Allen Pike

UX Entropy

2025-09-30T23:45:30+00:00

In the olden days, video calls were hard.

Circa 2012, if your next meeting was online, it was important to start the process 5-10 minutes early. The process, at that time, was some or all of the following incantations and rituals:

Find the meeting URL
Find the meeting passcode
Download a specific videoconferencing app
Agree to and accept various things
Dial in separately to get audio
Troubleshoot your audio or video
Wait for an update to download
Wait for the videoconferencing app to restart
Wait for your whole computer to restart
Repeat some of the above steps, now that your computer has restarted

With luck, you would eventually be in the meeting. The other participants, often, would not be. Regrettably, each participant also needed to do the incantations, and they might not have started early. They might even be stuck.

For example, the person you’re meeting might think they’re waiting for you, so they’ve multi-tasked to another app – but surprise! GoToMeeting or WebEx or whatever actually needed them to click “OK” or “Update” or “Ẓ̴͝a̴̡̕l̷̙̓g̶̫̔ó̸̻” to continue the joining process. After 5-10 minutes you would politely email your colleague, asking if they were still joining. Often enough you’d find yourself attempting to help people troubleshoot the above steps via email, which was… not enjoyable.

This was all obviously bad. Any user could see it was bad, but it seemed – oddly – like the companies supporting these apps were kind of blind to it. Or, at least, their enterprise customers weren’t demanding better.

As the story goes, Eric Yuan, then an executive at WebEx, was aware how clunky these product experiences were, and was ashamed of it. He felt that customers deserved a more user-centric video product, with excellent call quality, that ensured anybody could join a call with one click.

In January 2013, his new startup launched Zoom 1.0. They employed some clever tricks to make sure Zoom seamlessly installed and stayed up to date, so anybody could always join a call in one click. They pushed hard to ramp up the video quality. They prioritized UX at all costs.

Zoom as it once was.

The formula worked. A few months after launching 1.0, Zoom had 1 million users. In April 2019, they IPOed with $600M of revenue, were profitable, and were doubling yearly. By then they were well-known as the video app with the best call quality and UX, so when the pandemic happened the following year, Zoom was propelled to household name status.

Today, they have over $1B/yr in profit, and continue to grow. Zoom is one of the great startup success stories.

It’s also slowly falling apart.

Enterprise rot

Success at scale always causes problems. Enterprise software success, doubly so.

The first hurdle for Zoom, shortly after their IPO, was security issues. These ranged from underpowered encryption to leaky analytics to the revelation that their legendary one-click meeting flow was itself a security vulnerability. With market dominance in hand and billions of dollars of enterprise revenue on the line, Zoom started to unwind their approach of usability at all costs. Zoom founder Eric Yuan on this shift:

One-click is important. However, you need to make sure there’s not any potential issue, any potential violation of the operating system. Sometimes we have to sacrifice usability for privacy or security, that’s exactly what we did. We now think security or privacy [is] even more important than that.

And objectively, this is good! We want the software everybody uses to communicate to be private and secure. But it’s also a change in mindset from what made the product great in the first place. The defaults get locked down, the settings panels balloon, and Zoom is that much less likely to incubate the next team communications breakthrough.

Zoom was also one of the companies most thrashed around by the pandemic. While from the outside the surge in usage might have seemed like a blessing, it ultimately caused Zoom more trouble than it was worth. Yuan again:

I really wish there was no COVID. Zoom would be a much better company today. COVID, I do not think really helped us that much except for the brand recognition. For everything else, I feel like there was a negative impact to our business in terms of culture, and growth, and the internal challenge, or the competitive landscape. Everything else… I feel like it’s not good for us.

When your company goes from 2000 employees to 6000 in 2 years because of an event outside your control, you’re gonna have a bad time! You’re also going to get even more settings screens. How many settings, you ask?

The first two layers of Zoom’s admin settings now offer 63 sections and sub-sections worth of settings. These sub-sections are further divided into as many as 17 sub-sub-sections, which are then divided into as many as 12 sub-sub-sub-sections.

Developing a clear and coherent product is hard. Developing a clear and coherent product with 6000 other people is even harder!

