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Tyler King

@tylerking.app
1.1K followers 135 following 862 posts

Professional hater. Co-founder / CEO of Less Annoying CRM. I talk about bootstrapping, tech, entrepreneurship, and business practices that annoy me. Podcast: startuptolast.com 📍St. Louis, MO, USA

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Tyler King @tylerking.app · 25/09/2026
Agreed. The way I've phrased it to the team is: Most companies are choosing to be 4x as fast, but half as good. We want to be 2x as fast, and just as good as before AI. Replace 2x with whatever multiplier is actually realistic (1.5x? 1.1x?) but yeah, we're betting that quality still matters.
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Tyler King @tylerking.app · 25/09/2026
We recently started getting tons of unsolicited job applications (we aren't hiring). Not sure if we got added to some list or AI just makes it easy for people to spam applications to every company on earth. Either way, it makes me very nervous for the next time we do try hire.
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Tyler King @tylerking.app · 25/09/2026
Works great for me, but I might have different priorities (flexibility isn't at the top). I love that one person set the whole thing up and our whole team can use it. Love being able to run multiple agents in parallel and each gets its own VM (no worktrees).
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Tyler King @tylerking.app · 24/09/2026
True. I guess I specified AI companies because I haven't found the changed to other products especially compelling. Either they haven't changed much (higher quality, less new cool stuff) or they have (lower quality but without the utility I'm getting from AI companies)
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Tyler King @tylerking.app · 24/09/2026
I'm mostly asking as a customer: will the software I use ever stop sucking. But as a business owner, yeah, I 100% want faster development. Pre-AI I certainly wasn't upset by the devs on my team with above average productivity.
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Tyler King @tylerking.app · 24/09/2026
AI companies are building very cool stuff insanely fast, but it's not lost on me how bad it all is. I've started using Amp Orbs this week. Total game changer *and* I run into a "pull my hair out" lack of polish at every turn. Will it be possible to move that fast without compromising quality?
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Tyler King @tylerking.app · 24/09/2026
Having said that, I have cancelled my Netflix subscription because everything they make is absolute shit. But Hulu, HBO, and Apple TV are all well worth the money for me.
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Tyler King @tylerking.app · 24/09/2026
People complain that because Uber and streaming services cost the same as taxis and cable subscriptions used to, we're no better off. Do you remember trying to hail a ride without an app? Do you remember having to watch whatever is on tv + commercials?Price was never the primary benefit.
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Tyler King @tylerking.app · 23/09/2026
fwiw we're now more focused on the number of accounts than the number of users. Users maps to revenue which is important, but our recent decline is mostly just one giant account shrinking. Long-term business health is about getting more accounts in the door and ignoring fluctuating users.
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Tyler King @tylerking.app · 23/09/2026
A few years ago, we passed 25,000 paying users and threw a huge party to celebrate. Over the last 24 hours, we've gone below and above 25k multiple times. Does this mean we get a few more parties?
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Tyler King @tylerking.app · 22/09/2026
My writing would be completely ruined if AI found out about parenthesis
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Tyler King @tylerking.app · 18/09/2026
We're about to add an AI chatbot as a support option. This is the warning we're showing users before starting the chat. It's pretty minor, but I love injecting a bit of humor and personality into the app like this.
A warning shown in our app before you start chatting with an AI support bot. The copy says: Sometimes AI is dumb. We've worked hard to train our chatbot to answer whatever you throw at it. But if it gets weird, come back to the help center to talk to a real person.
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Tyler King @tylerking.app · 18/09/2026
I wouldn't put that past them, although currently, it seems like lack of compute is one of Anthropic's biggest business challenges. It would be dumb to deliberately waste tokens until later in the "monopolize then monetize" process (but they've done other dumb stuff so, who knows).
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Tyler King @tylerking.app · 18/09/2026
We had a dev team meeting to share how people feel since switching from Claude to any harness of their choice with GPT models. The main feeling people shared: Claude's writing had gotten super annoying and GPT is much more pleasant to work with. What a dumb failure from anthropic.
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Tyler King @tylerking.app · 17/09/2026
As a former programmer that's now mostly a manager, it's tough to decide when to weigh in on tech stuff. 90% of the time, my ideas don't work, and I'm just a distraction. 10% of the time I suggest something way simpler than what the team would otherwise do and it saves a bunch of time.
