#774 WP-Tonic This Week in WordPress & SaaS: With Special Guest Rob Walling of TinySeed & MicroConf

August 15, 2023

We Discuss The Secrets of a Successful Startup in 2023

We discuss Rob’s new book, “The SaaS Playbook” What is the critical message that Rob wants people to get from the book?

Rob has been helping non-venture-backed startup founders since 2005, and now I run the first startup accelerator for SaaS bootstrappers, TinySeed.

Rob has invested in over 125 startups, but I don’t believe raising money is the only way to start a SaaS company.

For context, Rob has built six businesses to six- or seven-figures in revenue without taking outside funding.

#1 – So, Rob, what triggered the new book?

#2 – What are a couple of new key areas that the new book covers?

#3 – What would be the main message you want readers to get from the book?

#4 – Some of the spin around AI is dying down, so have you had enough time to consider how this new technology will affect startups in the next 12 to 18 months?

#5 – What have been some of the biggest online influences or personal mentors connected to your business career development?

#6 – If you return to a time machine at the beginning of your career, what essential advice would you give yourself?

This Week Show’s Sponsors

Zoho: Zoho.com

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Episode Transcript

Welcome to the WP-Tonic This Week in WordPress and SaaS Podcast, where Jonathan Denwood interviews the leading experts in WordPress, eLearning, and online marketing to help WordPress professionals launch their own SaaS.

[00:00:00.000] – Jonathan Denwood

Welcome back, folks, to the WP-Tonic this week in WordPress and SaaS. It’s episode 774. I feel so old audience, but there we go. We’ve got a real friend of the show and a personal friend. He puts up with my madness. He just looks back at me and smiles with the experience of dealing with crazy people like me, we got Rob Rowland with us again. Rob, we’re going to be talking about your new book, Secrets of a Successful Startup—the SaaS playbook. I like the cover. It’s great.

[00:00:56.790] – Rob Walling


[00:00:57.300] – Jonathan Denwood

I paid a lot for it. I’m sure you did. Would you like to quickly introduce yourself to the new listeners and viewers, Rob?

[00:01:05.680] – Rob Walling

Yeah. Thanks so much for having me on the show again, man. I feel like I’m becoming the Steve Martin on SNL. He has the most appearances. That’s what I’m gunning for. I’m on WP-Tonic.

[00:01:15.580] – Jonathan Denwood

Well, they’re great discussions. I think you enjoy them as well.

[00:01:19.300] – Rob Walling

Don’t you? Always. As a way of introducing myself, I used to be a software developer. I wanted freedom, I wanted to be an entrepreneur. The Silicon Valley Path didn’t make sense to me, and I didn’t have any connections. I was an outsider, so I just started building little software products. This is almost 20 years ago. I made invoicing software for. Net developers. I just created little random things. Eventually, I owned all of my time, about 120 grand a year, 150 grand a year, and I just had products. Then I realized as I started blogging about this, a bunch of other people were like, Oh, my gosh, this is cool. You should talk about this. Then I started a podcast called Startups for the Rest of Us. I started a conference series in a community now called MicroConf. I’ve written four books now on entrepreneurship. That brings us to today, which is the full-time now I run MicroConf, and I run Tiny Seed, which is a startup accelerator for SaaS. As Jonathan said, I write books.

[00:02:17.290] – Jonathan Denwood

That’s fantastic. I’ve got my co-host, Kurt. Kurt, would you like to introduce yourself to the new listeners and viewers?

[00:02:24.880] – Kurt von Ahnen

Absolutely. It’s great to be back with Rob again. I have a small company called @MananaNoMas. We specialize in membership and learning websites and helping other people find their space online and working with WP Tonic’s on them.

[00:02:39.320] – Jonathan Denwood

We’re going to be discussing what triggered Rob to decide to write this book, what key things he wants people to get from the book, what Rob thinks about AI. It’s dying down a little bit, so I think we’ve had a little bit of time to reflect on it. In many other subjects, it should be a great discussion. But before we go into the main meat and potatoes of this great interview, I’ve got a break for a couple of my major sponsors. We will be back in a few moments, folks.

[00:03:10.530] – Rob Walling

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[00:03:14.380] – Rob Walling

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[00:03:43.190] – Jonathan Denwood

Hi there, folks. It’s Jonathan, Denwood here, and I want to tell you about one of our great sponsors, and that’s Zolo. Com. If you’ve got a WordPress website, a membership website, and you’re looking to link it with a great financial management package, Zolo can provide this solution. So all your bookkeeping needs are done through Zolo. If you need new inbox email functionality, and you don’t want to pay the high charges that Google will charge you, Zolo offers a great email inbox platform. They’ve got over 50 apps and services that all integrate fantastic with WordPress at great value levels, and they almost always offer a fully functioning free product as well. It’s just amazing value. Also, if you’re a WordPress developer or agency owner, Zolo are looking for great partnerships in the WordPress space. To get all this information, all you have to do, folks, is just go over to zolo. Com, and they have the products that you’re looking for. Thank you so much, Zolo, for supporting WP-Tonic and the Machine Membership Shows. It’s much appreciated. We’re coming back, folks. I’d like to point out I’ve got some great special offers from the major sponsors, plus a created list of all the best WordPress plug-ins.

