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TK Tyler King Co-founder and CEO of Less Annoying CRM, a bootstrapped CRM for small businesses he started with his brother Bracken in 2009.

“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.”

Startup to Last · Bootstrapped & Indie SaaS · October 2026

“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

Context

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.

Transcript

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.

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