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Shane Cultra and Sean Markey of Winterline.com discuss domains, branding, SEO, and running successful online businesses.
SHANE: It's our first Winterline podcast. We haven't come up with a name yet, but I like Sean and Shane — that's what we go by. You don't answer to Shane, but I answer to Sean.
SEAN: No, I don't answer to Shane.
SHANE: Yeah, I've been called that my whole life. But we're gonna have some fun — go over domain names, digital assets, business, things in the news. Get our takes from a domain standpoint, a marketing standpoint, and from yours, a SEO standpoint.
I'm Shane Cultra. I've been in the domain space since 1999, active since 2008 — and when I say active, I mean actually making money. So it took me a decade to figure out what I was doing. Sometimes things take a little long. I'm known as Domain Shane, but also Garden Shane, and various other things. So I'm a master of nothing and good at everything. I'll chime in on things from a high level. Let me let you introduce yourself, Sean.
SEAN: Yeah, I'm Sean Markey. I've been doing SEO for about 15, 16 years now. I worked at agencies, built my own affiliate sites and sold those. I've been writing — I guess a critically acclaimed, commercially not-so-acclaimed — SEO newsletter for probably six or seven years now called Rank Theory, and I also co-own the Advise Marketing Community.
SHANE: I'm gonna start right out of the gate here with AEO. That's something we're hearing all the time. With domain names, you're hearing people say, "Oh, it could be the end of domain names" — although we've heard that for 20 years. QR codes were gonna kill it. Apps were the big one. Nobody's gonna need domain names because we're all going to apps. Obviously none of that materialized. I use the analogy that we're always gonna buy food, but how we get the food will change. So I think we'll always need domain names, but what leads us to those actual sites will change over time. What's your take on domains and the overall atmosphere in search?
SEAN: I think domain names will continue to be important, and I know I'm biased saying that as someone who's interested in them and wants to help people buy and sell them. But even with AI — maybe the domain name matters less upfront — I think what the LLMs are trained on will still default to domains that look trustworthy. Something with three dashes in it or a .cx extension, versus a oneword.com or a .ai or even a .org. The training data has a bias toward clean, recognizable names.
SHANE: Visually, we say it all the time: it's about exuding trust. At a glance, majorkeyword.com gives most people the signal that they're probably going to a legitimate site rather than something with three words and a weird extension. Would you agree with that?
SEAN: Yeah, yeah.
SHANE: So I think the highest-premium names are going to be more valuable than ever because they're a visual, quick-trust signal. And the word trust comes up constantly. When I'm going to conferences and talking about AI and agents, that's what they're talking about — security, trust of the agents. Because everything's "agentic this, agentic that" — you don't have to do anything, your agent does it. But there's a liability in allowing something else to act on your behalf. People are going to look for trustworthy things, and the domain name is going to be one of those trust signals under the caption of your search result.
As far as content goes — you write a website, put out all this content, and AI scrapes it and throws it into their LLM. You're still putting that content out there only to have it land somewhere else, hoping it comes back to you. Are you more inclined to put out better content or pull back? What's your take?
SEAN: I think there are kind of two buckets. You want to put out good, trustworthy, authoritative content so that when people read it they trust you and want to hear what you say — and because the LLMs are going to read it too. Unless you block them. But I don't think you should. I think authoritative, good content will still matter.
SHANE: Are you writing for LLMs or for people? I know that sounds cliché because you're always writing for people, but what's the real answer when you're building a site?
SEAN: I think there's a balance. And the other part of it — I own a marketing community — we don't allow any AI writing in there. It's all human-authentic. I think that's where premium, valuable content is moving: behind a paywall in a curated, managed community.
SHANE: Yeah, that's how I see it going. People will pay more or give more direct clicks if they feel the content is human. Is that moving to Substack, to newsletters? That's the only place I feel like I can find a real writer now — a private newsletter.
SEAN: Yeah, even then, I constantly see emails like "I've made a new newsletter system — just tell it what you want and it feeds stories." So it depends. A writer like Ben Thompson from Stratechery — that's not AI as far as I know. Really dense, valuable content. That's what people are going to keep paying for. Because trying to rank on generic stuff? That's mostly going to be AI. Not very valuable.
