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So the first thing I think is shifting from an audience mindset to a community mindset. Step two is build trust and strategy first, and then monetize later. My third bet is you have to know what your arbitrage is.

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I wanna know if there's three things that five years ago were really valuable in the creator economy and now have lost value. The first one I think, which is a no-brainer, is just short form.

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I think a second one is, and this one I gotta be careful how I say it 'cause it's podcast. Welcome back to the Creator Spotlight podcast. My name is Frances Year, and today we're speaking with Jordan DiPietro.

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Jordan's career includes a few of the most famous and successful new media businesses out there.

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He spent twelve years at The Motley Fool, starting as a writer and finishing as VP of Growth, then led The Hustle when they were acquired by HubSpot, and most recently served as the CEO of Hampton, the high-ticket private community Sam Parr founded after leaving The Hustle.

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He's now writing his own newsletter, Signal/Noise, and consulting founders and operators on their businesses. Jordan is a really smart guy, really sharp speaker. This is a really good conversation. I really enjoyed it.

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I think you will too. So you promised to tell me the three moves that you would bet your next ten years on as a creator. Yeah. Walk me through these three moves. Okay.

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Um, so the first thing I think is shifting from an audience mindset to a community mindset, and so I think in the last five, ten plus years, whatever it's been, people have mostly developed very one-sided transactional relationships.

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So they build an audience, um, and they transact with that audience. They post something on socials to get likes and comments. They have an email list they send emails to.

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You know, it's just like very one-way and transactional, whereas a community relationship is, is by nature a lot different. It's more of a, you know, two-way kind of reciprocal relationship.

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And I think that the more and more people start thinking about this from the very beginning of their business or their, you know, whatever th- it is that they're starting, I think just the better, um, things are gonna be in the future 'cause I think we're just moving dramatically away from just impressions for im- impression sake or reach for reach sake.

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So I think that's kind of step one. Step two is there, there was a philosophy that kind of said, "Build an audience, and you can monetize it later," right? Mm-hmm.

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So many people I think, especially in the beginning days of YouTube especially, built huge audiences, and they figured out monetization down the road, or they built huge followings on Instagram, and they, and they figured out monetization down the road.

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I don't think that that works nearly as well today, but I deal s- I, I do still think that you should build first, but I think that you should build t-trust and strategy first- Mm-hmm... and then monetize later.

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I-- There are way too many people that land in my inbox or that I see building businesses, and they're already trying to monetize.

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Like I have no idea who you are, I have no idea what your credentials are, um, I have no idea if I can actually count on you to fulfill on whatever the value prop is that you've shared with me, and it just feels too presumptuous.

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Mm-hmm. So I feel like there needs to be, you know... There just needs to be more, um, more trust built in the initial part of whatever it is. And I think that there's a really easy way to do that, and, you know, I mean,

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not that m-my way is the way to do it, but I've been working for twenty years before I've really started to produce content or kind of ask people for any sort of value exchange.

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But I think that in doing so, right, people know that they can trust me. There's, there's a, a reputation there, and there's trust built up over the years.

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So I think, I think that's another thing is not trying to monetize too early. Mm-hmm. Doesn't mean just like build an audience blindly, uh, and cross your fingers.

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Build a strategy around the future thing that you do wanna monetize for, but don't feel like you have to do it right out of the gate. That's-- So before you get into the third one actually- Yeah...

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real quick, I wanna, wanna pause on that. Yeah. Um, it's reminding me of something that our mutual friend Matt McGarry said when I had him on, uh, where I, I forget exactly what I'd asked him.

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It was something about like if he identifies as a creator, and, and he said he didn't.

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Um, and part of why is he said he-- anything he's going to create, any content asset that he's gonna put out there, he's always ha- he always has a way to monetize it built in first.

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There's never content without some sort of monetization attached, though maybe this is where it connects with what you're saying, even if that's kind of down the line and downstream.

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His newsletter, for example, it's all... It's not directly monetized. The monetization is i- as a top-of-funnel for his course and then his agency services. Right.

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So I don't know if that, if that conflicts with what you're saying. But, um, I feel like I talk to more and more entrepreneur st-type style creators who, who always have the monetization tied directly to the content.

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Right. And then I talk to a bunch of more like creative or like sometimes from the journalist world style creators, and they don't-- they're really just content first. Monetization comes later. Right. It's less attached.

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Right. Well, I think it's important to note kinda two things.

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I, I mean, I do think of course like everything there's, there's different ways to do stuff, but I think you're looking at Matt McGarry twenty twenty-five point in time today- Yeah... and, and what he says he's doing.

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But I can't remember, God, what year we hired Matt at The Hustle. Let's say it was twenty eighteen or- Mm-hmm... I don't know, some-something around there. Something like that. But, you know, Matt

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built his chops at The Hustle.

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Then he went over, I think, post-acquisition at HubSpot for a little while too, and then the, he spent some amount of time there, you know, having enough confidence in himself that he knew what he was doing from a, a, a paid media to build up newsletters till he went on his own to do the agency, right?

