What is The Future of SaaS & WordPress in a World of AI In 2025
With special guest Rob Walling, Joint Founder of Tinyseed, the presenter of the popular SaaS Podcast “Startup For The Rest of Us,” and the founder of one of the largest annual bootstrap startup conferences, MicroConf.
How will AI shape SaaS & WordPress by 2025? Find out in our in-depth analysis of the future of these technologies. Click to learn more.
What does the future hold for SaaS and WordPress as artificial intelligence evolves? In this engaging video, we analyze the impact of AI on these platforms by 2025. Learn how AI will reshape how businesses operate and thrive online, from personalized user interfaces to automated workflows. Gain valuable insights and tips to stay ahead in this dynamic environment. Click to watch and prepare for the future!
With special guest Rob Walling, joint founder of Tinyseed and the presenter of the popular SaaS Podcast “Startup For The Rest of Us,” and the founder of one of the largest annual bootstrap startup conferences, MicroConf.
#1 -Rob, can you give the audience a more detailed introduction on how you got involved in SaaS and online business ownership?
#2 – In a recent episode of your popular podcast, “Startup For The Rest of Us,” you discussed the possible threats and opportunities in the age of AI. Have you had time to have some additional thoughts on this subject that you are willing to share with the WP-Tonic tribe?
#3 – In another episode ( This Pricing Strategy is DISASTROUS (unless…), you discussed your general dislike of the Freemium pricing model, which is very popular in the WordPress professional community. Can you outline the main dislikes connected to this pricing strategy?
#4 – In this episode, ” 6 Lessons From My MOST SUCCESSFUL Investments in B2B SaaS,” you outline some essential principles for building a successful SaaS business. I wonder if you can give/share some additional insights connected to this with the tribe.
#5— What AI tools do you personally use to help you run your business?
#6—If you had your time machine (H. G. Wells) and could travel back to the beginning of your career, what advice would you give?
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The Show’s Main Transcript
[00:00:00.000] – Jonathan Denwood
Welcome back, folks, to the WP Tonic Show. This is episode 953. I might have done more episodes and our guests on the show, but I don’t know. He runs a very popular podcast. I’m not sure if he’s up to 953. I’m sure he will tell me. How are you shaking? He’s shaking his head.
[00:00:39.700] – Rob Walling
He probably is. 770. I think it was recorded yesterday.
[00:00:42.440] – Jonathan Denwood
Oh, there’s just one thing I’m beating you on, Rob. There’s nothing else that I can say.
[00:00:48.500] – Rob Walling
He hangs his head in shame.
[00:00:49.820] – Jonathan Denwood
Yeah, I don’t think you got any much to worry about. We got a friend of the show, Dr. Rowling, with us, the joint founder of Tiny Seed. A company that invests in bootstrap startups. He also founded the popular podcast Startups For The Rest Of Us. Plus, he does many other things, has a fantastic wife, has a nice family, and it’s done all right for himself. Yes, it’s sickening, isn’t it, folks? But somebody’s got to work hard and be lucky, haven’t they? But there we go. It ain’t me. But I’ve accepted my fate, folks. I still live in the It’s a possibility. So there we go. Also, Rob, you got a new book out, haven’t you? What’s the book about, Rob?
[00:01:38.320] – Rob Walling
The book is called Exit Strategy, The Entrepreneur’s Guide. As far as I know, it’s The Entrepreneur’s Guide to Selling You Without Regret; I co-authored it with the wife that you mentioned. And it’s all about the mental and psychological process of thinking through selling your business. And then, as you’re going through it, and once you’ve sold, how do you think about what’s next?
[00:02:01.730] – Jonathan Denwood
Right. This episode will discuss some of Rob’s podcast posts and videos over the last few months. We will start discussing how Rob sees how AI might affect the startup world, which also affects WordPress. We’re also going to be talking about the Thrinium price model. I think in your video, you call it pricing strategy. It’s disastrous in capitals. We’re going to be discussing that. Plus, we’ll probably be talking about its book as well. It should be a great show. Kurt, would you like to introduce yourself as well?
[00:02:49.210] – Kurt von Ahnen
Sure. Kurt von Ahnen, owner of MananaNoMas. We focus largely on membership and learning websites and working directly with WP-Tonic and the good folks at Lifter LMS.
[00:02:59.730] – Jonathan Denwood
That’s fantastic. Before we go into the meat potatoes of this great interview, I’ve got a message from one of our major sponsors. We will be back in a few moments, folks. Three, two, one. We’re coming back, folks. Before we go into the interview, I also want to point out we have a great free resource for WordPress power users and freelancers. We created a list of the best WordPress plugins and services that we tested ourselves, and we use them daily, weekly, monthly, and yearly. It’s a great resource. It will save you a ton of time. You can get this free resource by going over to Wp-tonic. Com/deals, Wp-tonic. Com/deals. Plus, there are some special deals from the sponsors. What more could you ask for, my beloved tribe? Probably a lot more, but that’s all you’ll get from that page. They love me saying that, Rob. I get more comments about that little statement than anything. I can get away with it because I’m English, right? I can get away with that nonsense, can’t I? So, Rob, you’ve been on the show multiple times. You’re a glutton for punishment, aren’t you, Rob?
[00:04:23.110] – Jonathan Denwood
You keep coming back for war, don’t you? But you need that type of determination if you’re an online entrepreneur, don’t you, Rob? But can you give the tribe new listeners and views? And we’ve had quite a new load of new people lately. Can you briefly introduce your background and how you got into the crazy world of online business building, Rob?
[00:04:49.120] – Rob Walling
For sure. Yeah. Software engineer is really how it all started. And working a day job and as many people experience, it just wasn’t as fun as I wanted it to be. I am unemployment That’s what I now call myself.
[00:05:01.900] – Jonathan Denwood
No, you are. You’re interviewing somebody that truly is unemployment, Rob.
[00:05:07.420] – Rob Walling
Yeah.
[00:05:07.940] – Jonathan Denwood
You are. I’m not, Rob.
[00:05:10.170] – Rob Walling
I worked several jobs, and I was always really good as a developer. I would manage people, I would lead them, and I hated the job the whole time, and I pissed off my managers. I never got fired. I never was disrespectful, but I just was so unhappy with the way things went. I hated the politics. I hated all that. So I started building little businesses on the side. 2004, Three was the first one I launched, didn’t work. Four, launched another one, didn’t work. ’05, finally had a little bit of a success, and then built it up from there. Stairstepped my way up. I was blogging along the way about doing it, and it was me. I was the only one at the time. Well, Joel Spolsky was before me, and then I started. And then two years later, Patrick McKenzie, Paddy 11, started. Peldie also started in ’07, I think. Jason Cohen in ’08 and ’09. These were the bootstrapper. I know Jason Cohen is technically not a bootstrapper, but he really is He thinks like a bootstrapper, and he can talk to what we do. So that was it. And then at a certain point, I realized, Man, I like building businesses, but I think I like as much as building them, I like talking about building them.
[00:06:12.970] – Rob Walling
And so that became the blog, and then I wrote a book in 2010, and then the podcast Startup For The Rest Of Us. I started a few SaaS apps after that. But I’d like to say I started six companies, five of them bootstrapped. I’ve written five books now on entrepreneurship.