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Tyler King @tylerking.app · 16/09/2026
ChatGPT doesn't have that limitation, so we just switched away from Claude so that we get the benefits of subsidized subscription pricing with the freedom of not being locked into any single LLM. This won't last forever (OpenAI will follow Anthropic's lead eventually), but for now it works well.
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Tyler King @tylerking.app · 16/09/2026
That type of thing, but not from the actual llm provider. I want my harness to be llm-agnostic
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Tyler King @tylerking.app · 15/09/2026
Beautiful. Exactly as it should be.
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Tyler King @tylerking.app · 15/09/2026
And how was it?
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Tyler King @tylerking.app · 15/09/2026
I know there are a bunch of third-party AI coding harnesses (Amp, OpenCode, etc.) but does anyone have a recommendation for that type of thing as an alternative to Claude Cowork? Like, non-coding workflows that still require file manipulation and ongoing projects vs on-off chats?
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Tyler King @tylerking.app · 12/09/2026
We do hear that a lot but it feels great every time. I love that it turned into a customer for you too.
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Tyler King @tylerking.app · 08/09/2026
That would be amazing, but it's not about who's in charge. That makes it seem like a new CEO might change things, but it's systemic. Apple has to grow at x% per year so our retirement funds can grow. There will be pressure from shareholders to grow regardless of who the CEO is.
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Tyler King @tylerking.app · 08/09/2026
It does exist, but it doesn't really do anything. It just means they are allowed to care about other things if they choose to, but who's doing the choosing? The shareholders! Think a bunch of VCs and public shareholders will choose to make less money?
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Tyler King @tylerking.app · 07/09/2026
The "good products will turn into more revenue" logic works at a smaller scale. But at the scale of Apple, Google, Meta, and Amazon, it breaks down. There are no more customers to win. You already have them all. The only way to grow 20%/year is to extract more from your current customers.
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Tyler King @tylerking.app · 07/09/2026
There are very few companies like #2, and they rarely have dominant tech offerings due to economies of scale. So #1 is probably the more realistic option. Just hop from startup to startup letting VCs subsidize your consumption. I wish it didn't work this way, but this is the system we live in.
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Tyler King @tylerking.app · 07/09/2026
If you want to buy stuff from a non-enshittified company, there are two options: 1) Buy from a company that's young enough to still be in the "capture market share" part of the journey, pre-enshittification 2) Buy from a privately owned company that has decided to make less profit than they could.
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Tyler King @tylerking.app · 07/09/2026
It was adorable how so many people thought the new Apple CEO might stop Apple's enshittification. His job is to maximize shareholder value! That's why they put him in charge! Not sure if this specific news is true, but it's definitely true that Apple is going to keep capturing every $ they can.
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Tyler King @tylerking.app · 07/09/2026
What I hate is that it punishes companies for being honest. There's no realistic way to communicate "we're $x/month which matches the annual price of the competition but it's much cheaper than their month-to-month price"
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Tyler King @tylerking.app · 04/09/2026
I don't have the motivation to leave them, but I get mad at 1password on a weekly basis because of some kind of UX nightmare that was totally avoidable.
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Tyler King @tylerking.app · 28/08/2026
And very important: I want them all to fail. I much prefer a future where AI is a commodity to one where Sam or Dario have a monopoly.
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Tyler King @tylerking.app · 28/08/2026
I mostly agree. I don't want to switch every week to chase whatever people think it's currently state of the art. It's all good enough. But being able to switch occasionally to keep them competing on price seems long-term necessary. Anthropic is waiting for the right moment to 5x the price.
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Tyler King @tylerking.app · 28/08/2026
Same (we're keeping Claude, just downgrading most people to the $20 tier). But that would change if they tried to charge what they *need* to charge to justify their valuations.
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Tyler King @tylerking.app · 28/08/2026
But in order for them to justify their valuations, everything has to go perfectly. Even if a few big players split the market, OpenAI and Anthropic probably still fall short of today's valuations. They can be hundred billion dollar businesses and financial failures at the same time.
