The Bootstrapped Founder

Peter knows how to get good domains and turn them into businesses. He's selling onions, helps dude ranchers get clients, and will share his approach to monetizing domains as well as purchasing them on the cheap side. Peter's been building online marketplaces for a while, and he'll teach you how he approaches setting up profitable businesses.

00:00:00 Peter’s unique approach to building a business.
00:02:59 The right mindset to become an entrepreneur.
00:05:46 Getting into domain name investing.
00:11:11 The domain name investing path.
00:16:20 The importance of having a domain first.
00:20:08 What’s a directory marketplace like?
00:26:43 The domain-first approach is genius.
00:30:00 The importance of no-brainer pricing.
00:33:37 How to use a domain portfolio to build your business
00:39:22 Peter is not afraid of going into a new industry.
00:44:21 The importance of having a good domain name.
00:52:13 Industries to avoid
00:58:48 Peter's world

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Arvid Kahl
Empowering founders with kindness. Building in Public. Sold my SaaS FeedbackPanda for life-changing $ in 2019, now sharing my journey & what I learned.

What is The Bootstrapped Founder?

Arvid Kahl talks about starting and bootstrapping businesses, how to build an audience, and how to build in public.

Arvid Kahl 0:00
Today, I'm talking to Peter Askew, domain investor and onion seller. Peter has a great approach to building businesses. He just looks at expired domains, grabs the good ones, and builds businesses around them. We'll talk about working in industries that you have no idea about, building up a portfolio of very different projects and the importance of having a good domain. Here's Peter.

I've always been interested in how you were approaching building a business because there's so different to what I know business building to look like. That's kind of what I wanna talk to you about today.

Peter Askew 0:34
Yeah, listen, I'm fortunate, you even just wanna talk out and I don't mind sharing because I took a very strange path into all of this. And didn't really intend to be or become a builder. I kept getting laid off. And I wrote another big essay about just how I got to where I am. And then lo and behold, I started building. I was like, gosh, this is a lot of fun. What else can I learn? Because I didn't come in through the coding side. I kind of came in, sort of through the startup side in the late 90s. And then got into mainly the marketing and advertising side through paid search SEO and then got on to analytics. But the more I started, like just scraping the surface, like a little bit deeper and I was like, well, what is this graphic design stuff? How do you make a logo? Well, I got to figure out how to make a logo. And I was originally in paid search. And then, you know, paid searches, you know, essentially half of the search engine result page. And so I saw SEO and I was like well, what is this? This seems pretty important. But okay, in order to get a site to rank you got to start building and adjusting the text on the page and each one's and you gotta have a good host. Hopefully, it's fast enough and so that all started boiling back down to the domain name so when I started building sites to teach myself how to do just basic coding HTML, build tables, add text, change the background color for me, for you because I know you have a development background. It'd be laughable but for me I was like, how does this? What happens if I remove this semicolon? The whole site breaks and so I found that fascinating and then I started leaning on WordPress to speed up development and you can make a pretty great look in the end especially these days are great looking very capable, robust back end on WordPress is what I tend to lean on these days. But yeah, it's very strange and I don't have a business background, never took a coding class. I just mainly self taught through YouTube videos or just really honestly just getting in there pulling raw code, opening up a text editor and like making changes and seeing what happens on the page. What happens if I do this? Oh, crap oh, geez! Site's down, let's change it back and push it back up to the site and see what happens. But

Arvid Kahl 2:59
That's just the right mindset, right?

Peter Askew 3:02
Yeah, I didn't really have a guide. So I was just more wandering around because I was still working a nine to five as a product manager at a few, I still got I got hooked on the internet. So I kept working day job nine to five and then I'd come home and monkey around on the internet just like okay, well, what do I do today? And so I'd need a topic. And so one of the first topics I picked and it didn't make any sense. But I picked the bed and breakfast industry. And I decided to build a little marketplace directory just if you wanna find a bed and breakfast in Alabama or up in Canada or in Washington State and so I put in. It was just like, it looked like the original Yahoo is just a bunch of lakes or click a state when I got really fancy I included an image and then I hotlinked specific states. I thought I had really gotten advanced when I hotlinked a specific state, you click the state and you go to Georgia, like oh my gosh! I'm really stepping it up now.

Arvid Kahl 4:09
I remember this, like this time when the internet was just people experimenting with HTML, like the whole MySpace and geo cities where people just customized things and figured out oh, wow, I have a lot of control. And that like fueled a lot of interest in programming and then turn people into self taught coders. I kind of come from the same background. I also did that when I was young, I guess and had no idea how all of this work. I just I noticed that people seem to be able to do something with it that is technical, but doesn't require like complicated machinery. It's just like software, right? That's when I understood oh, wow, I have this immense power. And then I went right into coding. But what I was gonna say here is that you seem to have this kind of spirit of oh yeah, I can learn this, which is such an important spirit when you wanna become an entrepreneur, right? Just the mentality of hmm, what is design? Or wow, what is SEO, right? That the kind of oh no, this is not in my domain, pun intended. But you know, this is actually something that I want to learn to expand my knowledge of things. And I see this in what you're doing right now and what I've read and learned about you have been doing for quite a while. And I kind of wanna talk about this history that you just kind of hinted at from coming from one particular background going into another one. Because what you're doing right now, as I guess you call yourself a domain name investor? Is that what it is? That seems to be a widespread field of many different activities that you all combine on the one personal business brand. Can you tell me more about this? What is domain name investor? What are you doing there?