[00:06:26.260] – Jonathan Denwood
Would you say Building Drip and selling it was That was one of the biggest turning points for you and your family and your career, really?
[00:06:35.740] – Rob Walling
It was. Yeah. It’s interesting. I wanted to build Drip. I wanted to build my next thing. This is late 2012, and I was like, I wanted to be 10 times bigger than the one before it, and just to see what it was like, and to prove that I could a little bit to myself. It turns out I could do it, and it turns out it was pretty tough. I didn’t have all the expertise that I needed to do it, but we figured it along the way. We sold it in 2016, and that was the moment that I could have retired. I was like 40 years old, maybe, somewhere in that range. I took six months off after I left. But obviously, folks like us are not. We’re not retiring. We’re going to keep cranking.
[00:07:15.620] – Jonathan Denwood
You’re not into playing golf all the time, Rob.
[00:07:18.190] – Rob Walling
I got to be doing something, man. I would write books, podcast.
[00:07:22.150] – Jonathan Denwood
Just laying on the beach, just deteriorating slowly. Just playing golf. Six days, seven days. That didn’t appeal to you.
[00:07:29.250] – Rob Walling
For about a For you, Rob. Yeah, about a week. And then it’s like, all right, what am I doing next?
[00:07:34.640] – Jonathan Denwood
God, that would be a snore fest, wouldn’t it, Rob? That would be that you must be dead, weren’t you? There we go. Over to my fantastic… Kirk He’s laughing. I still surprise old Kirk. He’s been my co-host there for what, two and a half, three years? That’s good. It’s good. It’s good for me. I don’t think it’s good so quick for you, Kirk.
[00:07:57.900] – Kurt von Ahnen
I was just thinking, if some people’s definition of retirement would be laying on a beach or hanging out at state parks and making a podcast from the beach or from the park, right? I just see things from a different perspective.
[00:08:13.600] – Jonathan Denwood
You only got one life. Well, I actually think you got multiple, but that’s more to do with me. But there we go. So over to you, Kurt. You got the next question.
[00:08:27.180] – Kurt von Ahnen
Yeah. So obviously, Jonathan and I are both fans of the Startup For The Rest Of Us podcast, and you discussed AI more than once, obviously.
[00:08:38.690] – Jonathan Denwood
You’ve never invited me to the show, Rob.
[00:08:41.060] – Rob Walling
You should show up. I showed up in Riverside, and you just never came. So I recorded a solo episode instead.
[00:08:48.520] – Jonathan Denwood
Sorry, Kirk. I won’t interrupt. You’ve never asked me, though. You’re going to have to hit, hit. There we go. All right.
[00:08:56.000] – Kurt von Ahnen
Wink, wink, nudge, nudge, animal, animal.
[00:08:57.690] – Jonathan Denwood
I’m so subtle, isn’t I, Rob?
[00:09:00.130] – Kurt von Ahnen
So your thoughts on AI, you portrayed it as possible threats, but also opportunities. And I think it’s this little echo thing that some of us have. But have your feelings on AI reshaped over time since talking about it on the show?
[00:09:18.870] – Rob Walling
I think they’ve reshaped in the sense of the gestalt seems to be on social media that it’s panic time and SaaS is dead, and SaaS is over, and that hadn’t happened when I recorded it. I agents started becoming a thing. Here’s the thing about the lack of subtlety on social media is it’s either this new thing is going to totally kill X, let’s just say, SaaS, or it’s going to have no impact on SaaS. And you know what? Neither of those is true, just like with no code. Remember when no code came out? No more developers, no more SaaS. Everyone’s going to build their own thing. It’s like, no, that’s not true. But also, let’s not ignore no code because it has changed things. It has an impact. And maybe there’s 10 or 20 % fewer SaaS companies that need to be built or that can be sustained because no code allows… Like my team at Tiny Seed Microcomf, we have, I think, at least three or four full-blown line of business apps that help us with YouTube production and podcast production. Prior to this, we would have paid for a SaaS, but we just built them in an air table in two weeks.
[00:10:22.420] – Rob Walling
So it is having an impact. Does it mean there’s no more SaaS? Saas can’t exist. No, that’s bullshit. And the same thing with agents and AI is there’s There’s so much FOMO around it, and it’s people who want to be able to make a big headline and it’s engagement farming. So it’s super annoying. So that is how I’ve become less subtle about it where I was like, Oh, let’s look at the nuance of this. Saas will change because of AI. And if you ignore it, you ignore it at your peril, basically. I think that people are developing faster using it. So if you’re a developer, and get your developers using it because you can roll out features more quickly, integrate it into your day-to-day operations, et cetera, et cetera. But what I I wasn’t saying is, Oh, my gosh, it’s going to end or it’s not going to change anything. Now I’m just saying everyone, simmer down. Saas will exist. Agents are not going to put SaaS out of business. In fact, I just recorded a YouTube video that goes live probably next week, next week or the week after. That is exactly It’s like 15 minutes of me walking, trying to logically and sensibly walk through this rather than just throwing my hands up in the air and running around like the blow up doll in front of the used car lot.
[00:11:27.140] – Kurt von Ahnen
Yeah. I just think about my own inbox, in the 15 to 20 spam messages a day, I get from some new fantastic AI product that’s going to be the end of YouTube or something. But then on the other hand, I think about clients I interact with. And so many people’s expectations of what AI is or the hype that AI has presented. Some of these people think we’re literally in the days of enterprise. You go into the cafe in enterprise and go, make me a hot chocolate, and it goes, there’s a hot chocolate. That’s not how the internet works. And I think there’s a big gap between what AI is really doing and what people envision it to do, and then what all these other spammers are trying to tell us it’s already doing that it doesn’t do.
[00:12:12.370] – Rob Walling
Yeah. And that’s the thing is the folks who are in it, if you’re in it day to day, and if you’re using WindSurf or Cursor, and you’re using ChatGPT, I search at least 50 % fewer searches on Google than I used I go to ChatGPT now. I know it’s less energy-efficient. I don’t really want that to be the case, but a lot of stuff is so possible. If you’re in it, it’s cool and you can see the possibilities, but you very quickly see the edges, which is what you’re saying. There’s a lot of edges, and hallucinations have gotten better, but there’s a lot of things it can’t do, and it doesn’t do very well, like writing long-form content. This is very plain vanilla, right? It’ll get better at that. But to your point, if you’re in it, you see the edges, and if you’re not in it, you think it’s magic, is what my experience has been. And the answer is probably somewhere in between, but it’s closer to where you and I are, if you’re, again, in it a lot.
[00:13:14.490] – Kurt von Ahnen
Nice. Jonathan?
[00:13:15.660] – Jonathan Denwood
Yeah, I think I get a feeling it’s a a hybrid situation because it seems to have elements of the early days of the internet before the boom bust. But it also has elements in the way it’s coming across to me, Robert, of Bitcoin and that whole… Which is reared its head again. But you’re the only person that’s ever made any money from Bitcoin. I personally know because you told us that story last time you came on. But do you sense that it’s got elements of the internet just before the bust of the internet. It’s also got elements of Bitcoin and Bitcoin exchanges and that whole crowd as well.
