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[on-hold music] I do think there'll, there will be a rebundling, to your point. Um- Yeah. Yeah. I mean, here's a quick, like, funny kind of anecdote.

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When I joined The Hustle the first time around as an advisor, one of my first meetings with the whole company where I was getting to know people, um, somebody asked, um, "Hey, what...

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Like, what's a newsletter that you like right now?" And I said, "Oh, I've been... I just started reading this newsletter called Good Better Best. I love it. It's written by this guy named Rob.

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He talks about, like, pricing and, um, pricing psychology and stuff like that." And literally they were like, "Oh my God, we love him too."

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And, like, two months later we were able to get Rob to actually stop doing his own newsletter, and now he's a full-time writer for The Hustle.

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[on-hold music] Welcome to the Rebooting show. I'm Brian Morrissey.

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This week's episode is brought to you by Bombora.

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The digital advertising industry breathed a sigh of relief last week when Google said it would once again push back the deadline for the phase-out of the third-party cookie in its Chrome browser.

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Deadlines force focus, and the human tendency when a deadline gets pushed back is to, well, stop working, and that's a major risk for publishers at this moment in time.

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Instead, they need to accelerate their digital transformation by getting in place systems that will leave them prepared for the eventual end to the third-party cookie.

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Here's how Steve Lilly, SVP of Global Data Partnerships at Bombora, put it for me. You know, we're essentially a massive data ecosystem, and our business model is really nothing new. We're, we're, we're a data co-op.

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And so there's a lot of problems that we solve for data as it relates to sales and marketing, predictive analytics.

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But as it relates to our publishing partners specifically, there's two primary problems that, that our model solves, uh, which is unknown audience.

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We still see, you know, just about every publisher we speak with has a massive percentage of unknown audience and no real cost-effective way to, to address that.

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The other in terms of B2B marketing or B2B audience targeting is understanding what businesses are visiting your site and what those businesses are in market for.

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Listen to my full conversation with Steve at the end of this week's episode, and find out more about how Bombora helps publishers on their digital transformation journey by visiting bombora.com/publishers.

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That's Bombora, B-O-M-B-O-R-A. Thanks, Bombora. [on-hold music] Before my conversation with Steve, I have a chat I did with Jordan DiPietro. Jordan is the head of The Hustle.

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My former colleague, Shereen Pathak, writes about brand publishing at Toolkits, and you should check out, by the way, Toolkits, um, for what she's doing, as well as my other ex-colleague, Jack Marshall, uh, who writes about subscription publishing.

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Um, but, uh, I have a healthy skepticism, I would say, of companies acting as publishers. I know for a fact how hard it is to be a publisher without also, um, building and selling software.

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But I wanted to have Jordan on, uh, to get the details of how this is working for, you know, one of the case studies I keep hearing mentioned, um, which is The Hustle, a daily business news, uh, brand, mostly newsletters, uh, at least when it was bought by the Hu- by HubSpot in February 2021.

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Jordan talks about the model and how The Hustle now doesn't need to sell ads, but instead it needs to ultimately drive leads for HubSpot software.

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We also discuss how The Hu- how The Hustle is expanding into podcasts, video, and the creator economy with its own creator network. Um, and we also try to get into the mind of Jordan's, uh, boss, Kipp.

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Um, it'll make sense in the conversation, promise. If you have feedback, please shoot me a note. Um, always interested in hearing what you like, what you don't like, and guest suggestions.

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My email is bmorrissey@gmail.com. Another thanks, by the way, to Bombora. Um, they've been really great partners and supporters, um, and, uh, it's always, uh, great for me to have. Here's the conversation.

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[on-hold music] Uh, Jordan, welcome to the podcast. Really appreciate you doing it. Thank you. Thanks, guys, so much for having me. [laughs] Okay, so you're, you're the head of The Hustle, right?

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And The Hustle, like, lives now within HubSpot. And for those who do not know The Hu- um, just give the elevator pitch of what The Hustle is. Sure. Um, The Hustle is a newsletter.

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It's a newsletter brand, and we've got over two million subscribers. It's a newsletter that focuses mostly on tech, entrepreneurship, startup news. Yeah, like, oh, that was very succinct. Thanks.

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Usually people, like, I'm like, "Oh God, I can like, uh- Rambling on and on... you know, have a cup of coffee," 'cause they, they go on for like 10 minutes. This is gonna be really good, Jordan.

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[laughs] Um, so, like, I always thought of The Hustle as being, like, you know, you always need, like, two players in, like, different things to play off one another, and there was, like- Yeah...

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Morning Brew and, like- Yeah... The Hustle.

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And, like, you know, Morning Brew, to me, was, like, the, the kids who were majored in business at the business school and, like, and, like, The Hustle was, like, a little bit more feral. Yep. Yeah.

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No, I think- [laughs] Is that fair? I think that is- Differentiation? Yeah, no, [clears throat] I think that's, I think that's pretty fair.

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Obviously- 'Cause Sam Parr, anyone who doesn't know, Sam Parr founded The Hustle. He's, he's a character. I, I- Yep...

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have only spoken to Sam a couple times, but, like, you know, anyone who's, who's, who's listened to his, what is it, My First Million podcast- Yep... or followed him on Twitter, like he- Yep... he sort of...

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You can see the ethos of the brand, I believe, in Sam. Yeah. Uh, I think that's true. We...

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One of the first kinda actual meetings that I had with Sam, um, when he was talking to me about potentially joining the team was, you know, differentiating The Hustle between all the other newsletter brands.

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And the way that he kinda described it at the time is he was like, "There's a lot of other newsletter brands. Some of them try to do X. Some of them try to do Y.

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We, we kinda wanna be the brand that's, like, business and tech, but it's, like, a little bit punk rock."

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And, you know, whether or not that's the exact right, um, description, I don't know, but that kind of appealed to me- Yeah...

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as, like, somebody, I think, who just always was-A little bit counterculture-ish and was trying to- Sure...

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work for companies that I thought were, like, a little bit contrarian, a little bit different than the norm, and I think that's what The Hustle was doing. I think that, that ethos definitely went through Sam.

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I also think it, it really went through all of the writers, too, that worked at The Hustle, who have, um, who have all been tremendous writers in their own right, but that also kind of share that same sort of vibe or ethos.

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Yeah. So, I mean, one of the things I think particularly with, like, niche brands is, like, having, like, i- in mind the type of person, right?

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Like, I mean, like, I think about the rebooting, it's like the type of person I wanna reach is, is the people who are operating day to day, building sustainable media businesses, big and small, right?

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So de- describe the person, and you know, obviously there's a lot of other people around, but you have to, like, focus on, on something that you're... someone, I think, a, a type of person you're after.

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Like, describe The Hustle reader for me. Sure. I think, I mean- Who's a Hustle reader?... The Hustle reader, I don't, I...

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It's probably not dramatically different than some of the audiences, um, that you might serve, but, you know, they're, they're knowledge workers.

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They're typically in technology and marketing, um, engineering, and they're, you know, there's, I think there's a combination of people that are, you know, maybe middle management or, uh, executives and stuff, and you know, people that work at companies.

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And then I think there's a pretty big, um, category of people that are also startup founders, startup operators. Um, and then I think there's also a growing segment of, like, your more aspirational builders, you know.

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Might not be somebody that works at a startup yet, but maybe they want to. Or might not be somebody that's launched their own company yet, but they want to.

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But I think the other important thing that you kinda touched on when you talked about ethos was it's not just for people who are looking to just stay in touch with the news. I think there's a lot of- Mm-hmm...

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other newsletters that will do that. I think you come to The Hustle also for the stories that you don't find somewhere else.

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So if, like, if your objective is to make sure that you are on top of, like, everything that's gonna be in The Wall Street Journal that day, or what are the five big stories, The Hustle isn't the best place for that.

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I think The Hustle is the best place to find the stories that you don't typically find somewhere else when it comes to technology and entrepreneurship. Okay, so give me an example. Give me a Hustle story.

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So what's a story that, like, you could take off the branding and, uh, you would read it and be like, "This is a Hustle... This is a Hustle story"? Oh, man.

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If you, if you have read anything by Zach Crockett, um, who does our Sunday Stories, you could, you could check out any single one of those.

