Over the weekend, I spent some time perusing my old journals, reviewing stuff that I had written about Readup over the course of the last several years. I do this occasionally, to get a glimpse into the brain of “old Bill.” Or perhaps I should say “young Bill.” You know what I mean.

Anyway, I felt quite lucky to stumble upon a glaring transformation of thought, a massive shift in perspective. The contrast is stark, which makes it interesting: In the past, I feared simplicity. I hated it. And I venerated complexity.

At one point, back when Readup was still called reallyread.it, I wrote:

reallyread.it is on a quest to save complexity, to bring back nuance, and to help people see that simple is stupid, and maybe even dangerous.

That’s pretty raw. And that’s what makes it interesting to me. I certainly no longer believe that “simple is stupid,” but I’m interested in the feeling behind the language. So, in this blog post, I’m going to explore the dichotomy between simplicity and complexity and, of course, I’ll tell you how things have been going this past week. To get started, let’s see if I can make a case for the value of complexity. Then I’ll tell you why, right now, it’s making me crazy.

Complexity is good.

The structure of this blog post is itself a case for complexity. In order to understand any topic, one must explore it from all angles. It’s a good habit to learn how to play devil’s advocate with yourself. Charlie Munger once said, “I never allow myself to hold an opinion on anything that I don’t know the other side’s argument better than they do.”

As soon as I feel like I have a healthy understanding of a topic, I try to zoom out or zoom in - whatever it takes to confuse myself. Where there is complication, there is learning. Navigating complexity is like solving a puzzle. It taxes the brain in a healthy and enriching way.

These days, all political discourse gets boiled down to simple binaries. Either you’re for something or you’re against it. Guns. Abortion. Masks. Immigration. Our political and media systems reinforce the illusion that we disagree on everything, but I don’t think that’s true. In reality, we agree far more than we disagree. Imagine a photo of two hundred elephants and one of them is pink. You’ll see the pink one. We don’t recognize our similarities as quickly as we recognize our differences.

The result of our collective inability to grapple with complex realities is abundantly clear. On many major issues, we’re deadlocked. Take immigration for example. We can’t not recognize our borders. That would create chaos, especially for our neighbors to the south. On the flip side, our borders can’t be absolute. They must be porous or we’ll have a different kind of chaos - a profound recession and, probably, we’d all starve. We need something in between. Instead, we have stalemate. We have nothing. The most recent major immigration reform enacted in the United States happened in 1986. That’s a year before I was born. I’m 33. That’s insane.

Conclusion: Blame simplicity. Reject the binaries. Embrace complexity. Embrace fluidity, abstraction. It’s the only way forward.

Now wait. Complexity is also a nightmare.

Over the weekend, Apple slapped me in the face with the dark side of complexity, the dystopian reality in which we all currently live:


No. I didn’t read it. And not because I don’t want to, but because I literally can’t. I tried. It’s too dense, too confusing. I have an English degree from Stanford. I have worked in tech for over a decade. I have written several privacy policies. This. Stuff. Makes. No. Sense.

It’s too complex.

So no, I don’t agree. Yet, again and again, Apple keeps forcing me to agree. To lie. And there’s no doubt that they know (or should I say “it knows”) that I’m lying.

But also, I really need to use my computer.

This stuff freaks me out. This level of complexity is synonymous with Orwellian bureaucracy, Doublespeak, and the result is human automation, giving in, giving up.

So perhaps, after all, simplicity is the answer. That’s the approach that we took with our Privacy Policy. After all, in order for truth to be true, it needs to be coherent. If it’s written down, it needs to be readable.

Readup is still too complex.

We need to simplify.

This is my fault. I can remember specific instances where I said, “If people aren’t willing to take the time to understand what we’re all about, we don’t want them in our community anyway.” That’s bullshit. That’s a cop-out.

It’s also one of the reasons that Readup, as a whole, is still borderline illegible.

Many companies claim to be innovative. Few truly are. Readup definitely is. As a result, we’re inherently complex. New and novel things often are. The downside is that we don’t have a single value proposition. Instead, we have a long list of capabilities:

  • Readup is a community of free, independent, critical thinkers.
  • Readup promotes deep, meaningful civil discourse.
  • Readup is a way to read anything you want without ads or distractions.
  • Readup is the best way to discover high quality articles and stories.
  • Readup is a great way to track and improve your reading skills.
  • Readup helps you spend less time skimming and scanning and more time finishing articles.
  • Readup is the first social media platform to offer a viable alternative to surveillance capitalism.
  • Readup has no echo-chambers, no black box algorithms, and no moderators.

And soon, we’ll launch the final piece of the puzzle:

  • Readup is saving the journalism industry. It’s the easiest and best way to support writers and journalists, directly, with real money. You pay what you want, and Readup takes care of the details.