Peter Askew 5:44
Yeah. So essentially, if I dovetail off the topic, please push me back on. So I'll try my best to explain how I got into domain name investing. So as I started teaching myself to code, I started. It took a long time to get a site up on its feet, to get it monetized to get traffic. And then my brain started thinking, well, gosh, what's stopping me from just finding somebody else's website? This is 2004-2005. What's stopping me from just reaching out to somebody and saying, hey, can I buy your website for $5,000? And if I can look at their traffic, I can determine maybe from a conversion standpoint, can I sell a product or service? What if I add Google AdSense on there? If I get a specific click through rate from AdSense, I can monetize the traffic if they don't have AdSense on there. So I started acquiring websites, I find, I look up high search volume terms like travel and tourism terms or specific. One site I purchased was Appalachian Trail, which is a hiking trail up the east coast in the United States. So it actually didn't resolve. So I found the domain, the guy just pulled it off. No, I correct myself, I'm thinking of a different domain I purchased. This one was still alive. It only had a few pages of content on it, reached out to the owner, see if he wanted to sell it and then acquired it from him. And as I started buying and selling these sites and transferring all the content, you know, all the pages, the domain, I started understanding the importance of the domain name. So when I'd make a transaction, I would say the first thing in my head would be I need the domain. If I own the domain, I control everything for this because even if they give me the domain, don't transfer the content to me. I can either go screen scrape the content through the internet archive or through other sources. So if I get the domain, that's the biggest hurdle. And I kept coming back to this domain name. I was like, this is a really, really important aspect. And I started kind of witnessing the impact that I could make being an outsider and buying a really good keyword descriptive domain name, like Appalachian Trail. People started assuming that I was an expert on the Appalachian Trail just because I own this domain name. They'd be asking me questions, where should we hike? Or where should we camp out on mile 105? And I don't know. I need to find some experts on this because I can't answer this question. And people will just automatically assuming and I was like, man, the trust and authority with these really good dotcom domains is impressive. And at this point in my career, Arvid, I was 35 or so. And I sort of felt like I was a little late into this development side. So when I noticed this domain I was like, gosh, this kind of gives me a little fast forward. It gives me a quick, unfair advantage. And I can quickly start building some of these products and services on really good domains, like how do I find a really good domain? I can't go buy them from the original purchasers, you know, years ago because typically original domain investors, they're gonna want 50,000, 100,000, a million dollars for a really good domain. And then I uncovered the domain expiration world where so many doesn't renew their domain at the registrar. It goes up for an open auction on the internet. And it's simply you just bid within a browser you set up an account. The two popular ones when I first started word NameJet and SnapNames. And essentially, domain expires goes back to them. They placed the domain up for auction before they rerelease it, if there are no back orders and no one's interested, then it suddenly just gets rereleased for open registration. And every day, roughly 50 to 100,000 domains expire. And so every day, I found it to be like a silent auction but it's also like a treasure hunt. And so you're like sifting through these domains looking for really interesting topics. And what I found as I started digging through them, certain domains were inspiring me to build little projects. I would find one, oh gosh, what were some of the early ones. I mean, I would start building anything on just, you know, C Minus domain names if you're on a grading scale. I buy one, I build one on, you know, baby carriages. I did one on the on llamas and llama wool. But they weren't the best domains. And so I kept building these kind of piecemeal sites and getting a little bit of traction, but I wasn't terribly inspired by some of the projects. And then my brain started morphing into, well, what if I just kind of pull back? And I was still working nine to five. So I had a salary. I was like, what if I just stopped this piecemeal and I save up, you know, 5, 10, 20,000 bucks and I just sit and wait and wait for an interesting domain. I got time because I thought that time was on my hand. I was like, I'll just wait. And I'll just monitor every single day and wait for a domain that might strike my fancy and might fit into a business model that I enjoyed. And I'll get back in the domain investing world. But and that's when this was when I kind of made that decision, it was late 2017-2018. No, no excuse me, this is 10 years before 2008 ish and I waited about a year and a half. And that's when expired. And the Dude Ranch vacation industry is really popular out west in the United States, where you can go visit an operating ranch. All Ranches are different. But you can either help herd cattle on the ranch, you can go shoot shotguns if they have a gun program, hike, fly fish, always compared to it's like summer camp for adults, essentially. You get to do all those kinds of activities. And so I saw it and since I built the directory on my little bed and breakfast, I was like this would fit really well into directory. I will help guide people to a dude ranch that matches their interest. So I waited on it and then acquired it for roughly 18,000 bucks, 17,949 bucks. I bought it at auction. And I wrote a big essay on one of my sites on how I found it, my rough ideas on what I thought I could afford, or hopefully what I could acquire it for. And that kinda took me down this domain name investing path on well, this is interesting once you kinda get into the monitoring expiring domain names. It's for the certain type of person, if you like auctions or treasure hunts, is very, very addictive. And it's something I do regularly almost every single day. I'm always pulling up and right before we spoke, I was digging through just a few what's coming up today. It's like, almost like my morning newspaper.

Arvid Kahl 5:45

Peter Askew 13:11
Yeah, yeah. So from a domain investment standpoint, there are kind of two different camps. There are some folks who will buy and treat domain names like real estate really, buy it and hope that it appreciates in price and then sell it a few years down the road for hopefully a profit. And when I started down the domain name, I tried all three different. There are essentially three different paths that you can take, buy and hold, and hopefully it sells at a higher value down the road. Buy and keep it and hopefully the existing traffic say if you own You'd assume a fair amount of people are just going into the browser bar and typing in water and adding dotcom at the end looking for maybe a water provider. And you can have Google Adsense or any kind of advertising marketplace provide ads on the page and you get a certain percentage of that advertising revenue. And then the third is development. And there aren't many domainers who develop. A lot of debaters are somewhat lazy. They just wanna set it up, set it and forget it and get their mailbox money every single day. So I tried the buying and flipping. I wasn't very good at it. And I found it kind of boring. I could never find a domain that was generating enough type in traffic to generate any revenue from just an advertising perspective. But each time I started building, it was fun. And to your point, I'd build a very, very rough site, but I'd learn just a little bit from building that one site. And then I'd try a new site. I was like, okay, I learn that but what if I added a you know, a map on the homepage, instead of just a whole bunch of links to all 50 states. I'll put a map and make it fancy, make it a little bit interactive. And then mobile came around. I was like, well, how do I make it mobile responsive and make it really fast on a mobile device? How do I do that? I I need to figure out how to do that to make a, how do I find a really fast host because now it seems folks are staying on my site longer if my site is more responsive and is a little bit quicker versus the shared hosting account that I had on my old. Yeah, so that started kind of taking me down. So I started slowly moving away from the investment side. But the interesting thing, Arvid was when I'd try a project on a good domain name. And if the project didn't work, my downside was not kept but it was somewhat limited because oftentimes, if I could buy the domain at auction, I'd be able to sell the domain sometimes at a profit. I'd try it, so the only thing I really lost is just my time and sweat equity and trying to build the project called tracking is a good example of this. When I tried to build a call tracking application with a friend of mine. I thought it was gonna be a competitor to call rails a big company in the Atlanta Georgia area. Now I thought I'd build a kind of a stripped down simplified call tracking application tried it. And as laid an egg, there wasn't a very good match for what folks were looking for. But I bought the domain roughly for 20,000. And then I sold it for roughly 120,000 even after the whole project failed and I sold it to Call Rail.