[00:05:22.290] – Jonathan Denwood

If you’re looking for a Pacific plug-in for a client’s job, you don’t have to tour the internet. You can go just to this list and you can get all these goodies by going over to wp-tonic-deals, and you find all the goodies there. What more could you ask for? Probably a lot more, but that’s all you’re going to get from that particular page. Rob, busy life, family, micro conference, tiny seed, not enough on your plate. Plus, you go on crazy podcasts with people like me. You decide you’ve got to write a book. What was the trigger to add more to your plate, Rob?

[00:06:14.460] – Rob Walling

It was a difficult decision, and the trigger was a conversation I had with a good friend of mine. He’s the founder of Signwell. His name is Ruben Gamez. I was kicking it around. I’ve written three books, and they’re always very painful and take a lot longer than I want them to, and they’re a distraction for my day-to-day and all that. But I was telling him, I said, I have someone for an AI project where they wanted to pull in every word that I’ve spoken on YouTube and my podcast, and it was like a million words, and he was feeding it into an AI engine because we were trying to build like a robot that we could query. I said, That’s a million words. A, that’s a lot of stuff, but B, it’s too many words for anyone to follow. That’s hundreds and hundreds of hours of content. I said, I would love it if I could condense that into something to 40,000 words, which is what this is. I was hearing hawn about it, and Ruben said, You know what? Our community needs this book because right now when people come to me, him being Ruben, and say, What are the best books?

[00:07:15.730] – Rob Walling

What should I read for bootstrapping SaaS? He was like, I just don’t. I name April Dunford’s book for positioning, and I name so-and-so’s book about copywriting, but there’s no core book that I recommend. He said, I would love it if write this book because I will recommend it to people. That was a weird moment of clarity of like, I need to do this. That was two and a half years ago, though, and that shows you how long these things can take.

[00:07:42.880] – Jonathan Denwood

I want to mention over to you, Kurt.

[00:07:46.390] – Kurt von Ahnen

Yeah, Robb. What are a couple of the key areas that the book really dives into and covers? You just mentioned it does the overviewing arc of it, but where does it focus or lead people?

[00:07:59.200] – Rob Walling

Yeah. What’s funny is I didn’t start with… I wanted this to be a general… There’s no bootstrapping SaaS book that has been out in the past five or 10 years. All of them tend to be old. I wrote one 13 years ago. They’ve all aged. I set out to cover things that the most common questions that I get from my tiny seed founders and from MicroConf. There’s a whole chapter on pricing. There’s only six chapters. Each of these covers the key. It’s pricing, one of them all about mindset because that’s a huge deal, whether you’re transitioning from developer to entrepreneur or whether you’re just dealing with the day-to-day of questions of, should I be doing this and how this is so hard. Then, of course, marketing. That may be the big one. Pricing and marketing are probably the big two chapters I think people have commented the most about. For marketing, I say this on my podcast all the time, there are only 20 B2B SaaS marketing approaches. That’s it. That includes high-level things like I’ll say PPC, pay per click ads is one. Now, under that is Google AdWords, Facebook ads, Instagram, whatever, LinkedIn, Twitter. But PPC has one.

[00:09:03.290] – Rob Walling

There’s only 20. People were saying, Well, what are they? I was like, Well, I have this list here written on this paper, and I put it in the book. That’s my understanding of pretty much, aside from some edge case, it’s about 20. I talked through when to use each of them, how to think about using, how to prioritize each of them. That’s a big question. There’s more to it. Those are three of the top chapters that I keep hearing about. People tell me, Oh, this one really impacted my thinking.

[00:09:28.420] – Kurt von Ahnen

Nice. I found that my personal experience, I tend to be more of that bootstrapping mindset. But then I found myself working on projects for clients that were the opposite, that went out and did the fundraising thing. It’s always blown my mind. I was used to blood, sweat, tears, the whole thing. Then I’d start a project for someone else and they’d come back to my office three months later and be like, well, our first round, we raised 400,000 dollars for this, this and this. And you get lost a little bit in like, okay, so what’s the right way to do something?


[00:09:59.240] – Rob Walling



[00:10:00.660] – Kurt von Ahnen

It looks like your book’s got some guidance in that.


[00:10:03.050] – Rob Walling

Well, that’s the thing. This book, I call it, the subtitle is, Build a Multimillion Dollar startup without venture capital. Honestly, there are a bunch of venture funded SaaS founders who have bought this and told me this applies mostly to what I’m doing. The only sentiment in the book… I’ve never been anti-venture and I’ve never been anti-fundraising. I think funding is a tool. Being anti-funding is like saying I don’t like hammers. When I have a nail, a hammer is the right tool. When I have high growth ahead of me or when I want to get there faster, funding is a tool to get there and you have to know what you’re giving up. There is no one right way, but I think of it, I do have a mental framework for it. I call it the 1-9-90 rule or framework or whatever that I think around in terms of tech companies, I think around 1%, maybe should, or should is not the right word, should consider venture. That’s where you’re going for a billion dollars or bust pretty much. I think about 9% should consider some type of funding that’s not venture, which is like Tiny Seed has indie funding that’s not venture.


