Ep. 3012: Personalized LinkedIn Ads at Scale

Two founders discuss AI tools like UserGems and Karrot.ai that personalize LinkedIn ads at scale, showing 7-20% ROI lifts. They share insights from a YPO retreat about founder loneliness and go-to-market confusion, then analyze how AI platforms are disrupting WordPress and reshaping the SaaS landscape.
Chapters
So let's talk about personalizing your LinkedIn ads at scale. So I was sharing an image with Eric a few minutes ago. There's a company called User Gems, I believe it is.
Mm-hmm.
And they'll say like, hey, NP Digital, but they won't write NP Digital. They'll actually slap in our logo.
Mm-hmm.
And the example I sent Eric of these screenshots, they have variations for all like, hey, AVI, SPL, hey Frontier, hey CGS. I don't know all these company names, but in essence what they're doing is they're running targeted LinkedIn ads to each and every single company with an image just for them, which obviously you can do really quickly because of AI. And when I was showing Eric, because he has Karrot, which is not karrot.com, what's the URL?
karrot.ai, K-A-R-R-O-T.ai.
Yeah, so when you check out Carrot, and we were talking about this, because with LinkedIn ads, they're super expensive, but you know, we all know personalization is important and targeting specific corporations that are your ideal fit is important, especially if you're going to do LinkedIn ads because of the cost. But why not just do creatives that are super personalized at scale? I did not actually check out their ad library, but someone on my team's like, they have thousands. And I don't know if they actually have thousands or they're using that as an expression, but yeah. Yeah, you can, you know, personalization's nothing that's really new, but you can just do this with ease now while before you couldn't. And I was asking him, I'm like, have we done this for any clients? What were the results? And they were just like, yes, it produces for when we tested it out and we've done it for a handful of customers, they were saying that it produces anywhere from a 7 to a less than 20% better ROI for the same spend, which isn't bad. Every little extra dollar really does add up.
So what are you guys using to personalize LinkedIn ads at scale?
We use your solution. Oh, you do? Yeah.
Really?
Yeah.
Wait, how do you use it?
We use it.
Huh?
Glass half full.
What?
Yeah.
That's not possible.
It is possible.
But you're not paying for it.
That's good. Yeah, we're not paying for it.
Okay, that's good. That's good. Okay, good. It's good to know that. So it's good to know that you're using Carrot because here's the thing. Here's the interesting thing here. Personalized especially in AI world, people want personalization. They want to feel like they're being spoken to like a human, right? I actually think, you know, so User Gems has one, there's another competitor in the space, they're coming out with one. And these— so User Gems, I was just checking their LinkedIn, I think they're Series B. Let me just look that up. Series A, $20 million, okay? And then there's another player in the space, maybe raised $50, $60 million, and then—
Wait, User Gems raised how much? $20 million?
$20 million, yeah. And then there's the player in the UK who copied us pretty quickly on this feature. This is the feature that we came out with in November, Wow. So these people ship relatively quickly, right? That, that's a whole thing we can talk about in a second. Like in SaaS, you're, you're better off just looking at what seems to work and just copying very quickly. Like no feature is too safe.
But these ads I think would work really well for you guys.
They do. So here's, here's what we've seen from a number standpoint. We have one customer who's willing to pay about $1,500 per lead, right? Because they're, they're enterprise SaaS. They're getting leads using Carrot for $500 a pop for these LinkedIn personalized ads. And then we have another customer, they were struggling to get this large beverage beverage company that everyone knows. And they actually ended up shaking it loose from their pipeline and getting that deal done, right? So they know it's driving customers. What I'll say to any of these people who are listening to these, this personalized LinkedIn ads thing is nice. It's not enough. It's not enough as a feature, right?
Yeah.
So that's why, you know, we copied other people, which is like the personalized landing pages, right? And then we're adding in website de-anonymization, which there's a lot of products that have that. But then we're also adding in, like for example, if I engage with one of your posts and I'm part of your ICP, we'll reveal that it's your ICP engagers happening and we'll say, hey, do you want us to customize the outreach? So there's a lot more that we need to build within this, but the very start of this personalized LinkedIn ads at scale, yes, it works.
It definitely does work. And when you're saying you're de-anonymizing visitors, you're talking about providing their email address because you know who's visiting what site, correct?