Arvid Kahl 16:20
That sounds like a good

Peter Askew 16:21
I'm not that good of an investor. That was a very lucky I happened to the guy who ran CallRail at that point. So he loved the domain. He kind of kicked himself for not seeing it within the auction. Well, I'm glad he didn't because I was assuming reason I was able to grab it. But I tried it, it failed. I didn't quite go down the path that I was expecting. But then I was able to sell it for a profit. I was like, well, this is kind of good even if the projects don't work, chances are hopefully cross my fingers, I can sell it for the same price I bought it and then move on to the next project and try something else.

Arvid Kahl 16:57
It's interesting because it's an asset, right? Like a domain, having the ownership of the domain is already an asset no matter if it's super valuable or not. But it's not just an idea. And that's kind of you know, that's the difference that I see to many other approaches in building a business. If you get a domain first, like you're doing it like intentionally that particular domain, not come up with a random name, try to find it, but like see your domain and think, okay, this could be a business, then ownership of the domain itself is already like you said, incredibly valuable just for the authenticity that dotcom domain suggests to your potential customers, the trust that they have in the authority, the SEO juice that's already in it. Like who knows how much or how good it's already made the ranking, right? I find that super interesting because it's really completely orthogonal to what I understand entrepreneurship as, which is why I love talking to you. Because it's just so different to my perception because I come from this whole go into your community, understand what your future audience needs, their problems, figure out a problem you wanna solve, find a solution for that that fits into their workflow. And then think about a product and then think about a name and then think about a domain, right? It's like

Peter Askew 18:11

Arvid Kahl 18:12
On the furthest other side. And that seems to work too. But I love how you completely flip this around. And I would like to talk to you more about this process from finding a domain to getting your business up and running. Because I feel lots of people out there are probably they see something that they find interesting. Whenever I go through my Namecheap, outing myself as a Namecheap customer here. I see interesting things happening there. And I see domains that I hadn't thought about even like versions of the things that have already happened, like, oh, yeah, that could be interesting. And then I dismiss it. Because you know, I have a different process. But I know that there are lots of people out there who might be interested. So how do you go from domain to business? How do you pick all your business models and figure out what you actually wanna do? What business might be feasible for that particular domain?

Peter Askew 18:56
Yeah, it's a great question. So here's how it essentially started boiling down the more small projects I've started building. And I'm very much, Daniel Vassallo and I have a very, very similar frame of mind on building these small projects, finding getting small wins where I learn more from small wins than I do from any type of loss or any kind of failure. The more small wins I have, the more I'm learning of what other customers or products and services need to do to meet market demand. So as I kept building these small projects, I found roughly three models business models that seem to work well within my lifestyle. I tend to build solo or I'm solo and then I partner with a subject matter expert. So Vidalia is a good example where I bought the domain, but then I partner with my farmer and Vidalia and he is the Vidalia expert and I am just the web guy. Sometimes I call myself the CTOO, the Chief Technical Onion Officer, Arvid. And so I tried to go down that path. So the three models that I roughly found that I enjoyed building were the directory marketplace. It's a very, very good fit for a solo builder, a solo founder, where you're simply aggregating information and making it easy for people to find products and services, hopefully a good high ticket item like dude ranching was very attractive to make as the typical Dude Ranch vacation ranges in price from 10 to $20,000 for a family of four. It's a big ticket item. And I was assuming that the dude ranchers were getting roughly 30%, maybe 50% margin on that. And they already actively advertised in online, offline, on radio. And so they're already comfortable with the idea of advertising online so it'd be a little bit easier for me to pitch the product and service to them pick the service to them. So directory marketplaces I love and so for Dude Ranch, it was simply where do you find a dude ranch in Colorado? What kind of dude ranch do you want? Do you want one with a pool? And do you need a tennis court? Or do you want one that strictly really hardcore, herding cattle and riding horseback rides, you know, twice a day and then just try to filter some of those options for the searcher. And that kind of goes into paid search SEO, which was my old world, which I can apply some of that expertise. The second was simply honestly, Arvid, a lot of this I was stealing ideas from other people, other people that built products and services. A friend of mine built a job board for the nursing industry in Atlanta. And it was very successful site. And he had a very good exit on it for just nursing. So this idea of running a job board, he was doing it solo. He's a PHP developer, so he just built the whole thing himself. But then I discovered job themes and job board themes within WordPress. I was like, oh, hang on now. I don't have a job board yet, don't have the topic yet. But job boards, I'm simply not packaging anything up. I'm not shipping anything out. I'm simply sharing information, just like the directory marketplace. I am allowing jobs where I'm either seeding the jobs and also taking in free or paid listings for so job boards, big, big fan of job boards. And each time I do a lot of searches, there's always seems to be a lot of opportunity out there, Indeed and Simplyhired and Monsters. They have too much, they've covered way too much ground in my opinion. There's so much opportunity out there in my opinion for the job portal, small operator if you focus on one industry and be able and it allows you to really and I've been able to do it through the ranching industry through my whole cycle ranch work and just posting ranching or equestrian focused or outdoors focus types of jobs or job boards I'm a big fan of and then the boutique small kind of product service, mainly product and Vidalia fits into this one. Primarily, hopefully, it's a product or service that is tough to find or does not appear on Amazon or makes it tough for any of these big Walmart's Amazon's if it's more difficult for them to sell or if you can serve an existing community at their search volume against it. So you can always search Google to see if there's demand or people, I always wanna know are people standing at the door waiting to buy and product and service? And can I build something to serve that market? And I can look at that through Google. I can look at search volume. How many times are people searching for Vidalia onions? How many times are they searching for buy Vidalia onions online or buy now. Sometimes they're looking for them, you know, at their grocery store. But they're very, very difficult to find around the United States. They sell out really quick. They're a very boutique item. There's built in scarcity just from Mother Nature. So when our season starts, onus is on my customers. You need to order. If you don't order now, then you're gonna be out of luck when the season ends because we're gonna be out and my customers call and complain or they moan and groan at the end of our season. They don't either get my last email or they waited too long and our season ends. And it's over until next season. If you don't order right now, we're out of luck. So this I started falling into these three directory marketplace job boards and boutique products and services. So as I'm scanning, but there are lots of other ones. There's forums, I've always been interested in forums. My brother restores old Porsches of all things. And so he is an active user and this small, tiny forum for Porsche aficionados and a strange side. I think it's called Pelican parts. He hangs on this thing all day long everyday talking to Porsche guys. Hey, do you have a muffler I can buy? Hey, would you have a steering wheel for a 1967 911 S. I'll buy it for you $500. Or maybe he finds a barn find and it has some wheels that he doesn't need. He'll put the wheels up for sale on the forum. And you just need a moderator. And oftentimes the folks that I've seen that run forums, they just become the moderator. And they're just making sure people are being nice and not yelling at each other. And then you can monetize certain aspects of the forum. So as what I found myself doing the weird thing, Arvid is, as I started going, none of this was intentional. I kept just kind of stumbling forward. And as I started monitoring these domain name auctions, my head just kept talking to me, that domain would come up with like, huh, that's pretty interesting. You could probably fit a job board on that or maybe a boutique product and service, this Like, oh, gosh, rum cakes, you could package them up. They have a pretty good shelf life. They're very popular around Christmas time. Maybe I could find a chef. I can't make him but a lot of people make really good rum cakes. And I could ship them out and charge this and pay the provider this and maybe I could work. So I just naturally just started, you know, reverse engineering business models on these domain names to see if they could potentially work and looking at search volume. Yeah, so those are kind of the three that I started kind of falling into.