[00:14:13.460] – Rob Walling
Here’s the thing with Bitcoin and crypto, and I’m not super into it, but I did buy some early just to take a flyer. And as you said, I made more money than I thought I would, almost as much money as I did selling my company. So the thing with crypto- That is a bit of money, is it? It was bizarre. Hard work, luck and skill, right?
[00:14:36.330] – Jonathan Denwood
So with crypto-What were you telling me? I should forget about building companies and this punter on Bitcoin.
[00:14:40.950] – Rob Walling
I couldn’t have bought the Bitcoin if I hadn’t sold the company. That’s why. So the thing is with crypto is they’re really still to this day, it’s like there is not a great use case that everybody needs it. My mom and dad are 80 years old. They don’t need to know about crypto at all. Most people just don’t. And that’s the bottom Fine. Ai. My brother runs an electrical construction firm, and he doesn’t own any crypto, doesn’t need to. There’s just no need. There’s no pull. I showed him ChatGPT when it came out 18 months ago or whatever, and he uses it daily now. He’s just an everyday dude who runs a construction firm, and he’s like, This is incredible. So the use case is there. So Jonathan, I think crypto is very different than the early days of crypto, very different than the early days of the Internet. You know what I mean? I see those, too, as crypto was so much hype. The internet was a bunch of hype, if you remember.
[00:15:35.890] – Jonathan Denwood
Yeah, but there was something to it, wasn’t it?
[00:15:37.360] – Rob Walling
There was something to it. But remember, when it crashed, it got overhyped, and we had pets. Com selling bags of dog food, and we had stupid crazy stuff happening, and cosmo. Com with a K, K-O-Z-M-O, which was the delivery service that went out of business. But then we had DoorDash and Uber Eats and Instacart, and I use all those things. So they were too early. And when the crash happened in In 2000, in 2001, people said the internet’s done. By people, it was journalists trying to get views and clicks. It’s done. It’s done. It’s hype. It’s hype. And then guess what happened? It wasn’t hype. The internet has absolutely changed our everyday life. I think AI, and let’s say chat interfaces and generative AI and AI that categorizes all the stuff we’re using it for. I think there’s absolutely a hype cycle. There’s way too much money being pumped in by venture capitalists, and a bunch of that is going to crash, but there still is a massive, massive use case. You see it through… The number is OpenAI’s revenue based on people paying the subscriptions. How many people are actually paying and sticking around?
[00:16:43.910] – Rob Walling
It’s a lot. I And they should be charging more than $20 a month, by the way. I would pay so much more. There’s a lot there, but it’s going to stick around. I keep saying, ignore it your peril. Especially if you’re an entrepreneur, you need to know, Hey, do to integrate AI into my product itself? Maybe, maybe not, but at least evaluate. Do you need to integrate it into your day-to-day operations and workflows and software development? Yeah. I don’t see that there’s any… There’s just no argument there.
[00:17:14.220] – Jonathan Denwood
Right. Back over to you, Kirk, for the next formal question.
[00:17:18.820] – Kurt von Ahnen
Well, we said way perfect with your comment, Rob. You said you thought $20 was way too small to charge for AI, $20 a month. If we talk about your ideas on pricing strategies and how disastrous they are, again, we’re referring to another episode from your podcast. But talk to me a little bit about freemium, the freemium pricing model, and then where you think the value of products really falls.
[00:17:47.900] – Rob Walling
Yeah. So here’s the counterintuitive thing or the, I don’t know, maybe the thing most people don’t know about me. Fremium is amazing. I love freemium. The problem is it doesn’t work the time. And what I don’t love is the myth around it that I see, usually it’s on Reddit or on ex Twitter, of just everybody launching with freemium because that’s what OpenAI does, right? Or that’s what Facebook did, or that’s what Reddit, or who else? Dropbox is a famous freemium. If you have $100 million in the bank of venture capital funding, then go try freemium. And if you don’t, then don’t Don’t do it, usually. That’s my default. There are bootstrappers who make freemium work. It is just specifically with SaaS. I’m not talking about WordPress yet. I know we may want to get there because it is the default, really, in WordPress. And so if you don’t do it, I think that’d be a challenge. But freemium is a distribution strategy. It’s a marketing strategy. It’s not a pricing strategy. And I believe Patrick Campbell from Profitwell came up with that idea, but it totally is. It’s not about price. It’s about how do I get this thing into people’s hands such that I can then own the lead until And then they decide to convert.
[00:19:01.760] – Rob Walling
And there’s four things that need to be in place in order for freemium to work. You can listen to the podcast. I won’t go through them all here. But one of the big ones is that people don’t think about or don’t… It’s virality. If you don’t have some type of viral loop, Meaning that everyone who signs up, winds up telling someone else about it. And usually, a good example is SavvyCal. This is Derek Reimer, my drip co founder. He built a competitor Calendly. So SavvyCal has a viral loop. Because when I sign up for SaviCal and I send the two of you my link to book me, you’re like, Oh, hey, what’s this thing? Click through. Hey, powered by SaviCal. That’s an interesting viral loop. It’s not the strongest viral loop, but it is a viral loop. If you don’t have that, I really don’t think I’ve ever seen premium work without that. And so people just do it. It’s cargo culting. Well, if the big company did it, it worked, I should do it, too. Rather than saying, why did it work? And in what instance as well, you need 100 million in the bank or five million in the bank.
[00:20:00.140] – Rob Walling
You need some money in the bank to do freemium, usually. And then what are the other criteria?
[00:20:05.690] – Kurt von Ahnen
I think about freemium models that I experience in the WordPress space, and one very directly, because I work directly with the Lifter LMS folks. That’s a freemium model. But Lifter’s freemium product is potent. It works. You can use it. It’s a full thing on its own. And then the add-ons give you features for expansion and growth and all those things. A lot of the freemium things that I see in the press space. I think to your point is to try and hit that. It’s obvious that it’s for distribution. It’s obvious they just want space in your plugins list. And the freemium model really doesn’t do a full example of anything you need. You got to buy something to make it function or work or do what’s purported to be the feature of the product.
[00:20:51.420] – Rob Walling
Right. And look, open source is a a different conversation. There’s approximately zero open Open source SaaS companies. There are a few, but there’s not many. And so open source itself, which doesn’t imply it has to be free, but really it does. I mean, open source stuff is free. That almost forces a type of freemium. If you came into WordPress and tried to not… If I had a plugin or a theme, didn’t do some type of freemium, it would just be really counterintuitive. But as a result, it shrinks the market. What if WordPress core and all the plugins, what if there was no freemium? It was all seven-day trial. It’s just hypothetically. Obviously, you can’t go back and change it. But at the scale it’s at now, if it wasn’t free, if everything was charged for, it would be the market would be so much. I mean, it’d be billions and tens of billions of dollars larger than it is right now. There would just be more money in it. It would be easier to build a business, especially as a small operator. There’s a reason that SaaS and… Well, there’s There’s a reason that a lot of the small WordPress, I know a bunch of bootstrappers that do WordPress, they struggle to charge more than $100 a year, $200 a year.