I was looking at Zapier's blog today. Really high-quality content, but it's not saying anything special — "the 10 best productivity apps." They didn't do five months of research. It's just, "This is going to rank on our DR 90 blog. Let's make sure it's not terrible." That's what people write for because that's how discovery works.
SHANE: Discovery is the key word. Without getting discovered, no new people are coming to your site. You hope that once someone's there, they don't have to go back through engines again — but you do need new customers. You need ideas generated from your content, and you hope they think, "That was good. I'll go back there instead of using the AI."
SEAN: Right. And to bring it back to domains — I'm not a very technical guy, but think about all the data these LLMs were trained on. Where did that data come from? It came from well-known brands. All those well-known brands have really good domain names. They probably weren't training on terrible dashes and weird endings and misspelled names. So there may be an inherent bias in LLMs to recognize and trust clean, authoritative domains. I don't know if that's definitively true, but it feels true.
SHANE: Yeah. When you can see where the weight is — they're going to Reddit because it's the most natural human conversation, unfiltered opinions and statements. YouTube is heavily weighted too, same reason: people putting out content that's valuable and informative. And that all translates to: a good name gets there too. They picked their training data to filter out AI-listicle slop.
SEAN: It's getting that way. There are already really effective services that will post on Reddit for you, find places where you should be mentioned and post there.
SHANE: So they figure out what's weighted, then the system adapts, and it evolves. Something that started out authentic becomes a little less authentic.
Well, that's pretty much everything in the world. I've always been about authenticity — I'm looking for the people who are. Not that they can't be paid or have biases — that's human nature — but I want to find people who curate better than others and go to them for answers.
Let's switch it up and talk about digital assets and domain cycles. There's no doubt that when money floods a market — blockchain, crypto, whatever cycle we're in — it changes how much gets spent on domain names. A good business market drives names up. When Trump was putting tariffs on things, when we're talking about war, when there's uncertainty, people are less likely to spend big money on anything that doesn't derive immediate value.
So let's talk about SpaceX and all these new IPOs. Do you think the trillions of dollars getting into the hands of tens of thousands of people will affect the domain market?
SEAN: It may a little bit, but I think this is a different situation from when crypto was running. You had a lot of people making crypto businesses, they wanted good domain names, and they were well-capitalized. I don't know if the people who work at SpaceX are super entrepreneurial in the "I'm going to go start my ideal startup on a hot domain name" way. You might see it with the VCs and the people who put capital in — they're interested in starting and growing businesses, and maybe they have more capital to deploy. But I don't know how many entrepreneurs at OpenAI want to start a business and need a premium domain. What do you think?
SHANE: That's a good point. A lot of the money's going to people on W-2s who will probably continue to work there since it's so lucrative. But you're right — there are a lot of VC companies that had money in these, and that will come back to them. They'll deploy it back into other startups. They do what they do: take the winners, invest in another handful, throw the darts, and they'll all need domain names.
Which brings me to YC Combinator. It's a great incubator to watch for what new companies are doing with names — what TLDs, what extensions. There's something pretty obvious by looking at the spring and fall batches. Something like 90% — probably not literally that high, but it feels like it — are ending in AI. Almost all of them are agentic something. Have you looked at what's coming out of YC lately?
SEAN: Yeah, we put a list together. It's interesting to see all the AI names. It's very stark — "Oh, it's definitely AI, that's where everything's going." We knew that, but it's one thing to know it and another to see the list. They're all very much startup names. Misspellings, modifiers — try, use, get — in front of a keyword they want to own but can't afford yet. Super interesting.
SHANE: Anytime I see a big keyword, like Hyper for instance — I know out of the gate it's not going to be hyper.com, and I would've guessed hyper.ai. Hyper is a new company coming out that's a "self-driving company brain" — basically an AI manager for an entire department of your business. Like a division manager for all these different brands. And they went with heyhyper. Which again — we knew it was going to be Get Hyper, Go Hyper, Find Hyper, and that's exactly what they did. That's across the board for most of them.