Arvid Kahl 26:43
That's so cool. Because initially I thought like your domain first approach sounds like so there's a gambling component to this on that there is a business model that fits. But now that I hear you talk, you had it all in the back of your mind. Like you didn't even look at just the domain name. You look at the domain name through the eyes of somebody who could immediately apply three plus different models of a system that potentially could turn into a good business, like you had all of this already in there, which makes this kind of a framework first approach. The domain is like the second part because you already have these things in your mind. If you're looking for the opportunity to implement them, which is genius. I love this because another thing I just learned from you telling me this was not only did you know how to look for like supply and demand kind of things where you could position yourself in the middle, a directory is exactly that, right? There's supply on the one side the demand on the other, and you kind of facilitate that or even a boutique service where you sell somebody else's products to an eager audience or a job board where you connect people who seek employment with the employers. You are finding these bots to mediate supply and demand. And with your knowledge in the search space, you know how to measure it. That's genius. I'm just blown away by how you use all this knowledge and all the skills that you acquired to immediately spot opportunity, which makes this something that I want to talk to you about, that seems to be an actually quite complicated process. And it looks easy. Find the domain build a thing, but if you look at all the other steps that you took before, understand how you could potentially monetize it, even before you buy it, that is not easy. Do you think it's hard to do this? Like do you consider this a rather complex occupation?

Peter Askew 28:37
It's weird. I mean, coming from my background, it felt natural to me. So I just kept taking these baby steps. And like I mentioned earlier, none of this was intentional. I'd never sat down one day and said, I'm going to start buying domains and then I'm gonna start applying these business models on them. Originally, it was I kept getting laid off at my company. So I realized I needed to save myself. I can't rely on corporations or even the small startups that were raising tons of money trying to go public. And then I get fired out of no fault of my own because they blow through all the money on 50 full page ads in the Wall Street Journal. And then I'm suffering from some of this mismanagement of these companies. So I was like, I gotta save myself. I need to figure out how this works. So that's what really started this path that I was on. And then I think how do I save myself? I need to figure out how to run, build a business. I'm already hooked on the internet. I need to figure out how to do this on the internet. Well, how does this work? And that's when I just started doing. I need to learn how to code, just rough not even fancy coding. It's just very rudimentary coding. And then started taking me down this path of okay, well how does this work? Okay, how can I monetize that and make it very worth the price of admission? Oftentimes I want my pricing to be just no brainer pricing, where it's just oh my gosh, this is a course for dude ranch when we built it and I was assuming roughly the transaction was 10 to $20,000. I wanted our pricing just to be absolute no brainer pricing. So when I started it was, you know, 250 a year, 500 a year where it was just throw away money for the dude ranch. Of course we're gonna advertise on And that's what I got when I first went to the first so I attended their conference Arvid so they have the dude ranchers host yearly conferences and so I bought a booth got a tablecloth and physically showed up. This was in Tucson, Arizona and showed up. And that's when I started really seeing the impact of a really good domain. Dude ranchers were just walking up to me, looking at my tablecloth, this had big And then I had my laptop there, opened up on the good enough looking website and like, okay, that seems to check out and you're here. I can shake your hand. Okay, how much is it? And I started signing up people at the table. They didn't know how much traffic I had. They didn't know whether I was gonna convert. But I was there at the conference. I had a website and I had the domain. I was like, holy cow. This works. Okay, this domain name thing is real. And I get to bake in this fun travel aspect. I was like, oh my gosh! At that point, I got really, really hooked on it, Arvid. And yeah, I did that for 10 years on the dude ranch side. But and I've gone on a tangent. What was your original question, Arvid?

