Tyler King

Things Tyler Says on Podcasts

Co-founder and CEO of Less Annoying CRM, a bootstrapped CRM for small businesses he started with his brother Bracken in 2009. Grew up in St. Louis and studied computer science at Washington University, and talks regularly about bootstrapping, small-business tech and the parts of entrepreneurship that annoy him. Hosts Startup to Last, a podcast on running a small, sustainable software business without chasing venture funding. Has also appeared as a guest on The How of Business, Indie Hackers Podcast, The Panel and Searching For SaaS.

Where to Find Them

Tyler King hosts and writes Startup to Last and writes The How of Business - How to start, run, grow and exit a small business. . They have also been a guest on Indie Hackers Podcast (2 times) , The Panel and Searching For SaaS .

Recently: “A new cross-sell opportunity” on Startup to Last (October 2026); “What’s the difference between a harness and an agent” on Startup to Last (September 2026); “What to do with extra marketing budget” on Startup to Last (September 2026); “R361 – Start and Grow Without Investors with Tyler King” on The How of Business - How to start, run, grow and exit a small business. (August 2026); “R361 – Start and Grow Without Investors with Tyler King” on The How of Business - How to start, run, grow and exit a small business. (August 2026); “Affiliates” on Startup to Last (August 2026).

What They Said

“We previously paid for a tool that would draft emails in front for us, and then a CRM coach would review it and hit send… the reality is we do customer service in such a unique way. No off-the-shelf tool is built for us. Michael, a non-programmer in one week, vibe coded something that works quite a bit better.” — Tyler King, Startup to Last

Discussing the hedges Less Annoying CRM could build and how hard it is to find a moat, Tyler offers this example: his head of customer service replaced a paid AI support-drafting tool in a week. Tyler calls it cool but scary.

Startup to Last · 2026-10-29 Permalink → Listen →
Startup to Last Around 28:23 into the episode
Tyler King

…just a big financial weakness in the company is we're paying a team of eight people really good money when we we could get away with a team of four. A team of six would be fine. We have eight. So what do we do with that excess capacity? So, these are the two thoughts. We need to cross. And, well,

Rick Lindquist

and if you invested more aggressively in AI support, potentially you need even fewer CRM coaches. Great

Tyler King

point. So, we already have this. So, one of the God, I have so many things I didn't even have time to say. Michael, the head of customer service, built this thing we're calling Scribe during Cupholder Week. We previously paid for a tool that would draft emails in front for us, and then a CRM coach would review it and hit send. The tool was resolved 24-7. I have good things to say about it. I liked it, but the reality is we do customer service in such a unique way. No off-the-shelf tool is built for us. Michael, a non-programmer in one week, vibe coded something that works quite a bit better. I'm not saying it would be a better product to sell to someone else, but for the way we work, how personalized, how tailored it is, it's the CRM coaches. Like, this is much, much better.

Rick Lindquist

That's so cool.

Tyler King

Yeah. It's cool, but it's that's scary. Yeah,

Rick Lindquist

it's, it's, it's a, it's a, it's, it's the threat to less anointing CRM in a box. Yeah. But it's also very cool. But

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“The last two years have been unreal. And not just because of AI, like even before Claude Code came out, our product has gotten so much better. We've been executing. We've been doing our job. And it just doesn't matter. Like the demand for CRM, I think, is definitely declining, is what I'm seeing.” — Tyler King, Startup to Last

Following up on his finding that trial signups are down and churn is up, Tyler had reviewed everything the company shipped since 2020 and concluded the product wasn't the problem. He adds that the market is still big and he isn't saying there's no hope.

Startup to Last · 2026-10-29 Permalink → Listen →
Startup to Last Around 17:54 into the episode
Tyler King

Yeah. Because they're like, they're the

Rick Lindquist

ones in the market.

Tyler King

Well, it also strongly implies if it's kind of weird to be like, I signed up for a CRM trial and I canceled because I don't need a CRM. Like, how many people didn't sign up for the trial in the first place? Yeah. And that's another thing. Our free trial pipeline is down. Our churn is up. Like everything kind of points to not that we're doing anything wrong because a different thing I did in this presentation is I went through our execution since 2020. What did we ship this year? What did we ship this year? And on and on. The last two years have been unreal. And not just because of AI, like even before Claude Code came out, we were our product has gotten so much better. We've been executing. We've been doing our job. And it just doesn't matter. Like the demand for CRM, I think, is definitely declining, is what I'm seeing. Still a major question of like, I could tell a number of stories for why we're going to be fine. Like just because the demand's declining doesn't mean like the fact that we're the cheaper option, the fact that we could do this or that, but like we, the market is…

Rick Lindquist

And I, I, you started this conversation with like something about a 30-year business, right? Like, yeah. And I, I just, I, I, to me, like, have you done the like, what the world, like, not, not even 30 years, but like 10 years from now, what does the world look like? Like, have you done that deep…