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Mark Dent, who's a great writer for The Hustle, just, um, wrote something not too long ago about, like, the psychology of free stuff. Um, that was a tremendous article. But [clears throat] I think the, the main

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point that I'd get across is, like, in any, in every single newsletter of The Hustle Daily, certainly you're going to get the tidbits of what's going on that week, what, in finance and tech, et cetera, but you're also just gonna get, I think, stories that have a slightly different- Yeah...

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point of view, and also that it's not just a regurgitation or a curation of what's going on. It's like our, our writers have a point of view. Yeah, and it's not an aggregation email. Right. Like, right?

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There's a lot of- Yeah... people out there that have really focused on, and I don't mean, like, it as a knock, 'cause I think there's a lot of different formats, but on basically smart aggregation of the news.

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We'll get you... And the, the promise is that, right? Like, we'll get you... We'll give you the stuff you need to know, like, in five minutes, and sometimes- Right...

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it's literally that's what they say at the top of- Yeah... the email newsletter. And that, that's when you see, like, a lot of bullet points and stuff like this. And I like- Right... bullet points. I use them.

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[laughs] Um, but I think that there's a different class of, like, of, of email newsletter, and I think The Hustle might be within that. I mean, you're telling, you're telling stories.

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Like, these are not, like, you know, just, like, a bunch of bullet points about, like, what happened at, you know, with the, the interest rates rising yesterday, stuff like that. Right. Yep. Yep, absolutely.

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But also, like, the brand, like, I, I always think about brand DNA. And, and it's interesting.

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I wanna get to that 'cause, like, uh, Sam is no longer with the brand and, and I think sometimes, like, you know, building a brand, and particularly when it's, like, a, a very strong personality like Sam, like, you know, then you start to wonder does the ethos, you know, get diluted afterwards.

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Sure. But, you know, The Hustle didn't begin as a newsletter, right? It began as, like, Hustle Con, [laughs] which is just like, I love the name, by the way. Yeah. Hustle Con. Right. Yeah, that's...

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I, it's, I don't, [clears throat] I don't know that part of the history particularly well, but yeah, I think, you know, Sam, uh, maybe acquired the name from somebody else and so it started as an- Right...

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event business, and then kind of, you know, I think he was getting incredible attendance and thought, "Well, what can I do that's- Yeah... a little bit maybe better than an event business?"

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And kinda turned it into a newsletter. But, um- Okay, so you joined-... one thing I do wanna say is, like- Yeah, okay... so Sam actually, Sam still is with The Hustle.

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Um, so he, he obviously doesn't play the same role that he did before, of course, but he's still on My First Million, which is owned by HubSpot- Mm-hmm...

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and he still helps out with other things, so still, still part of the branding. Right. Still, still part of the DNA. Yeah. Well, but it's, it's also, it's very...

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I mean, it's, it's tricky, though, to, to handle that transition, um- Yeah, totally... uh, from, you know, because he's n- it's, I'm sure the, the involvement is, is less than it was, like, when he was the- Totally...

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sole or mostly- I think if-... uh, full owner. Yeah. I think if you looked at, like, if you looked at pre-acquisition, kinda the set list of, like, all the employees who was working at The Hustle and Sam- Yeah...

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and then you looked post-acquisition, you'll see 80% of the same names. Yeah. And most importantly, I think a lot of the people that are on the editorial side are still the same.

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And so I think that's why, I think that's how we've been able to still keep a lot of that, like, editorial integrity and that brand and that feeling and that vibe the same is because we haven't lost a lot of the most important folks on The Hustle, which are the ones that are creating content every day.

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Yeah. I know at, uh, one of my final hires at Digiday was someone from The Hustle 'cause, and I remember in the interview being like, "I'm mildly obsessed with The Hustle." [laughs] Oh, yeah?

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Who, uh- 'Cause I wanted us to be better and, uh- Can you say who it was or no? Ah, I'd rather, I don't wanna- Okay. Yeah, no worries. Um, he was at our retail brand. Um, anyway, it was a long time ago. It was years ago.

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Yeah.

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Uh, but, um, so you joined when it was still independent, pre-HubSpot, right at the end of its independent days, yeah?Yeah, the, the short story is, um, Sam had approached me pre-acquisition to, basically to come and be the CEO of, of The Hustle.

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And so he and I, I, I was still trying to finish things up at my other company. I had a lot of projects I really wanted to see to fruition.

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So what we kinda decided on was I was just gonna be an advisor, um, for a couple months and see how things went.

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So I was kinda working with Sam and the Hustle team for about three or four months, kinda nights and weekends, being an advisor, getting to know the team.

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Sam and I would be talking about, like, our long-term vision for the company, and we were getting close to a point where we were gonna, you know, decide to formalize it when, um, of course, HubSpot reached out to Hustle and made an offer, and Sam came to me and was like, "Hey, remember all that stuff we were working on?

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Psych." [laughs] So, um, so I was like, of course, I understood it was a great, you know, it was a great opportunity for him and for the Hustle team. So we kind of parted ways, um, and, you know, I said, "Good luck."

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Um, I went back to all the things that I was working on.

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And, and then it was maybe six or seven months later when Sam texted me and said, "Hey, actually, HubSpot is looking essentially for the same sort of role that you were already gonna do." Okay.

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Um, so he got me in touch with the folks at HubSpot, and we started exploring things, and now here we are. Yeah. So at that time you were at Motley F-Fool?

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Um, it gets a little bit fuzzy, but- Is that- I was at the Motley Fool. Um, I left in... God, I'm blanking exactly, but we'll say sometime in 2021.

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I had a, um, a brief stopover at a venture studio where I went over to be head of- Yeah... growth. I was only there for about three or four months when the Hustle and HubSpot folks reached out to me.

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So, uh, yeah, there was a, a little bit of a pit stop in between, but essentially. Yeah. Yeah. Okay. Um, so what were you doing at, at, at the Motley F-Fool?

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'Cause I'm, I'm interested in, like, how you carried over your experiences there and, you know, to The Hustle, which is, like...

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You know, it's, it's a different, particularly now, I mean, you know, being part of a software company is different, I think, than being a, uh, uh, an independent publisher. Absolutely.

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Um, so I was at The Motley Fool for a little over 12 years, so, you know, that's like an eternity today. I started at The Motley Fool as a, as a writer/editor.

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You know, I was covering media stocks, tech stocks, entertainment stocks.

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And, you know, over 12 years obviously I've had a lot of different roles, but, you know, managing editor, you know, head of product, head of marketing, um- Mm-hmm...

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and, you know, when, when I left, you know, I think my title was chief growth officer, but I, I over the course of 12 years, I really kind of did it all inside of that publishing subscription business. Yeah.

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And you saw, you saw... I mean, 'cause I think The Motley Fool, I haven't had anyone from The Motley Fool on, and I really want to because, um, it's, like, underrated story- So underrated...

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success story I feel like, right? Totally.

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And yeah, and I think that Sam is a lot of things and, and one of the things that Sam Parr is great at is, is, like, really, really underappreciated or undervalued businesses, and I think that he was kind of honestly obsessed with The Motley Fool 'cause he, he knew through research and reading and other things that they had really built an incredible business.

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And so I think that's honestly kinda how he found me in the first place. Um, but yeah, the- Yeah... I mean, The Motley Fool is, they are near and dear to my heart. I love to talk about them.

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They're one of my, you know, favorite companies of all time. That's where I came up. But yeah, they... I mean, they are an incredibly large- So give me the playbook. Give us the playbook.

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But- What's the playbook for- The-... The Motley Fool playbook? Uh, just- Like, what makes them unique and, and super profitable? Man, so many things make them unique.

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Um, I mean, The Mot- m- many people don't know The Motley Fool's been around since 1993.

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So the owners of The Motley Fool, David and Tom Gardner, like, they literally launched The Motley Fool inside of an AOL chat room, um, in the early '90s.

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And so, I mean, to summarize the playbook would take, like, a long, long time. But I think it starts with the, the value prop that The Motley Fool gives is incredible.

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The stock picking that they provide members with is incredible, and it starts with that, and obviously they do a lot of other really, really things well. I think our, our direct response marketing is incredible.

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I think our stock picking and our analysts are incredible. You know, I think the personality and the brand and the ethos that we're talking about of The Motley Fool is really incredible.