[00:11:05.950] – Rob Walling

There’s debt financing, they’re friends and family, there’s angel rounds where they don’t expect you to raise venture. Then I think the other 90% should probably bootstrap. It’s like the 80-20 rule where it’s made up, but it gives you an idea of how I think about it. There is room for each of these. I’ve started six companies in my life. Five of them were bootstrapped, and the sixth one, we’ve raised $42 million for Tiny Seed. I see successes across all of them. Funding, I will say, does make it easier. That’s the thing. Whether it’s a cheat code or whether we say bootstrapping is hard mode, however you want to call it, I’ve done both. Bootstrapping is harder, but bootstrapping, you’re in control. You don’t answer to any of you. There are pros and cons to each of those, which I discuss a little bit in the book as well.


[00:11:52.150] – Kurt von Ahnen

Nice. Jonathan, back to you.


[00:11:54.850] – Jonathan Denwood

Just remark, me and Kurt had a discussion about page builders last week. It was the internal show. We had an example of this actually, Rob, in the WordPress space, about three, four years ago, there was a page builder called Beaver Builder, and there was another Elemator. Elemator has grown into a six million user, took VC money, and Beaver Build is still going, still a great company, still great founders, and they chose not to take VC money. I’m just saying, I just remarked to Kurt maybe it was the wrong decision for them and maybe they should have taken VC, but on the other hand, maybe they were totally happy where they are. I’m just put you by. It really depends where you want to go with your own business journey, really, doesn’t it?


[00:13:01.860] – Rob Walling

That’s right. You can go in one direction. Let’s say I bootstrapped for six months, a year, five years, you can then always raise funding. You can’t go back. You know what I mean? Once you’re raise VC, once you raise angel, if it’s not VC-focused, you can still hang around there. I’ve seen some people, like Wistia, bought out their angel investors. They literally went backwards. It’s uncommon, but it happens. But man, once you go venture it’s very, very unusual that you don’t just take it to the moon or bust type of thing.


[00:13:35.810] – Jonathan Denwood

Obviously, people can have their own takeaways after they read the book. But if somebody read the book and you bumped into them and they mentioned the book and you said, What was the main thing you got from the book? What would lighten your heart if somebody said the main message they got from the book?


[00:13:59.850] – Rob Walling

That’s an interesting question. I’ve gotten a lot of feedback on Twitter already, and I think some of the things that made me happiest were someone said… Well, a few people said that their pricing, the book made them realize that pricing is all screwed up, that they’re underpriced or the value metrics off, they just don’t have it structured correctly because pricing is the single biggest lever in SaaS. That is the first thing you should think about. If I can get someone to increase their price or to change the way they charge, that can make or break a business. It can make a quarter million dollar business into a million dollar business if you’ve just changed this one thing. I’ve seen it. I’ve been part of it. That would probably be the number one. The number two is there’s a mindset chapter at the end. Of course, I throw it at the end because a lot of people are like, Oh, mindset. Why is he talking about this? But there’s a bunch in there about the grind, about burning out, about disputes, co-founder disputes, about taking founder retreats and recharging. I think if someone told me that that took me from being a crazy, stressed, overworked founder and made my journey easier and just made my life as a founder easier, my relationship’s better, that would also make me really happy.


[00:15:12.810] – Jonathan Denwood

That’s fantastic. Over to you, Kurt.


[00:15:16.300] – Kurt von Ahnen

Well, I feel like I’m going to go off the range just a little bit. But when you decide to write the book, Rob, and I know that you said that someone else had said, Hey, if you write this, I’d like to recommend it to people. But in my personal writing, I find that my brain gets just so overwhelmed all the time. If it’s constantly there, if it’s just constantly buzzing, for me, the writing is like it’s the release. It’s the, if I write it down, I can let it go and then get more productive on other things again. What’s that energy like for you? Was it a struggle to focus on the content or was it like, Thank goodness I’m finally getting this content out?


[00:15:53.560] – Rob Walling

For me, it was a struggle to focus on the content because I had already gotten 80% of this, 75% of this out over 675 podcast episodes and 52 YouTube videos a year that I record. A lot of it has been said somewhere in some interview at some point, you know what I mean? I was actually trying to revisit a bunch of my conversations to say what were… I listen back to 100, 200 of my own podcast episodes.


[00:16:21.730] – Jonathan Denwood

Oh, well, that’s horrible, isn’t it? It’s terrible. It’s terrible. I can’t listen to me.


[00:16:27.960] – Rob Walling

But I would pick up, I’d like, Whoa, I said that, and that was really smart. I never said that again. It just occurred to me at one moment. I said it and it was gone. I said, That is an entire section of the book. Just that thought. That’s what I was trying to do, was pull it in. The writing was… Theni was almost retreading ground I’d already treaded, which I don’t like doing so I wrote half the book on my own, about 20-something thousand words. Then I stalled for almost a year and I got writer’s block and I pulled a writing coach in who helped me flesh the rest of it out. Without her, I just don’t think the book would have been finished.