Tyler King

Oh, I mean, we're all

Rick Lindquist

I have not like, like, I have not thought 10 years ahead. I mean, I

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“I do think stability maybe matters more than like shipping velocity, arguably. Stability of the code base. And these companies that are like vibing real hard, they are putting out a lot of shit. And if what you want is the max features, like I want to be on the cutting edge. I just want all the functionality and I can handle some rough edges, then that's fine. But I don't think that's the business we're in at Less Annoying CRM.” — Tyler King, Startup to Last

Asked whether his new AI bug-fix workflow could eventually run without a human developer, Tyler explains why his company keeps a human reviewing the code. A CRM people rely on every day, he argues, needs stability more than speed.

Startup to Last · 2026-10-29 Permalink → Listen →
Startup to Last Around 13:34 into the episode
Tyler King

…solution is approved by the CRM coach, all the dev has to do is just glance at the code and be like, this is a good thing. Sometimes it's like, this is 5,000 lines of code. That's wrong. Sometimes it's like, this is 10 lines. Nothing looks horrible. Ship it. Like, I don't even need to do anymore.

Rick Lindquist

And could that be done by an agent at some

Tyler King

point? Yeah, I think probably. If I'm being honest, I think the biggest hurdle to that is cultural, not technical. But at the same time, I'm there's for a business like Lesson Wing CRM. I do think stability maybe matters more than like shipping velocity, arguably. This is another theme kind of connected to something else. Stability of the code base. Yeah. And these companies that are like vibing real hard, they are putting out a lot of shit. And if what you want is the max features, like I want to be on the cutting edge. I just want all the functionality and I can handle some rough edges, then that's fine. But I don't think that's the business we're in at Lesson Wing CRM. But yes, I think that I don't think the full thing can fully get replaced. Sorry. If the CRM tests a fix and we could probably have an LLM that's like, here's how you decide if it needs a human review or not. And it's like, if it's a simple front end change or whatever, like we could probably codify, here are the things that could be done automatically. But it's already like, I don't think it's like a huge game changer because the reality is before the dev was just telling their agent to do it. It's not like the dev was doing it by hand. It's…

Rick Lindquist

No, I get it. It's great.

Tyler King

It is the first time I've ever built, like you've talked a lot about agents on this podcast. I've talked a lot about like, well, coding. I've talked about coding agents, cloud code, et cetera. You've talked a lot about like, I built an agent in Slack to do whatever.

Rick Lindquist

Yep.

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.
“The number of people canceling their accounts because they vibe coded a CRM in Claude Code. This thing that all these big brain geniuses on Twitter are like, it's never going to happen. No one's going to vibe code a SaaS tool.” — Tyler King, Startup to Last

Tyler, who runs the bootstrapped Less Annoying CRM, used an LLM to sort cancellation messages and found a new category: people leaving because they built their own tool. He says it went from about one a month to roughly daily in a few months, though some are free-trial users.

Startup to Last · 2026-10-29 Permalink → Listen →
Startup to Last Around 16:03 into the episode
Tyler King

…Since then, they've almost doubled in size and they have not canceled. The other one that was the biggest one shrunk and shrunk and shrunk and shrunk. And I think the whole company went out of business. So they're gone now. Yeah. That's my quick updates before I get into my meaty topic. That's

Rick Lindquist

a lot of stuff, dude. All right. What's your meaty topic?

Tyler King

Okay, here, let me clear out all these topics from our notion board so I don't get distracted here. I'm just knocking them out. Okay, so I gave, as you know, every six months, I and the other, like the leadership team at the company gives a six-month presentation to internally at Less Knowing Serum to the employees. Sometimes this feels like a real drag on my time. It normally takes like a week of full-time work to prepare for this. And oftentimes I'm like, I don't know if it's worth the week, but sometimes it's really valuable because like a lot of times I don't know what to say. I'm like, you know, we've got a plan. We're only halfway through the plan. So it's like, what am I going to go up there and say, let's keep doing it? Like, that's not a very rousing speech to give. So I always like have to think about what I'm going to say. And in doing so this time, I often have to go into the, I just, it's a forcing function to make you like, I'm going to go run through our numbers real quick and make sure all the…

Rick Lindquist

code. We said it about no code. We said no code will never replace a CRM. But I don't know that we ever said it about.

Tyler King

Well, and even that, it's interesting you say that because the way I presented this in this presentation is like, I didn't say who said there. Replacing us with AI. I said, who, you know, I used an LLM to categorize all these cancellation messages and group them into categories. The category wasn't…

Rick Lindquist

I would probably be the best feedback loop, too.

Speaker names come from our own diarization. The position is estimated from where the line sits in the episode.

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