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But I think the thing that really, really separates The Motley Fool from a lot of other companies historically was before it was really all the rage to have a subscription business, that's what The Motley Fool was doing, you know?

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And so, I mean, I, uh, when I started at The Motley Fool in 2009, I started learning the nuts and bolts of what you need to have a, um, a really successful reoccurring subscription-based business model, and they were doing it before everyone was like, "Oh my God, SaaS multiples are amazing, and this renewable cash is amazing," but The Motley Fool's been doing it for a really long time.

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Yeah, yeah. Um, and at the time, I guess when you started, you know, talking to Sam and stuff like this, the, you know, uh, The Hustle had trends, and I remember, like, um, Piano was, like, our- Yep...

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provider when I was at Digiday, and- Yep... I w- they were always using The Hustle as examples of what we should be doing [laughs] because they were like- Yeah...

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basically they were saying, "These guys are way more successful than you are." Oh, that's funny. Um, I think that's, that was the message I got.

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Um, but, like, what, what did you see, like, that attracted you to, to The Hustle when it was part of HubSpot? Because that's a different proposition, right? Like when, um...

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Yes, it's about, like, subscriptions and stuff, but I would, I would imagine then the media becomes about, like, generating leads and stuff.

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It, it becomes less about, you know, getting people to pay for the media itself. Yep. Um, so when they reached out to me post-acquisition, there was a couple things.

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First and foremost, I kinda felt like I had unfinished business because I had started working with the team before the acquisition, and I got really close with a lot of the folks on the team, and I was, you know...

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I mean, this was, I was about to be the CEO of a company that I loved. That was incredibly exciting.

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So then when it didn't happen, it was like, oh man, obviously I went and, you know, continued to do other things, but when they came back, it kinda felt like, all right, this is a second chance to do the thing that I wanted to the, uh, the first time.

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I also, I mean, if you are in marketing of any sort, you know HubSpot. You know, I mean, they are kinda like the gold standard for inbound marketing.

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They've got an incredible company, incredible team, incredible culture. So it wasn't just, like, some random SaaS company that had gobbled up The Hustle and now I was gonna, you know, go and be a part of this machine.

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It was, um, a company that I really, really kind of respected in the marketing space.The other thing was, as you know, being in the publishing game when you're focused on ad dollars, like, that is hard. That is a grind.

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And pre-acquisition, that's...

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I mean, sure, The Hustle had Trends, and, and certainly our plan was to really, really accelerate the growth of Trends, but still a lot of our revenue came from advertising, and that's just a different beast.

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And so once it was acquired by HubSpot, the pressure to not have to sell external ads, but instead to focus on, you know, basically being our own media buyer was actually really, really, really attractive, especially knowing the business model behind HubSpot and the capital and the resources that HubSpot had.

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It was actually like, like, "Is this serious? Is this, is this actually a thing?" Yeah. "I get to go and do the thing I wanted to do before, but with more stability, less chaos, and a longer runway?"

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So it was kind of a no-brainer for me. So, so you thought that was like... So what was...

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I mean, 'cause, like, I guess from my standpoint, I would be worried, like, any time a publishing venture is side, a side thing, right? Like, I mean, HubSpot makes software. They don't- Sure...

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they, like, they're not, they're not a publishing company. Like, Conde Nast, it's publishing. Right. It's all publishing. Like, this is what you do. [laughs] You wake up, everyone at the company wakes up.

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Now, companies, particularly in B2B, are doing a bunch of different things. Sometimes they're events companies and do publishing on the side, too, so- Yep... I understand that.

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Um, but explain, like, what the sort of pitch was when you sort of...

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'Cause, I mean, you sort of, you know, originally connected with, with The Hustle a- as an independent business, and there's up- and, and there's upsides and downsides to that, like you said.

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Um, but being within, like, a far larger software company is a totally different proposition. You might not need to sell ads, but, like, I, I would think that it comes with its own set of challenges. Yep.

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I think, I mean, certainly it's, it's a leap of faith.

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Um, but it's not like we didn't have a lot of conversations before I accepted the job with, you know, Kieran, who's my boss, the VP at HubSpot, and Kipp, who's the CMO of HubSpot, of, like, what their vision was for the team that I now lead, which is called HubSpot Media.

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And, you know, they had just acquired The Hustle. It was pretty, you know, sizable acquisition for HubSpot.

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Uh, it was the first acquisition they made of a publisher, so it wasn't also like they were just selling me something, like, arbit- You know, they had just made an acquisition, and we talked a lot about what my budget was gonna be, you know, what kind of resources I was gonna have, the things that they wanted to do, not just with publishing, but also growing HubSpot Podcast Network.

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Um, we just launched a, a pretty large creator program this year, so, you know, what they described to me that they wanted to do, sure, I know it's not gonna be core, like a core part of HubSpot's de- like, current demand e- engine, but it's a long-term bet that they're making.

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And I guess at the end of the day, like I said, a little bit it's a leap of faith, but I totally trusted and bought into what they wanted to do and believed that they would give me kind of the resources to do it. Yeah.

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So you said there's two million subscribers. I know you said you weren't gonna talk numbers, but you said it without me asking. [laughs] Over, over, over two. I believe there was 1.5 million. [laughs] Over two. Over two.

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See? There, it's more. [laughs] At least 2.1. So I believe there was 1.5 million at the, uh, acquisition, which is in February 2021.

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So explain exactly how, if at all, The Hustle's mission has changed since February 2021, when it was acquired by HubSpot, both on the editorial side, but also, like, what your KPIs are as a business unit. Sure. Um,

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I wouldn't say that the mission has changed. Um, yeah, I don't know that the editorial part of what we're doing has changed. I'd say that where we focus is more expansive.

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Um, so, like, uh, I guess I'll answer it in two ways. The first part is we're just focusing on a lot more things.

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So previously we had The Daily, which you mentioned, had 1.5 re- 1.5 million readers, and that was a really, really big focus in addition to Trends, that was obviously growing.

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Now, we have put a lot of time and energy and focus into The Hustle Daily Show, so a little plug for my podcast there. Um, we have put a lot of time and energy into that podcast. We... I don't know if I should say this.

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We just crossed a million downloads. We launched it in February, um, and we just crossed a million cumulative downloads. Like, that podcast is doing a tremendous job.

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And we're also, um, going to be launching The Hustle YouTube channel in the next couple months. Just hired a really, really incredible executive producer, um, to join the team there.

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So we're focusing on different things. It's not just all about the newsletter. So that's one. Yeah. And then two, you're right. We, we do have different metrics.

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I mean, the main metrics before, of course, like any publishing company, we were looking at, um, you know, opens and clicks and CPMs and ad revenue.

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You know, and a really high level metric that we look at now is, of course, leads, to your point. Yeah. Yeah. So how do... Let's, let's, let's break this down. Cool.

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So both the, the product expansion into different areas going well beyond, like, a newsletter and, and podcasting, I mean, The Hustle was already doing podcasting, uh, is, was that changed at all?

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You think at all, uh, like, if The Hustle... If you had joined The Hustle, like, um, uh, with the original, you know, and it was still independent, that, would that product roadmap be any different, or do you think...

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I mean, it's really hard to say exactly. Or are you able to make, um, different types of decisions? And, and I mean that, like, for instance, like, you mentioned YouTube, right? And- Mm-hmm...

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you know, it's not on here, but Jay is, is, uh, the producer of the rebooting show and is always bugging me to do more videos, so. [laughs] Right. Because I should bring him in for this conversation.

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Because, like, my thing with, like, video is, is in a, for a B2B audience, it generally doesn't... I, I don't see examples of it working well.

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I go on these, like, YouTube pages of, like, business, and I'm like, "Oh my God," like, "you should at least hire a bot." Like, only, like, 63 people [laughs] have viewed this thing. Right. It's not a good look.

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Um, but and that's because it, it's a slow burn. It takes, like, a long time. Like, you can start a newsletter and get a lot of traction really, really quickly, okay?Start a podcast, way harder. Like way harder.

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And I think that's why you guys have your podcast network, um, because, like just like this podcast, like, you know, it's growing slower for sure than the Rebooting newsletter but then I go onto one of these services and they're like, "You have the top...