Another one is Parrot. It's for insurance. If I asked you what Parrot was, would you have any idea?
SEAN: No.
SHANE: Maybe something that talks? Maybe squawks?
SEAN: Yeah, I was gonna say maybe something about squeaking.
SHANE: Yeah. It's actually a voice AI for the automotive industry — it takes calls and negotiates insurance claims on your behalf. Supplements, parts, coordination. And their domain?
SEAN: It's their domain — is it Parrot.ai?
SHANE: It's useparrot.com — a .com. Which is interesting. I wanted to note that Hey Hyper went .ai — heyhyper.ai, not .com. I looked it up and hyper.ai is already in use, looks like an open-source project, so that would've been harder to acquire. But heyhyper.com is for sale at around $3,800.
SEAN: Oh, yeah.
SHANE: It's interesting they went with the modifier plus .ai route. I haven't seen as much of that. Normally it's a .com several levels down — you start with hyper.com, can't get it, go to hyper.ai, that's taken, go to modifierKeyword.com, and at $3,800 it doesn't seem like a huge cost to get heyhyper.com. But that's the choice they made.
SEAN: And the difference is what? $79 a year versus $3,800 and then $10 a year. But that seems to be the norm across the board — although UseParrot did go .com, so they're at level three on that scale.
And honestly, maybe Parrot is going to negotiate your insurance claim for you — because that is a pain in the ass. Imagine just going, "Here are 20 pictures of the damage. Call the insurance agent and handle all of this." Nobody's gonna have to have any crucial conversations anymore. Your agent has all the crucial conversations.
SEAN: I'm here for it. Yeah.
SHANE: That's perfect for you. They're gonna say, "Oh man, Sean was the nicest guy." And you'll be like, "Oh no, that wasn't Sean. That was Sean's AI trained on—"
SEAN: Yeah, trained on AI.
SHANE: A couple other ones I thought were interesting. Apollo Atomics — they did go with apolloatomics.com. It's a modern nuclear company. Their take is that nuclear power takes too long to set up — five to ten years — and their version is a reactor 50 times smaller but with the same energy output. How do you like that?
SEAN: You mentioned Chernobyl, but what decade was that thing built? If technology and innovation scale, you can in theory take a proven energy concept and do something innovative with it. But yeah, it's nice to have something tried and tested that's not going to blow up.
SHANE: Well, smaller is definitely smaller. Maybe those movies where there's a little nuclear reactor sitting in the back room are becoming a reality. They said setup time is going to be 18 to 24 months — just a huge, huge difference, and that would change the game if it becomes real.
My stocks wouldn't actually be very good, because a lot of my Bloom Energy positions are based on needing fast deployment. If you can throw out a nuclear reactor in a couple years, that changes things. But it's a YC Combinator company — just started, so it's probably more theory than a working nuclear reactor in the backyard.
SEAN: Probably worth setting up some Google Alerts so you could sell when it gets traction.
SHANE: Exactly. Small nuclear reactors — we've seen them in movies forever. In Fallout they had one in a little tube that powered a whole city. Maybe that's coming.
There was one more that was really interesting: Amborus. One of the very few with an exact-match .com. But it's A-M-B-O-R-U-S, which was probably pretty easy to get.
SEAN: Yeah, it's not a great name — because what vowels are those? If someone's listening, how do you spell that before they've seen it written down?
SHANE: Yeah. Anne... Borrass. I—
SEAN: Because the tendency is going to be to say amber-ass. Or ambor—
SHANE: Em—
SEAN: It doesn't mean anything as far as I can tell, and it's not clear which vowels go where.
SHANE: Yeah. It's another agentic one — you connect your Shopify store and hand it over, and it constantly optimizes, analyzes conversion rate, changes things. Essentially you hand it your store and it monitors and adjusts everything. That's going to be huge, because Shopify changed the world for small businesses. But if you're competing against a company running this and you're not, everything on their end is being optimized constantly. That's going to be tough.
SEAN: I agree. I thought that was pretty cool.
SEAN: I want to talk about one more. I want you to try and pronounce this one — I said it was a strong brand name. It's right above it on the list I sent over.