Yeah. More than that though, it's saying, hey, we found this person over here. Here's what we think you should be messaging this person. And then the more integrations we have, we can say, okay, you emailed this person like 12 months ago. Here's the conversations you've had in Gong or like email. Here's the recommended outreach we think you should do to revive this lead, right? So we think B2B, it's just like, how do you make it easier? Because, and this could be the next topic, I just came back from a B2B SaaS founder retreat where there's a bunch of 8, 9-figure founders there.
You didn't go to Vegas?
No, I want to go to Vegas. Oh no, no, Vegas is, no, no, no, don't reveal Vegas, but Vegas is supposed to be this weekend.
It's supposed to be?
Uh-huh.
So that means no go on Vegas.
Well, that's because our mutual friend was going to come, but we might do it the next weekend because The hotel rooms are $3,000 a night for this weekend.
And I get that.
I went to perplexity. I was like, why are the hotel rooms $3,000 a night? And it's like, oh, 'cause it's like a U2 farewell concert or something like that.
Yeah. Oh, at the Sphere or something.
Or no, AC/DC. AC/DC. Yeah, yeah, yeah. And that's, that's like the— I remember Beavis and Butt-Head. I think Butt-Head used to wear the AC/DC. Yeah, yeah, yeah, yeah. So, okay. You want to, you know what, want to know what I learned from this, this little retreat?
So before I want to know what you learned, I want to know The type of people that were there, roughly how many. And when I'm saying type of people, I'm talking about like their roles, but also company size. And the reason I want that is, is I can then, you know, think about the learnings respectively for company size and if it could be applicable.
Yeah, totally. If you're in B2B, here's the deal. LinkedIn account-based marketing sucks, but it doesn't have to. With Karat, it allows you to create personalized ads towards your customers and also personalized landing pages that align with the ads. So you're going to have higher conversions and influence pipeline reporting to prove that your ABM works. So if you want to learn more, just go to karrot.ai and you can join the waitlist. Again, it's karrot.ai and we'll see you on the other side. So this event, I was there from Sunday to like middle of the day Tuesday and we did it in Temecula. So it was easy drive for me. Some people had to fly from like Toronto, some people from Miami and all that, and a 2-hour drive for me. But so the group, one, I'll just give you kind of the breakdown of some of these people. So there's, they're all founders, okay? They're all founder CEOs. And I would say that some of them have built their SaaS companies to 9 figures and then sold it. Some have built to like mid-8 figures or so, call it $40, $50 million or so. Some have sold their companies for like $50, $60 million or something like that. So everyone is, they're all part of YPO. So there's a certain level. And then one guy in the group, he actually helped build Calendly. And so, you know, Calendly became like a big thing as well. So that is the setup of the group. It's a group of guys and then we just ended up chilling in like a home in Temecula.
So all 8 figures, some 9 figures, a lot 9 figures or more so like maybe 4?
Let's just say like 2 out of 8.
Got it. So most of them are 8 figures, call it like $10, $20 million-ish in revenue.
$10, $20, some like $40, $50.
Okay.
Yeah. So that's the groove. Like what? And then let me just give you something to take away.
Wait, and they were all founders or they were hired guns?
Everyone. It seems like everyone's a founder. Maybe one might be a hired gun, but that's a different story because he works with his spouse. So, yeah. And then the spouse like founded like a really big company in the past and sold for like, I think a healthy 9-figure amount.
Good for them. Yeah.
So here's what I learned, that the big thing Is people in B2B SaaS, they have no idea what to do with go-to-market right now. Zero clue. And a lot of people, it's like a sunk cost fallacy. They're like, oh, but I invested so much in SEO. I'm like, so what? Doesn't mean you deserve traffic right now. All right. So everyone seems to be confused about go-to-market, but what, where I kind of left them all is like, guys, like it is the search everywhere optimization thing. I said, guys, you have to be creating content like in some way, shape, or form. I don't care if you hire an in-house influencer and pay them like $200 plus or something like that. maybe give them some upside, or you have to figure it out on your own. Well, I don't like being on camera. Well, I'm like, so stop being selfish. Like, your job is to figure out how you can help other people with the knowledge that you have. And we started talking about the Clue.ly people, right? And then one of the guys in the group, he has like a, basically it's like, it'll screen for weapons in a school, right? Imagine that. Like, there's a lot of school shootings that happen.