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one of the top 1% of podcasts." Yeah. And I was like- Oh... "Really?" Because [laughs] like, man, 99% of podcasts, like nobody's listening to those things. Right.

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It's not like nobody's listening to this, but I'm like, my God, you get like a couple thousand downloads and like you're all of a sudden like- You're in the top 1%... top 1%. Totally.

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And I'm like, that, that tells me something about the podcast industry. And then, I- video I just find really difficult to wrap my head around, and I've always found it difficult for, for business news.

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I think you guys are doing a little different thing. But I guess my question is, are you making different types of bets because you don't have the ad revenue pressure?

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You have a different type of pressure, but like you don't have the ad revenue pressure? 100... I mean, 100%. It's, it's totally different roadmap. I mean, when I was going to join pre-acquisition,

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Sam and I talked about what our kind of three-year objective was. And for the most part, I think the objective was to generate as much revenue as possible to achieve, you know, the highest multiple at, for an exit.

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And that's, that's what Sam was most interested in.

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So our roadmap was focused on certainly scaling up the newsletter, but also, and I think it's probably a big reason why Sam was interested in my experience, was growing Trends because obviously there's a huge overlap, right, between Trends and The Motley Fool.

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They're both membership communities. Yeah.

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So it was, that was going to be an insane amount of our focus was how do we get Trends from, you know, it was probably 8,000 paying subscribers to 30 or 40,000 paying subscribers, and then maybe launch a back-end product off that, o-off the front end prod- you know.

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So that was really, that was gonna be the roadmap.

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Now, they had launched My First Million, so it's not like they weren't interested in podcasts, but it was this, that was more of honestly a creative outlet I think for Sam and Sean in the, at the very beginning.

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Um, so things have dramatically changed because now we don't have that same sort of pressure to only look at revenue. In fact, revenue's not really one of the things I'm judged on at all.

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So the podcast play and the YouTube play and some of the other things we're doing, they're all top of funnel. And like when you're a startup that's just trying to find an exit in two, three, four years, you're...

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I just don't think that you have the luxury to go as top of funnel sometimes as, as we do now. Yeah. And you can't...

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I mean, the, I always found like the hardest part, particularly like in bootstrap business is like, um, you can't hi- you can't like spend too much ahead of revenue.

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And like the reality in media is like revenue is, is a lagging indicator of brand. And like build, you build brands, and you have to do stuff that doesn't immediately generate revenue.

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Like, I think people now with the popularity of performance marketing, and they sort of take that mindset to, to media and like the reality, at least maybe I'm just not good at it, but like [laughs] the media business is like you gotta like you gotta stay after it and like you...

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a lot of times you don't immediately generate revenue 'cause it's a chicken and egg thing. You don't have the audience, so you're not gonna have the revenue, and like you gotta just keep after it to build the audience.

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Um, but like I wonder how the decisions are affected because like you do... It's not like you, you're, you've got some sinecure where you don't have like to, to meet any goals. Sure.

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Like I would guess that you're, the, the CMO is, is I know how B2B works. Right. And it usually comes down to leads. Yep. It's like how many qualified leads are you delivering? Yeah. No, absolutely.

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So my, so my team, HubSpot Media, is responsible for all of the HubSpot blogs,

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all of the HubSpot, um, YouTube channels, our HubSpot podcast network, which includes all of our original shows, but then we also have like a creator program where we have emerging podcasters and we also set up licensing deals with established podcasters.

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Um, it also includes our newsletters, so not only The Hustle, but we also have HubSpot blog subscriber email lists as well. And then, what am I missing?

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So across all of those channels, my two main metrics that I'm responsible for, high level, one of them we'll just call monthly media engagements.

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So that's how many unique engagements we get across all of those channels every single month. So that's kind of your more like brand awareness. Oh. How many impressions are you getting- Yeah... across everything?

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So for instance- Okay... la-last month we'll say 35 million literally unique brand engagements with HubSpot that our teams have created.

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The other metric that we're responsible for, which I think what you're more interested in, is leads. So obviously HubSpot blog- [laughs] Oh, it's not that I'm more interested in it.

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I think I forgot the CMO's name that you had mentioned before, [laughs] but- Kip. Yeah, the Kip, yeah... this person. Kip. Yeah. Kip. I'm talking for, I'm speaking for Kip right now.

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Kip is interested in both, but he's also interested in leads, of course. And yeah, we, I mean we- I've got, actually I got Kip in the other room. I'm gonna bring him in. [laughs] Kip says you're fired.

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Um, yeah, no, we- Kip, Kip's gonna come in like, "Where are my leads, Jordan?" He, uh, he does. And we generate, every month we generate leads from the HubSpot blog.

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We just recently launched a Hustle blog that we're gonna be, uh, utilizing to create Hustle content outside of just the newsletter. So we create leads from that. We create leads from YouTube.

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Uh, we create leads from the Hustle daily newsletter. So, you know, the Hustle daily newsletter, let's just say it sends five days or six days a week every week.

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Those, every single one of the daily newsletters used to be filled with an external ad spot. Obviously- Yeah... we don't have to do that anymore.

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So sure, we could just stuff every single one of those ad slots with HubSpot content.

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But it's probably not the best idea because we would honestly just dilute our brand and piss our readers off, but I'd say probably five to 10 times a month, we include something about HubSpot.

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You know, a HubSpot offer, whether it's a template or a guide or the state of marketing report that we just released or whatever it is. And honestly- Mm-hmm...

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we have been exceeding HubSpot's expectations when it comes to the leads that we generate from The Hustle. Yeah. So I joked about Kip being here. Yeah. He's not actually here. Um- Good stuff. Good stuff...

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don't worry, you can speak freely. [laughs] Uh, but um, I am interested, since he isn't here, we can talk about, you know, how you manage that, like internally, right?

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Because like I think of HubSpot as, I remember like actually-Right before I, I spoke at the, their, like, Inbound conference one time. Cool. Like, and it was a massive conference. Yeah.

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And I feel like HubSpot has always been really on the forefront of, of truly acting like a publisher.

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I know a lot of people, like, claim that and stuff, but HubSpot to me was always, like, one of the cases of a, a B2B software company that put a lot of resources into...

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I mean, it was called Inbound because, like, they really believed in the power of content to attract people. Like, there's inbound and then there's outbound, which is- Right...

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like going out to prospect on LinkedIn- Right... and stuff like this. Yep. Which I might have to do because I have to sell ads. Right. Um, but it's different, right?

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Like, because B2B, a lot of the inbound stuff, and, and I think HubSpot did a lot of the good job. It's like, give us your information to download this white paper. Come to this webinar and stuff.

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And like, we've all seen it and stuff like this, and like, I personally, you know, one of my life's missions is to reinvent the webinar. It's not that glamorous, but, um, I wanna do it. Right. Um, explain how...

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Like, that's not a publishing mindset, right?

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Like, when you're, like, you know, as, like, an editorial person, you know, I feel like, at least I'll speak for myself, as an editorial person, when I would see the kinds of content marketing that people are doing, I'm like, "Ew."

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That's, like, kinda different. Like, I understand what it does, but that's not what, like, what, quote-unquote, you know, real publishing does. Right.

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[clears throat] I, I think that what you're getting after is, like, one of the main reasons why HubSpot wanted to acquire The Hustle in the first place and why it, it doesn't feel as challenging to me as it might seem on the outside.

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Like, so HubSpot essentially kind of created the whole inbound marketing movement, right? So they've been, like- Mm-hmm... dominating that for the last 10 years, which is what you said. Create valuable content.

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People that have problems that are searching for solutions will find that content. Yeah. They'll download your white paper. Yeah. They'll grab your guide, whatever. [clears throat] Let's just- Let's get good at SEO.

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I mean, a lot- Let's get-... of this stuff is SEO, let's be real. Yeah. Uh, no, of course. [laughs] And so, and I mean, inbound marketing is essentially two things.

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It's, it's being great at SEO and great at paid search, and both of those things are just dramatically getting saturated and more and more competitive, right? Like, search- Yeah... CR click.

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It's just, it's harder and harder to rank. Paid is just... It... We don't need to go into that here, but [clears throat] the whole inbound marketing playbook, I think has, like, 10X'd in difficulty.

