People often tell me we need to be on top of AI or we'll get left behind. That doesn't make sense. Being a fast (or even slow) follower is way more sensible. For example, we're building a mobile app right now, about 15 years "late". It's fine.

As each generation ages, they struggle to understand the culture of younger generations. That's not new. But is this the first time that younger generations seem to agree with old people that culture used to be better? Most young people I meet wish they could have grown up in the 90s like me.

My co-founder (and brother) started out just doing dev ops and I handled building the product. Eventually he switched to full stack which has been great. Ironically, his dev ops work got *better* after making the switch. Why? Because now we work on projects based on need.

I mostly think the various AI chatbots don't have much of a moat, but I will say, it's very nice how ChatGPT knows stuff about me. I used to have to explain every detail of my business (product, bootstrapped, team size, etc.) over and over, and now it just knows and gives me personalized advice.

lol Google Slides now has a "Beautify this slide" AI button. It just generates a static jpeg of a nice-looking slide. You can't edit it. It doesn't apply a theme to your whole presentation. Your original slide is still there. How is Google so good at tech and so bad at product?

It seems to me like more and more people are canceling their free trial rather than just letting it expire. This is great for me because most of them leave an explanation for why they're canceling. Not sure why it's happening more now, but I won't complain.

Workflow for writing emails with AI: - Write it by hand - Realize it's not very good - Ask Chat to improve it - Hate what Chat does - But that makes me realize what I actually wanted to say - Type that up by hand - Send

I hate how Thanksgiving and Christmas make every metric I care about nosedive for a few days. It makes it much harder to understand what the data is saying, especially if you do trailing averages (e.g. trailing 6 months) to smooth things out.

I'm not sure why, but I've been using Loom really heavily recently, both for internal and customer conversations. It's feeling great. I just feel like there's way less room for miscommunication and it adds a personal element that email/Slack misses.

I feel bad for all the industries getting decimated by AI except one: SEO spammers. Oh, you noticed my blog isn't getting enough traffic and you want to help so you decided to spam me? Have you not noticed that giant meteor headed towards your entire industry. Don't look up, just keep spamming.

Somewhere along the line, it seems like the feature to open links in the appropriate app on your phone just completely stopped working. YouTube, Amazon, slack, etc links all open in the browser instead of the app. What's that about? Is this an iOS issue? Just my phone?

Possibly the most frustrating support question is when someone is migrating away from us, but their new CRM has terrible support so they want *our* support team to handle the migration. I'm sorry but that's going to be a fuck no from me

I get why everyone wants subscription revenue (that's how I make all my money!) but there are so many sites I'd be happy to make a one-time donation to that there's no way I would ever subscribe to. But the subscription business model has mostly killed one-time payment options 👎

Let's say companies A and B can both use AI to get the same done in half the time. Company A lays off half their people and gets the same done. B doesn't lay off anyone and gets twice as much done. Company B wins. I don't see how efficiency improvements justify layoffs aside from certain job roles.

Help me understand this disconnect: Many people claim AI helps build software 10x faster than before. There are many examples of individual features/projects getting built 10x faster than before. None of the software I use has been improving faster than it did pre-AI.

It's that time of year where you buy three Christmas gifts online and receive a combined 350 emails updating you on the status as each individual strip of tape is applied to the box.

Given how similar all the AI chatbots are, it's hard to pick between them. So I'll just go with whichever one adds my main feature request first: Make it so enter/return is a line break, not "submit message". I'm getting real sick of hitting shift+enter all the goddamn time

I love Notion, but they've been having far too many bugs with their editor recently. Sometimes I literally can't type a full sentence without it freezing or moving the cursor to a different part of the document. I normally don't care about it being "slow" as the haters say, but this is too much.

So many PE/VC firms outsource founder outreach. Not that I'm interested in talking with them anyway, but come on, can you put just a little effort in? What else are you doing all day? Is it like a point of pride that if you have enough money you can avoid doing anything remotely useful?

Crazy to me that many people feel overwhelmed by email notifications, and their solution is to instead get the exact same notifications as pushed via every single app. No centralized inbox that lets you manage things. Just "I'll remember it".

It's always strange to me when customers get offended that we don't offer a discount for annual billing. Like, I don't care if you pay annually or monthly, so why would I reward one way vs. the other? Totally reasonable to ask, but annual discounts aren't some god-given right.

Users are in equal number demanding that we add AI features and demanding that we don't add any AI features. Cool. Cool cool cool.

All businesses are hard in their own way. You have to choose what type of hard thing you can do that your competitors can't/won't. Selling to low ARPU customers is a real challenge, but it also weeds out a ton of the competition because they also don't want to deal with the headaches.

Tried unsubscribing from emails from a SaaS I use. The link just took me to their dashboard. Annoying, but why would they bother fixing it? Loom just sent me an email with a link to upgrade billing. I clicked it, and it took me to the dashboard. What does it take for these companies to give a shit?

Two kind of scary things we're trying: 1) A user forum 2) Sharing more about the inner workings of the company with customers I just recorded this walking through everything we have planned for the next ~6 months. We'll see if customers actually care! forum.lessannoyingcrm.com/t/product-ro...

