The crash landing of the Southwest brand

I recently flew what may be one of my final Southwest trips ever. This is crazy to say, since Southwest has been my default airline since I was a kid. (My family used to fly them often, and that loyalty carried over to my adulthood.)

Back in the 2000s, Southwest hedged fuel costs and locked in great deals before fuel prices shot up. So between their legendary service and low fares, there was no reason not to choose Southwest. While they no longer have the advantage on significantly lower fuel costs, I've stuck with Southwest because of the brand factor.

In fact, Southwest has been more expensive than other airlines in recent years, but I was still happy to pay a premium for friendly service, flexible terms, free bags, and most importantly, the ability to grab any seat I wanted to.

On top of that, there were countless other small moments throughout a journey on Southwest that sparked joy and made them different from every other airline:

$8 for wifi all-day, super important since Southwest has fewer direct flights and more layovers. You didn't have to pay per leg.
Free live TV
No change fees and credits that don't expire
A boarding process that actually made boarding faster
Exit row seat configuration (with only 2 seats)
Actually friendly flight attendants who didn't appear to hate their lives and take it out on the customers
Sometimes if you made a flight attendant smile, you might even get a free alcoholic drink
Got an expired drink coupons? Yeah they'd still take 'em.

And for me, someone who is constantly working on a laptop, they were one of the first airlines that generally turned a blind eye to typing away during takeoff and landing.

In fact, there were ways to "hack the system" as a frequent traveler, and Southwest turned a blind eye.

In 2013 when my co-founder and I frequently traveled from Southern California to the Bay Area for our startup, he would book weekly trips even if he didn't plan on using them. He'd book in case of an opportunistic investor or customer meeting ("I'm actually going to be in town tomorrow!"). If nothing important came up, he'd cancel the flights and use the credit later. (You could cancel up to 10 minutes before the flight with no penalty.)

It's this sort of flexibility that earned Southwest so many fans.

Combining this experience with the perks of the Southwest credit card (free upgraded boarding passes and annual flight credit) has made Southwest my airline for decades. It wasn't even worth comparing prices in most cases - I flew Southwest for the experience that couldn't be matched by the likes of the other national carriers.

But then Elliott Investment Management got involved...

Leave it to Wall Street to destroy a once-iconic brand. When Elliott flexed their muscle, bought up 10% of the company, and took control of the board, things immediately started going downhill from a customer experience standpoint.

One of the first things to go was the $8 all-day wifi. Now you'd have to pay per segment.

Sure, $8 isn't much in the scope of things. But also... isn't $8 not much in the scope of things for Southwest? How much did they grow revenue by charging an extra $8 for wifi for people on multi-leg journeys?

Since Elliott took over, here are some of the other things that have changed (or are changing in the near future):

Charging bag fees (except for frequent flyers)
Assigned seating
Division of cabin classes/premium seating
Flight credit expiration

In other words, they're becoming just another airline. And it might be profitable for them. But they lost what made them special, and what earned them customer loyalty.

Have you ever taken a bus or train where you were enthusiastic about the brand or experience? That was Southwest. Now they're becoming just another bus in the sky.

I'm sure Elliott's bet is that the American consumer will typically go for the lowest price or best route option, in which case will still very often be Southwest. Does brand have that much of an impact on an airline? You could make a case on both sides of this argument.

Other airlines have perks for frequent travelers, the most common of which is first class upgrades and code sharing. (Have you ever met a Delta loyalist? They are rabid.)

Seat upgrades were never needed on Southwest because a) the routes were typically shorter and thus had less of an impact on passengers, oh and b) there was only one fare. In a sense, they diversified how they earned customer loyalty, and found it in many different ways. (I mean hello, I'm still stuck on the $8 all-day wifi, because to me, it's about not nickel and diming.)

So how much of an impact will Southwest's sabotage of brand loyalty actually have on the long-term business? Maybe less than I'd hope.

But at least for me, I'm canceling my Southwest Visa card and will no longer default to opening southwest.com when I'm booking my next flight.

My domain registrar (DNSimple) tried to 5x the cost of my reseller plan

TL;DR: DNSimple eliminated our "legacy plan" and tried to increase our annual spend from $810 (plus domain registration fees) to $4,000 (plus domain registration fees).

Over ten years ago, I started using DNSimple's API to register domains for my side project, FolioHD (an online portfolio service). At the time, it cost $10 for a .com domain along with a monthly reseller fee of $50.

Recently I got an email telling me that my plan was being deprecated, and unless I hopped on a sales call to look at an enterprise plan, my new annual spend would be $9,616.70, up from $4,913, representing a 96% increase in total cost.

