Rob Walling
Serial entrepreneur who has founded six companies over two decades, five of them bootstrapped, including Drip, which he sold.
“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.”
Ditching Hourly · Agency Business · October 2026
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."
Transcript
…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.
…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?
…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…
Yeah. What was the, what did you say about orthon vertical and orthogonal? Orthogonal. Yeah. What is that?
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…
That's one of the biggest,
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