SHANE: Claimy?
SEAN: No, below that.
SHANE: Oh — Astria?
SEAN: A-S-T-R-A-E-A.
SHANE: Astraea? Astri... Astraea. That's it.
SEAN: That's it. And the fact that they couldn't get the .com or the .ai and had to go with TryAstria — that tells you something.
SHANE: It's a Greek goddess of justice, innocence, and purity — if I'm getting this right.
SEAN: Never heard of her.
SHANE: On the one hand, it's nice. Greek gods and goddesses make solid brands. But that's way harder to pronounce, and it's not a well-known one. It gets 3,800 searches per month in the US.
SEAN: Yeah, they probably put it in an AI and said "Give me a Greek god name" and that was the last one on the list. You could probably have put try in front of a lot of Greek stuff and gotten those names for cheap.
SHANE: What's the business?
SEAN: Smarter, faster, safer clinical trials with agentic AI.
SHANE: That's a big deal. I mean—
SEAN: Nothing to do with purity and justice. It's just a complicated name for no reason. I guess I'm a hater. I don't know.
SHANE: No, I'm right there with you. I love the business model. But as people who do naming and branding for a living, you shake your head. Not because we don't understand that finding the perfect name is hard — but there was a whole bunch above this. And they're going to tell us "It's more important what we're doing" and so on. But at some point, the name matters if you want to be found.
SEAN: It's hard to tell your friend about this. It's easy to tell your friend about GoodRx.
SHANE: Yeah. And that's not a premium name by any measure, but in terms of memorability it's enormous.
SEAN: That's what you're looking for. It tells you exactly what it does. Nobody is ever going to misspell GoodRx.
SHANE: Exactly what they do.
SHANE: Let's talk about drugs. We can't be in the world of the internet without talking about peptides. I was curious myself, and I'm sure every domain name investor has been looking through peptide names that are available. So I looked up who ranked for what and gave you a sheet.
Does the word peptide make a difference? Are there any exact-match domains that perform better than others? And when you look for "buy peptides" — what would you search if you were buying them, Sean?
SEAN: These days I would go to Gemini and be like, "Hey, this is what I want, how do I get it?"
SHANE: Where can I buy peptides?
SEAN: Yeah. And it'd probably come back, "Sorry, I can't help you with that — medical—"
SHANE: I've done that. I didn't put that in the sheet. But I did ask Gemini one time and it actually responded: "I can't tell you how to mix your water and Retatrutide because it's not FDA approved." I'm dead serious. It wouldn't tell me how to do it. So I had to go over to Google Gemini, and it was like, "Over here — I'll tell you all about it. You got a needle? Show me the needle." Completely fine. I don't like morality in my AI, honestly.
SEAN: But they don't like lawsuits, so.
SHANE: No, I get it — especially with medical. I guarantee they'll give it out if you prompt it right.
So for "buy peptides," the top organic results are Phoenix Peptides, Biotech Peptides, GenScript, RPeptide, and Biosynth. Three of the top five have peptide in the name, and I imagine they're killing it.
Did you visit phoenixpeptides.com?
SEAN: No, I didn't even go. Is it—
SHANE: Pull it up. Tell us what happens.
SEAN: Am I about to see something sketchy?
SHANE: No, it's safe for work.
SEAN: Okay — "Orthopedic regenerative"? Wait, did I type it in right? It's going to Grace Orthopedics, forwarding somewhere.
SHANE: 301 redirect. I don't know why.
SEAN: Ha — good buy. Let me see what they're doing in terms of... Oh, phoenixpeptides — Phoenix Peptides doesn't have any—
SHANE: Oh—
SEAN: Search — once I click on it, it goes to Research Peptides, antibody, and assay kits. It does go to a site. Did I type it in wrong?
SHANE: Phoenix... pub trades?
SEAN: Yeah.
SHANE: Maybe it's in the sheet wrong.
SEAN: Oh, I know why — it's singular. It's not plural. Man, I don't run a good show.
SHANE: So Phoenix Peptide is singular, but Biotech Peptides is plural. Look into any others that have peptides — no. I think that's a good branding lesson: own both, singular and plural.