[00:22:08.430] – Rob Walling
It’s inexpensive, $10, $20 a month, maybe, if they can charge monthly. I believe it’s harder to build a business. And in fact, when we started microcomp, and we started getting attendees, we’re like, Oh, you have WordPress plugins, you have SaaS, you have mobile apps. There was all this stuff because it was 2011. I didn’t know which of those was the best business, and I didn’t know which of them would become the big thing. And SaaS did. And it’s because you can charge a lot. It’s because the market hasn’t been shrunk to the point where it’s like, Oh, I can only get maybe 10% of the value that otherwise I could. And WordPress is like that because it’s open source. Now, that’s a good thing as well. It’s good that it’s open source. It wouldn’t be as big as it is without being open source. But it’s a headwind if you’re a bootstrapped entrepreneur trying to build a business in it, if I’m being honest. I’ve owned stuff in the WordPress space, so I’m not against it. I think WordPress is amazing, and I still use it for the podcast website. And I was an early investor in WP engine.
[00:23:05.630] – Rob Walling
I have history with it, but it’s tough. Yeah, go ahead.
[00:23:09.780] – Kurt von Ahnen
No, I was just going to say there’s a great use case right now that we see in real time, where There’s a Wu commerce developer that is now branching out into Shopify development, and she’s being very transparent about the work. And she’s like, Yeah, the margins are great. There is more funding, there’s more money. People are more apt to to purchase rather than just trying to manipulate a piece of code for free. It’s a very interesting mindset, I think, to look at. Jonathan?
[00:23:42.730] – Jonathan Denwood
Yeah, I’ve got some views. I don’t really I don’t really totally agree, Rob, but I’m going to leave my views to the second half of the show. We’ve had a great discussion so far, but we’re going to go for our middle break, and we will be back in a few moments. Three, two, one. We’re coming back, folks. We’ve had a great discussion with the friend of the show, Rob Ryelling. It’s always a blessing to have him on the show. We always have interesting discussions. Before we go into the second half of the show, I just want to point out if you’re a freelance or a power user and you’re looking for a great hosting provider that provides all the best plugins, the best WordPress technology, so you don’t to have arguments with your clients about buying all the right plugins for the project, plus really powerful secure hosting. Why don’t you look at building something with WP Tonic We’ve got some great deals for you, the freelancer power user. You can find more by going over to WP-Tonic. Com/partners, WP-Tonic. Com/partners. Partners, and we love to build something special together. Well, I see where you’re coming from, Rob, but I think one of the problems with the pricing was linked to the foundations of WordPress as a free blogging platform that basically got traction because it replaced a paid blogging platform that was getting into trouble.
[00:25:33.760] – Jonathan Denwood
I forgot the name of it. It was so long ago. Do you remember it? What was the name of it? I can’t. Blogspot?
[00:25:42.140] – Rob Walling
Pardon? Was it blogger or blog spot?
[00:25:45.060] – Jonathan Denwood
No, it was called something else, actually, a typo or something. I remember this.
[00:25:49.960] – Rob Walling
Typefully. Typefully?
[00:25:51.950] – Jonathan Denwood
Something like that, wasn’t it? It was so long ago, Rob. I’m ancient. And I think it’s traditions. But I think I do know some plugin providers that are providing more specialized services, especially to the business to business. One comes to mind is WP Fusion, and there’s a couple of others that are charging reasonable amounts of money. And there are some other plugins. I think it really depends on your target audience. Also, I think you’re slightly discounting. You might have to charge a little bit less depending on the broadness of your market selection. But being part of the WordPress community ecosystem, you’re saving a lot of time and energy when you are placing your product, then having to go out there and actually market Which I had last time I interviewed Jason with WP Engine. He told me it took him three years to get 300 clients. And this is a person technically and got the marketing chops. And it’s still, and I don’t think you… I think I took it. He’s a very honest individual. So it took him three years with WP Engine to get that first 300 clients. But I think a lot of the problems with WordPress is its historic placement.
[00:27:41.410] – Jonathan Denwood
I think in the business, the business world, there’s a lot of clients that got legacy software that’s now coming up for redundancy. When they look at the costs and locking of buying Bastoke custom software solutions, and then they look at a hybrid solution of maybe looking at WordPress, it’s more attractive when they look at the pricing of a full customized locked in Bastoke solution. Am I making any sense, Rob?
[00:28:17.230] – Rob Walling
Yeah, you’re saying that for custom line of business in-house software, whether it’s managing content management system for their website or other stuff, that by building on WordPress is better or can be less expensive and or just they have more control because it’s open source.
[00:28:33.840] – Jonathan Denwood
Yeah, but you’re trying to build something totally. You can use the core, the interface elements, but then you can add, you can customize it, but you’re not fully locked in to a fully-persuade solution. And deal with that ego of those developers, Rob.
[00:28:48.800] – Rob Walling
Yeah, think about that. I think of it more, see, I’m a product person. I stopped doing consulting and freelancing back in ’08. That was the last time I did it. And what you’re What we’re talking about is going in and doing a consulting engagement, right? And building something out for someone. And in that respect, I think you’re correct. But if I were to be deciding, should I build a plugin or theme business, or do I want to build a SaaS, I would obviously go towards SaaS because I believe it’s a better business model.
[00:29:18.760] – Jonathan Denwood
Yeah. Over to you, Kurt.
[00:29:22.360] – Kurt von Ahnen
Well, it looks like I get to jump back into another episode of your podcast, and the one that was titled sixth Lessons from my most successful investments in B2B SaaS. You outlined a lot of important principles for building a successful SaaS business. I was hoping that you could share with us just some of the insights with the listeners of the show.
[00:29:45.920] – Rob Walling
Yeah, for sure. I have a couple of bonus ones, actually.
[00:29:50.190] – Jonathan Denwood
We like bonuses.
[00:29:51.560] – Rob Walling
I mentioned them in another place, but I did not mention them in that particular.
[00:29:55.790] – Jonathan Denwood
You get 10 stars for the bonus.
[00:29:58.030] – Rob Walling
Very nice.
[00:29:59.580] – Kurt von Ahnen
We’re going to have to pimp the book for sure.
[00:30:01.410] – Rob Walling
Very cool. So there’s an interesting pattern we’ve seen. So across Tiny Seed, we’re a startup accelerator for SaaS companies, Ambitious SaaS Founders, and we’ve invested in 192 SaaS companies. And one of the patterns, that’s where I pulled all these learnings. I think I put six in that video, and then I had eight more, nine more that I put in the podcast. But one of the ones that struck me is really interesting is that horizontal SaaS SASS, meaning SaviCal is a good example of that. Anybody can use it, any industry, any business, versus we have invested in a lot of vertical SaaS. So vertical SaaS example would be Jimdesk. That’s a company of ours that sold recently, a portfolio company. And It’s like an operating system for your gym, martial arts, dojo, fitness studio. It does all the stuff, soup to nuts. And what we’ve seen is that in general, the horizontal plays face headwinds, especially Essentially, in the early days, if they get traction, great. They get to half a million, they get to a million, and then they start to really see headwinds and they plateau more often, and they have higher churn in general than our vertical plays.
