Rob Walling

Things Rob Says on Podcasts

Serial entrepreneur who has founded six companies over two decades, five of them bootstrapped, including Drip, which he sold. Co-founded MicroConf, a community for SaaS founders, and TinySeed, a B2B SaaS accelerator, and has personally invested in more than 240 startups including WP Engine and Sparktoro. Author of several startup books including The SaaS Playbook and Start Small, Stay Small. Hosts Startups For the Rest of Us, a podcast with hundreds of episodes on bootstrapped SaaS growth, and has appeared as a guest on Indie Hackers, My First Million, Build Your SaaS and Tropical MBA.

Where to Find Them

Rob Walling hosts and writes Startups For the Rest of Us , hosts The Art of Product , writes UI Breakfast: UI/UX Design and Product Strategy and hosts Smart Bear Live . They have also been a guest on Indie Hackers Podcast (6 times) , Tropical MBA: Entrepreneurship & Founder Lifestyle (3 times) , Built to Sell Radio (3 times) , Creator Science with Jay Clouse , Indie Bites , Moneywise , The Bootstrapped Founder , The $100 MBA Show , Ditching Hourly , Build Your SaaS , The Koerner Office - Business Ideas and Deep Dives with Chris Koerner , My First Million and Offsite .

Recently: “Episode 855 | The Eight SaaS Moats that Still Work in the Age of AI” on Startups For the Rest of Us (October 2026); “Episode 854 | How to Find Startup Ideas (Sneak Peek Chapter from My New Book)” on Startups For the Rest of Us (October 2026); “Rob Walling - Stop Building Stuff Nobody Wants” on Ditching Hourly (October 2026); “Episode 853 | How to Become the SaaS That AI Recommends” on Startups For the Rest of Us (October 2026); “Episode 852 | Getting Big Name Customer Case Studies and More Listener Questions (with Ruben Gamez)” on Startups For the Rest of Us (September 2026); “Episode 851 | The Messy Middle of a SaaS Pivot” on Startups For the Rest of Us (September 2026).

What They Said

“Since AI has come out, the number of words translated and transcribed in this world has gone up what, 10X, 50X… So the activity itself, the volume of transcription and translation has gone up. But if you were building software for translation agencies, transcription agencies, you're done. There's no market there anymore.” — Rob Walling, Startups For the Rest of Us

Rob Walling on the "demand side" threat to SaaS: will your customer still exist at all? The activity can explode while the businesses that used to perform it, and the software sold to them, disappear.

Startups For the Rest of Us · 2026-10-20 Permalink → Listen →
Startups For the Rest of Us Around 21:29 into the episode
Rob Walling

…it's not going away but it is being dramatically impacted right exactly so attack number six is that the model itself like the llms the foundational models basically absorb your product they kind of turn you into an obsolete wrapper it's not going to happen to everyone but we've seen it already it

Einar Vollset

…seed where someone really smart had gone along and they like fine-tuned their own model and it was like perfect for this it was like state of the art and then like i think chat gpt released a new version it was like oh out of the box zero shot it does a better job it's like well then you're screwed

Rob Walling

yeah we've seen a handful of companies within our portfolio experience this so now let's look at demand side and these are the ones there were a couple on the supply side that were surprising to me but the demand side was the one that i hadn't thought of so there's four here right so attack number seven is will your customer still exist at all and And the idea of, let's say there's an agency out there that used to either translate words, text, audio, or they would transcribe words, text, audio. So since AI has come out, the number of words translated and transcribed in this world have, what do we 10X, 50X, whatever. I transcribe everything now because we can, and it's really good. The agency revenue for those businesses is effectively going to zero. If it's not going to zero, it's going to a tenth of what it used to be because everybody knows we can just use AI to do it. So the activity itself, the volume of transcription and translation has gone up. But if your customers, if you were building software for translation agencies, transcription agencies, you're done. Like there's no market there anymore.

Einar Vollset

Yeah. I mean, this sort of reminds me of my favorite conspiracy theory that dentistry is basically just a fraud. They fixed it in the 1970s and then they decided, you know what, we can't get all these dentists unemployed, so we're not going to distribute the solution. But it's a similar thing. Like…

Rob Walling

Yep. And that, I mean, that leads us into the next attack, which is like, there's two that are very similar, but this one is, are your seats going away? Meaning, like Zendesk is a great example of this, right? If you're charging per seat for customer support software, you used to have six, 10, 15…

Einar Vollset

This is sort of kind of the problem with like, and HubSpot has other problems too, but HubSpot's a similar thing, right? Like it used to be per seat for human writers to write things and SEO optimize and all this stuff. And now it's like, it just, no, like the thing is AI slop. You just generate…

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“I have gotten some pushback from developers being like, well, now that I can build it in two days with AI, I should just build it and launch it. And it's like, no, dummy. Do you realize that you're going to build the wrong thing? … I guarantee you that your plan for your product will not survive contact with a real customer.” — Rob Walling, Ditching Hourly

Jonathan Stark asked what developers tempted to build a SaaS product with AI agents should do first. Walling, a developer himself, lays out his "2-20-200" sequence of market research, then customer conversations, then an MVP. He says AI changed the advice less than people think.