His SaaS will screen for weapons?
Yes.
How? Like through a metal detector or something like that?
Something like that. Yeah, I don't know enough details, But I basically started telling people, I was like, guys, like what, what's like the most outlandish stuff you guys can come up with? And that guy was like, oh, I'm just going to walk into a store with a cowboy hat with a gun and see what happens. I'm like, that's a little outlandish. Like you might get in trouble for that.
Depends on the state, but yes.
Texas, it'll work. It'll work in Texas. You can carry in Texas, right? Yeah.
But that's what his current software does.
Yeah. Yeah.
That's a cool concept.
Yeah. And so everyone has like interesting stuff, right? Where they have a lot of data. Some might be in like KYC, which is know your customer. Some might be in like real estate where they can offer you a deal. Where like, for example, if I register, okay, let's say I register for an apartment. Let's say you're the landlord, right? Let's say you reject me, but I had to go, you pulled my credit, you did all these things, right? I did a lot of work. You rejected me 'cause I'm too risky. But what if Noah over here and like 3 other people all of a sudden can appear and say, hey, you've already done the work, we're going to approve you, right?
Yeah.
So that's a really cool offer. I'm like, how do you not just float that offer everywhere? And so I think it's just pushing these people a little more, but Everyone seems confused on go-to-market right now because the game has changed so rapidly from a marketing standpoint. So that's number one. Do you have any follow-ups on that before I go through some others?
No, keep going.
Okay. I think the second part is it's everyone wants community, right? Like we've talked about this quite a bit, like human to human, and it's apparent that a lot of people don't. I think I've gotten lucky with, you know, being in part of these different groups, right? Where I'm able to meet with multiple people once, Like 2, 2, 20 years. Wait, let's back up.
Are you talking about they want community for their customers want community or they themselves want?
For the team.
So they themselves as founders and operators want community.
Yeah, it's lonely. Yeah, 'cause they say they don't really have, you know, hangouts like this, right? Whereas I have like 2 other groups at the minimum.
But they're in YPO, no?
They are, but they don't have, so in YPO, we actually talked about this a little bit. In YPO, their forums, their core group back home, they don't really talk about SaaS and business all the time. It's more like personal stuff, right? So you would actually like a group like this 'cause all we talked about was business the whole time. So that's what I would say.
But their YPO group is mainly personal.
Correct. Yeah. And the same thing with mine. My YPO group is more personal and my YPO group likes to, they like to go out and party, right? And so like, you know, every group is different.
Yeah. You mentioned that when you guys travel, you want to go to sleep and they want to drink.
Drink or yeah, you know, it's, they like going out.
Yeah.
Yeah. So I think it's, everyone's looking for community. It's about founders. It's a very lonely game. And I think the other piece is everyone is— I'll tell you one other thing I learned. I don't want to reveal this person, but it just reinforces the fact that you don't want to have outside stakeholders as much as possible. Like some of these people have raised multiple times and sold multiple times, but they would prefer not to, because one company was forced to sell by not necessarily their investors. Well, you can say investors, but a bank forced them to sell. Because the bank thought the business was too risky, even though the business was starting to take off, the bank forced them to sell. Isn't that crazy?
That means they had debt and they were struggling to pay the debt or else the bank would've never forced them to sell.
It was a combination of debt, but also it was, their contract sizes were not like pure-play SaaS. You had some that were like government contracts that were like maybe like one-offs and then maybe like only a portion of it was like actual recurring revenue SaaS.
Yeah, but they breached their covenants. For the bank to put pressure and be able to force a transaction, that means they had debt. From the bank.
Yep.
And something went wrong and they weren't able to make their payments.
But we talked about this too with, with, you know, you, we were talking about this a little bit. It's like ideally, ideally, ideally you don't, you don't have these covenants. And ideally, what did Charlie Munger say? You go, men go broke through 3 things, ladies, liquor, and leverage. And the first 2 are for fun. So it's really leverage.
Yeah.
Yeah. So it sucks 'cause like he clearly had something going, right? The other thing I learned too is there's one guy in the group He has leveraged everything, by the way. So we're talking about leverage, right? But I don't— again, I want to—
What do you mean, say leverage everything? Like give an example.