SEAN: Yeah. And right — if you're selling more than one thing, which peptide do you want? I think I'd rather have the plural.
SHANE: Let's see. So peptide singular has 52,000 searches per month in the US—
SEAN: Yeah.
SHANE: —and peptides has 203,000.
SEAN: Largely the same Google results — Google treats this as essentially the same keyword. But based on volume, the way people actually search and speak is plural. So Phoenix Peptide singular is a bad choice based on this.
SHANE: Yeah — kudos to their SEO team for ranking number one on "buy." But they're not taking advantage of it. I guess they could get sued, but still.
SEAN: Just looking at how their SEO looks overall.
SHANE: Yeah, it's—
SEAN: Not super strong, no surprise. But they are starting to pop off in AI citations, which is an interesting thing to look at.
SHANE: They're definitely putting in the work, there's no doubt about it.
Now, I broke it down for Retatrutide — nobody calls it that, they just call it Retta. So if you type in "buy Retta," you get five companies that don't have Retta in the name: MyBioSource, Medika Depot, Magellan Rx, GoodRx — I'm surprised they weren't in the peptides results too — and Novo Pro Lab. Nobody just pushing Retta sales is in there. It's companies that have done a great job ranking broadly. Once you have a great DR, you start hitting all the good keywords.
SEAN: Yeah. Just looking at the results — almost every single one is not a company that just sells that one thing. They sell a lot of things. So it's product pages ranking for these keywords, at least.
SHANE: Yeah. And I looked at peptides.com — we just said it — that's a multi-million dollar name. Ten, fifteen million dollars at this point. Maybe more, given the sales you could pump through it. But it looks like it's not even a real site yet, just a staging page.
SEAN: I think it was probably recently sold based on the "coming soon" and how hot this space is, with all the disclaimers at the bottom. I actually did some SEO work for a peptide site about two years ago, and they're closed down now. The regulations were too much to overcome. They just said forget it.
SHANE: Across the board, I've noticed a lot of "DM me your order" type operations when it comes to peptides. And there are testing labs that will test anybody's peptides for free and publish the results. The ones that score 90-95 out of 100 are always sold out. We're in the Wild West of peptides. It's a huge market — billions of dollars. Retatrutide is in phase three and will probably be FDA approved by 2027. You can't scroll TikTok without seeing some bro talking about his peptide stack.
I also noticed peptide.com is out there and working, but it's ancient — not modern at all. They've evidently had it quite a long time. And buypeptides.com is for sale.
SEAN: Did it say how much?
SHANE: A lot of peptide names are for sale. I didn't inquire about buypeptides.com.
SEAN: Probably not the niche to play in unless you're super well-capitalized.
SHANE: Yeah, that's going to be a big-boy game.
I pulled up the top peptide domain sales of all time according to NameBio. Want to give thumbs up or thumbs down on the name and take a guess at the price?
SEAN: Okay — go ahead. Give me the name first, go in order.
SHANE: Okay. PeptideLab.com.
SEAN: Hmm. That's a great one. Would the plural be better?
SHANE: In this case, I like the singular. I think either works, but Peptide Lab feels like an entity — "The Peptide Lab." When you call a business the lab, you're not necessarily expecting it to be a literal lab. It's just a representation of a business. I like Lab a lot. That's a good one. How much do you think it sold for?
SEAN: Depends on when. What's the story?
SHANE: After NamesCon last year.
SEAN: Oh, so — 50 grand?
SHANE: $24,995.
SEAN: That's a good pickup. Not a bad guess for how late in the cycle of popularity that happened.
SHANE: Yeah, that's a great one. All right — peptide.co.
SEAN: Hmm. Feels more like a domainer buying it than an operator. We already said peptides is way better. I'll say $10,000.
SHANE: Five.
SEAN: Yeah.
SHANE: And I don't love .co.
SEAN: Same. But that one has a site built out on it and Peptide Lab still says "coming soon."
SHANE: Yeah — someone might have hit buy-now thinking they got a $100,000 name. But if they get any sales at all with good margins and they can stay afloat and not get sued, they'll recover that $5K fast.