[00:17:03.880] – Kurt von Ahnen

Thank you for the insight. That’s great. I actually have new clients now out of Canada. That’s what they do to help people finish their books. It’s a whole industry.


[00:17:12.500] – Rob Walling

Onto itself. Surprisingly helpful. I resisted it because I’m a writer, after all, I’m not going to let someone else… At a certain point, I’m like, look, do you want the book to get done or not? They’re all my thoughts. They’re all my ideas. For the most part, they’re all my words, although she wrote some of them because she would interview me about things. She’d watch the video, she’d say, I have questions around this. Then she would write a rough draft of sections. Then I would go in and change the tone and be like, Oh, didn’t quite get that. But that’s why the book is done, is because I let her do that. I run two companies. I put out 52 podcasts a year and 52 YouTube videos a year. To think that I had the time and the focus to write the book was, I’ll say, a little misguided. In the end, I cut myself some slack to be able to do it, and I’m happy that I did.


[00:17:53.990] – Kurt von Ahnen

That’s awesome. That’s awesome. Jonathan, I’ll kick.


[00:17:57.000] – Jonathan Denwood

It back. Thanks. I’ve got a question here. I do another podcast. I’m going to do a show tomorrow and it’s more focused around my business. It’s the membership machine show, Rob. We’re going to be… We talk about membership and building a successful membership website, and we talk about WordPress, but we also talk about SaaS solutions. Tomorrow, we’re talking about ClickFunnels and some of the competitors. I’ve been doing a fair bit of research, Rob. You would think in 2023 that most markets were saturated. That it’s very hard. But doing this research, ClickFunnels 2.0, they have tried, I think they were in a pincer. There was new competition and they also wanted to go into the land of Kajabi. They’ve built out ClickFunnels too, and they’ve thrown a lot of extra functionality. But a lot of people criticizing the core functionality is degraded. Then I looked at the competition, I looked at something called Go High Level, which is more aimed at agencies. Then I looked at something called System. Io, that’s System, System-E, I don’t know how to pronounce it, and that seems to become the darling of some of the influencers that supported ClickFunnel. I know this is long-wining, but what I’m saying here, you would think there seems to still be bandwidth, even in something so competitive as landing page CRM, there seems to be a lot of people, competitor, established play like ClickFunnel, they seem to be having problems, but none of the other competitors have quite got it.


[00:20:11.630] – Jonathan Denwood

Is this something you regularly see that there’s still a lot of possibilities there even in markets that you think are very- Saturated.


[00:20:24.820] – Jonathan Denwood

Yes. Yes.


[00:20:26.910] – Rob Walling

We had to add Tiny Seed, we had- That was a very.


[00:20:29.240] – Jonathan Denwood



[00:20:29.800] – Rob Walling

Question, wasn’t it? No, but there’s three reasons for it. I’ll go into them in a second. But at Tiny Seed, we’re a startup accelerator for SaaS bootstrappers, and we back between ’50 and 60 early-stage SaaS companies a year. We’ve backed 131, I believe, to date. There’s a couple of different opportunities we see. One, of course, it’s just verticalized. It’s like, I’m going to build Salesforce, but for hair salons, for lumberjacks, for whatever other vertical. The other thing is you go into these horizontal plays like landing pages, email marketing, email service providers, CRM that anybody can use. There are still corners of those markets that you can get to by positioning yourself. We are like ClickFunnels, but our performance is way better. I don’t know what’s wrong with ClickFunnels, but you figure out what is ClickFunnels, Achilles, Heal? What is everyone complaining about? Your H1 on your homepage is we’re not that. Becoming the opposite, and that’s how you position yourself in a corner of a market. Every big market always has these positioning quarters where you can say, We are the low price leader, which I don’t recommend being, but you can say we are the easiest to use.


[00:21:54.160] – Rob Walling

You can say, We are the one with the best support. Think of what Zappos did with customer support. That was their one thing. They weren’t the cheapest. Zappos just said, Our support is incredible. We FedEx overnight both ways. Some SaaS companies have taken up that mantle. Yes, there’s opportunity. It’s more crowded than it was 10 years ago. It’ll be more crowded in 10 years. I believe there’s always opportunity. Those were two. The third thing is markets mature and apps mature. You saw ClickFunnels come out. It was new software. Oh, my gosh, this is the best thing ever. Software gets old quickly, and the lifecycle of it, if you don’t rebuild it gets real crusty. Think of Mailchimp and Salesforce. I’m not saying Mailchimp is crusty, but it is old. It’s 20-something-year-old software. That’s what made an opportunity for me to start Drip, for other ESPs like ConvertKit to come around, is that Mailchimp got old. Similarly, it’ll happen to everything, ConvertKit, ClickFunnels, anything we name today that’s like everyone’s using it, give it five years, give it seven years, it just doesn’t move fast. Some upstart could come in. I could could start an ESP today and grow it to a multimillion dollar business in a few years, I’ll say.


[00:23:06.370] – Rob Walling

It takes you one or two years just to get to table stakes features. But given that software ages so fast, it ages itself out. Unless someone’s really on top of it, like Base Camp, for example, where they rewrite everything, there’s massive opportunity for an Upstart to come in and replicate, but innovate in a way that the existing incumbents aren’t able to because of the age of the product.