Let's take a step back. When we started registering domain names for FolioHD around 2012, it was a manual process on Godaddy. We paid $7.49/year for these domains, but had to configure them manually.

As FolioHD grew, this became unmanageable ("Do things that don't scale") and so we looked for an API that would allow us to register and provision domains automatically. There weren't a lot of options at the time, so we chose DNSimple because they had a straightforward API and fees that weren't exorbitantly expensive. Out of the gate, our costs were going to go up, but DNSimple provided a service that we could justify.

Godaddy: $7.49/domain → DNSimple: $10/domain

In 2019, DNSimple raised prices to $14/domain, then $14.50, and now it stands at $15.50. So I'm now paying over 50% more per domain than when I signed up.

Domain registration has never a profit center for FolioHD. I never wanted customers to have to decide if they wanted to save money by registering a domain on their own and configuring DNS to work with our service versus doing it directly through FolioHD. So when Godaddy domains cost $7.49 to register, we charged $12. When switching to DNSimple, we had to adjust this cost to $15/domain.

To this day, I've never raised prices on customers for an ancillary service. I just think it's the wrong thing to do, especially on a subscription service with lock-in.

Domain registration is a sticky business. If you ever want to leave a domain provider, you have to pay another company to renew the domain which extends the registration another year.

Aside from that, the process of transferring a domain includes unlocking the domain so it can be transferred, sending an auth code which then has to be confirmed, and going through a transfer period. In its entirety, it's not a streamlined process.

So if you have a large portfolio of domains you need to move, not only is there a significant cost involved, but it also takes a lot of time.

And that's partially what makes me so pissed off about this entire experience. For a company I've been with for over a decade, to receive an email out of the blue telling me that my price is going to increase 2x-5x – with no rationale – is infuriating.

On top of that, DNSimple's core product is actually kind of terrible. They don't provide an exact date a domain name will be renewed, instead just saying a domain will renew within 30 days of its renewal date. This makes it particularly hard to allow customers to cancel their domain renewals until the last minute, as is common with every other registrar. So my choices are a) potentially eat the cost of a domain renewal if a customer decides they don't want to renew after DNSimple has renewed the domain, or b) charge customers early for renewals. (I ended up going with the latter option.)

So to summarize, not only does the product not work as expected, but now they want to exponentially increase my cost.

Why would I stay?

I've put up with a lost of cost increases here, and I fully understand that when your services are dependent on an upstream provider, you have to pass along cost increases, but for a heavily commoditized business like domain registration where the value that DNSimple is providing me is no different than the product I started using ten years ago, I see no justification in the money grab.

This reminds me of when Intercom switched from being a product-led organization to a sales-driven org. In that case, my cost was going to 10x. In Intercom's case, they made the right move by making exceptions for long-time customers where the risk of brand damage was greater than the amount of revenue they'd add.

The same is true here. In my (potentially uninformed) perspective, DNSimple should have just bit the bullet, grandfathered in long-time customers, and looked for growth opportunities with new customers and in new product development.

Without receiving any communication from them explaining the reasoning, aside from an email within 3 months of a cutoff date, I have nothing to go off of other than assumptions. Those assumptions are: they hired a new head of sales who has a plan to "10x revenue", they're looking to get acquired and need the numbers to look more attractive, or they never operated at a profit in the first place (doubtful, given the premium prices).

I will admit I don't know the first thing about being a domain name reseller and the challenges that are involved in a business like this, but without any other perspective from DNSimple, the only takeaway I have is that this is yet another example of a predatory price hike in a product segment that has natural lock-in. I can think of zero people who enjoy being on the receiving end of enterprise sales, and it was worth it to me to spend an annoying amount of time to move off of DNSimple than just roll over and accept a 5x increase in cost for the same (subpar) services.

Bias for impact

One of the things I love about working at PostHog is that one of our core values is Bias for impact.

If you want to make a change to posthog.com, there's no linear process you have to follow. You don't need approval from a specific person. Anyone can see your proposed changes and merge them at anytime.

It's a great example of this core value in action.

As a designer, I want to keep the bar high for our website. (As the self-described webmaster of posthog.com, I have to continually tend to the site's design and messaging if I want to maintain the title.)

Many updates I make on the PostHog website go through some stage of wireframe or mockup. This is because I very deliberately want to craft copy, tone, layout, and design – because we believe it makes a difference.

But this desire inherently conflicts with the value, Bias for action. When less design-oriented people make changes, you can't always maintain your level of quality.

But for me, that's a worthwhile tradeoff.

When someone goes to the effort to create a pull request against the posthog.com GitHub repo, it shows they believe the change was important enough that they didn't ask someone else to do it - they took it upon themselves.