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So HubSpot kinda looked at things and said, "We kind of in- invented this inbound marketing thing a decade ago. Let's start again with something new, and let's do inbound media."

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And so the way that they're looking at The Hustle acquisition and what, what I do and what the rest of the media team is, let's just create incredible editorial content, media focus, publishing content across lots of different platforms, whether it's newsletters, YouTube, or podcasts, and let's just get in the mind share of these people.

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[clears throat] They might not have a problem at that exact moment for which they are searching for a solution, so they're ready to download the guide and get your white paper and convert into a lead today.

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Maybe it's a longer putt, you know? Maybe, like, we just have to be in the mind share of listeners f- who don't even currently need HubSpot, and maybe we're gonna do that for a couple years.

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But when the point comes where they do need a CRM or something that HubSpot offers, we're top of mind. So it's just, it's a longer-term play that I think, you know, inbound media is. Okay.

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So it's not like I sign up for The Hustle and then, like, uh, four days later, I'm getting an email from, like, HubSpot.

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Like, I'm, I'm in the system in order to, like, set up, like, a one-on-one meeting in order to go- No... over my software and stuff like that. No. No.

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I would, I would urge you after this to go and re-sign up- [laughs]... for the daily. And h- I mean, honestly, unless you were, like, in a- No, 'cause all, we've all gotten into that, like, cycle. We know how it goes.

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Oh. Like, you put your, like, email into something, and then all of a sudden it's like you're in the flow. Um, and, like, B2B companies know that only 3%, like, or so, like, end up being, like, qualified sales lead.

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But this is just how it's always been done. Like, that's- Yeah... it- it's just always been done. You, like, pour a bunch of leads into, like, a funnel basically, and then they come down. Right.

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Like, and you know, the truth of the matter is 97% of them don't go all the way down to the bottom, and that's just... You know, it's not about the fish that get through the net. It's about the fish that get on the deck.

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Yep. Yeah, I mean, it's absolutely a distribution play. I mean, that's what The Hustle acquisition was, right? Like, you only have so many distribution channels. And like, and like we talked about, search, harder.

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Paid, harder. Direct sales, harder. Okay, so then let's look at media, and let's own and operate a bunch of different media products.

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And sure, absolutely, we need some of those people in our media products to convert at some point down the funnel, but I think they are...

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And when I say they, I think we'll talk about Kip again, who's in your closet or your back kitchen or something. [laughs] But, like, I think they, they are smart enough- He's having coffee in the kitchen.

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[laughs] Getting revved up.

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They're, they're smart enough to know, like, if we hit you over the head when you join The Hustle with, like, HubSpot, then hey, now you're all of a sudden, you're in a one-on-one call with a guy trying to sell you a CRM.

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It's just not gonna work. [laughs] So just, it's just a longer-term play. I c- I'll just say this. Again, Kip is not actually in my kitchen.

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But, like, that kind of awareness is actually missing at a lot of, um, a lot of, uh, technology companies, I believe, and that's why I wonder whether... 'Cause I think, you know, look,

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the, uh, HubSpot acquiring The Hustle is, like, part of a lot of, like, conference presentations I'm sure, and, and usually those people are trying to sell some- something, uh, as most conference presentations are.

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But, you know, I wonder how unique it is. Like, 'cause HubSpot is not a typical company. There's a lot of companies who, who talk about, like, acting like publishers. Like, I will, I will give specifics.

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Coinbase, for instance, okay? So Coinbase, that guy, Brian Armstrong, he might be a, a... I'm sure he's a brilliant guy. He just comes off like a total jerk. Yeah.

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Um, and, like, the arrogance o- of him being like, "We're going around the media, and we're gonna create this blah, blah, blah." Guess what? They're not doing anything. Right. You know? Their stock is down 80%.

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This guy was talking about setting up movie studios and stuff. You know, he's, he's gonna be working for-That, uh, that dude with the crazy hair in the Bahamas pretty soon. He'll, he'll be like a VP at FTX.

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And, and to me, that's the part I can't get at. Right. I think about Shopify, okay? Shopify started Shopify Studios. Yeah. They're gonna tell the stories of entrepreneurship and stuff like that. Right.

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I don't think they're doing much with that. Their stock's down 75%. Right. So I just wonder w- about the wherewithal for a lot of these companies thinking about this as a template, because I think this...

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And tell me if I'm wrong. I feel like this is unique from what, from, a- a, from other types of efforts, whether it's Salesforce or MailChimp or whatnot. Yeah. I, I totally agree.

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Obviously, I'm biased on the inside, but we, like, we could go through the list you just started to name of, like, unsuccessful or boring or fucking totally lame, you know, companies trying to be a media or- Or just send out a press release and then do nothing...

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right, or just do nothing. Or... And I think that the, I think the way that HubSpot decided to do it was right, and they, they made an acquisition. They realized, "We don't have a certain type of talent in-house."

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Sure, we could take five or seven years or whatever to build that talent, but instead they decided to go out and acquire it, and then they largely have left those folks alone to do what they really, really like to do.

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And, you know, there were a lot of conversations on branding. Do we call it The Hustle HubSpot now? Do we leave The Hustle logo? How do we do that? Like, I mean, God, it was exhaustive. Like- Oh, I can imagine...

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how do we keep that Hustle ethos that you mentioned at the beginning, how do we keep that alive, but still give a nod to Hub... I mean, you could go in the wrong direction.

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You know, not to name competitors, but Schmels, S'mores, Schm- You know, like, they decided to name their media business after the parent company. You know? And- Ah, Salesforce, yeah. Oh, yeah. Okay, yeah.

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Yeah, I guess that's it, yeah. So, like, I think what HubSpot is doing is really smart because they're letting The Hustle stay front and center, and that's what people love.

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They love Hustle the newsletter and Hustle the brand, and so that's front and center. Yeah, but I think that's, like, the issue, right? Like, I'll say Salesforce.

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Because, like, anytime, my experience, like, you know, one of the biggest problems of, like, big companies is when you're sitting in some... If you have a tower, like, that affects your thinking, right? Yeah.

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If you're sitting in the Salesforce tower, you think the world revolves around Salesforce. If you're sitting in the Coca-Cola tower, you think that, like...

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I remember covering this as a reporter, 'cause I'm like, yeah, oh, Coke is starting, like, a social network to compete with Myspace called SpriteYard, and I'm like, "Who in their right mind would want to, like, interact with people in SpriteYard?"

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Like- Right. Yeah... I don't really even need to, like, learn much about this. This'll never work. Right.

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Like, and anyone [laughs] who is not sitting in the Coca-Cola headquarters or is an agency trying to, like, wring more fees out of, uh, Coca-Cola would know this, I feel like. Um- Right...

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so, like, I do, yeah, I d- I do wonder about, like, a- about how much this is necessarily a template, because it's one of those things that it sounds good in theory. Yeah.

256
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And like, you know, it's good on paper, you know. But I remember early on in my career someone saying, "Yeah, communism sounds good on paper too." Sure.

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But, you know, when you start to do it [laughs] it's a little different. It doesn't work, yeah.

258
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[laughs] So, I mean, my, my decade plus at The Motley Fool certainly, um, got a lot of experience in publishing, but also had a lot of experience of, like, the economics of the business. Yeah.

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And one of my things that I learned was, like, never stray too far from the revenue is, like, one of the best, like, kind of axioms that I could say for, like, any leader, and that was definitely an important part of coming on was I didn't wanna just operate a media business that was kind of t- gentle to the core business.

260
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And, and we actually didn't, we weren't responsible for leads. We were just responsible for impressions.

261
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Like, I wanted to be responsible for all of the blog properties, because those properties create leads, and those leads turn into revenue for HubSpot. Yeah. Yeah, 'cause then otherwise you get...

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You, you become, like, again, the, like, the, the side, literally side hustle, if you will. Yeah. Um, [laughs] that could've been the rebranding, Side Hustle. [laughs] Uh, [laughs]

263
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I'll just, I'll bill you for that later. Um, but, like, the... Like, I think about that.

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Like, you see, like, Netflix with Tudum and stuff like this that, I mean, I guess they're still continuing it, but they got rid of, like, you know, their team and they're restarting or whatever.

