Tyler King
@tylerking.app
Professional hater. Co-founder / CEO of Less Annoying CRM. I talk about bootstrapping, tech, entrepreneurship, and business practices that annoy me.
Podcast: startuptolast.com
Podcast: startuptolast.com
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.
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.
November 21, 2025 at 7:29 PM
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.
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.
November 19, 2025 at 6:57 PM
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'm getting real sick of hitting shift+enter all the goddamn time
November 19, 2025 at 1:48 AM
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'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.
I normally don't care about it being "slow" as the haters say, but this is too much.
November 11, 2025 at 6:45 PM
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.
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?
Is it like a point of pride that if you have enough money you can avoid doing anything remotely useful?
November 7, 2025 at 9:38 PM
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?
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".
No centralized inbox that lets you manage things. Just "I'll remember it".
November 5, 2025 at 8:51 PM
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".
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.
Totally reasonable to ask, but annual discounts aren't some god-given right.
October 31, 2025 at 1:58 PM
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.
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.
October 28, 2025 at 2:46 PM
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.
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.
The lower the ARPU, the higher the churn.
The lower the ARPU, the more the tech support (esp. relative to ARPU).
The lower the ARPU, the less likely to upgrade to higher ARPU later.
Going low $/mo for high N is not a bad strategy, but there are consequences.
The lower the ARPU, the more the tech support (esp. relative to ARPU).
The lower the ARPU, the less likely to upgrade to higher ARPU later.
Going low $/mo for high N is not a bad strategy, but there are consequences.
October 23, 2025 at 2:54 PM
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.
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?
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?
October 22, 2025 at 8:29 PM
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?
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...
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...
Product roadmap - October '25
Hey there! I wanted to share an update on what the LACRM product team has been up to. Here’s a video walking through our main projects right now: If you have any questions or feedback, set up an ac...
forum.lessannoyingcrm.com
October 17, 2025 at 2:41 PM
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...
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?
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?
October 16, 2025 at 3:22 PM
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?
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
- 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
October 9, 2025 at 8:51 PM
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
- 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.
We need an "I know how to use a calendar" option when booking reservations.
October 9, 2025 at 3:17 PM
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.
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
October 8, 2025 at 6:20 PM
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* didn't make it political. That motherfucker bought my favorite social network and forced his dogshit politics on my feed.
October 6, 2025 at 8:47 PM
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* 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?
October 4, 2025 at 7:33 PM
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.
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.
October 3, 2025 at 2:13 PM
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.
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.
September 28, 2025 at 2:21 PM
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.
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.
September 23, 2025 at 4:10 PM
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.
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.
September 18, 2025 at 8:47 PM
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.
September 18, 2025 at 8:43 PM
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.
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.
September 10, 2025 at 9:32 PM
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.
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.
September 10, 2025 at 2:56 PM
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.
August 27, 2025 at 9:25 PM
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.