Home, home, everything. Like, you know, you leverage out the wazoo for like your— you basically, you've pushed, put all your chips in the middle for your business. Like—
So he's maxed out his mortgage, his car loans, everything.
Everything.
Yeah. But no investors. That means—
He has investors too. And he's— I think he's like pulled Like some crazy terms too. Like I think the interest rates are astronomically high. Yeah, we're talking like 30%. I don't have the exact numbers here, but it's insane.
Wow.
But it's like, this is like, oh man, you have really put all your chips in the middle and like, I applaud you. I'm scared for you, but I applaud you for having the guts to do it.
I couldn't do it.
I can't do it either. I just, I think that would hang over my head.
Is that person married with children?
Yeah.
Oh, I definitely couldn't do it. If I was single, not married, no kids, it's a different story.
But you know, his whole thing is like, I look, no matter what, it's going to be a great story. I'm like, that is true. It's going to be a great story, whether it's good or bad, it's going to be a great story.
Imagine your kids not having a roof over their head. That is not a good story.
It's not a good story, but hey, but it's still a story. Yes. Yeah. So those are just a couple of high-level things I'll say.
And by the way, I wish that person the best of luck and I'm knocking on wood for their luck. I don't want—
I think they've got something good and I hope they can figure it out. One final thing I'll say here and then we can move on. So there's one person in the group. You know how you and I talk about like the, we've had to learn our lesson with focus, right? How long did it take you to learn your lesson of focus?
More than 10 years.
Okay, same for me, right? More than 10 years. Now there's one guy in the group and let's just say he has a couple businesses, right? More than a couple of businesses. And he was basically like, what am I supposed to do with all this? Like, you know, he wants like a very big outcome at the end of the day, right? But You know, we, I kind of shared my experiences and everyone in the group was basically like, you're going to have to kill some of these things, right? But he's like, well, there's an opportunity here. There's an opportunity. There's opportunity here, right? And even though the lesson was focus, I don't think he necessarily is going to take that advice or that those experience shares. And what my conclusion afterwards was like, dude, maybe that's okay. Maybe he enjoys having all these different things and maybe he says he wants the multi-billion dollar outcome or whatever, but maybe he doesn't really want it inside. I think he enjoys what he's doing already. So just let him do it, right? There's no like right or wrong, but it's, I don't genuinely believe he wants a huge outcome and he already is doing really well. And so I'm like, maybe just keep doing what you're doing. Like forget whatever we shared, just do what's comfortable to you. I just learned that I get less anxiety from focusing.
So. Yeah, focusing makes things easier. I agree with you on that, but some people perform well with a non-focused business. It kind of can be focused. A great example of this is we have a mutual friend named Syed who lives in Florida. Most of his businesses around the WordPress ecosystem, but he has a lot of businesses. He invests in quite a few, doesn't always own majority from my understanding. Sometimes he does, or sometimes he owns 100%. Most of the time, no. And he also owns businesses outside of tech. And I look at him as an entrepreneur. I'm not saying that'll limit his earning potential because I don't believe, you know, I've seen people not have focus like private equity funds and people become billionaires from that. And they just continually buy a lot of different businesses in different verticals.
We both would agree that they're, that is their business.
That is their business. But I look at like Syed, for example, I think he thrives in that environment and enjoys it. I think you get bored with just one business.
I think so. I look at Syed as more of an investor. And the reason I say that is because the forum that he's in, in YPO, is like a fully invest— decked out investor forum.
Okay.
Right. And I think you're going to like—
I agree with this. This is minority owned for a lot. I mean, I'm not saying he's a minority, although technically he is in the US classification. But I meant more so when he's investing, he's taking a minority chunk.
He's very much a student of Warren Buffett and Charlie Munger. And so, and when he, even just when he talks in general, he thinks like an investor. And if he has to roll up his sleeves, Every now and then, like he'll do it, but for the most part he stays pretty hands-off. So I look at private equity, I look at Syed more as investors. I look at this guy as he really likes getting involved in all these different things and I'm like, okay, yeah, you know, I would say focus, but just do what works for you.
Yep.
So yeah.
On a random note, what do you think's going to happen to WordPress with all these changes with AI and like Lovable and all these solutions that can just—
Are you talking about this because of the thread? I saw a thread the other day on Twitter.