[00:31:12.900] – Rob Walling
Just the numbers- Can you quickly explain Can you explain the two concepts to the audience? Yeah. Horizontal just means it’s across any industry. And then vertical means you build software for exactly a single industry. Now, there’s a third time. This is the other thing that I’ve coined this term last year because I started realizing we have invested in a company called Code Submit. And what it is, is it’s for HR managers to help evaluate developers. So it’s like coding challenges and quizzes and this and that. That’s horizontal, technically, because any company can use it in their HR. But it’s different than Savvy Cal. It’s different horizontal. And I was like, What’s different about it? Well, what’s different is that it targets a particular role or title at a company. So I started, I was I was asking ChatGPT, what should I call this? It’s role-based and title-based. And these are all awful monikers. So eventually, since vertical and horizontal, I came up with orthogonal. And the reason is because it is horizontal, but orthogonal, meaning it only hits one piece of it. Basically, it’s role-based or title-based SaaS that operates and behaves more like vertical SaaS in terms of the net negative churn is easier to get there.
[00:32:29.330] – Rob Walling
You know who to market to, you know who to cold outreach to. It is a lot easier than when you plateau at a million or a million and a half and you’re horizontal. What do you do? It’s really hard to get around that versus if you’re orthogonal or vertical. I won’t say it’s… I think it is easier, actually. It’s easier to know what the next steps are to try to get out of a plateau.
[00:32:52.640] – Kurt von Ahnen
Well, it’s akin to… If you listen to the Membership Machine show with Jonathan, a topic that’s common is know your niche or know your avatar, know your audience. Instead of trying to make a membership or learning project that is, to your point, horizontal and good for everybody, it’s like, if it’s good for everybody, it’s good for nobody. That’s So if the more that you can niche into something, the more you can target your audience and find success. But it’s interesting that software is like that. So if I had a CRM tool for service managers in the automotive field, that would be like, bam, bam, bam, like very direct. And you think that would probably be stronger than, say, a CRM tool for any manager.
[00:33:40.480] – Rob Walling
Yeah, I do, especially to start with. And here’s the thing, there’s a Venture dollars go into very big markets. And so as a result, they get really crowded, and venture-back companies can lose money for a very long time, and they can outspend you. It doesn’t mean they’ll win, but there’s headwinds there. If you start with a vertical, and you get a lot of traction, we have seen a number of companies then add another vertical, add another vertical, add another vertical. You can do that if eventually you plateau because you’ve tapped out the entire vertical. It’s extremely rare to do that, but there are some that are so small.
[00:34:13.970] – Kurt von Ahnen
You hit an interesting It’s a good point. That’s always been a thought for me. When you say add another vertical, so like I said, service managers in the automotive business. So they might say service managers in the marine business, service managers in the motorcycle business. You could just keep adding those on. How many people do you feel in the software space that you’re in, in SaaS, take their success almost for granted? They think they’ve topped out a vertical, but in reality, they still have half that vertical to go. Do they abandon too early and get out too early and miss the opportunity? Or do they get impatient?
[00:34:51.270] – Rob Walling
Yeah, they get impatient or they say, well, nothing I’m doing is working to generate more customers. So therefore, I must have tapped the entire market out. And the answer is almost never. If you’ve tapped the market out, you tend to know. We’ve invested in a company called Senior Place, and they are SaaS for senior placement agents, which are like realtors for senior living facilities.
[00:35:16.340] – Jonathan Denwood
I thought you had said Senior Police.
[00:35:19.720] – Rob Walling
Senior? Yeah, no. Senior Place. Senior Place. Anyways- I thought it was Retirement Police, but- That would be a good SaaS. Apply at tinyc. Com/apply if you start that business. But But anyway, Senior Place, they have a very small market, and they know it. I forget what the number is. I think it’s 3,000 senior placement agents in the country, and they know that’s the market. So they’ve been from day one, they’re like, they have to charge quite a bit of money to make it worthwhile, and they know they’re going to top out it, whatever. They haven’t hit it yet, but they know that. And so they’ve already started being like, All right, so do we offer more stuff, more products, more add-ons, more whatever to this existing audience that we already have, the existing customer base? Or do we add a second vertical. That’s usually the decision.
[00:36:03.590] – Kurt von Ahnen
So just one more follow up, and then I’ll pass it over to Jonathan. In those examples that you’re giving, do you find it is more financially advantageous to add services to the existing vertical market, or do you find it more advantageous to graft on another vertical market to the same product?
[00:36:22.400] – Rob Walling
I mean, it probably depends. Let me think. I think it depends, but I would tend to lean all things being equal It would be nice to not have to build a bunch of new stuff. You don’t want to build a bunch of new stuff if possible. And so if you have this product for one vertical, and it’s not a ton of work to go to the second, then great. Code-based stays generally the same. You change some whatever’s, add a little feature in there. Now, you do then have to start the marketing engine. And so if you’ve only been doing realtors, now you want to do mortgage brokers, you probably have a little bit of reach in there, but you do have to extend it. So I think my it depends is, with the caveat of, it depends on if you think that marketing into that new vertical is going to be harder than building a second product or a bunch of add-ons for your existing one, and if that’s feasible. And if you have ideas for that, you may not. So that’s the strategy call. If I were with a founder, we’d spend 45 minutes just spitballing this.
[00:37:24.600] – Rob Walling
How long do you think it’ll take? What ideas do we have? You have to have a hypothesis for each of these, and that would a decision. It’s a complicated decision in the end.
[00:37:33.300] – Jonathan Denwood
Yeah.
[00:37:34.450] – Kurt von Ahnen
Jonathan?
[00:37:35.970] – Jonathan Denwood
Yeah, I just want to touch something. I think a lot of people don’t really understand. Well, I wonder why you stuck with tiny seed, really, because it’s not the traditional investment model, is it? I presume you do it because you’re not totally interested in money. I think the money gives you freedom and gives you and your family choices. But I don’t think… Because the reason why I assume this, because people don’t really understand the traditional venture capitalist model, which is one in 10 of their investments will get big, and the actual business model is to find really extreme, wacko founders that are half crazy but got a big idea and you punt with them. And long as you think they’ve got some chance, of those 10, one might get big and you might get a trade sell, some of the others, so they break even. But you’re looking for that real big idea and that real semi-crazed, wacko founder. Bootstrap, and Bootstrap investing is about miminising risk, which is the normal model of business. If you got any sense, you go into businesses and you attempt to reduce your risk because business tends to have a very high failure rate.
[00:39:18.830] – Jonathan Denwood
And so really, it’s about finding a business model that reduces your risk. But venture capital is a totally different business model, isn’t it? Which I still think a lot of people don’t I understand that, do they? But why have you stuck in the bootstrap? Because you could have gone, you’re quite capable of going the traditional route. I just wondered why you chose to stay in the tiny seed I believe.
[00:39:45.590] – Rob Walling
Yeah, it’s because there’s a gap in the market and we’re the only one filling it. And there’s potential here in the long term to make money on these investments. In the near term, I mean, what people don’t understand about venture capital. I wouldn’t be doing tiny seed if I hadn’t already had the big exit with DREP because I take a salary, and that’s it. Any of the big returns that you think about are all down the line, because you have to return all your investor money. We’ve raised $42 million that we’ve invested into companies. We take out a management fee, of course, but then we invested in these companies. We have to return $42 million before we get a dime, me being the owners of Tiny Seed. So that’s years down the line. It’s at least 10 years from our It’s our first investment until any type of real significant money comes back, to your point. The reason I’ve stuck with it, though, is because I really do believe. I believe in what we’re doing, and I think it has the potential not only to, like continue to catalyze this ecosystem, because my mission in life is to multiply the world’s population of independent self-sustaining startups.