The other day I had to log in to Zoom to change one of these myriad settings. Shown below is what Zoom looks like today when somebody at a 2-person startup logs in.

Now. In your opinion, what is the ideal number of times this screen should try to sell a startup an upgrade to allow over 100 people in a meeting? Maybe… 6 separate upsells? (The sixth is hard to spot, it’s partially hidden by the popover for the 5th upsell.)

There are even more upsells below the fold.

Of course nobody at Zoom decided 6 was the right number. While there is probably somebody at Zoom thinking about the 2-person startup UX, there are clearly 20x as many people concerned about increasing the number of customers who sign up for 500-person meetings. This dashboard is a veritable <marquee> banner that says “Our KPI is selling Large Meeting add-ons.”

Which I’m sure is logical! At least in the short term.

At the same time though, this stuff gives users the ick. “Avoid the ick” is not an OKR, and “% of users that hate navigating your settings” does not appear on your KPI dashboard. But it still accumulates.

When this kind of rot happens, it’s obviously bad. Any user can see it’s bad. But, importantly, enterprise customers don’t demand fewer settings, nor sane marketing position toward startups. So, often, these situations degrade.

It’s a tale as old as time. Occasionally a market leader who’s gotten off track will rally – especially if they’re still founder-led – to save themselves from fossilization and reinvent. In theory, Zoom could lever their position, in the center of billions of work meetings, into becoming a critical part of future AI-accelerated work.

More often, the gaps grow large enough that they spawn new startups. Blind spots and product debt compound until they recreate the situation that inspired Yuan in 2011: the market leader’s UX will be bad enough, and the potential for what could be will be compelling enough, that a worthy successor will launch. People will love it, and it will grow like wild.

Either way, we’ll look back on today as the bad old days, and appreciate how much better software has gotten. Customers will continue to demand better, and eventually someone will provide.

It’s the circle of life.

Building Something Big

2025-08-31T23:45:30+00:00

When I talk about building Forestwalk, people who’ve long known me are sometimes surprised that I’ve been using terms like “runway”, “venture-scale”, and other jargon more associated with the VC world than indie or lifestyle businesses. And indeed, I do have a secret to come clean about.

You see, for most founders, most of the time, it’s logical to build a “lifestyle business” rather than a venture-track one. The good lifestyle is right in the name.

Unluckily for me, working for a lifestyle was never that motivating. I love building software and teams and companies – if I earned enough to retire, I would just keep doing that. So instead of centring my first business around my lifestyle, it was focused on building great products and being a great place to work. Still, our ambitions were generally sized to ensure we didn’t need to make tradeoffs like working late nights, bringing on investors, or taking big risks.

This mostly achieved my goals. For a while.

Yet a standard human foible is that, as we achieve our dreams, we generate larger ones. A decade in, I didn’t just want to build great apps with a small team of good people. I wanted to build great products that had a positive impact on a lot of people, and I wanted to do that with a highly ambitious team.

Over the years I’ve had the chance to work with some really incredible folks – driven, passionate, smart, and ambitious. People who are unhappy with the status quo, and who rally their peers to do better work and set their sights higher.

As I was working last year towards founding Forestwalk, I realized that a core motivator for us was building with these kinds of people. But how the heck could we afford to do that?

Alex MacCaw highlighted this dynamic in his generally excellent Lifestyle business FAQ:

Pros of lifestyle businesses:

Fairly straightforward way to get rich

Earn while you sleep; escape the 9 to 5 rat race

Focus on other pursuits, like writing, traveling, family, etc

Cons of lifestyle businesses:

Unreliable source of income (at least initially)

Does not force ones self-growth (unlike venture-backed companies)

Most likely you won’t work closely with incredible people (can get boring/lonely)

There it is. If you want to constantly be learning, and attract and retain a team full of world-class people who are driven to push you to do so – the sort of people you dream of working with – the best way to do that is to build a venture-scale business. So if you’re a weirdo who cares more about that than you do about your own stress levels, you should swing big.

So that’s what we’ve been doing.

