R
Rob Walling
Entrepreneur
4
APPEARANCES
4
PODCASTS
012
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Sep 4, 2026
AI Pricing: New Costs, Old Rules
22:34

Marcos RiveraHOST
When I think about the landscape changing, how are entrepreneurs, how are they positioned to really grow their SaaS companies in this new landscape, in this changing ecosystem? Are they better off, worse off? Tell me what's your point of view as the world shifts?
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22:50Rob WallingGUEST
Yeah, I think anytime there is a seismic shift like this, like when businesses move from exclusively brick and mortar to being online when the internet, you know, really World Wide Web started in the 90s, whether it was a lot of folks moving to mobile when the iPhone came out in 07 or 08, whenever, 06, 07, whenever that came out.
R
23:11Rob WallingGUEST
to now AI, these seismic shifts are really uncertain in the near term, right? And they're pretty scary.
R
23:22Rob WallingGUEST
Think of all the stores, the clothing stores that in the 90s don't exist today.
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23:27Rob WallingGUEST
And really, it's because I buy a lot of my clothes online, right? I think a lot of us do.
Ep 561 The $40M Earnout That Never Got Paid, and the One That Did - Rob Walling and Garren Hilow
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33:34Rob WallingGUEST
Like I, I, I maintained product and engineering, but everything else, support and sales and marketing, all of that I gave away, and I knew that was coming.
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33:44Rob WallingGUEST
I had literally written every line of copy, like that was on the website and all that, and so it was all my voice.
R
33:49Rob WallingGUEST
And for them to take it over, which they told me they'd do, was still difficult.
R
33:52Rob WallingGUEST
So for me to have someone to talk to that was not my co-founder and not my spouse was really, really helpful.
18 MINS LATER
The Remote Work Tribe Podcast: Rob Walling
11:53
38:52

Jessica MalnikHOST
What are you seeing working today? And what, if you were to having to like bet money on it, what do you think is actually going to keep driving attention and distribution in the future?
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12:10Rob WallingGUEST
Like if you have a desperate problem and you're like, I need software to solve this problem, right? Or I need, you're running a gym and you need software or you want an operating system to run it.
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12:26Rob WallingGUEST
You need to be in the place that they are searching, right? So Let's put distribution more in that area.
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12:32Rob WallingGUEST
But like attention is, that's me on, that's you recording a podcast, that's me recording a podcast or a YouTube video or whatever.
26 MINS LATER

Jessica MalnikHOST
And on the flip side of that, now that you can pretty much build any feature way faster, how do you know what you should be building when anything can be done way faster without ending up with like gigantic, like a product bloat nightmare?
How Rob Walling Raised $59 Million to Fund Bootstrapped SaaS Founders
17:00
Jared BaumanHOST
I can tell you from interviewing individual SaaS owners over the years, that's something that they always mention and talk about.
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17:08Rob WallingGUEST
And, and in, in the interviews w-we will often say, I'll say, "Look, if, if you wind up working with us at Tiny Seed, taking money in, I'm, I'm gonna really lean on you to like triple your price.
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17:17Rob WallingGUEST
Like you are so far underpriced based on what you should be." And I see people, I'm, and we saw somebody charging, I think they had, it was like $50 and $100 were their two price plans.
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17:27Rob WallingGUEST
And I was like, "No, this is a $500 and $1,000, like $1,000 a month product." They were literally a 10th.
10 MINS LATER
