhaps pricing Substack subscriptions like one of the more function-based services made it feel more like a transactional purchase.”

It would have never occurred to me to ask people for money and not make sure that the people paying gets something extra. It doesn’t seem fair to them. Yet, it works.

Perhaps the deeper difference between me and the more successful solopreneurs I follow is I worry too much about the functional aspects of the exchange in value.

I do want to make money by being useful and I hope my customers get their money’s worth! But that made me too narrowly focused on making that happen.

People give money for all sorts of reasons and all kinds of value. And that obsession made me forget this simple fact.

I think too much in bright, straight lines and not enough in fuzzy, curved lines.

What are my options then?

In front of me are two paths I can see:

1. Either I change myself and practice being less rigid in my approach.

2. Or I change my area of focus and forget about emulating the solopreneurs I follow on Twitter. That is, double down in areas where the exchanges of value need to be straight and clear. Areas where my kind of rigid, straight-lined thinking are highly prized, rather than merely adequate.

I haven’t decided which path to take. But, this is certainly a new line of thinking that I never thought of until this counterintuitive experimental result by Substack.

Thank you for your subscription to my newsletter. And as always, I wish you and your family good health and good fortune.