I recently discovered a change to some content on our Book a demo page that sort of threw off the layout of the page, but it was still a good change.

Our Book a demo page

I spent a long time iterating on our demo request flow. In the end, this is the page you'd react after clicking a "Book a demo" link.

This page reflected a lot of work to distill down exactly who needed demos and for what. In my eyes, it was perfectly balanced and exactly accomplished the mission.

But over time, as we grew our go-to-market team, someone eventually added a demo type and changed the page. This meant stuffing in a button in a place where I might not ~~generally~~ ever put a button.

The page now looks like this:

Gone was my perfectly symmetrical page, and in was a third call to action. More buttons to read, more places the eyes need to travel, more decisions for the user to make.

But it's okay, because it solved a problem.

A reflection on a favorite moment in my career

A decade ago, I co-founded a B2B SaaS company. My co-founder was the developer and I designed and some front end code.

When we added a new feature, he would throw data on a sparse page, and it was my responsibility to figure out how to present that information. I loved this delineation of roles, because we had a shared vision and allowed each other to do what we were good at.

With many companies, to make a change to your website, you have to get a lot of buy-in - and that's if you have any say at all. After you get buy-in, you might have to talk to a product manager or run it by marketing or design. PostHog is different.

I love it when my colleagues make changes to the website. Anything they change to the website has our customers interests in mind. And even better for both of us: I don't end up slowing us down.

To me, it's not the end of the world if a button looks out of place for a few weeks. If it solves a purpose, it's a good change, and that will always be more important than perfectly consistent design. Like in my startup, I'll always be here to follow behind them and polish things up afterwards.

Now if you'll excuse me, I have some buttons to redesign.

Dear Android design team: Please stop making things worse

Designers always want to leave their mark. I get it. You want to have something to be remembered by.

This is no different within Google. Android has been significantly improved in recent years. It's finally on par with iOS design. (And it only took a decade and a half!)

But there's a point where designers start redesigning things that weren't broken, and we've hit that point. Moreso, they're actually making things worse.

Exhibit A: Redesigning the dialpad

This new feature provides transcripts when calling businesses, among other features. But they reduced the keypad to a single row that overflows off the screen. Now, choosing a menu prompt above the number 4 requires an additional gesture and cognitive overhead of having to learn a new UI, vs the tried and true traditional keypad arrangement. (The number "1" also comes before "0", which is a different pattern than a normal dialpad.)

Exhibit B: Buttons that change shapes?

The goal is to get creative with the active state, but this adds nothing and is a weird one-off in the entire OS.

Exhibit C: Random square buttons

Somebody decided it would be fun to make the primary CTA button a rounded square. I fail to see what was wrong with the round buttons they've been using. But hey, a designer's gotta design, right?

Exhibit D: Removing the wifi Quick Settings tile

Arguably the biggest annoyance in all of Android 12 is the removal of the option to toggle wifi on and off. It was so elegant. Need to toggle wifi? One swipe, one tap. Done. That's all it took!

But our great overlords at Google decided they would fix something that wasn't broken and combined it with Cellular data into a new "Internet" tile. So now when your wifi is spotty and you want to turn it off, you must swipe down from top, tap the Internet tile at the top of the screen, then head to the very bottom to toggle wifi, then tap Done. Great, right?

This change has received so much backlash by users that a Google Community Manager had to defend it in the forums, and there's even a post on how to root your phone to bring it back.

This was supposedly done to help you remember to turn wifi back on? Not really sure how this solves anything. Other users tend to agree, and Google has been getting ripped in comments:

"The Internet panel solves nothing, at least not the "problem" you are describing. If you use the internet panel to switch from WiFi to Cellular Data, how does that make it more likely that the user will remember to switch back to WiFi. You've made the experience much more unpleasant to switch between the two that it is probably more unlikely a user will manually switch back to WiFI.Why does Google feel like it has to fix things that are not broken? What used to be easy and intuitive is now difficult. I hate the Internet panel. Adding it to the lock screen will also not help anything. Since when do users want to switch back and forth when their phone is locked?"

"I'd like to see some hard numbers on who wants this change, or what your user study really showed."

Exhibit E: Making Quick Settings tiles harder to use

For those not familiar with Android, you can swipe down from the top of the screen to access Quick Settings. Before Android 12, you'd have six customizable options at a single tap. Android 12 reduces this to four options. An additional swipe down reveals four more tiles with extra info nobody really needs.

Google decided to add a subtitle to each tile, with information you don't really need. Color already indicated whether an option was on or off. Now many of the tiles list out whether they're on or off. This seems like a great option, but provides little value to anyone after their first week on Android. I don't need text to tell me my flashlight is off, my hotspot is off, my auto-rotate is off, airplane mode is off, bluetooth is on, and that my night light turns on at sunset.