Arvid Kahl 31:37
Actually, I wanna keep talking about this because you just mentioned this as a 10 year project. How long do you usually run these little business experiments on top of any particular brand?

Peter Askew 31:46
No talent, I never know. I just keep so I'll be going into my ninth year of Vidalia next season. I ran dude ranch essentially. Sold dude ranch to my friendly competitor that he and I work together. He owns I wanted to fund, another directory that is still struggling. And to your earlier point, I am far from you know, 100% you know, baseball hitter. I'm only really sharing the ones that work. And I've had so many crash and burns and ideas I try to push out don't wanna work, call tracking was one that didn't work. I tried to build a nationwide directory or nationwide search platform for restaurant health inspection scores. I thought that would be fascinating information to look at and failed incredibly on that. But some of these odd ones. But you know, it is like baseball, you just keep taking a swing, keep taking a swing. So what's gonna connect?

Arvid Kahl 32:48
Nothing wrong with that, right?

Peter Askew 32:49
Yeah, I'm spoiled where once I started building these dude ranch projects, I was like, man now. For me, it's not even the success the product or project. Now I'm very stingy on the projects that I approached, like, if I'm not like, what's the term? Does this project spark joy? Like, do I wake up in the morning want to go jump on that project and start serving these customers? If that isn't there, do not bail. I don't care if it's making money. I'll sell it to somebody else. And I'm not gonna wake up and go to work on some project that is not, you know, firing my engines and getting me excited every day. Dude ranching did that ranch work. It essentially evolved out of my dude ranch work. One of my friends there own the domain. And he ran a job board on it years ago, but it kind of abandoned it. And I found it in his portfolios. He and I became friends. I was like, David, let me look at your domain portfolio. What do you have in here? You have some good names and I saw ranch work. It's like David, what's this? He was like, oh, I used to run a job board on it. I was like job board. Hang on. I know about Shane site, he ran a nursing site. What is this? Hang on.

Arvid Kahl 34:04
This is so nice. This is such a cool way of like figuring things out. But just pulling things from left, right and center. What a great integrative approach. I love this. So so cool.

Peter Askew 34:13
This is on ranch work. So David had the domain and tell me if you wanna go in a different story. So again, I wanna limit my downside as much as possible as I build these projects. So I didn't even buy it from originally. So I just said, David, hey, how about you just point the name servers to me. I'll build the site. I'll rebuild it on WordPress with a job board theme. If I make any job board revenue, I'll give you 25%. I keep 75% just to see if I can get this thing on the feet. And David Malo, friend partner in the dude ranch again, he's so great. He's very similar to me. He was like, let's do it. I'll do it. And he went in there change the name servers domain. So I was like, let's go. Let me start working on this site. So I started building it. It started getting reindexed, Google started searching and I started serving and within the first week or two, I started getting paid submissions coming through. And I was like, oh my gosh, okay, here we go. Let me just dote on these people. I mean, make sure if they don't fill the job within the 30 day, I'll rewrite it for free. If they email or call any kind of questions, how can I serve them to make their jobs easier? And it was a good niche that Indeed wasn't serving them. They were gouging them for, you know, $1,000 job listings on Indeed. And I was charging at the time I think I was charging 25 bucks for a job listing. And then I dote on make sure it was getting filled. So I had to do a little bit of paid search as well, in addition to SEO and then a little bit of social written not that much. But then years later started doing more paper advertising of all things and like, in cattle magazines, farming magazines and because I wanted to try to find these decision makers. In some cases, they aren't online, you know, the owner of the ranch is not online and he's making the decision. So how do I reach that guy? Maybe he reads progressive cattle, which is a big ranching magazine. So I started buying little thumbnail ads in there. But this goes back to Daniel Vassallo. I'm never making these bets that are gonna put me at game over making very, very small calculated bets, you know, buying $1,000 ad, testing it, seeing if there's any traffic with it, or seeing if the baseline goes up for revenue. If it does, okay, something's happening there. Maybe I can consider that as well. Never trying to put myself in a position where I have to go back to my old job. And I wish I could if worst case scenario, I can always probably go back and get a job as a product manager somewhere. But I want as many fallbacks as possible. So if ranch work has a rough year, hopefully birthday parties or Vidalia or another project comes up and can help support me if I have one rough year and or if Vidalia goes down ranch work maybe support me and help kind of build this little nest egg.

Arvid Kahl 36:47
Would you still actively monitor the whole expired domain space? Like every single day, you're still doing it?

Peter Askew 37:15
I do. It's a bad addiction. Yes, it's fun to do. And so oftentimes, you may see me share them within Twitter. So when I find the one like a recent one, that was pretty neat., that was like, gosh, that's a lot of people. And when you go into search volume, there's a lot of people searching primarily in Florida, California. But even if you just built the site for just those two states, you might have a fun 10 to $20,000 little side business you run. And hey, then you get business trips down to Florida, get to hang out on a few yachts, meet some interesting people on the yacht industry. And so that one seemed interesting. So whatever I find when that seems like a fun side project to build because I see how building these small little projects helped me. I try to encourage other folks is to try little projects because you can learn so much versus reading. I tend to learn best by you know, jumping in the water and learning how to swim when I'm there versus reading a book on how to swim. I just jump in, start figuring out how this works. So yeah, so that will come up. So whenever I come up, whenever I stumble across other domains, I'll just dump them on Twitter and say, here's a rough idea. Maybe somebody else is out there. There's nothing in this for me. I just found this. I'm addicted to looking at domain names that are expiring, they're fun. Or even sometimes I'll find some that are for sale. Like what was it was for sale for a pretty reasonable price. So it was, I can't remember Arvid, 14 or 15,000 bucks, a lot of search volume, a lot of business go into it. It was beach ball. I can't remember if it was singular or plural. But that one was like, hey, if you are ready to pull the trigger on a big project and you wanna have a physical product that you box up and ship out, here's an interesting one's pretty reasonable price. I'm surprised the domain investor hadn't bought it yet. Yeah, so those pop up but the wholesale price on expired is always attractive because there you can buy them at a somewhat steep discount.