Except here’s the thing. It has proven to be insanely complicated to make that as simple as it needs to be in order for it to work. And that brings me to what Jeff (Readup’s CTO) and I are working on right now. For starters, let’s break it down into a few key feature sets:

  • We need clear, simple pricing. And we need to collect credit card information before we allow people to read.
  • We need to allocate a percentage of payments to the writers.
  • We need to show the readers where their money is going.
  • We need to show the writers how much money they have earned.
  • We need to have a way for writers to “cash out” their earnings.

Seems pretty straight-forward, right? Not so fast.

Let’s start with the first point. Initially, we wanted a donation-based system. We even had the UI — a slider bar, to emphasize “sliding scale” — and then, a rude awakening: Apple said no. We can’t not be in the App Store, so we’re at Apple’s mercy. So we were like, Oh shit. Okay. Well there goes that idea.

We were forced to create tiers: $5, $15, and $25. But Apple’s not down with that either. Prices need to end in .99 cents. (I’m not crazy about that, but no big deal. I’m learning to pick my battles.) So we ended up with $4.99, $14.99, and $24.99 - a budget plan, a standard plan, and a super-supporter plan. With that locked, we dove into the rats nest that is billing cycles.

Our initial plan was to put everyone on the same billing cycle - calendar months. And if you start in the middle of the month, your bill would be prorated. No can do. Apple doesn’t allow prorated pricing. And beyond that, we need to allow people to upgrade or downgrade at any point in time. That makes the writer payouts hella confusing.

But, alas, confusing is the one thing that’s not an option here.

Making this stuff simple has been extremely complicated. And, frankly, it feels like the future of Readup rests on our ability to reduce all of this madness into something that readers can look at for just a few seconds and think: “Cool. There’s my money, and there it is going to the writers.”

The basic mechanics of the writer payouts are kinda-sorta clear at this point.

  • When contributions get divvied out, article length is taken into account.
  • We are never going to pay writers for articles that readers don’t finish.

So, let’s say you read five ten-minuters and one fifty-minuter within one pay cycle. In that case, the author of the fifty-minuter gets one quarter of your total contribution, and the other five writers split another quarter. Then Readup gets the other half.

Oh, and reality check: Apple takes one third of everything. (What?!) Obviously that has to come out of Readup’s half, not the half that goes to writers. So - uh oh - are we even making that much money here?

Doesn’t matter. Keep forging ahead.

There are more questions to answer:

  • What happens if an article has multiple authors?
  • What happens if an author is dead? (Are we supposed to pay Ernest Hemingway?)
  • What happens if the system doesn’t recognize an author? (Jay Vidyarthi, for example, is a Top Writer on Readup, but our system fails to pick up any author metadata in some of his blog posts, like this one. Can we fix that? Probably. After the close of a billing cycle? Maybe not.)
  • How do we verify writers? (How do we know that “Glenn Greenwald” is the Glenn Greenwald? What about Andrew Sullivan? The latter is, frustratingly, a fairly common name. We already have writers in our system with duplicate names. Oh lord.)

Anyone who has ever built software knows that edge cases can be a nightmare.

The only way to solve all of this stuff is…

…to solve all of this stuff.

Day after day, Jeff and I are on the phone for hours at a time, reviewing all of this — and oh so much more — and making as many decisions as we possibly can, to the best of our ability.

This past Thursday, at the very end of one of these marathon phone calls, Jeff brought up something that I had never considered before.

“One more thing,” he said, as my eyes were literally drooping with exhaustion. “What if one of our existing ‘free’ readers upgrades to a paid account, but then they decide to switch back to free? Do we allow that?”

Then I asked a really stupid clarifying question: “Would you need to, like, build that?”

Somehow he maintained his composure. “Uhh, yeah,” he said. “If legacy readers can switch from free to paid and back again, I’ll need to build that.” (God bless Jeff for being so patient.)

Hastily, I replied, “Fuck that. If you’re a legacy reader and you upgrade from free to paid, you can’t return to free. That’s just annoying. Either keep paying or leave.”

There was silence on the other end of the line.

I’m pretty sure that Jeff had already spent a few minutes considering this and arrived at the correct (and opposite) answer. And in order to help me get there, he humanized the conversation. He mentioned a few readers by their usernames and I immediately felt horrible. I pulled a one-eighty.

“My god,” I said. “You’re totally right. We can’t lose [my favorite Reader.] Okay so: existing readers need to be able to upgrade to paid and, if necessary, switch back to free.”

So, that’s how that decision was made. In about 30 seconds. (And sorry for cursing.)

Then, after I hung up, I realized that I hadn’t considered something else: We have users all over the world. How would we handle local currencies? I’ll bring that up later. And, in the meantime, I’ll sleep okay, because it’s probably something that Jeff has already figured out. Or Apple’s just going to tell us what to do and we’ll do that. We just need to make it all sound simple.