[00:23:28.970] – Jonathan Denwood

Yeah, because I’m trying to think. I think if you’ve got a certain market share, there seems to be a temptation to add more and more functionality. As you add more and more functionality to the core of what led people to your product, your service, it actually deteriorates in general. But it’s understandable in a way because you see it as a way of making your product more appealing?


[00:24:05.110] – Rob Walling

It’s a pain in the audience. You want to keep growing. No matter how big the idea, there’s something called the S-curve, which in Darmesh wrote a really nice thing about this. Jason Cohen wrote a good thing about this called the Elephant Curve. But basically, your app starts off and it grows and then it inevitably plateaus. The market is only so big and it might plateau at a million dollars a year. It might plateau at 100 million, but it plateaus. Even W. P. Engine, I know their story pretty well. I was an angel investor in the first two rounds. I’m friends with Jason. At a certain point, just WordPress hosting, they had enough of the market that it’s like, well, we’re going to start to plateau unless we expand. That’s the same thing with ClickFunnels, same thing with Leadpages, who was the big… Leadpages was the leader until ClickFunnels came along. Leadpages was starting to plateau because they had sucked almost all of the market in. Yes, it’s inevitable that you’re going to plateau, and so you have to add either services or teaching, because I know ClickFunnels does a lot of the education stuff, or you add new product lines.


[00:25:09.110] – Rob Walling

Think of HubSpot. Remember, HubSpot used to be all-in-one marketing. It was like Google Analytics mixed with Squarespace, mixed with, I think they had some… They didn’t even have email marketing at the start and they bolted that on. What really caused a ton of HubSpot’s growth was when they added CRM and went against Salesforce. Talk about adding five things, and then they kept growing. To your point, Jonathan, is the product very good? I don’t know, I don’t use it. I hear people don’t like it. A lot of these things like ClickFunnels or whatever, it’s the deterioration of the core product. I think it is. Inevitables, may be too strong of a word, but it’s certainly common.


[00:25:46.090] – Jonathan Denwood

I’m not having a basher. I just don’t think any of this is particularly easy, which is not surprising, is it? We’re going to go for our mid-break. We’ve got some other great topics to discuss. It’s always a great to have Rob on the show. They’re always interesting discussions. We will be back in a few moments, folks.


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[00:27:14.790] – Jonathan Denwood

Your show. We’re coming back, folks. Just want to point out, if you’re looking for a great WordPress hosting provider and partner for your projects, especially if you’re building out complicated membership and community websites and WordPress, why don’t you look at becoming a partner with WP Tonic? You can find all the info and the special deals we do with our industry partners by going over to WP-Tonic/partners. That’s WP-Tonic.com/partners and find out all the info there, folks. In some ways, I’m so bored with this already, but AI, God knows how many people have approached you with startup. I hate to think how many emails, conversations you’ve had in the past six months of our day. Are you sick of it? I’m not sick of it either way. Obviously, unlike Web 3.0, I definitely think there’s substance to this, but I also think it’s much, much more complicated than what people were thinking. People seem to have a clear roadmap, and I think it’s much more unchartered territory that we’re entering. I think the hype’s died down a little bit, so maybe you’ve had enough time to think about, do you have any thoughts about this AI road trip that we go there?


[00:28:59.150] – Rob Walling

Yeah. I think the top-level summary is AI is going to be like any… I’ve likened it to a web development framework like rails for Ruby or Jango for Python. When you first see it, you’re like, Oh, my gosh, this is an advantage and it’s going to make me move so much faster. That’s true. But it’s also an advantage everyone else can use. It’s less of an advantage and more of just an accelerant. It’s more of something that helps you move faster. Certainly, our horizontal AI is going to be owned by a couple of massive players. We can probably predict who those are, but it’s anyone’s game, I suppose, at this point, although OpenAI has the edge. But then the uses are already starting to be verticalized, I’ll say, or they’re starting to be use case driven, where you see it’s like, oh, it’s specifically for marketing images and it’s specifically for this and that. Now, my intuition is that the people who are going to succeed in those spaces in the long term are the ones that are already there. It’s like if you look at Buffer or Hootsuite, why wouldn’t they just build in the ability to generate marketing copy and generate marketing units?


[00:30:19.250] – Rob Walling

You don’t need a third-party tool to do that. They already have the customer base, they already have the momentum. Similarly, I guess what I’m saying is I see a lot of AI tools being built that it’s like, Oh, this is a cool idea and AI can generate that. But it’s going to be a feature of a bigger product that’s already there. I looked at Vimeo and Wistia, these big video hosting platforms. There’s a bunch of, again, feature apps that it’s like generatevideoscript. Ai and generatevideoscriptsummary. Ai and whatever else. Now like Vimeo released yesterday, you can generate a video script and you can generate a video summary. That’s all just built into the main tool. It’s not a differentiator. It’s just something cool now that makes me going to stick with Vimeo. Those are my short term thoughts and I think over the next 12-18 months it’s going to just continue to evolve that way. Unless we see another big step like OpenAI when they drop chat was like, Oh, my gosh, now we’re all shocked and it’s this new thing. I don’t know if another new thing like that will come out or not.