265
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And, you know, a lot of these things are, particularly when times are good, you know- Yeah... there are, you know, they're great ideas. Yeah. Like, you know, and

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a lot of these companies, particularly technology companies, I have this theory they're just completely overstaffed and they got tons of marketing people who come up with these ideas, and usually it flatters the CEO or the boss's, like, you know, grand notions and stuff like this.

267
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And then, and then times get tough, and then you see the thing. They're shutting this down, they're shutting this down. They laid off half the, the team there. Yeah.

268
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Because any time when the economy turns, the fir- the last thing you cut are the main drivers of the business. Totally. It's the absolute last. That's why sales never gets cut.

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Like, that's why editorial gets cut first- Totally... is because you do not cut the people who are driving revenue.

270
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And the challenge for, I feel like, a lot of people in this model is if they're too far away from the, the, literally the core of the business. Yep. Yeah. No, I agree.

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I mean, we're, we're already seeing that and we're gonna continue to see it play out, obviously.

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We're, you know, whether we're calling it a recession or not, it's, it's happening across, you know, tons and tons of different companies. And it's not that we don't feel belt-tightening too.

273
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Um, it's certainly a really challenging macro environment. But the great thing, like, you don't need that many people to make an incredible media product or media products.

274
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The challenge is always with the business model. So we, like, it's not like our team is... I mean, in the whole grand scheme of HubSpot, my team and our budget, it's, it's a blip in the radar.

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Like, it, it wouldn't even be worth it to come and say, "Slash half the team." Like, we're just not that massive. Um, but the business model allows you to continue fueling that growth. I mean,

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I, I think to one of your early questions, like, is this a template? I think it absolutely is for people, especially the parent company, who are willing to do it right. Yeah, well, the, that's the tricky part.

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That's the hard part. The second part. Yeah. Yeah. [laughs] 'Cause you gotta find- And what, um, the right companyTotally. And I'm, um, what am I? Eight, 10, I don't know, 10 months in, so who knows?

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You know, maybe next year they shut me down, and they, they rip apart all of our budget [laughs] and our... But, you know, f- so far so good. All right, I'll have a talk with Kipp. It'll be fine.

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Um- Let me, let me know, let me know what he really says. Okay, so final thing is, is let's talk about this creator network, 'cause I, I go back and forth, uh, on this thing. I know, like, I, I have...

280
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I, I'm, like, working on, like, a grand theory of this, of, of all this creator stuff 'cause I, I can't totally wrap my head around it. But- Yeah...

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I sort of think about it as, like, the sharing economy for media in that, like, it sounds like this wonderful little thing, but it's actually a way to sort of, like, disenfranchise, like, you know, actual, like, workers and make them, like, just, like, you know, more of a precariat and, like, feeding these algorithms and machines and stuff like this.

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And, like, you just... It just all sinks to the bottom. But that's my theory about it. But explain to me- Okay...

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like, what you guys are doing on this, like, and I always use quotes around the, the sort of creator world. Sure.

284
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Um, so the, the objective of what HubSpot is doing with our creator program is instead of, you know, most big brands like HubSpot, they will go out and buy, you know, media placements in other places, and they'll spend millions and millions of dollars getting brand advertising in different media, um, agencies and networks.

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And HubSpot has said, "Actually, screw that. Why don't we just build our own media network? And we can put whatever sort of ads we want. We're not restricted to, like, this 30-second spot or this way to do it."

286
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So what we are doing is we have... There's two parts of our creator program.

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First part we call, like, our established program, and it's basically that's where we go out to established, um, creators, and we create licensing deals with them.

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So Entrepreneurs on Fire, My First Million, Being Boss, these are podcasts that have established audience, and we're going out to them, we're, and we're basically paying them a fee in order to have HubSpot ads, uh, in the, in their, um, podcasts.

289
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The other thing that- Is that, like, exclusive? Let me just jump in. Is that exclusive, like, or is that just a- Yeah, there's an ex- Yeah, there's an exclusivity deal- All right... um, that they'll have with us.

290
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All right. And it's, like... So the rebooting could be in the creator program. Oh. And so there's a lot of things [laughs] that you're like, "Oh, thank you." Now we're talking. Kipp, get in here.

291
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[laughs] So there, there's a lot of, um, there's a lot of things that add value to the creators for being in our network. It's not just a fee.

292
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We also support them operationally with marketing and blah, blah, blah, lots of other stuff.

293
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The other thing that we have is the, um, emerging part of the program, which is more of what you hear about, um, like, if it's, like, Spotify's, um, Spotify's or LinkedIn as a creator program, Pinterest as a creator program, TikTok as a creator program.

294
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And that's where we're basically... And we go out to people that don't have audiences, but they wanna start their own podcast, or they wanna start their own YouTube show or whatever, and we basically give them a shot.

295
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And it's, you know, it's a, it's... We're still super early stages. I mean, we just launched our first cohort four months ago with eight podcasts. Um, so, you know, we'll see how it goes.

296
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But our, our hypothesis is basically that, like, because of the scale of the HubSpot media team, you know, cross-promotion's one of the most beneficial ways to grow anything, whether it's a podcast- Yeah...

297
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or a newsletter. And so we just kind of feel like we have a massive advantage because of the scale of the HubSpot podcast network and all of the different HubSpot, like, media assets- Yeah...

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that we can help grow emerging creators at a much faster speed than they could on their own. So do you think this is gonna be part of the, like, the sort of rebundling? 'Cause, like, I just don't...

299
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I don't know how you feel about, like, you know, the sort of Substack, quote-unquote, "revolution" or something like this. I mean, I, I get the sense that it's sort of, like, hitting the wall and stuff like this. Yeah.

300
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And maybe it'll, it'll normalize, and like anything, like, it goes into this, like, sort of, um, trough of disillusionment. Um- Yeah...

301
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but, you know, like, as I said, like, media's a slow burn, and it's an endurance sport. Yeah. It's not a sprint. [laughs] Yeah. And, uh, all the cliches. Um, but it, it requires, like, time, and, and it's, it's hard.

302
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It's hard to build audience, and it's hard to retain audience.

303
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And so I, I think that that speaks to a sort of rebundling to some degree, but I think that it'll, it'll be different than just people saying, "Oh, forget this.

304
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I'm going to, I'm going back to, to work for X publication or Y publication." Yeah. Yeah, I think I, I think I largely agree with you.

305
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I mean, in the beginning during, like, the whole Substack phase, I was ecstatic and excited because there was so much good content coming out, and people were, you know, starting their own newsletters.

306
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Um, and it was just super exciting. Now it has gotten to that point where you're like, "I can't keep up. There's so much." Also, you can't... It's hard to know if somebody's actually a writer.

307
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You might sign up for a newsletter, and you get it, and it sucks, and you're like, "Man, this fucking blows."

308
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Like, so it is- [laughs] It does get harder and harder to separate, um, like, quality, and the quantity is overloaded right now. Yeah. But I do think there'll, there will be a rebundling, to your point. Um- Yeah... yeah.

309
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I mean, here's a quick, like, funny kind of anecdote.

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When I joined The Hustle the first time around as an advisor, one of my first meetings with the whole company where I was getting to know people, um, somebody asked, um, "Hey, what, like, what's a newsletter that you like right now?"

311
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And I said, "Oh, I've been... I just started reading this newsletter called Good Better Best. I love it. It's written by this guy named Rob. He talks about, like, pricing and, um, pricing psychology and stuff like that."

312
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And literally, they were like, "Oh my God, we love him too." And, like, two months later, we were able to get Rob to actually stop doing his own newsletter, and now he's a full-time writer for The Hustle.

313
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So things are gonna ebb and flow. You know, people were quitting their full-time jobs in droves to start their own Substacks.

314
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Now I wouldn't be surprised if people, you know, quitting their Substacks, going back to companies and publishers. Okay, so, okay. So this, I... We're, we're getting to 48 minutes, and, like, Jay- Cool...

315
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keeps telling me to keep them shorter. So I could do this all day. Okay. I could talk newsletters, B2B all day. Yeah. But the final thing is because, like, as I mentioned, like, very early on, you know, The Hustle

316
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and Morning Brew, like, I thought it was, like, Bloods and Crips of the newsletter world. [laughs] It's just, like, the, the, like, [laughs] nerdiest possible sort of beef and stuff like this.