[00:40:53.990] – Rob Walling
That’s what I want to do. That’s the rest of my life. That’s all my books. That’s MicroKopf. That’s Tiny Seed. That’s the podcast. That’s YouTube. And Tiny Seed is a big part of being able to do that. Now, I have to justify everything I do just in my head. Usually, money is involved. I have hobbies that don’t involve money. But if I wanted to be doing something professionally day to day and spending a lot of time and grinding, I do need there to be the potential to make the money. And to your point, Jonathan, why are we raising our third, technically, fourth fund right now to invest in more tiny seed companies? Because early results are really promising. I forget which fund it is, A&R knows all this, but I think fund one is in the top 5 %. Maybe 4% of funds of its vintage in terms of performance. That’s across all venture capital. There’s your Carta or Angel List numbers, I forget who, but really good early performance. And SaaS, specifically, sells at really high multiples. We don’t need outlier billion dollar outcomes. We can have folks who sell for 20 million, 30 million, 40 million, and our model works such that eventually, as more companies sell, we’ll provide great returns.
[00:41:57.000] – Rob Walling
When I say we’re early, 192 investments, I I believe 4% of those, maybe 5, somewhere between 4 and 5, have either gone to zero or sold where we got 1X back, like we got our money back. And then another maybe 2 or 3% have sold for seven, eight figures, like good outcomes where we make a return. That’s it. So across our whole portfolio, and we brought our first checks in 2019, six years ago, it’s only like 6%, 7% of companies are no longer in operation. It’s really small, right? So SAST is a long game. And so I knew from the start we’d have to be in it for a while in order to really prove it out.
[00:42:37.820] – Jonathan Denwood
All right, thanks. Over to you, Kurt.
[00:42:40.570] – Kurt von Ahnen
Well, that bumps us to our AI question, which is an extension of that second question, right? But you had mentioned ChatGPT and Cursor and a couple of others. But in the day to day, in the Rob Walling world, what AI tools are you personally using to help you in business?
[00:42:58.180] – Rob Walling
Yeah. So I’ll tell you, my team It’s called Roses Pod Squeeze, which we upload a podcast episode, and it writes first draft, of course. We human edit them, but it summarizes, writes show notes, puts all the time stamps in, et cetera. It’s quite good. It says it’s a significant amount of time. Of course, we all use ChatGPT, but a lot of folks on my team use Poe, P-O-E. Com, which allows you to switch between ChatGPT. It’s still $20 a month. This is like giving away a dollar to get 50 cents back. Ai is what I think. I don’t know, but Poe allows you to just switch to Claude in your interface and switch to OpenAI or ChatGPT and switch to all these different models. Now, I don’t actually use Poe because I found… I like ChatGPT. It’s fine. It works for what I need. I don’t use it so intensely. I use ChatGPT for a lot, though, not just searches, but for helping me brainstorm, refine ideas. I use it as a… I don’t know. I use it to get me halfway to a YouTube outline. I say, pretend you’re Rob Walling. Outline this video with this title.
[00:44:02.120] – Rob Walling
Try to make it non-generic. Try to make it Rob’s specific stuff, and it’ll spit it out. And it usually gets me 50, 70% of the way. At least their ideas. And oftentimes, there’s a couple of ideas on there. I’m like, I wouldn’t have thought of that. That’s cool. I’ll use that in the video.
[00:44:13.490] – Kurt von Ahnen
Yeah. Well, and the advantage of that is that you’ve got published books that it can refer to, too, right? The Voice of Rob Wall and all that.
[00:44:19.710] – Rob Walling
Books, podcasts, YouTube, all of that. It pulls.
[00:44:22.190] – Kurt von Ahnen
Yeah. So you’ve got that persona that you can nail into. It’s interesting that you mentioned the Po. I use a very similar strategy with a tool Magi, which is a paid AI service, but it’s got six or seven different tools that you can just live switch to. So it’s got Claude and ChatGPT and LLaMA and all that. And you can just, Okay, I want to do this, this, this. I find As weird as it is, I don’t consider myself an expert in AI, but boy, it sure is nice to be able to be in one screen and be able to pop into the different tools and do different things.
[00:44:54.700] – Rob Walling
Yeah, big time.
[00:44:56.370] – Kurt von Ahnen
That’s sweet.
[00:44:57.550] – Jonathan Denwood
Well, I’ve got a suite of tools because it’s helped me buy dyslexia, Rob. If only I had this 15 years ago. I’m actually not here, Rob. It’s actually artificial intelligence.
[00:45:10.050] – Rob Walling
I can see that. You’re being so nice today. I was like, what’s up with Jonathan? And it’s because of your AI.
[00:45:15.700] – Jonathan Denwood
I’ll take our next question. Will you be able to stay on or do you have to be off at the hour? Or do you can spend another 10 minutes with us?
[00:45:27.040] – Rob Walling
I’m looking. I can spend another 10 minutes. Yeah.
[00:45:29.820] – Jonathan Denwood
So we have some bonus content. Kurt’s got to be off before the hour because he’s got another commitment. But if you had your own time machine, you could go back to the start of your career and tell yourself one thing a little bit of voice to yourself, apart from not coming back on this podcast, Rob, you can’t tell yourself that. But anything else, anything comes to mind, some little hint or nudge that you could have told yourself, Rob.
[00:45:59.400] – Rob Walling
Younger Rob, be less scared. Be less anxious. Be less worried about all this. Ship faster, make more mistakes. Don’t be afraid to fail, move quickly. Because I was in my head for years and years and years, and it cost me years and years and years, not only of stress, but I just moved slow because I was hesitant about a bunch of things. It’s a pattern we see across our founders, the ones who really move quickly and are less afraid of failing. It doesn’t mean they’re not impacted by failure, but they just ship a lot of stuff pretty quickly and they take risks. That’s what I wish I was doing from the start.
[00:46:33.280] – Jonathan Denwood
I totally agree with you, but on one per viso, I just wanted to see if you’ve noticed this. I’m old now, but I just don’t accept it. I’m still young at heart. I’m actually fitter. I had a real serious health scare about three years ago, and I’ve lost over 120 pounds, Rob. Good for you. I exercise vigorously every day, and I’ve mostly given up on meat. That was shot, Kirk, you can’t cope with that. But I’ve noticed with Gen Z and millennialss, and I don’t know what the next one is, they seem to apply what you said to personal relationships as well. And I find that a little bit disturbing because obviously, if you’ve got friends that do something really appalling and they turn out not to be people that you think they should be. You obviously got to drop them. But normally, I have about half a dozen friends, and they can totally rely on me. I have a lot of acquaintances, but I have about half a dozen really close friends. But I find with a lot of people, they apply what you said about your business. You would have stopped worrying so much to move to next.
[00:48:01.080] – Jonathan Denwood
They seem to apply that to their personal relationships and people in general. How would you respond? Do you think I’m onto something or am I just that old gees of romanticizing about the past?