[00:31:21.670] – Jonathan Denwood

Do you think it will substantially, as it matures a little bit more substantially, help developers be more productive and to serate and lower the price of building apps and products, which is which is the tiny seed is a direct area that you’re interested in. Do you see that really happening?

[00:31:46.640] – Rob Walling

I do. Yeah, I think it will make them, developers, more productive, which in my business, well, maybe it’s decreased the cost of it, but really it’ll allow us to build more with the same budget because we’re still going to spend as much as we can and we’re just going to move faster. We’re going to build more in general. Because in early stage, you do need to build a lot usually to get to an MVP or to get to table stakes. But with consulting projects, if I was still a microagency, yeah, we would be way more efficient. Whether that number is 20% or whether it’s 50% more efficient, I think with tools like Copilot and whatever else comes out, I think it’s absolutely. There’s one that’s coming out that is you can type in a description of what you want to see and it generates all the tailwind, like a whole tailwind CSS of a page after you’ve described what you want it to look like. That’s crazy. It’s not going to get you 100%, but can it get you to 75%? You don’t have to hand-code all that anymore. It’s pretty crazy.

[00:32:50.440] – Jonathan Denwood

I have a tear cut.

[00:32:53.070] – Kurt von Ahnen

Well, Kyle has a follow-up to the idea that AI is the accelerant or that things can move faster. When you are looking at an incubator for SaaS. Do you foresee this being like it’ll hasten the churn rate? Do you think businesses will start and fail at a quicker rate because they’re the impatient of AI that push and push and push and then poof?

[00:33:18.150] – Rob Walling

I don’t think it will because businesses usually fail. Funded companies fail when they run out of money, and bootstrap companies fail when the founder runs out of motivation. Because that’s just how it works because bootstrap companies don’t run out of money because they just don’t have the… They don’t have burn, per se. I think AI, if anything, might help founders not run out of motivation because they are moving faster. Because that’s usually what happens is I’m just not growing, I’m not getting traction, nothing’s working, I’m going to throw in the towel and if I can help them move faster, maybe it’ll keep me going longer. But yeah, I don’t know. I don’t know how much of a difference it’ll make.

[00:34:02.600] – Kurt von Ahnen


[00:34:03.150] – Jonathan Denwood


[00:34:04.190] – Kurt von Ahnen

I like that. I was just trying to figure that out. The next question is, what are some of the biggest online influencers or personal mentors that may have had an effect on you?

[00:34:17.080] – Rob Walling

Yeah, there’s a couple. Jason Cohen is one. He was back in 2011. Let’s see, I started blogging in 2005. He started blogging, I think, in ’08 or ’09. I’d never heard of him. I was like, This guy’s really smart. This is way before W. P. And Jen. He was just very smart. He was touching on things that I was also thinking about. There were only a handful of us who were startup bloggers at the time. I was more of a micro bootstrap blogger. I wasn’t even a startup. I hadn’t started a bigger company. Then in 20… I wrote my book in 2010. I saw he bought my book. I was like, This is really cool. We’d never met, but apparently he was reading my blog because I certainly was reading his. He bought my book, he commented on it. Then when he went to raise funding for W. P. Engine, he emailed me and he’s like, Do you want a minimum is $25,000, but I’ll take whatever you have. I was like, I’ve never invested.

[00:35:12.850] – Jonathan Denwood

I wish you had five things.

[00:35:14.660] – Rob Walling

I don’t have $25,000, but I didn’t have the money. I had no big exits. I was like, Oh, my gosh, this is so special. I actually went and sold a small little product I had to raise 20 grand to invest in that first round of WP Engine. In fact, that’s the other funny thing. He sent an email and it said, This is the general idea of what I’m building and here’s the deck. When I clicked through to the deck, it was like a 404 or access denied or something. I never asked for access. I just said, I’m in. It didn’t matter to me. I just believed he would do it. Then he spoke at Microcom, we got to know each other. I have just watched him just basically hit the stratosphere, and I’ve always respected his logical way of thinking. Then the other one is a friend of mine. It’s the guy who encouraged me to write the book. His name is Ruben Ahmed. He started actually, he was reading my blog, he was working at Day Job, 2008 and ’09. Then he started this little sass on the side and he was asking me advice.

[00:36:13.960] – Rob Walling

Kind of like a… He was learning from me. Then at a certain point, I remember thinking, I think he knows more than I do now. I remember in 2011 being like, This guy passed me on the curve. Now I feel like in different areas, as any good relationship is, I’m ahead on some things, am I thinking in other things, he’s ahead on. Those two people have 100% shaped my journey.

[00:36:37.140] – Kurt von Ahnen


[00:36:37.380] – Rob Walling


[00:36:37.960] – Jonathan Denwood

It’s great to hear about Jason because Jason’s become a friend of the show as well. I didn’t know that you had a connection, but he’s come on the show regularly, and I think he would say that we’re friends like you, and he’s just a great, like yourself, very generous with your time. He’s just a great person. It’s great to have sucha lot of people that agree to come on the show, actually. I love this question because now I’m English, while I’m a dual national, but I used to watch a lot of Doctor Who when I was a kid. If you had to do a time machine and you could go back to the start of your career, this crazy sass, what would be a couple of things that you would say to yourself that would have helped you? If you do at the beginning, that would have helped you out, Rob?