I did not see a thread, but I've been messing around with Lovable a lot recently.
Yeah.
Um, and like Lovable? I was using it to help create a better version of one of the reports, uh, a design report that one of my product team ended up sending me for Ubersuggest.
Yep.
And I wanted to make, come up with my own variation. So I'm like, let me just use Lovable and see what I can end up creating.
You gotta use v0 for that by Vercel. Did you do that?
No, I did not. I'll, I'll, I'll do that next.
v0 is better for front ends.
Uh, and I did not get the best results with Lovable. Mm-hmm. So I was like, all right. But generally speaking, I'm just like, you know, WordPress as a business, I was starting to think about it. I still think there's a big ecosystem for them, just like I think there's a big ecosystem for Shopify still, and their stock price, at least with Shopify, shows it. But I think their model is going to have to change on how they adapt. Shopify is easier because they'll just create partnerships with like the ChatGPTs if they already have it. make it easier to buy within ChatGPT, which is great for them. But WordPress, I would say, is much more slower moving organization, in my opinion. I don't have any data on who's moving faster, but like when I actually look at releases and progress, I've seen Shopify make way more progress over the years than I've seen WordPress make. And it's not to knock WordPress. They've built a bigger company than I have built. So I'm not trying to be negative here, but I don't know how they're actually going to adapt to this new world.
So I was reading this the other day, but I think it was Jason Lemkin that made this point. But basically, if you look at Lovable, you look at Replit, you're basically paying $20, $200 a month or whatever versus what used to be free, which is WordPress, right? So it is going to— I think it's going to take some time. I do think WordPress will eventually, quote unquote, become dethroned or won't be the king in this space anymore because they power 40% of the web right now still, right? Websites. I think that's going to continue to go down because people are now willing to pay for what used to be free. And that's, that's again, you look at Lovable Replit, like that is happening now, right? So I think the model will eventually become disrupted. I think you and I—
Well, let's go back. I don't think they're willing to pay for what used to be free because what used to be free to get what they want a lot of times involved paying someone to help them. Whether it's a full-time employee or developer or designer. I know you can do a lot with WordPress for free, but A lot of the people using Lovable, from my understanding, are doing stuff that would've required them to pay an engineer or a designer.
Yeah, I'm looking for that. Okay, so, okay, here we go. Here we go. This is what I, I pulled it up. So Jason Lemkin, WordPress powers 40% of the web. Lovable and Replit are targeting that market and more, but they get to charge you $25 a month and for every token you use. WordPress in its most basic form is free outside of hosting. And your argument is it's not free because you do have to find developers and people to figure out what you should do. Yeah.
And even with the plugins and all that kind of stuff, if any business running on WordPress, Majority of them that I talk to, when I say majority, I'm talking about like 99 out of 100, pay people to manage their WordPress, to design, create plugins, tweak code, all that stuff.
Yeah. Now to continue here, much as ChatGPT gets to charge for what Google provides for quote unquote free, Lovable and Replit get to charge for what WordPress provides in many cases for free or very cheap. That adds up to a lot of money very quickly. AI is getting us to pay for a lot of what we used to get for free, for more value, no doubt, but a lot more than what we used to. So like, I think your argument is fair. Like I didn't actually think about that, like you do have to pay developers and people, like you do have to pay for plugins, hosting, and all this stuff. It starts to add up. And there's mental bandwidth to figure that stuff out too.
Dude, we spend for all our WordPress instances throughout our organization, and I don't know how many sites we have, but if I just look at our main 3 websites, I would say we easily spend like $300,000+ maintaining them per year, easily.
I still think though, even if most people start to move over to Lovable and Replit, and Replit can ship and deploy these websites, 40% of the web plus pricing, that's a large amount of revenue that's gonna come out.
Yes.
And I do think though, even if you deploy something, Lovable, Replit, you're still gonna need something to manage. So whether what used to be developers or someone that's actively on the site, I think that's probably gonna be some AI agent doing it. But I also think that's gonna happen for WordPress too.
Yeah.
I think costs will come down for both sides, actually.
Yeah, I think costs will come down for both sides.
Yeah. So like, I think, I think, I think our conclusion here is WordPress is probably going to lose market share. Um, and it's fine. You know, things change over time.
Unless they adapt. I just haven't seen WordPress really adapt.