This screen is now harder to scan, harder to find the options I'm looking for, and requires more swipes to access options.

This was a worthless change that solves no real problems for anyone who uses Android on a frequent basis, which tends to be everyone who has a phone.

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Like I said, designers gotta design, but maybe we can find real problems to solve instead of alienating loyal users by changing things that weren't broken just to leave a mark.

Facebook’s community standards censorship has far-reaching consequences

Update: After some retweets about this issue, my domain is finally unblocked. (More details at the end of this post.)

Facebook censorship has effectively barred my business from their platform and is materially impacting the livelihood of my customers.

For the past decade, I’ve run an online portfolio business on the side called FolioHD. (You get a subdomain on the platform to host your portfolio, like mine at watilo.foliohd.com.) The entire foliohd.com domain has been banned from Facebook and Instagram because someone shared something that Facebook didn't like.

Unfortunately I have no insight into the offending content, and the offending content can be anything from a nipple to now apparently even a MAGA hat.

Now I am personally blocked on Instagram from liking photos or sending DMs. I can’t sign into my company Instagram account. And Facebook has reached into my Page’s support inbox, removed private message between myself and customers, and has blocked my website's integrations to import photos from Facebook's and Instagram's APIs.

The worst design trend of 2018: Stacked, label-less navigation

App designers are always trying to stay on-trend. The problem is that sometimes these trends tend to take design backwards from a usability perspective.

The last horrible design trend (2013)

A few years back when Apple decided to change iOS icons from filled in to outlined (in iOS 7), many believed this to be a step in the wrong direction, as outlined icons increase cognitive load.

The image and quote below are from Aubrey Johnson's analysis of the change:

Take a look at the example above. The red lines indicate areas where cognitive load is occurring. Your brain traces the shapes on the first row an average of twice as much. Your eye scans the outside shape and then scans the inner line to determine if there is value in the “hollow” section.

Forcing users to spend more time to decipher an icon is never a good thing, and unfortunately, many designers have followed this trend "because Apple did it", which is a horrible justification.

The latest horrible design trend

A free UX review for Postmates

The vast majority of the hip, cool Silicon Valley-based startups have products that work decently well.

The one outlier in this category is Postmates. I have no idea what they're doing over there, but every time I try to use it - between errors, poor UX decisions and outright bugs - the whole experience is a disaster. And this is from a company that has raised over $326 million!

So in an effort to improve the internet and not just complain, here's a free UX review for Postmates:

An incredible customer experience

I spend a lot of time ranting about businesses that treat customers poorly. I have a rule on Yelp that I have to post more positive reviews than negative, and while this isn't Yelp, I figured it was time to highlight someone doing something right.

So I was in Jersey City, NJ - just across the water from Manhattan, with the French Bulldog in tow. Since I didn't exactly want to leave her for more than a few hours, I looked up doggy daycares in the area. Turns out, there was a highly-rated place not too far from where I was staying, so I took her in to check the place out. (It's rare you see a place with 5 stars on Yelp, but this is one of the few.)

How Silicon Valley's elitist mindset affects product design

TL;DR: Did you know you can't plug a Pixel phone into a TV to mirror your screen? Google purposely left this feature out because they want you to buy a Chromecast and have decided that wireless is the future, and to not build for the thousands of edge cases in the meantime.

Silicon Valley decides how we use technology. Since they make the products we all use, they have the ultimate say about how we will use our devices. Overall, we benefit from the decisions they make for us - in how we are forced to embrace technological advances that they deem necessary.

Adobe Flash is a great example of something that Apple and Google collectively decided to force out of the market, due to security concerns, battery life issues, and more (if not also for competitive reasons). While I don't know anyone who firmly believes Flash should still be around, it's a marquee example of how Silicon Valley businesses altered how we use technology because they decided it was in our best interest.

But where is the line between what's "good" for us, and what they say is good for us?

Redesigns: Stripe UI 👍🏼, Stripe UX 👎🏼

When companies produce redesigns, the intention is usually to make things easier to use, make features more discoverable, and often to provide a visual refresh. As we all know, people don’t like change, so usually their is some level of revolt. This revolt usually subsides over the course of weeks or months and everyone moves on. But not always...

Stripe recently released an update of their dashboard. Initially I didn’t like it, but I decided to give it some time before passing judgment. It’s now been 2 months, and I still believe this is a huge step backwards in terms of usability. Stripe has managed to add additional steps to many steps of my typical workflow. Here are a few examples:

Dashboard

The old dashboard had 3 charts visible at all times: Volume, Charges and Customers Created. It was great to be able to quickly glance at all 3 metrics.