[00:37:33.000] – Rob Walling

I would say don’t be so scared. Make more mistakes, move faster. It took me way too long to get where I was going because I was so scared I was going to do something that I would look back on and regret or that would be a mistake, or that I would waste time building something and it would never take off, or that I would say something or build something online that would get criticized or that people wouldn’t like or that people would get mad at. Is here, here I am 23 years later after starting my career as a developer, and I wished I had gotten here faster. I could have if I had just taken bigger risks and not tiptoed around all this stuff and I had all this anxiety and stress around, Should I do this? Should I do that? The more I shipped, the better I got. The more I shipped, the faster I moved. In the early days, I was so tentative to ship anything. I mean, ship code, I mean, ship websites, I mean, ship blog posts, ship podcast, ship books, ship opinions, whatever it is. These days, I have gotten over that fear because I ship all…


[00:38:38.950] – Rob Walling

Some would say I ship too many of those things, but that’s the place that I find myself at now.

[00:38:47.660] – Jonathan Denwood

Yeah, it’s a difficult one. I always felt you were very focused. I think that’s one of the main things, isn’t it? In this age, it’s effortless to become unfocused.

[00:39:04.030] – Rob Walling

I was unfocused for a while, though. Because I was launching, if you think about it, Drip and any SaaS app I ran was this company and it was pulling me in. It was all the energy I could muster. Then on the side, I was writing books and doing podcasts and running micro conference for startup. I was not focused, and that was actually pretty stressful. The most focused I’ve ever felt in my life in my professional career started in 2018. I’d sold Drip in 2016, worked for them for a couple of years. I left in 2018, and I looked at what I had, and I had podcasts and I had MicroConf, and then decided to start Tiny Seed. I realized, Oh, these are all the same thing. The mission of those three things I’ve just named is to multiply the world’s population of independent, self-sustaining startups. That’s the podcast, that’s Tiny Seed, that’s MicroConf. They do it in different ways. They’re different tool. One’s a hammer, one’s a screwdriver, and one is a rake. But the mission of each of them is to do the exact same thing. This is by far, even though when people ask me what I do on a day-to-day basis, I’m like, I work on a lot of things.

[00:40:08.850] – Rob Walling

I’m like, I do all these YouTube videos, and then I do podcast interviews, and then I manage a team ofMicroConf people, and I manage a team of Tinyseed people. But I feel more focused than I ever have been because the mission aligns all three of those.

[00:40:21.660] – Jonathan Denwood

Yeah, I think so. They are all linked, aren’t they? There is, you can see some clear linkage to the madness because I’m not sure about my madness though, but there we go. Most people… Because we’ve got enough of five minutes before you’ve got to go off. Quick question. Most people give up too soon, but when should you give up on a startup, on an idea? I’ve got a project that’s got some traction. It’s another business. I’ve been at it on and off for about five years, but that’s been mostly down to my madness. It’s just starting to get some traction. I want to know if I should call it a day and just concentrate on. When can I go to insights? Because like I say, most people give up too early, but there must be a time where you should give up on something.

[00:41:25.950] – Rob Walling

There’s definitely a time when you should give up. Five years is a long time. The question I have before giving up on an idea is, is it the idea itself or is it that I haven’t given it the attention it deserves? I haven’t pivoted it. I haven’t focused on it enough. It’s been a side project for years and years. You’re not giving it a full chance if you really want it to work. There’s this myth in the Indie hacker community, I’m going to do one project a month and whatever one catches on is 12 projects, and one of them is going to catch… It’s bullshit. It never happens that way. I say never, meaning like 99% of the time. It’s an Indie hacker dream to think that I’m just going to throw these things out and they’re just going to catch on fire. You’re meaning catch like a rocket ship.

[00:42:13.840] – Jonathan Denwood

It almost never happens that way. Well, what was that saying? Overnight success takes about 10 years of effort and sweat. Exactly. I’ve got the say right.

[00:42:22.070] – Rob Walling

If I’m honest with you. The companies I see that are amazing and have all this growth and the profit and whatever else we would want in a company are the ones where someone focused on it and they fought through and they pivoted and they changed and they realized, Oh, this is not working, and they made another change. It wasn’t some autopilot thing they launched. I think before I would close something down, I would ask myself, have I given it its due? It’s due focus? I would also ask myself, am I done with this? Am I just totally… Sometimes you’re just done with a topic or an idea or a tool and you as a bootstrap founder or even as an investor, if you’ve raised funding, you get to make that call of like, I just want to cash it in. I just want to be done.

[00:43:10.130] – Jonathan Denwood

Yeah, it’s been one of my weaknesses in my life and accepting when business relationships or more personal relationships. I think everything’s got a time and place and there’s a place where you just got to accept things that are nothing lasts forever. We die. Everything dies in the end. Or a business, they expect business will either die or it’ll be sold or nothing goes on forever, does.