No, there's, I mean, I think, I'm sorry, I think their founder is distracted.
So. I don't know much about what's happening with the founder, but, um, when I look at the overall progress that WordPress has made. I haven't seen really much improvement from Tumblr, that acquisition. Maybe they acquired it for other reasons. They've acquired a few other companies in the last year or 2 years that I read about. I forgot exactly when, but I was looking at some of these acquisitions. I was like, why'd they even buy them? And it was like the same thing. Like we both love HubSpot, but remember the rumor that was going around that Google was going to buy HubSpot?
Yeah.
And I was like, it doesn't make sense for Google to own HubSpot. And I don't think that rumor was valid and I don't have any proof or data on this. I know Dharmesh, but not well. But, and I don't think that Google's really circling it. It doesn't fit into what they're trying to do. If you look at Google and Facebook, they're trying to paint this story of you don't need agencies and marketers, just use our software and we'll do it all for you. And then when people don't get the results they're looking for, they turn to agencies.
Yeah, I'm looking at, by the way, I'm looking at Grok right now. I'm like, what's going on with Matt Mullenweg, which is the founder, or I think he's still CEO?
I'm pretty sure he's the CEO.
Yeah. So the loss— so they got in a lawsuit with WP Engine, which is like a hosting—
Oh yeah, that's right.
So WP Engine, by April 2025, a US district court granted WP Engine preliminary injunction forcing Automattic to restore access and lift discriminatory measures. Because I think WP Engine was going out to market there. I think they're trying to sell. And then I think WordPress, Automattic, they said they— Matt Mullenweg said they wanted a piece of it. And, you know, they got in this lawsuit and then I just, I think You know, this stuff is a distraction. And in January 2025, Matt Mullenweg disbanded the WordPress Sustainability Team. He deactivated WordPress.org accounts of several contributors, including Joost de Valk.
Yes.
Yeah. And just calls for him to step down have grown, but he's been there, right? So I think a lot of this is distractions versus when you look at Dharmesh, for example, he's always posting to LinkedIn, he's posting to Twitter, sharing new experiments. He's like, he bought agent.com, he bought this domain over here, he sold this domain. He's always trying new things. And I think that's always a good signal of whether a company is kind of on top of it or not versus like for him it's more he's either not posting or you see it like it's like lawsuit-related stuff.
Yes, and Dharmesh, a lot of the content that he's posting is even new features and news related to OpenAI and ChatGPT and stuff that they're doing. But what's interesting there is I think he'll make a killing from—
OpenAI shares?
OpenAI shares. I don't know what his net worth is and I'm not here to try to predict, but I'm guessing he may make more from that than he did from all of HubSpot.
I mean, imagine getting $15, $20 million or whatever, just all in OpenAI stock. And this was like a year or two ago, 'cause he was selling chat.com.
I think he sold it to ChatGPT.
So you figure $15, $20 million for that, right? Let's call it $15.
I'm assuming he got a good deal for him. And it's probably worth hundreds of millions easily based on their latest valuation. It'll probably go to a trillion-plus dollar company. The interesting thing with HubSpot, he's done an amazing job building a great company, him and Brian Halligan. I don't know the lady who's the CEO right now, but when you look at—
He's Indian.
She's Indian, right? When you look at HubSpot, they built an amazing company that's roughly worth $30 billion. I'm looking at their stock symbol right now live. It's like $29.34 billion, which is amazing and very hard to do. Do you still own any? Do I what?
Do you still own any HubSpot?
No comment. So, and then what? you end up seeing with this company is, is it was not only hard to build this big of an organization, but what people don't always realize is, is Brian and Dharmesh, to build this kind of organization, had to pump in a lot of cash. So they had to take in tons of investor money over the years. And when I say tons of investor money, I'm not talking about like the amounts that like the Ubers or the ChatGPTs raised, because the time when they created their startup, which is similar times to when I was, you know, getting started and raising capital, people didn't raise as much money. It's like if you raise like $100 million, you typically would go public, not in one round, in total, right? And I don't know exactly how much HubSpot raised, but I don't think it was that much. I don't think it could be more than a few hundred million dollars before they went public, but it took a lot of capital to build the company that they did. And it's actually worked out quite well.
Anyway, that's it for today, guys. And we'll see you tomorrow.