317
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I mean, give me your honest evaluation of what you like about Morning Brew and what drives you nuts about it. Um, God, I knew you were gonna try to rope me into this.

318
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First of all, I will say, like-Friends with all the guys at Morning Brew. All right. There is no beef. Cut that out, Jay. Cut that out. Okay.

319
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This is, this is what, uh, I will say that I really, really like about Morning Brew is that every single day, you do know exactly what you're getting.

320
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It is structured and organized really, really well, so that when you o- open up Morning Brew, like, you start to develop your own reading habits. Oh, I like this part. I'll skip back to this part. I skip...

321
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Like, it's highly skimmable. Like, it doesn't surprise me, honestly, that their growth, um, exceeded the Hustle's growth at a certain point, because I just think it's built a little bit more for the masses.

322
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And I don't say masses in a negative way, it's just I think that more people are interested in, I gotta keep up with the news. Um, I, you know, and it... You just develop a better reading habit, I think, with them.

323
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Um- Yeah... so I, I think they do an excellent job at that, and I... Yeah. If I- You're basically saying it's very tem- it's very templated. I think that's what you're saying. Nope. Nope. No, I'm not saying that at all.

324
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I like Alex and Austin, so. [laughs] Not gonna lure me in. I refuse. [laughs] I re- [laughs] I refuse.

325
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Well, no, I do, I- [clears throat] I'll just add, but I, like, I think it's always, like, a challenge because, like, you think about, I'll take it to, like, Axios or something like this, right? Sure.

326
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So, like, everything gets boiled down into a, a format or a template and stuff like this, and it, it allows for, like, immediate consistency and familiarity- Yeah...

327
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and habit, like you said, and these are amazing things.

328
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I think the downside ends up being, it's like, you know, is it almost becomes a parody of, like, with Axios of the like, you know, it's like, "Why does this matter?" You know, "Go deeper." Right. Like, you know- Yeah...

329
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two-minute read. And, like, not everything. I think one of the, the parts that I chall- I, I struggle with is, um, is the importance of, like, having a unique format.

330
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A- and that, like, I think the best brands, if you took away, like as I said earlier, if you took away the logos and you took away the packaging and stuff like this, people would say, "Oh, that's a Hustle story."

331
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You know, "That's, like, the rebooting. That's, uh, Morning Brew," or something like that. I'll put myself in there. Why not? [laughs] Uh, a- and I think the challenge ends up being is

332
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it, and particularly as you scale, is it can become very templated. Like, I, I know this, like, just... I'll use, like, my past experience, like, at Digiday with doing events.

333
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It was impossible to do unique events when you were doing, like, 80 a year. You e- if you're doing that many of anything, it becomes an assembly line. It's the only way you cope. Yeah. Yeah. I mean, I don't disagree.

334
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I think there are... You can try to balance. I mean, I... There was a point at which- Yeah...

335
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I was looking at the Hustle newsletter, and I really did think that we needed to move a little bit more towards what The Brew was doing.

336
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There was a point at which the Hustle content was terrific, but every time you opened it, you, it was like, holy sh...

337
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Like, there's this story, then there's 25 emojis, and this thing flashes across, and there's gifs- Yeah... and you're like, holy shit, like, this is like taking acid.

338
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You know, like, you do need to make it- In a good or a bad way?... a little bit, you know, a little bit of both. [laughs] There's, there's always a g- a good part of the trip and a bad part of the trip.

339
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But, like- Okay... I, I do think that there's a, there's a balance there. Um, so I like having a predictable format. Yeah. I like the stories to be the things that really stick out and shock you. Right.

340
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Like, make the content- Yeah... the key part of what, you know, what you're doing. Yeah. I think that's like, 'cause it's like, um, I keep going back to, like, connective tissue.

341
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Like, and I think that one of the challenges... Actually, a, a Hustle, um, veteran, Adam Ryan, was on here a couple weeks ago. Um- Right...

342
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and one of the challenges I have with the Workweek model is what the connective tissue is between all these different creators, 'cause y- you can l- lean into individuals as much as you want, but if you wanna build, like, a brand, there needs to be- Right...

343
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some connective tissue other than you're just aggregating a bunch of people who have audiences. That's, that's an ad network. Yeah. That's not, like, a media brand in my view. Yeah. Um, and so- Yeah...

344
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developing that connective tissue is really important, and I think a very blunt force is we're gonna boil everyone down into this, like, templated format, and, like, you write to the template. Right. Get...

345
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You'll get, like, consistency, but you also might get uniformity. Yeah. Yep. No, I agree. So.

346
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I don't, I don't know a ton about, um, about their business model, but yeah, there's a difference between a network and, and a media publisher, right? Like- Yeah...

347
00:53:23.214 --> 00:53:32.504
and, and that they're j- they're different business models. They have different objectives, and so one is just- Yeah... trying to aggregate creator. It's kind of like our cr- HubSpot's creator program. Right.

348
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We're not trying to make the creator program have a personality. There doesn't need to be a whole lot of connective tissue. We're trying to do something where we aggregate creators in order to scale and blah, blah, blah.

349
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The, a media brand is publishing content with a point of view that's original to them. Yeah, and like, I... It's like Dive, Industry Dive, as we're recording this, like, I, you know- Yeah...

350
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think they, they sold at a 500 million plus, uh- Yeah... valuation. And I think- Right...

351
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one of the things that Industry Dive, like, I, I'd written about this, that I think they got, quote-unquote, "right" that I personally was not super into, was really templating these things out across industries.

352
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Like, I mean, if you- Yeah... open, you know, there are some variations, but if you... I, I'm not on, on the Waste Dive one, but, like, you know, Retail Dive and Marketing Dive, like- Yeah...

353
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yeah, just, like, this, the sites are the same, and so there's a lot- Yeah... when you simplify things, there's a lot of leverage that that creates, but there, it comes at a cost, like anything. Right. Yeah. Yeah.

354
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Just depends what you're optimizing for. Like, people are talking a ton about the Industry Dive, um, acquisition, 'cause it's awesome, and, you know, congrats to them. But I'm just... They weren't... I, I don't know.

355
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I guess it just depends what you wanna be doing. For me, I'm like, I think that's incredible what they did, but I w- I don't, that's not the world that I wanna be in.

356
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I just personally enjoy being in a more editorial-driven world, um, where you're actually- Mm-hmm... writing content that's, yeah, just a little bit more interesting, I guess, and less templated than that. Yeah. Okay.

357
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All right. I gotta, I gotta check on Kip back in the kitchen, see how- [laughs]... see how his cor- corditos are doing. This is gonna go terribly, terribly wrong for me after the podcast.

358
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[laughs] Try, try to get an insertion order or f- part of this- [laughs]... uh, program and stuff like that. Anyway, Jordan- Oh, fuck... this was fun. I really appreciate- Yeah... uh, you doing this. Thanks, man.

359
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Thanks for having me. I appreciate it, guys.Thanks a lot for listening to that conversation.

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Up next, I have a ten-minute bonus conversation with Steve Lilly of Bombora about why publishers should be out there kissing a whole bunch of frogs in advance of the demise of the third-party cookie.

361
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Trust me, it makes sense in context. [upbeat music] And I mean, it seems like it's kinda like putting together like a jigsaw puzzle, right? Like, I mean, it's like there's a lot of different pieces.

362
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Some are more valuable and useful than others. You wanna find the corner pieces, so there are only four of the corner pieces. But you're gonna need to piece together the puzzle with different...

363
00:55:50.192 --> 00:56:01.782
There's a whole bunch of different pieces together. So the final topic I wanted to talk about, and this is a little bit broad-brush, but what do you see as, like, the steps that publishers that are successfully...

364
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'Cause y-you mentioned, like, you work with publishers that are farther along on this journey.

365
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So, like, and I think, like, one of the interesting things about this field, and maybe every field, is how much, like, publishers can learn from each other in particular.

366
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But, like, most of them, like, don't have visibility into other people's businesses. That's why I've always liked talking to people like yourself because you see, like, inside a bunch of different businesses, right?

367
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So give me, like, the sort of characteristics of a data-centric publisher that is setting themselves up for this future, uh, of data transformation. Yeah.