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Tyler King @tylerking.app · 27/08/2026
I'd never give money to Grok for other reasons, but all the people excited about them are just saying "they're subsidizing my subscription even more than Anthropic/OpenAI". Price is the *only* differentiator right now. What do Sam and Dario say in internal meetings? What is their plan?
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Tyler King @tylerking.app · 27/08/2026
Our team of ~8 devs is switching from entirely Claude Code to a mix of different agents with a ChatGPT subscription providing the inference. No idea if this is better or worse, but I *love* what this says about Anthropic/OpenAI's future. Neither one will ever be able to charge a premium.
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Tyler King @tylerking.app · 26/08/2026
It's neat the Bluesky has a way for accounts to label themselves as bots, but the natural next step is to let me block bots from replying to my posts. Why would I ever want a reply from a bot? If my post is meant as a question for AI, I would have just asked it to an AI directly.
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Tyler King @tylerking.app · 26/08/2026
Most recently, Notion, Loom and Figma have been doing AI stuff for free that they previously wanted me to pay a lot for. Maybe it's just a taste in the hopes that I'll pay, but I haven't hit any limits yet.
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Tyler King @tylerking.app · 25/08/2026
I love the whiplash of SaaS companies going from "pay us double to use AI" to "please please please use this free AI feature".
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Tyler King @tylerking.app · 25/08/2026
Agreed. What I did yesterday was good I think. But it made me realize that years ago, I spent so much time on that stuff that it went way beyond a break. It became the focus during large chunks of the 2014-2019 years.
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Tyler King @tylerking.app · 25/08/2026
Back then, we spent hours coming up with the perfect floorplan, and shift desks around every quarter to mix up who sits next to who. We over-thought policies, wrote detailed wiki docs, and discussed "company culture" a lot. In retrospect, 90% of that time should have been spent building and selling
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Tyler King @tylerking.app · 25/08/2026
I spent all yesterday alone in the office upgrading our wifi and rearranging the desks. It was a lot of fun and reminded me of the old days. But it also reminded me that in the old days, I spent way too much time on crap like that. I was so excited to "build a business" that I let it distract me.
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Tyler King @tylerking.app · 25/08/2026
I'm very jealous of your one request per day
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Tyler King @tylerking.app · 20/08/2026
It frustrates me so much knowing that there are other easy wins just waiting to be had, but I can't predict which tiny things will delight people like that.
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Tyler King @tylerking.app · 20/08/2026
As tech people, when designing features, we tend to get overly clever. But then when you talk to normal people using the software, the things they actually care about tend to be way more basic than you'd ever expect. Keep it simple.
A screenshot of text saying in all caps: I love the way it emails me early in the morning about clients birthdays
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Tyler King @tylerking.app · 19/08/2026
I really with Bluesky had a "location" field on user profiles the way Twitter does. So many posts are directly or indirectly tied to a person's region (weather, traveling, taxes, regulation, etc.) and it's nice to be able to quickly see where they are so I can contextualize the post.
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Tyler King @tylerking.app · 15/08/2026
And yet, it does catch up with you eventually. I don't think Amazon would be worth what they are if their website still looked like this. I agree that redesigns are probably needed much less frequently than they actually happen.
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Tyler King @tylerking.app · 14/08/2026
This page is a fun example of Google sucking: developers.google.com/identity/bra... The top section recommends using the first image as the logo. The next section shows the second image, a "G" with a gradient. Below that, it says that the first image is using an outdated logo which isn't allowed!
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Tyler King @tylerking.app · 12/08/2026
Yeah, that was also high on the list. Ultimately, we didn't have the appetite for the money and time it would take to do that right, although that was when I assumed Ring would be super easy to use which ended up being completely wrong.
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Tyler King @tylerking.app · 12/08/2026
We set up Ring cameras at the office after there was a break-in, and wow is the admin panel terrible. So many things are straight-up broken. Redirects pointing to redirects. I can't even subscribe to a plan because it redirects me back to my dashboard every time I hit the billing page.
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Tyler King @tylerking.app · 05/08/2026
Fuck making money, this is what it's about: "As a long time user of LACRM I couldn't be more impressed with how you do business. What other company in America has customer support that actually answers the phone with a real live person. You are always improving an already great product"
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