[00:48:14.150] – Rob Walling
I don’t think I can comment on whether it’s a generational or whatever. What I will say is, to be clear about what I said, I meant it certainly for business, as you’ve said, but also there’s just a list of things that I think are implicit in any comment like that, which is be moral, be ethical, don’t hurt your fellow humans, be good to other people. You know what I mean? When I say, Hey, ship fast, do you think- Do you think you can be an effective business individual with those in Sybil’s role? I am. Yes, you can, and I know several. We’re invested in a bunch of Tiny Cee founders, and the vast majority of them are good people. Jason Cohen is a great guy. Heet and Chou is a great guy. I know decamillionaires, I know centimillionaires that are good people, and I know some that aren’t. There’s a mix. I think people who are dismissive of other people’s feelings or who don’t include the thought of, Hey, I might be hurting this person or these people in their calculus, I don’t hang around with those people.
[00:49:23.360] – Jonathan Denwood
No, I agree with you. I think this propaganda that you got to be a certain type of individual I think it can be very effective, but I also think it suits the personality of that individual to have that attitude around business. It’s a mixture of it suits their personal It’s a biology, doesn’t it?
[00:49:46.590] – Rob Walling
Yeah, I think so. Do I think it’s easier to make money or to be successful if you screw everybody over in the short term? Probably in the long term, I think it comes back to bite you. But do I think that’s worth it? No, I have a code of morals and ethics that I’m going to live by. I’m not going to do that to people. I believe in humanity. I think generally most people feel that way, though not all. Yeah.
[00:50:10.010] – Jonathan Denwood
All right, we’re going to wrap it up. Kurt’s got to go off to his other engagement. So What’s the best way for people to find out more about you and what you’re up to, Kurt?
[00:50:19.380] – Kurt von Ahnen
For business, anything that’s Manana Nomas. We’re Manana Nomas on X, on Facebook, and of course, manyanonomas. Com. If you want to make a personal connection, just connect through LinkedIn. I’m on there almost every day.
[00:50:31.820] – Jonathan Denwood
And Rob, what’s the best way to find out about what you’re up to and your latest thoughts on SaaS and business in general?
[00:50:41.230] – Kurt von Ahnen
And his latest book.
[00:50:42.810] – Rob Walling
Yeah. Latest book, Exit Strategy.
[00:50:44.480] – Jonathan Denwood
Which we’re going to be I’ll be fussing in the bonus content in a bit more detail.
[00:50:47.660] – Rob Walling
Now available on Amazon Exit Strategy. Keep up with me. I put out free content every week. So youtube. Com/microconf. You’ll see a video about every 14 days. And then Startups with the Rest of Us, or type that into Spotify, Apple Podcast, wherever greater podcasts are served. I’m on episode 760 something, and that comes out every week like clockwork since 2010.
[00:51:11.430] – Jonathan Denwood
We’re going to wrap up the podcast of the show. I’ve got a question. I’ve had some thinking. I know this is going to be a big surprise to you, tribe. I’ve been thinking about SaaS and AI, and I’ve got some ideas which I’m going to put to Rob, and he’s going to tell me that I’m a lunatic, but he knows that anyway. He’s worked out and his wife told him I was a lunatic anyway. But I’m a decent lunatic, I know. I can’t be totally wacko because I know I’m a wacko, don’t I, Rob? There we go. He shokes, he doesn’t care. But You’ll be able to watch the podcast and the bonus content on the WP tonic YouTube channel. And think about subscribing. I’m always putting new content around on the channel every week. And we will be back next week with a great guest interview. We’ll see you soon, folks. Bye. Bye. So bonus content. So I was thinking about AI and SaaS, and I’ll put this concept to you. You have AI product, and you’ve gone through in a number of your discussions on your podcast that SaaS products that just keep building out more and more new features to them can lose their way because they haven’t really worked out who their target audience is, the language that that target audience uses and the real problems.
[00:52:49.760] – Jonathan Denwood
You’ve covered this numerous times between a painkiller and a vitamin. You can succeed with both, but it’s best to go with the painkiller, especially if it’s your first SaaS product. But I think there might be the possibility of you have your SaaS product and using AI, you can customize the product to a more stoke solution for each client to a way that would be non-profitable and not very attractive. So you have the core of the SaaS product, but using AI and agents, you have the ability, which you might be able to charge more to actually customize it. So you have the core SaaS product, but it becomes a hybrid. So it’s SaaS with consultancy.
[00:53:48.730] – Rob Walling
All right. Yes and no. That’s how I think. So I think if you’re Are you impressed with that? I think- I like the idea, actually. Yeah, no, I really like this. I think if you You have a core SaaS and you are using AI to generate additional code for each client, then I don’t like that idea because it’s just not repeatable. And the maintenance is more of a headache than writing. I mean, it’s just such a… You’re creating yourself technical debt down the line.
[00:54:15.320] – Jonathan Denwood
You wouldn’t touch it with a barge pole, would you?
[00:54:17.310] – Rob Walling
Exactly. But if what you’re talking about doesn’t involve actually new code, that it is a model, an agent or something, an LLM that is changing, I think that’s really interesting. I actually talked to a SaaS founder the other a tiny founder who is thinking about building agents into their SaaS, building their own agents into their SaaS to help to do this. And that, I don’t know if it’ll work. I don’t know if the market will care about it. I mean, it’ll work technically, but I don’t know if the market will value it, but it’s really intriguing, as you said, to get this next layer. So it potentially offers a lot more value to your end customer.
[00:54:56.580] – Jonathan Denwood
Right. On to the next question I’ve been thinking about, Shackora. So you’re in a way with, not formally, but you’re definitely… I place you there, and I think you’ve done this consciously through the conference, through your podcast. You’re in the education area in the informal way. So you influence people and you attempt to educate them, and through your books, through your podcast, you attempt to build influence, but you do it through education. One of the things that has disappointed me is that I thought the internet and having something like Wikipedia have out there and having other… Having information at your fingertips, I thought it was going to equalize the educational outcomes, because When you look at… I don’t actually believe in IQ, really. I understand why it’s utilized. But when you look at the science, or I would classify it as semi-sudo-science, But other people disagree with me. But when you look at the IQ levels of most people, they are very stupid IQ people, and there’s a small minority that have a very IQ. But when you look at the outcomes of people that got very high IQs, a lot of them aren’t very successful because it needs other factors, grit, determination, focus, personal relationships, which a lot of these highly IQ individuals don’t have.
[00:56:53.260] – Jonathan Denwood
But the bulk of us are in a very similar IQ range. But I the internet and e-learning and having access to information would even outcome an opportunity, but it hasn’t really panned out. You could argue the reverse has happened. Have you got any thoughts of why that has happened, or do you think there’s any insight in what I’ve just laid out to you, Rob? Only small questions, aren’t they, Rob?
[00:57:26.850] – Rob Walling
Yeah, I can answer this in one sentence. No, let’s start with… If we have time, I’ll address the IQ thing, but let’s start with the question you asked, which is, access to information. Why hasn’t that normalized or equalized things more? My thought comes back to, I say, success as an As an entrepreneur, is one part hard work, it’s part luck, and it’s part skill. And what can I control of this? I can’t control luck, but I can control my own skills, my expertise. I can learn over time. I can control my hard I can put in a lot of time. I can focus. And then maybe luck will come, and maybe it won’t. And that’s usually a multiplier on your success. I’ve seen people have zero luck, not even get unlucky, but just have zero luck and still build good businesses. And maybe if they got lucky, it would have been a great business. But I think it’s a similar thing with information. It’s like, just because there’s information available, it doesn’t mean that everyone’s even going to consume it or internalize it or put in the hard work to build their skills up, a skill of just understanding the knowledge and learning.