368
00:56:37.912 --> 00:56:49.162
So I think the first sign that things are gonna go well with a partner for us is, um, A, they recognize all the things we do to de-risk the ec- the ecosystem.

369
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If you're paying, if you're paying attention and your, your InfoSec folks know what they're doing, we're able to go through that process very quickly under the auspices of, "Let's just get the data in and look at it."

370
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You can spend a lot of time kinda out in the ether saying, "It could do this, it could be this conceptually, it's this, that, and the other thing."

371
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And the reality, like, until it's in your pipes and you're looking at it, either and you're visualizing it, either resources that we present or in we're sort of platform-agnostic third-party tools, you really don't know how it relates to you.

372
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And so a first sign of success is folks that recognize that the privacy stuff is, is really a, a non-issue. Um, we anon- we anonymize the sources. We don't ingest PII.

373
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We don't ingest proprietary sort of behavioral insights, if you will, and we return these highly scalable resources that really should go straight into whatever BI tools exist to start to figure out what does this mean for us.

374
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So the first thing is putting your hands on it, moving quickly to just get it into a system where it can start to be met is the first sign of, like, just recognizing that spend a lot of time guessing what it is, and it really isn't anything until it's in a system and you're starting to overlay it against first party and start to figure out where are there areas of strength, where are there areas of weakness, what insights can you...

375
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I think the other thing too is, and so I kind of house that under this concept of PSI, that, um...

376
00:58:14.952 --> 00:58:25.512
And I'm, and as you already know, I use some of the worst analogies out there, but one of the ones I can't avoid- Wait, what's PSI? Well, people have built a lot of pipes to move audience data around, right?

377
00:58:25.552 --> 00:58:29.792
To do marketing automation, right? Mm-hmm. And CDPs and DMPs.

378
00:58:30.232 --> 00:58:36.762
But, you know, a lot of times, if you only know a lot about twenty or thirty percent of your audience, it's like you have pipes where there's not a lot of water pressure.

379
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And so I often look at ourselves as we're a highly scalable quality resource. You just inject that into a system matched against first-party audience, and it just sort of adds PSI.

380
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So whatever wheels, bells, and whistles are going to run, they run at capacity versus, well, what could they be if we had information on the other seventy percent of the unknown audience?

381
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And so I often think of the, the first problem is getting enough data into these pipes so that they actually crank wheels. I mean, you actually get measurement of things, or you're measuring things at scale.

382
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There actually is the opportunity to see trend. And so going back to complacency, one thing we've seen, if people say, "Yeah, we get it. We, we get it. You've got ninety-nine percent retention rate.

383
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Nobody gets hurt," yadda. They're like, "You know, we just don't wanna mess up this first-party strategy. We're afraid to screw this up." And we're kinda like, "Do you have no...

384
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There's no better thing you can do but to get more information matched against the first party you do have, both logged-in users and unknown users, to, to start to figure out what the strategy should be."

385
00:59:42.572 --> 00:59:47.872
And we're able to do that in a way where, you know, it's whatever. It's a tenth o-of the cost it might be.

386
00:59:47.932 --> 00:59:58.332
If you went out and bought the standard three or four data points we can overlay over most, uh, publisher's audience, it'd be a three dollar CPM in most data exchanges. So nobody does it.

387
00:59:58.352 --> 01:00:10.762
But if you can get that overlay and really start to see, well, who is in this transient audience as it turns over, now you're in a position to actually understand a lot about something nobody really... It's a tough sell.

388
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"Hey, I wanna spend a half million bucks a month for six months, and I don't know what we're gonna find.

389
01:00:16.772 --> 01:00:26.452
I hopefully will monetize it, but by the time I know what we have, I'm three million dollars deep into this project." Right? No wonder nobody does it. It's too expensive- Yeah...

390
01:00:26.552 --> 01:00:30.092
to overlay a bunch of data to just see what you find.

391
01:00:30.332 --> 01:00:38.852
If you ha-- And, and granted, I was assuming an audience, you know, assuming, like, an audience of fifty million uniques, and you're overlaying thirty, thirty million of that. It gets very expensive very quickly.

392
01:00:39.392 --> 01:00:48.432
So the long and the short of it is, under the complacency thing, um, what are they doing well? They're know-- They know they need more data in the system to- Yeah.

393
01:00:48.872 --> 01:01:00.292
And my cheesy analogy is it's like driving a, it's like driving a jet ski, right? And so people in, in an abundance of caution to not screw up- Do you drive a, do you drive a jet ski? I should know this. I live in Miami.

394
01:01:01.672 --> 01:01:12.042
Poorly. [laughs] And that's why I know this, which is you wanna go slow to not mess up, but as you go slow, you lose steerage. And so the reality is that- Right...

395
01:01:12.072 --> 01:01:22.732
this goes back to you should be kissing frogs and piloting more things to figure out that stable of horses because that input from these different players is the PSI.

396
01:01:22.742 --> 01:01:34.311
It is the throttle that allows the vessel to still steer.And what you see people doing that are being complacent is they're taking their foot off the gas because they don't want to drop all the used to be silver, now gold eggs.

397
01:01:34.792 --> 01:01:44.562
And God forbid I drop a gold egg or give one away to the wrong third party. And so they go slow and they do nothing with it. When the reality is- So wait, they're on a jet ski and they've got like- With golden eggs...

398
01:01:44.562 --> 01:01:50.312
a basket of golden eggs. Okay, you're like painting an evocative fixture [laughs]. And they shouldn't slow down. I know. Yeah.

399
01:01:51.392 --> 01:02:08.432
My, my twist on that, that I do understand a little bit is it's kind of like when on a, a stand-up paddleboard, like a lot of people that are new, they end up like feeling like unsteady, and so they stop paddling, but that's actually when you're gonna lose your equilibrium.

400
01:02:08.472 --> 01:02:19.532
It's sort of like that. It's exactly the-- Yeah. It's exactly the same point. The reality is most publishers that haven't started their data transformation don't have enough data. They may not even have the pipes.

401
01:02:19.712 --> 01:02:25.842
If they have the pipes, great. Yeah. Push more through it so that trends mean something. Yeah.

402
01:02:25.892 --> 01:02:36.832
Indicators have value, and that actually informs the transformation and informs the needed strategy versus, "Hey, I, I can't hit the throttle and hold the eggs because God forbid I drop the eggs."

403
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[laughs] The reality [audio cuts out] the cookie's going away.

404
01:02:51.682 --> 01:02:55.952
And so start now figuring out all of these pieces so that to some degree

405
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y-you have some familiarity, you're as nimble as you can be when the cookies do go away, and personnel, right, are familiar with figuring out how to tell a story that connects the dots, that creates continuity and a clear value chain that inherently requires greater accountability.

406
01:03:15.652 --> 01:03:27.332
And I think that's the toughest part of it, is you're going through a transition that's gonna create more value for both the publisher and the advertiser, and there's gonna be fewer places to hide once you do it.

407
01:03:27.362 --> 01:03:41.592
And that's l- I-- Coming from B2B, I mean, that was the beauty of it, is we have top-of-funnel content, mid-funnel, low funnel, and if one guy consumes one piece of low-funnel content, oh my God, a Fortune five hundred company is now in market for this two million dollars piece of software.

408
01:03:41.632 --> 01:03:45.041
It's like, it's not actually how things get bought. Well, I remember- And-...

409
01:03:45.041 --> 01:03:57.832
the early days of the behavioral ad networks, like they were saying that like I forget how many people that they would claim every month were in market for a car, meaning that they were gonna buy a car in the next thirty days.

410
01:03:58.352 --> 01:04:11.652
But it was, well, like double the number of cars that were sold in the United States [laughs] in any thirty-day period. So data can be-- If you torture data enough, it'll tell you what you want. Tell you [laughs].

411
01:04:11.732 --> 01:04:20.952
[laughs] Say it and we'll let you go. Exactly. All right, Steve, let's leave it there. I wanna thank you so much, really appreciate, uh, your support, and thank you for having this fun conversation.

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[upbeat music] Thank you for listening this week. We will be back next week with a new episode. The Rebooting show is produced by Podhelpus. Podcasts are a great way to expand your client base.

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Podhelpus lets you focus on having engaging conversations, giving your brand the full stack of services needed for a professional look and sound. Start your podcast today at podhelp.us.

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