That’s why, earlier this year, when we concluded the LLM evals product we’d been working on could make a meaningful business but not a venture-scale one, we pivoted to something new (using what we’d learned as kindling). And why we’ll keep adjusting our plan until something clicks that we could plausibly build into something big. Not because building a huge company is inherently good, but because building toward something big is the best way to attract incredible people.

Of course, it might not work. Things are still very early. But I thought it was worth being straight: that’s the goal. We’re going to build something big, or die tryin’.

Wish us luck.

Getting Tied Up

2025-07-31T23:45:30+00:00

I never was a Boy Scout. As a kid, I leaned heavily toward papers, screens, and other indoor pursuits.

Despite this, I was always drawn to camping. Setting up in the forests of British Columbia for a few days, surrounded by trees and fresh air, always felt good. Worthwhile. Right.

While camping was always joyful, there is one aspect I long struggled with: I was bad at knots.

Okay, that is too charitable. I was incompetent at knots. All I could really do is tie the basic learn-it-when-you’re-five knot, repeated twice for good measure. Knot connoisseurs call this a “granny knot,” and it is an objectively bad knot.

These bad knots got me through most of life – they tie a garbage bag until it’s out of sight and out of mind – but when it comes to camping, they are not very helpful. They don’t stay tight, but they’re also hard to untie. They’re not adjustable for tarp lines, and they’re not useful when you only have one end of a rope to work with. They’re just generally bad, and they should feel bad.

I kind of knew this. I had camped every year for decades, and my knots were always a source of frustration. But I was never a Boy Scout. I missed the knot-tying part of life! And my dad moved out when I was a kid. And… I dunno. I’m a computer guy, don’t make me learn knots.

I mean, obviously I could learn knots. I learned long ago that we can learn anything at any age! Being bad at something is just the first step to getting pretty good at it.

But if you try to get started with knots, it’s… a lot. The Ashley Book of Knots documents 3857 of them. I downloaded the Knots 3D app, hoping it would give me some guidance. It explains 201 knots, but specifically calls out the “essential” knots: the mere 18 knots one must learn how to execute in order to survive.

You see, there are knots for binding an object down, hitching a rope to an object, adding a loop to a rope, joining two ropes together, stopping a rope from going through a hole, and making an adjustable tie. The ideal knot can vary depending on the direction of tension, the kind of rope, and the relative size of the ropes you’re using. Plus, many knots can easily be done incorrectly, resulting in a problematic bad version – like our cursed double-tied shoelaces.

But… I just wanna quickly tie tarps. And do basic camping stuff. There are a lot of things I’d rather spend my time mastering than knots! So I went back to ignoring them.

A couple years ago, after one particularly frustrating battle with a large tarp in the rain, I finally realized I’d played myself. By avoiding knot practice for so long, I’d let it become a gremlin in my mind. A thing I was bad at, not as a transitional phase towards being good, or even because I was happy to be bad at it, but because I’d let being bad at it become part of my character.

So, when I got home, I set myself down and learned one single knot. Something that would help with tarping. I spent a couple hours and learned the adjustable Tarbuck Knot.

The Tarbuck Knot. There are many others, but this knot is mine.

The Tarbuck Knot isn’t an ideal knot in any sense. But it’s adjustable, it’s reasonable, and I like it. And by going from knowing nothing – other than “I am bad at this” – to knowing literally anything levelled up my vacation every year. I now have nice little adjustable tarp lines everywhere.

Sure, I sometimes have things tied together with adjustable knots that don’t strictly need to be adjustable. But it’s quick and useful.

I guess the thing I learned – other than how to tie a knot – is that there is nothing so outside your wheelhouse that you can’t go 0 to 1 with it. It’s too easy to dismiss a topic or discipline as not your domain and let your ignorance slowly hinder you. One of the miracles of being human is that we can learn a little bit about everything.

I suppose there’s one other thing I learned. When it comes to the plain knot – the “I’m gonna tie my shoelaces” right over left knot – you should never double-tie it. Instead, tie the second one in reverse, left over right. That upgrades the bad knot into a Square Knot: stronger and easier to untie.

Little things can make big differences.