Arvid Kahl 39:22
I see how this can be addictive. Like particularly if there's this discount to be had and all the opportunity in the world, you know, for you to figure out what you could do with it. What I really enjoy about your approach to this is that you are not afraid of going into a new field like exploring a new industry. And what is even more impressive, particularly I guess to people who are introverts self declared introverts like myself, it's just like showing up to a conference or going trying to find somebody to work with that I think is a hurdle that many people are afraid to take like to throw themselves into something new. Fearing, I guess, failure, fearing, not knowing what to do, doing it wrong, like messing things up. All of all of this, like looms over my head, even just thinking about it. And I know that, you know, if you have an open personality and if you're just interested in stuff you quickly get beyond that stage and you actually get to results. But I see this is a pretty high barrier of entry for an completely new field. How excited are you to dive into these completely novel industries? Is that something that by itself is alluring to you?

Peter Askew 40:27
Ah, it was very difficult for dude ranch. A lot of imposter syndrome was going through my head when I started that project. I mean, I still remember walking into that first conference I mentioned to you. They had a like a cocktail party the first night I'd showed up at a cocktail party outside in Tucson. They had a Saguaro cactuses. Have you seen this like in the background of Looney Tunes of roadrunner and coyote those little all those in the background? All those are beautiful. The scenery was beautiful. So it's all these dude ranchers hanging out cowboy hats, jeans, all hanging out. And I have my name tag with Peter Askew, And I remember walking forward, I was like, oh, gosh! Okay, soon, he's gonna call me out and you'll kind of what your brain starts overthink and somebody's gonna call me out. I'm a fraud. How dare you have this domain representing our industry? Who were you? You're from Atlanta, Georgia. At the time I was in Atlanta. I'm in Savannah now. Oh, you're in Atlanta, Georgia? How dare you take this domain name, you assume but they are the most welcoming, but I had to just ignore that side of my brain and just almost empty mind. I like the whole idea of just going empty mind and just walk in there and see what happens. If somebody wants to yell at me and say I'm a fraud. Bomber. Let me just go maybe talk to somebody else and almost water off my back, trial it in just to see what happens. And so I was very uncomfortable walking into it. And one of the first people I've met at that conference was a guy that ran a ranch up in Montana, your Flathead Lake. And he either had some exposure to web and a little bit, but he owned the ranch. And so I walked up to him and said, hello, I'm Peter. I'm one of the vendors here. And so he looked down at my nametag, was like Peter Askew, And the first thing off his mouth was how in the hell did you get that domain name? And I was like, oh, wow, look, it's a long story. It expired. And this is before I even started signing up advertisers. He later became an advertiser. But I was like, it's like it's a long story. I was lucky a dude ranch abandoned it. They let it expire. It was a dude ranch up in New York State. And he was like, man, that's a good domain. I was like, yeah, I'm very fortunate. And I'm very fortunate to have it. I'm very fortunate to try to can use it for good help you guys, to help drive better leads, to lower hopefully your advertising expenses and provide another avenue for you guys to advertise online. And

Arvid Kahl 43:21
Yeah, that's what you do, right? That's your skill. That's what you can give to these people who are ranchers like they run a ranch. They don't have the time to build a complicated ad serving system or a network where people can connect with them like they are on their ranch, tending to their cattle tending to their horses. And you're the guy that was lucky. But it's also really interested in helping them. That's kind of how I feel about this, like you just showing up there. Nobody else did that, right? You did that. Like there was no other domain guy very likely showing up. So that's cool.

Peter Askew 43:56
And here's the crazy thing too, Arvid. On that site, outside of the whole imposter syndrome and trying to get out of my skin just walk into this conference and give it a shot. At the time, there were roughly three to four other dude ranch directory marketplaces. I was roughly the fourth or fifth one coming in. So I wasn't like the first idea to come up with this marketplace directory. I thought I can make a better one than some of the existing ones there. But number two, I had the name of the industry. So I'm in here trying to wedge myself into this industry but I didn't necessarily let that scare me away where I would have said it could have scared me away. But in some ways, those other sites had almost validated the directory marketplace idea for me. They're already paying, some of these ranchers are already paying. I don't wanna come in at the beginning the low cost option then slowly maybe stair step up some of my pricing. But I wasn't like, which kind of taught me I don't have to have, you know, the Uber ID or the next Airbnb. I can simply have a really good domain, find a business model that works that either tries leads or solves some sort of unique problem for these businesses. And then lien on that good domain name, almost as a co founder. Sometimes I say these domain names are my co founder because they're that important. They do that much heavy lifting for me because they're branding themselves in many ways. And then I can go on the back end and try to build the sites get some good looking logos, make them fast, optimize well, really look at the analytics. But yeah, there were already four, just for some of your listeners don't necessarily get thrown off if there are already three or four. There are always ways to create maybe it's just a little bit either different bells and whistles or make it simpler. But it is we're looking back after a couple of years. It was like, I'm surprised I haven't built that because there were like four or five others.

Arvid Kahl 43:56
It's validation, though, right? If they are already there.

Peter Askew 46:05
Yeah, yeah.

Arvid Kahl 46:06
There might just as well be a fifth one, right? If there was a fourth one and data survive that. Yeah, that is really cool. Let's talk about domains for a second here. Because I see you're very much established in the .com world and you recently tweeted something where you said you once developed the site on a dotnet domain, and you're disgusted and ashamed.

Peter Askew 46:27
Like self deprecation, so I like just making fun of myself.

Arvid Kahl 46:30
So what is it with top level domains? How important is that, the TLD for a particular domain?