My email is firstname@ not first.last@ but I receive both. If I get an email to first.last@, I know with pretty high confidence it's spam. I recently started getting marketing emails to first.last from Stripe. I want to give them the benefit of the doubt, but I think maybe they started spamming?

Typical support experience in 2025: - The app says "Error: Contact support" - Click the link which goes to the help docs, not support - Click through multiple links to get to contact form - Type my message - It's a chat bot that has no clue what I'm talking about YOU TOLD ME TO CONTACT SUPPORT WTF

Because so many people are so unreliable, every reservation I book using software feels the need to text me 17 times to remind me and confirm the reservation. We need an "I know how to use a calendar" option when booking reservations.

If an email uses a serif font, there's like a 95% chance it's spam

I'm getting really frustrated with the "you don't have to make everything political" crowd. e.g. people saying it's silly to not use Twitter because of Elon's politics. *I* didn't make it political. That motherfucker bought my favorite social network and forced his dogshit politics on my feed.

I'm seeing all these Sora videos, and while I'm happy that ya'll are having fun (sincerely, I miss when new tech was fun, and I'm glad there's something new to play with), what's the use case that will keep this relevant next week and beyond?

It's so hard to make customers aware of...anything. When someone signs up, first thing, we pop up a tutorial video. And the same video is at the top of the dashboard until you dismiss it. We also send a drip email linking to it. One of the top suggestions we get: I wish you had a tutorial video.

Is anything in life more frustrating than when you're in a rich text editor and you bold a line, then hit enter to start a new line, and start typing and the text is still bold. So you delete, hit cmd+b to unbold, and type and it's still bold. There's no way out of the hell loop and I hate it.

I've finished moving 100% of my investments from US to international index funds. Partially because the US economy seems like one giant grift right now, and partially because investing in a country's economy is in some ways endorsing that country's policies. I don't want to be a part of it.

Apple thinks I'm supposed to be able to read this.

Recently went with United over Southwest for a flight just because of the bag fee. Not even that the Southwest flight was more expensive, I just see no reason to use them if they're offering the exact same experience as everyone else.

It's crazy how often I stop writing a question to ChatGPT halfway through because I answer it myself as I'm writing it. Of course, the same is true when talking to real humans, but this way I don't need to waste someone else's time coming up with the answer.

How come sometimes when I mark an email as spam in Gmail it offers to block that address and sometimes it doesn't? I can't figure out the behavior.

Whenever an employee is writing something on my behalf, I need to train them not to use semicolons or em dashes because the real Tyler does not understand how either of those things work and would never use them in his writing.

I hate that Reddit seems to be going down the same growth hacking black hole that Facebook did years ago. In what world is it ok to send me this as a push notification? I've been getting more and more of these and don't see a way to turn them off.

I find Riverside's AI podcast episode summaries to be so funny. It really latches on to the small talk at the beginning of an episode. "Rick is considering whether or not to get a hot tub" doesn't need to be included in the two-line summary of the episode.

Hot take: "Ok" should be spelled like that. Capital O, lowercase k. "Okay" is also maybe acceptable. "OK" is wrong. It may have been an initialism at one point, but now it's just a word. Similar to how most people now write "Covid" and not "COVID". It should be capitalized just like any other word

I hate that when I abandon a discussion with ChatGPT in the middle, a small part of me wants to go back and explain why so I don't leave the robot wondering

An AI trick I've been enjoying: If you're trying to get an opinion on something, hint that you're already leaning towards an answer, but pick an answer that you know is wrong. If the AI has the conviction to disagree with you, I find that the odds of it being correct go way up.

I don't want to pick individual stocks to buy, but I do want to pick individual stocks to exclude from an index fund. I hate the fact that all these companies are buying bitcoin and getting a 2x valuation multiple on it, and I have to own that garbage because I'm invested in an index fund.

In some ways, modern tech has turned my brain to mush just like everyone else. My attention span is limited, and I probably over-rely on AI to do my thinking. But one thing saving me is that I still write a lot. Sitting down and writing a few thousand words at once keeps your head on straight.

People view Apple's past with rose-tinted glasses. They've *always* put form over function, even under Jobs. Remember when they said calls were dropping because we were holding our phones wrong? Or the butterfly keyboard? Or that trash can Mac Pro? Or the mouse that charges from the bottom?

So, bay leaves don't taste like anything, right? People try and tell me it "enhances the flavor" or whatever, but no one has ever said "that tastes like bay leaf" or "the chef put a bit too much bay leaf in this". The whole thing is a scam. You've all been lied to.

My normal rule is that I'll archived the first cold email I get from someone, but the second one gets marked as spam. But these days *everyone* is using automated follow-up tools so there's always a second email, so first emails now get marked as spam. This is why we can't have nice things.

This is one of those days where ChatGPT and Cursor keep alternating between being genius-level smart and being the dumbest motherfucker on the planet. It'll get several hard things right so I let my guard down and then BAM insanely stupid mistake on something easy.