SEAN: The third one is copper peptide.
SHANE: That's the biggest market — outside of Retta — when it comes to peptides. I'll say ten grand. But I know that market is probably as big as any of them.
SEAN: $5,000. Seto, March 24th.
SHANE: Yeah, no — that's actually the one I personally use. I'll tell you why without giving out my full health data. That's GHK-Cu — copper peptide — and it's for skin and hair. Women are using it, men now too. It's almost like collagen — it strengthens skin and reduces wrinkles. They're putting it in topical creams too. It's like the peptide facelift, they call it.
As someone who uses it and is trying not to lose his hair — I think it seems to be working. I still look old. It's not like I'm Brad Pitt. But there's something to it. And I think outside of Retatrutide and other GLP-1s, copper peptide will be by far the biggest seller once it gets FDA approved. Half a trillion dollar business in time.
But the technical name — GHK-Cu — is really hard to say. Copper peptide is much easier. So that $5K was a good buy.
SEAN: Definitely a goodbye. I'll do one more — researchpeptides.com.
SHANE: That plays into what we were talking about — people wanting trusted sources. It wraps up everything. People want to feel like someone's actually done testing and research. Whether that's true or not, it certainly comes across. I'll say three grand.
SEAN: In 2015.
SHANE: Wow. That was an early buy.
SEAN: Yeah. I tried to see if there's anything on the site, but I'm accessing from Europe and they blocked me.
SHANE: Peptide, peptide, peptides — that's the top sales.
SEAN: That's four of the top five.
SHANE: Of all time, publicly. Wow.
SEAN: After that, it's all brandables.
SHANE: It's incredible. If you think about the market — on social media it's everywhere — and yet the domain names haven't caught up. Doesn't bode well for people trying to hold those names in the short
term.
SEAN: I think it's still fairly early. You can't really buy these things online in any mainstream way. When I was in the cannabis and CBD niche in 2017, 2018, cannabis had been around forever so everybody had their nicknames — 420, weed, grass — but CBD was newer and there just weren't that many things people called it besides CBD or "canna-something." The naming conventions were really consolidated. I don't think we're there for peptides yet.
SHANE: Yeah. Everyone's still buying it from some guy on Telegram, not from a website.
SEAN: That's a great point. It's such an immature market. Remember NFTs used to be called Nifties before we even knew what they were? People were buying "nifty names" and then, "No, no, it's NFT now." Peptides — I think that name sticks. But I agree, the market is early and we're not monetizing it anywhere near what it'll eventually be.
Although — with Eli Lilly owning the patent on Retatrutide, whoever's in distribution with them will be the only ones with it. So the naming conversation for that specific peptide will eventually be a pharmaceutical one, not a domain one.
SHANE: I know people are buying peptides like crazy. I tried to buy peptidestack.com and peptide stacks, and they were asking not-terrible amounts, but definitely more than anything on those charts. I would've been the all-time high on peptide names, which I don't really want.
Can I ask — do you know any of these peptides? Like, do you know what BPC-157 is?
SEAN: I've heard of it, but I don't know what it does.
SHANE: It's an injury recovery injection — helps heal muscles, ligaments, tendons. Everyone I've heard from says it's a miracle drug. Now, anything that grows and heals non-selectively is not something I personally want to mess with, but people who've used it post-injury say it's better than stem cell injections.
As a runner — and us old guys always get hurt — we're always looking to heal faster because we're psychotic and can't sit on the couch waiting. So first you try PRP, where you spin your own blood and inject the platelets. PCP is a drug. PCP will f you up. That's totally different. Don't do PCP if you get injured. PRP is what the doctors will tell you about. Then there's stem cells — from umbilical cords or your own. And BPC-157 is kind of in that same realm of regeneration. But if you've got something else going on in your shoulder, that worries me a bit. I'm not one to tell people don't try anything — I'm taking Retta and GHK-Cu, so don't listen to me. Lab rat. All right.
SEAN: Nice.
SHANE: Popular one: Thymosin Beta — TB-500 as they call it. Do you know that one?