Peter Askew 46:35
I don't really lean on .com because so the more conferences I attended and physically hung around either the decision makers or even the general public. I would notice how ingrained this .com name is, how much it's been branded since the mid 90s, Arvid and how many marketing dollars have been spent educating the general public that it is the gold standard for websites. And what I started noticing and this was after I got into the domain investment world, but it even further entrenched me and solidified how important this .com name was. Certain times, a few times it was this dotnet domain or other domains, if I would watch other times other people's domains, sables .co or .io, which are perfectly fine extensions, not to say you couldn't build anything on any kind of domain, but it might require different marketing channels. You may have to market in advertising, educate the public that it's an IO and not a .com. But I would watch decision makers or the general public, I would tell them a domain. I would tell them to visit, say, maybe to use an example,, which I don't even think exists, but I would tell them, okay, go visit this And I would watch, I would be standing over their shoulder and I'll see them tight. I would tell them to go to .co. They'll go in there and just type .com, ignore what I said after the dot and they just type in .com or .io, anything. And I've watched them do this over and over and over again. It was like, gosh, this is how important that .com name is. Everything after the dot, they're gonna automatically assume. And if I have an alt TLD, I'm gonna have to really educate them that it is a .org or a .net because they're automatically gonna assume. And then guess where all my emails are gonna go. If they try to send it to me it whatever .net, they're gonna send them to .com. And I've seen that happened before, a really sensitive documents, tax reports. In a bank account statements, my university in Mississippi, their nickname is Ole Miss. And I helped them acquire And for a short period, I had the domain name under my control before I pushed it over to them. And oh my gosh, the emails that were, Ole Miss primarily operates on .edu. And the emails that were coming through, it was just I was like, oh my gosh, this is just people assuming they wanted to send an email to or Here's our bank account statements. Here's the check there. Here's my routing information from my bank to make sure that my payment to the university and like, gosh, this is another that didn't get talked about as much as the email aspect of having these private communication going back and forth for .co, .io, .com. So it really just solidified after I really gone into the .com world. It just solidified. I just need to focus on .com And that was more just a joke and not trying to smear anyone who's built on .net. I built on one but I was like gosh, this is hard. Now I'm spending half my time trying to educate everyone that I'm .net and not .com. Rather than just having the domain and everybody assumed when they look for dude ranch and the amount of type in traffic I got for was 50 visits a day roughly people just going up in the browser bar typing in dude ranch and adding .com because they wanted to either find one or maybe be inspired or be kind of pushed in the right direction to make their selection. And let's see it for I see for Vidalia and my friend built a site for the bobblehead industry. You should have one, Arvid. Warren Royal, he runs a bobblehead business and he was a lot of the inspiration. He was almost my North Star. So he bought the domain Any on singular and plural and bobbleheads. No experience in the bobblehead industry, he just bought the domain because he thought it was cool. So he bought it right before the 08 US election. And he started selling three bobbleheads. It was Clinton, Barack and John McCain. And he sourced him from other people in the prototype of in his basement. And he started selling out. Almost all of his traffic was typing traffic, just somebody wanted to bobblehead they go, where do you get a bobblehead? Just go to, I guess He had no SEO, no paid search, everything was typed in traffic. And I talked to him quite often. He's local here in Georgia. So I see him quite often. And he was like, yeah, that's how I got this whole thing on its feet. So he spent roughly 30,000 I think for the singular and then was able to acquire the, excuse me, he got the plural for I think 30. And they got the singular for roughly 20,000. So all in was in for around 50,000. And now he employs I think 13 or 14 people north of Atlanta and does almost all the Presidential figures. He's gotten relationships with all these kinds of foundation boards to make presidential figures bobbleheads. And does he has some contracts, I think with Walmart to make these collectible bobbleheads for them is fascinating. His office is just littered with bobbleheads everywhere. It's amazing. But yeah, so I quickly realized back to the .com stuff. In order to keep this moving, I need to keep this simple. I don't need to overthink it, focus on .com. And then try to find an interesting term that might be fun for me to develop, where I can really solve an interesting pain point, potentially. But be patient with it. I tried to make sure I was patient, wait for the right one, give it a shot. If it doesn't work, try my best to learn. I tend to learn best from projects that work. But if it doesn't work, don't beat myself up too much about it. Try to learn a little bit, see if I can sell the domain, move on, it's over, go to the next project and try something else.

Arvid Kahl 53:01
Yeah and I think you've gone through a lot of domains at this point, right? You probably had a lot of little projects here and there. One thing that I do wonder, as you had so much exposure to all these different fields, are there any industries that you would never go in or never go in again? After having some experience with that? Like, is there anything you wanna stay away from at this point?

Peter Askew 53:23
Probably as far as me doing, it would be like custom software development. I'm not very good at custom software. If I do it, I would either partner with a subject matter expert and let them do the custom software development and I can give feedback on how look and feel might be or maybe SEO or paid search lead generation, the conversion aspect. I learned that from call tracking. I wasn't very good at custom software development. And the hardcore sales the started noticing like the two different types of sales that at least that I'm getting exposed to is, I tweeted this out the other day. There's one type of business that I build that sometimes requires a face to face, dude ranch was an example. It helped that I was physically there shaking people's hands and making the conversion there versus ranch work where somebody is visiting the site. It's almost self serve. They come in, make the decision themselves, hit the purchase button, it pings Stripe, the money is pay. They take their cut and it gets deposited into my bank account. I vet and curate the listing and post it live. And what I found is I tend to prefer building these self serve models with maybe one project that is very front facing, birthday parties is that for me right now but it keeps struggling because I'm still getting out, it's getting better from the COVID aspect but it's that industry is so fragmented. I'm having a lot of challenges on how I find dude ranching, it was nice because they all hang out in this one conference that I could go visit and then I could go visit them individually when the summer starts, which was fun for me to do. The birthday party industry is typically like family entertainment centers so to be you know, rock climbing walls or go kart centers or batting cages very fragmented. And I'm working through this right now on how I try to find where do they hang out? Some of the existing places they hang out are

Arvid Kahl 55:35
Probably secret clown car somewhere where all the birthday clowns hang out. It's like in a really, really small confined space

Peter Askew 55:40
I would probably fit in very well there if I could find that clown car.