[00:43:45.120] – Rob Walling

It Rob? No. Everyone sells eventually. I say that a lot. There’s only a handful of companies that don’t sell and move on because you just get bored. You just get bored of stuff as entrepreneurs. Base Camp is really the only bootstrap company I can think of that hasn’t sold. I never thought Mailchimp would sell, to be honest, and then they did. I didn’t think I would sell Drip, and then I did. I didn’t think baremetrics would sell. I could go through this list of like, I bet they’re going to run that forever. Then someone comes along and they write you, they say, I’m going to pay you 20 times your net profit this year and to get long-term capital gains. By the way, you can fund all of your kid’s college funds. You can have enough money you never have to work again. Suddenly you’re sitting there like, Oh, I wasn’t even thinking about selling, and now why would I not? Jason Cohen has a great essay about this actually called Rich or King. He basically says, Do you want to be rich or do you want to be king? He talks about base camp wanting to be king and run their company and this and that.

[00:44:40.840] – Rob Walling

Jason Cohen said, Everything’s theoretical until you’re sitting at a taco joint and someone slides a piece of paper across and you look at the number and you say, Wow, I would never have to work again. Suddenly it changes your mindset. Anyways, that’s leaving a business on the good side. That’s leaving it when you exit. You’re talking about leaving it, shutting it down in essence, which unfortunately happens a lot more.

[00:45:07.510] – Jonathan Denwood

Yeah, I think, Jason; I’m pretty sure he said this on a podcast that I was hosting. He said that with WP Engine, it took him three years to get the first 1,000 clients.

[00:45:20.080] – Rob Walling


[00:45:20.690] – Jonathan Denwood

Wouldn’t- First 1,000. He knows what he’s doing.

[00:45:25.110] – Rob Walling

He had money. He had money, and was putting into it.

[00:45:27.880] – Jonathan Denwood

He knows what he’s doing. It still took him three years to get these first sales.

[00:45:31.500] – Rob Walling

And clients. That’s right. With Drip, which was my last SaaS app, it was an email service provider, it took us eleven months to get to launch. We had beta customers and we had early access and blah, blah, blah, but it took us eleven months to get to launch. Then we plateaued because we had really built something that was a commodity. People didn’t really want to pay for it. Then it took me about another nine or ten months of just pulling my hair out to find product market fit. It was about nine or ten. If you put that together, that’s like 20, 21 months from start of build till we were able to pour rocket fuel on it.

[00:46:09.370] – Jonathan Denwood

Yeah, because just to finish off, I don’t know if just to finish off before we go to go off, I think it’s really hard to really understand what clients really want. I don’t care, every surveys you do. It’s not easy to really work out what really, what customers really, really want. Would you agree with that?

[00:46:34.150] – Rob Walling

Yeah, because of people… This misattributed Henry Ford’s quote if I had asked… Henry Ford and Steve Jobs are known as implying they never talk to customers. Oh, so I should do that too, because I’m like them. No, that’s not what they did. Henry Ford’s quote was, and I think it’s misattributed, but whatever, if I had asked them what they wanted, they would have said a faster horse. It’s like, Okay, you’re a fucking product person. Don’t build them a faster horse. Build them a car. Build them; think about it this way. I want to move faster than a horse. Translate that. You’re a product person. I want to build; should I create a train? Oh, what if I made a train that wasn’t on rails? Well, that would be a car. You know what I mean? It’s like when people tell you, Jonathan, that I want a checkbox that does X, Y, Z. Usually, the problem they’re bringing up is correct, but the solution they’re suggesting is not the right one. You know what I mean? The problem is there, but they don’t know the right answer, and you, as a product person or as an expert, you have to be able to translate that.

[00:47:30.500] – Rob Walling

I believe that quote I just said was maybe from Chris Savage on Twitter last week, but I heard it, and I was like, That precisely encapsulates what it’s like being a product maker.

[00:47:39.790] – Jonathan Denwood

He’s coming to the show. That’s great. He’s coming to the show.

[00:47:44.890] – Rob Walling

September action. You have to listen to your customers but listen to their problems, not their solutions. That’s the summary.

[00:47:51.920] – Jonathan Denwood

Right. I think we wrap it up because you’ve got to go off. What’s the best way for people to learn about you and your fabulous new book?

[00:48:01.930] – Rob Walling

www.sasplaybook.com if they want to read about the book, and of course, start-up to the rest of us if you’re listening to this or watching this and you like podcasts, that’s where I’m at 30 minutes every week.

[00:48:12.770] – Jonathan Denwood

Thank you so much for coming on the podcast. I enjoyed the chat. I think it’s been as usual, very insightful. We will be back next week, folks, with another great interview. I’ve got some fantastic people that have agreed to come on the show. I’ve always been amazed at how I persuaded people to go on this. It’s the main reason why I continue. I love my discussions. I’ve learned so much from the podcast myself. We’ll see you soon, folks. Bye. Hey, thanks for listening. We do appreciate it. Why not visit the Mastermind Facebook group? And also to keep up with the latest news, click wp-tonic.com/newsletter. We’ll see you next time.


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