SEAN: I've heard of it — I worked on these pages — but I didn't really retain what it does.
SHANE: Yeah, that's repair and regeneration. Not as traumatic-injury-specific as BPC-157, but fitness people use it to recover faster. Work out, use this, recover quickly.
SEAN: Do you think taking a name like TB-500 — that's not a good brand, right? Like for comparison, going back to cannabis: Blue Dream is a great brand, but TB-500 is never going to be a brand someone builds.
SHANE: It's going to need to evolve. Like Retta — Retatrutide, they call it Retta. That works. GHK-Cu doesn't have that same quality. TB-500 sounds like a cleaner model number. It's not sexy. It'll evolve, and I guarantee there are domain investors trying to get ahead of it — coming up with something like Thymo-X or some brandable around it.
SEAN: Some brandables, yeah.
SHANE: And this next one I don't know well — tirzepatide. Oh, wait — yeah, I do. That's like Retatrutide. I've seen that. It's on the GLP-1 side, the semaglutides. Comparable to Retatrutide but probably more established — it's in the Mounjaro/Zepbound family.
SEAN: Oh yeah, it's all made up and yeah—
SHANE: All made up. The name can't mean anything at all. It has to be totally unique and defensible. That's why they're all such terrible brand names—
SEAN: That's why they're all such terrible, terrible brands.
SHANE: Exactly. And they try to rhyme it in the commercial — "Diarrhea, constipation" — and then they sing a little song and somehow make it sound fun. It is funny to watch them try to turn horrible side effects into a little dance.
The last one I don't know at all — Ipamorelin. Recovery, sleep quality, body composition, popular growth hormone secretagogue.
SEAN: Never heard of that.
SHANE: Yeah, I'm not taking any growth hormones at all. Not gonna touch it. But you can't deny it — in the world of domain names, we're always looking for the hottest segments. That's what people do. Personally I'm a word guy — I want open vessel stuff. I want a name that can be anything, maybe exudes a category, but is defensible and easy to spell. I'm a Rich Barton kind of guy — he's the Expedia/Zillow guy — where I want it defensible, easy to spell, maybe category-adjacent. I bought a lot of names ending in O — Cello, Weba — those kinds of names I think are great brands.
But it's hard to deny that a name like Parrot isn't a great brand. Those types of words are really good. The problem is when people don't have money for a one-word premium name — even a five-letter .com is now $2,000-3,000 — so they reach for new tech. They read all the latest publications and try to stay ahead of emerging categories. That's a little squatty, don't you think?
Nothing against Rick Schwartz — one of the greatest domain investors ever — but he was bragging today about intelligentglasses.com. To me, that doesn't make sense. What are your thoughts, especially since exact match is basically worthless for SEO now?
SEAN: I don't think they're worthless. If you know what you're doing with an exact match, it can still help you rank. It can help you get mentioned in ChatGPT — having an exact match site, even a .org or a .co, can still juice your citations. The easy money's gone, so everyone writes it off. But in my experience, there's still something there.
SHANE: So you're saying it's not worthless — it's worth less, as Brayden Pollock would say.
SEAN: Yes. But the domain itself — intelligent glasses — nobody says those words in that order. If anything, you call them smart glasses.
SHANE: Yeah, and I think—
SEAN: This is my smartwatch. Nobody says "intelligent watch."
SHANE: Smart glasses is better than intelligent glasses, for sure. But if you look at comparable technology, no one cares about a "smartwatch" either — they care about their Apple Watch. In this case, exact match isn't helpful, in my opinion, because no one is actually searching for that.
SEAN: And what do you even do with that name? You're selling other people's stuff?
SHANE: Basically.
SEAN: Can you even sell Apple products on a third-party site like that? Do people buy Ray-Bans or Warby Parker glasses anywhere besides the manufacturer?
SHANE: I think you could maybe at retail — Best Buy. And you already trust Best Buy. But I wouldn't go to smartglasses.com to buy an Apple Watch. I'd go to apple.com because I know they'll ship it in three days and it won't be fake. This is a category where if you're buying branded items, you buy by brand. If you're buying sunglasses, you buy Goodr, Roka, Oakley. And Luxottica makes literally 95% of all glasses in the world — so branding defines everything in glasses. Rick might have picked the worst category for exact match, because glasses is purely about brands. The only thing you buy un-branded in eyewear is readers.