Arvid Kahl 55:44
I bet there's forums somewhere hidden forums. I found this with lots of communities, like these special interests communities. There's some forums from the 90s, like PHP bulletin board that nobody knows, that's not even listed on Google because nobody ever links there. But there's a community of like, 20,000 people. I bet there's something in that particular industry too, but that's super hard to find, right? That's always the challenge is to find that one particular community to then inspect and build these relationships with people. Yeah, that must be hard.

Peter Askew 56:14
Yeah, so I did find those two and so I tend to try my best to focus on these products. Vidalia is a good example. They show up on the site. They see a picture of me and Aries, the farm, our pricing models where we ship within this timeframe. Hopefully they think the site is well designed and then they make the decision purchase and the order comes to me and then I go through and start fulfilling the orders and looking at or at least scheduling the orders to get shipped out versus the sale but what I found, Arvid is I learn a lot when I'm physically face to face selling when I'm trying to serve someone that's taught me a lot. So I do try to force myself into those situations because it does to your point it takes me out of my shell because I'm like you. I'm stuck behind the computer. A lot of times I consider like my job is my job working on this computer is to distance myself from working on this computer to get whatever I'm working on should be a key to get me out of here. In some aspect dude ranching, I go on 1000 mile road trips. I go visit dude ranches all around the rocky mountains, wonderful! Vidalia, I get to go hang out at an onion farm and Vidalia, Georgia and hang out with just these wonderfully, you know, kind and generous people that they work the earth and they grow this really amazing boutique onion. And they're just salt of the earth people really just great people to hang around. So I learned something from them. So that's what I've found is like, well, a lot of times when I look at domains, it's like, what adventure can this thing take me on selfishly? What are you gonna do for me? I know I can build you. What are you gonna do for me? Is this gonna teach me something? Can I hopefully support myself? Can I serve someone? Can I serve a farmer? Can I serve a dude rancher or a family entertainment center provider? But there needs to be a little in it for me. I want something fun. I don't wanna wake up, I'm like, okay, I gotta do my expense reports again because I did X, Y, Z. But birthday parties, hey, I'll go to an arcade because they're one of my customers and play a claw game all day. I'll do that. But I haven't gotten the thing to make money yet. So, but that seemed attractive for the birthday parties. I was like, I like claw game that's fun. And oh, gosh!

Arvid Kahl 58:42
I love that!

Peter Askew 58:42
My job could be going to visit places and play claw game. I'll do that. I'll try that and see what happens.

Arvid Kahl 58:48
That sounds like such a fun way, like quite another really fun way to approach building a business to look for the thing that's in it for you and everybody else. So in a very expensive kind of thoughts that starts with yourself is selfish and become selfless, like just through radiating out, empowerment and helping people serving people. And what I really, really appreciate about this is that you come back to mentioning the connection that you built with the people that you serve, either through going to conferences or making sure that they can get as low friction as possible in the things that they need or get the highest quality goods because you know that people who are working the soil, who are growing the onions. Connection is such a central part of entrepreneurship, done well. And I see you do this so well, even here with me and sharing your story. I'm really happy that I got to talk to you today. And I think you are a wonderful person to follow for advice for cool domain ideas even if there's a .net at some point. But where can people follow you? Where can people learn more about you and your journey and be inspired by you and your work?

Peter Askew 59:53
No, thank you. I typically hang out on Twitter @searchbound, which is a nod to my searched world paid search. So I'm always and then bound was Bound Search. I'm always other search bound looking for a product or project or a domain or SEO that's all search bound came around. And the .com was available. I could pay in registers. I'm like, oh good, I register

Arvid Kahl 1:00:18
There you go

Peter Askew 1:00:19
Primarily Twitter and then I write. Let's see, I write you can primarily find all these little essay things that are right if you type in it's a .org. So I have my last name .org, And then it's like a little homepage for all the stuff that I write or projects that I'm working on or just things that I'm building that are just simply fun. I just do it anyway, I don't care. I recently moved to Savannah. And there kind of central park down here is called Forsyth Park and has these live oaks, Arvid. It's beautiful and with moss hanging down from the trees and so I was like who is So I checked it. It had been owned for like 20 years and lo and behold they didn't renew it. Nobody backordered it so went out for open registration. So I don't think I'll ever make me any money but I bought for I was like, I wanted to learn how to build this website builder called dorks. I've built it on dork but primarily going back to your question primarily on Twitter, @search bound and then, will link to some of the essays if you wanna read like how I bought dude ranch, how I monetized ranch work, how I got laid off a lot and forced me into this corner. Like I didn't wanna be an entrepreneur in many ways, but I'm glad I am. And it taught me that I am. I write some of those essays through a site called Deep South Ventures. But it's linked on

Arvid Kahl 1:01:47
Well, I'm glad you are an entrepreneur. I'm glad you have been backed into that corner and you know, figured out a really cool, insightful and inspiring way to leverage the technology that exists to build things that people need. So thank you so much for being on my show today. That was an awesome and really, really inspirational conversation. I can't wait to look for domains now. Honestly, I didn't do this before. I'm now inspired to do this. It's really cool. Thanks so much.

Peter Askew 1:02:15
No, I appreciate you having me on. Thank you, Arvid.

Arvid Kahl 1:02:18
And that's it for today. Thank you for listening to The Bootstrapped Founder. You can find me on Twitter @arvidkahl. You'll find my books and my twitter course there as well. If you wanna support me and the show, please subscribe to my YouTube channel, get the podcast in your podcast player of choice and leave a rating and a review by going to ( Any of this will really help the show. So thank you very much for listening and have a wonderful day. Bye bye