[00:58:35.610] – Rob Walling
Because think about it, I was a construction worker in the late ’90s, early 2000s. I didn’t like it very much. And I had taught myself to code as a kid, but I hadn’t done it in many years. And I was at the library nights and weekends. The Internet existed, but it was not the easiest to learn how to code Pearl and PHP and ASP in 1998 or ’99. There were some tutorials, but to really learn it, I was at the library. And we’re Are all of my other construction worker buddies at the library doing it? No, they won’t. Did they have access to free information to learn to code? They did. Am I saying I didn’t have a leg up because maybe when I was younger, my dad… Of course, I had a leg up because my parents got me a computer when I was eight years old, so I’m not dismissing that. Maybe that’s part luck. I was a little lucky that that happened. But access to information does not… It lifts up those who have the desire and the Even the knowledge that new information can help them raise their stature in life or make them more intelligent.
[00:59:37.380] – Rob Walling
And there’s a bunch of people… My mom, self-admittedly, says, I haven’t read a book since high school. My mom’s 80 years old. She has not read a complete book since high school, and that’s just what she does. And I read through Audible. I have 907 books in my Audible account.
[00:59:52.310] – Jonathan Denwood
Well, I do the same because my reading speed is well below my intellectual I’ve had a report, psychological report, when I was a younger individual, and I’ve got quite a high IQ, which I don’t talk about because I don’t really believe in it anyway. So you’re saying it’s family background and motivation?
[01:00:19.800] – Rob Walling
Well, family background, it’s just like, A, if you go to a person and they don’t realize that learning more is a good thing or that learning this knowledge will help them, then they’re not going to do it. So there’s a knowledge gap of just even knowing that more knowledge is helpful. And then there is a motivation thing. I know folks who are unmotivated and who would prefer to sit around and watch TV or to smoke weed or whatever, rather than… These are folks that I used to hang around with the construction sites, and they were For whatever reason, I don’t know, I’m not judging them, but- I’m sorry to interrupt, but obviously, we only got 10 minutes of your time. Sure.
[01:00:54.630] – Jonathan Denwood
What was driving you to spend your time in the library as a construct? What was the driving How did that work?
[01:01:00.720] – Rob Walling
I wanted to raise my station in life. I didn’t want to work in construction my whole life. My dad worked in construction for 42 years. My brother now owns a contractor, but he was an electrician himself as well. I didn’t want to do it. I hated it. I didn’t want to work for other people. I wanted to do something that was more interesting, that maybe could make me more money because we came from a solid working-class background. That was it. I didn’t know if it would work, but I was willing to try it and put in the work. And if it failed, at least, I’m afraid.
[01:01:32.340] – Jonathan Denwood
But a lot of people wouldn’t be right. So it was that vision. It was that desire to do a bit better. Yeah.
[01:01:44.330] – Rob Walling
That was it.
[01:01:45.880] – Jonathan Denwood
So, last question before you go. You’ve invested, and you must be one of the individuals in North America who’s had a volume of discussions with entrepreneurs and possible entrepreneurs on the podcast. I don’t know how many conversations you’ve had over the last 10 years, but there must be thousands from a very diverse group of individuals, to say the least. Is there anything that you observe that has any linkage with all the types of individuals that you’ve discussed And that points to you that they might be successful in what they’re trying to achieve, Rob?
[01:02:40.020] – Rob Walling
Yeah, there are some commonalities. And it’s something I mentioned earlier, I think when we were still livestreaming, but it’s the thing we are still livestreaming. Yeah, it was in the prior, during the show. It’s that folks who succeed tend to move quickly. They tend to try a lot of things, and they’re right enough of the time. They’re right most of the time. They have a generally a good gut feel of if they get into something, anything, if I’m going to write a new book, if I’m going to try to go on LinkedIn, me personally if I’m going to try to launch a YouTube channel, I’m generally right about it. Why is that? Well, because I’ve put in hard work to learn the skills. These days, I often have money to hire a consultant to help us succeed. But even if I didn’t, I would still probably figure it out. And so the founders we see succeeding, not all of them, but most of them do things. You can get totally lucky, and none of this matters. But let’s put luck aside. Most of the founders work hard, they ship a lot of things quickly, and they’re right enough of the time.
[01:03:39.580] – Rob Walling
And they’re not always right the first time. Right when they launch something, oh, everything’s perfect. They then follow up for two to three months to get it to work. If they’re launching a new marketing strategy, they give it the time to properly breathe. That’s probably the number one. There are several others that just have the ability to learn things quickly. I mean, that’s as an entrepreneur.
[01:04:00.990] – Jonathan Denwood
Well, because I want to say I have to plod along, but I get there. I’m not the quickest to learn something, but if I’m motivated, I tend to learn it very well. Also, my own observation, and I think you touched on this, Rob, is a lot of people really concentrate on the external struggles, but I’ve observed in myself, that the real battle is the internal battle. It’s the messaging, the baggage, the stuff that’s going on in your own head, and if you can accept it and move on and improve, you’ll probably be in a better position than 90% of the population.
[01:04:50.860] – Rob Walling
Yeah, there’s two things there, I think. One is self-awareness and this self-knowledge. I know what my weaknesses are, so therefore, they’re not blind spots. If you have weaknesses and you keep tripping over them. You keep getting in your own way, you’re self-sabotaging, and you just never learn; then they’re blind spots, and they will keep you from having the success you want. I don’t believe I have any blind spot. This is years of therapy. This is years of being married to a clinical psychologist. This is years of making a lot of mistakes and being very self-referential or looking at myself to try to figure it out. So, I think self-awareness and self-knowledge are big deals. And then the second one that you’re talking about is almost… I say more than half of being a successful founder is managing in our own psychology. And what I mean when I say that is exactly what you’re saying: we’re all going to get in our own heads sometime. And being able to wake up, some days I wake up and I feel terrible. I’m either stressed, or I’m well. You’ve talked about this; you’ve had times where you’ve burnt out, and you’ve had to walk away a little bit, haven’t you?
[01:05:51.510] – Jonathan Denwood
Yeah.
[01:05:52.240] – Rob Walling
And knowing that and being aware of it is something that you want to learn. You want to learn your own strengths and weaknesses and not just go through life mimicking other people and not letting the hard times crush you because managing your own psychology is part of that, a part of getting up. And when you’re beaten down, it’s to be like, well, this isn’t permanent. I will succeed eventually.
[01:06:21.790] – Jonathan Denwood
All right. I think we end it now, Rob. As always, I think we’ve had an interesting discussion. I think you’d enjoy it, and that’s why you come back because I obviously listen to your content and I try and put interesting questions to you. I think we’ve had a fabulous discussion. Hopefully, you come back late in the year, and we will have another one. We’re going to end it now, folks. We will be back next week. See you soon. Bye. Bye.
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