But Rick knows what he's doing — he's done an amazing job over the years. This isn't me saying he's wrong. It was just the one that caught my eye.
SEAN: It'd be a rough build out.
SHANE: Yeah. And that's how I evaluate domains.
SHANE: How about Notion.so? They announced today that they're moving everything to Notion.com, and James Iles said they've owned the .com for a decade — they just waited until now to move. What does that do to the .so extension? Somalia was a bit sketchy to begin with, but Notion gave it social proof — people said, "Well, Notion's a billion-dollar company. If they can use .so, I can." What are you thinking?
SEAN: A lot of people went that route. I don't think the switch kills .so — I think it was just established. It's smart to go to .com when you can, though.
SHANE: Yes — in general, smart to grab the .com. That's good advice.
SEAN: Yeah.
SHANE: Going the .so route is risky and questionable long-term. But it clearly didn't hurt Notion at all. They were the poster child of alternative extensions doing just fine.
SEAN: Yeah, at no point did it seem to hold them back.
SHANE: And making a big announcement about finally moving to the .com — that shows how much a company cares about the TLD. They thought it was a milestone worth announcing. It was a big deal to them. "We're finally going to the .com."
That should be a goal for most companies — at minimum, own the .com to protect yourself from leakage. Even if you keep operating on the .so, have the .com pushing back to you. Claim all your assets: social handles, every relevant TLD. The big companies will spend whatever it takes to capture all the leakage — even the small stuff. If you have deep pockets, you do it.
And I'll be honest — I run a company too. I want the typos of my company. Because if someone types the wrong thing, I don't want my competitors to take it. And if they're smart, they will.
SEAN: Yep.
SHANE: Yeah. And is it even illegal — to buy a competitor's typo and forward it to your site? Not build anything, just forward it.
SEAN: I'm not sure.
SHANE: That's a Barry Hill question. I'm sure he has an opinion.
SEAN: Yeah, I'd like to know.
SHANE: Because that's what everybody would do, right? I'd buy all your typos. That's squatting a little — or a lot — but we are domain-oriented. Still, I know where I'd spend money on my runway. If I've raised $200,000, I'm not spending $100,000 on a domain name. That's not fair to your investors or your employees. They need operating capital.
I'm not the guy who says, "Don't pay your rent, but buy Bitcoin." If you've got two months of runway, buy the best .com you can afford — and even if you fail, you still have the domain. No. That's not how it works.
Now, if I'm a crypto company with a billion dollars in coins I just minted — that's different. Maybe you do spend some of the treasury. Azuki bought anime.com. Amazing investment. Whatever they spent on that name is worth way more in terms of value captured — especially since in today's coin value they probably got it for effectively nothing. If you're sitting on a volatile crypto treasury, spending it on a quality domain is actually a very wise hedge. A good domain only goes up.
SHANE: Well, I think that's a wrap on our first podcast. We kind of went all over the board — which is what we'll keep doing. We'll have some guests on. We've got some bigger names coming on to talk to us. But we wanted to start with us. I know at Winterline we're really happy with where we're at. I love working with you. We're two totally different people with two different areas of expertise, and we've had some great conversations.
SEAN: Yeah, it's been a lot of fun. I'm super excited about where we've gotten to in just a couple months since we launched. Pretty amazing, the names we're working with.
SHANE: It's been fantastic. Even the representations we don't get — we're getting the opportunity. And that's more than we expected. We have to earn our keep. We know domain names, we know the companies, we're a little older, and we know the product really well. But brokerage is different, and the other domain brokers out there are amazing — they've been doing this for decades and they've earned their position. That's just right.
But this is what we're here to do — talk about names and the industry, which is what we do every day. Looking forward to having another one of these.
SEAN: Yeah, this was a lot of fun.
SHANE: All right. Until next time, my friend. Well actually — I'll see you in about ten minutes.
SEAN: Yeah. See you.