Ditching Hourly · 2026-10-13 Permalink → Listen →
Ditching Hourly Around 11:04 into the episode
Rob Walling

…after I do them, but this one is so prescient and we want to like let SaaS founders know. I also gave eight moats that I believe will hold up in the age of AI for SaaS. And this is like stake in the ground type stuff. So that'll be up on my YouTube channel soon, youtube.com/slash at rob walling.

Jonathan Stark

…So they're new to the whole, they're sort of experienced developers and they built stuff for clients who are probably running a SaaS, certainly worked on SaaS projects. But what should they be thinking about in terms of the steps you walk them through in the book if they were going to get started?

Rob Walling

…from developers being like, well, now that I can build it in two days with AI, I should just build it and launch it. And it's like, no, dummy. Do you realize? Do you realize that you're going to build the wrong thing? You're going to just build something out of your head. The whole point of talking to customers is not to say, oh, will they buy it? Is there a market? Part of it is that, but also, I guarantee you that your plan for your product will not survive contact with a real customer. They're going to tell you, well, I'd use this, but not this, or I'd like it that way, but this way. Or you'll pivot to an entirely different idea altogether that is so much better. I have stories like that in the book that I, you know, I won't go into, but of folks who had one idea and were two engineers. And one guy just did cold call after cold call. And at cold call 35, he learned this idea…

Jonathan Stark

Yeah. I mean, back in the day when people were, when it took 200 hours to get something good, I would always say to people, like, well, okay, let's say it's built. It's 200 hours from now and you built it. What are you going to do? 100%. You're going to have to go do the thing that I'm asking you…

Rob Walling

Exactly.

Jonathan Stark

100%.

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“Don't sell to consumers. Stop. … I've just plain out stopped answering questions about B2C SaaS and about two-sided marketplaces. … I'll tell you how. Don't. That's my answer. And then I move on to the next one. … It's just a boulevard of broken dreams.” — Rob Walling, Ditching Hourly

Walling is describing the "idea graveyard" chapter of his new book, on ideas bootstrapped founders should avoid. He tells of a founder who bootstrapped a two-sided marketplace without access to either side, who said it was "like eating glass."

Ditching Hourly · 2026-10-13 Permalink → Listen →
Ditching Hourly Around 34:54 into the episode
Rob Walling

…their pricing. It's not that you need to be necessarily cheaper or more expensive, but you should have a mental map or a map in a notebook or something of all competitive pricing as you're doing this just to see where you fit because you're positioning and your pricing is part of your positioning.

Jonathan Stark

…So what's the, what do you think is the biggest insight in the book? What can we leave people with? That's that, you know, I think there's a lot of people who are probably your ICP in this audience. So what's the thing that you think is the most important thing for them to hear that's in the book?

Rob Walling

…a bunch of product to see what sticks. Focus on one. Don't try to define a new software category, et cetera, et cetera. So I think those are important because they're the most common. I mean, the reason they're so bold in the book and have their own chapter is that people just make the same mistakes over and over and over. And I see this. I've actually stopped. I do QA episodes on my podcast and I've just plain out stopped answering questions about B2C SaaS and about two-sided marketplaces. And when people write in, sometimes I'll even read them and I'll just say, yeah, they're like, how do I blah, blah, blah with this? And I say, I'll tell you how. Don't. That's my answer. And then I move on to the next one. And I'm being, look, I'm being cheeky about it, but I get so many. It's just a boulevard of broken dreams. I can just tell you don't. And I've seen, there was a guy on X…

Jonathan Stark

Yeah. What was the, what did you say about orthon vertical and orthogonal? Orthogonal. Yeah. What is that?

Rob Walling

Orthogonal is this term that I made up to. I was going through all of our, all of our investments and I was trying to just see patterns. I do this because it's, I'm nerdy as hell. And this is the stuff I think about. And I was looking at horizontal SaaS, right? Which is like e-signature. Signwell…

Jonathan Stark

That's one of the biggest,

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