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And then he was building the agency and hopefully seeing success with clients. It gave him more confidence that what he was delivering was of value.

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And then so it was a very iterative process, and it's like step-by-step when you are building trust, right? Mm-hmm. Which was the thing I said. And he was building out his strategy.

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I'm sure when he started at The Hustle, he had no idea, right, he was gonna have an agency and then be doing communities and all this other stuff. But over time, he built out trust, and he built out a strategy.

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So then you get Matt McGarry in twenty twenty-five who's able to say, "Oh yeah, everything that I produce has a strategy and, um, a, you know, a monetization- Yeah... strategy around it."

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But, you know, I think he would be the first to say, "Yeah, I didn't, I wasn't thinking about that in twenty eighteen." So I- Hindsight is twenty/twenty sort of situation. Yeah. I, I think it just takes time, right?

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Yeah. You gotta, you gotta put in the work to get to the point where you can be as intentional as he is. Um, you know, so that, I guess that's, that's kinda- Mm-hmm...

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my quick take on that.Um, okay, so the, the final thing, the third thing, your third bet Yeah. My third bet is you have to know what your arbitrage is. Mm. So this conversation, I'm gonna talk a lot about arbitrage.

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I think that there are basically three arbitrages as a creator, as a producer, as somebody in content or media. I think there's an attention arbitrage, there's a taste arbitrage, there's a trust arbitrage. Mm.

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So attention is obviously, you know, impressions, what's your distribution, what's your reach, how many platforms you're on, all that good stuff.

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And if that's your game, if that's what you're great at, virality or reach or whatever, awesome, then play that fucking game and do that all day long. Um, trust is different, right?

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That's a different sort of arbitrage that not as many people have. It's harder. It takes longer. Um, I think it's, you know, it's probably higher value in terms of monetization, but it's a hell of a lot harder to reach.

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But when people trust you, you have so many different... You really build optionality into your business. You know, I've had people tell me,

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"Hey, if you were gonna go and launch, like, a carpet business next week, I would probably just join you." [chuckles] Yeah. Like, that's crazy 'cause I don't know anything about carpets.

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But that does tell me that people trust me, which is a nice, nice thing, right? Yeah. So it, it builds a lot of optionality, but it's, it's different.

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You have to understand what you're good at and what you think your strength is. I mean, this is kinda arbitrage here is basically the same as saying, like, know, know what your strengths are and what your weaknesses are.

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And then the last one, taste, is, you know, do you have really, really exceptional taste? Um, are you good at curating things? Do people seem to really care about your point of view?

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If that is one of the things that you're good at and that you seem to, um, you know, get respect for in this space, then that's something that you should double down.

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So I think it's really important to just know from the beginning what you offer, you know, in a unique way and make sure that your, your vision for your company and where, where you're spending your time and energy is, you know, directly kind of correlated to which one of those you're kinda going after.

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Yeah. That's-- I think that's a really helpful framework.

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Um, on, on the inverse of this, uh, I wanna know if there's three things that you think maybe in the last five years or maybe five years ago were really valuable in the creator economy- Mm...

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and now have lost value or, or if they're being given as advice, maybe, you know, it's kinda bullshit.

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I think, you know, uh, pretty clear in your first item there when you said that community over audience now, it's not... I don't think you're saying that audience is meaningless- Sure...

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but you're saying that, like, audience for audience sake maybe five years ago was more valuable, now has lost a lot of that value. Yeah.

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Um, but yeah, the question is three things, three creator economy trends or tactics, strategies, whatever- Cool... that were good five years ago that you think are dead or dying now. Yeah.

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Um, so this one was ea- Well, it was definitely easy to think of the first two. The first one I think, which is a no-brainer, is just short-form content in general. Mm.

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Um, I remember when The Hustle was first acquired, and we went over to HubSpot, and so many people were just talking about short form.

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And I remember, like, there, there's a couple of people in particular kinda in my ecosystem who were incredible at short-form video, I mean, really, really skilled at this.

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But when you would go deeper and say, like, "Well, what's the business or what's the business model?" It's like the business model was short-form content. Yeah. I'm like, that's actually not a business, you know? Yeah.

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That, that's, that's a type of content on a specific- Platform ad payouts are not very high. [chuckles] Yeah. And it's just, it's not a busine- Yeah. It's just, it's...

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I think what we know now is it can be a great discovery mechanism, awesome, but it's not a business strategy. Mm.

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So I think some of the hype has just died down a little bit from just short form, you know, clips, uh, and, and video content in general. I think a second one is, um...

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And this one I gotta be careful how I say it 'cause it's podcasts, and I love podcasts. Yeah. Um, but if you look at, like, 2020 to 2022,

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you know, especially post, post and during COVID, something like two million plus podcasts, um, came on the stage, probably more than that, maybe, maybe two and a half million, something like that.

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And, and then if you fast-forward to, like, I think it was the end of 2024, only, I, I think 90% or more of those podcasts had less than three episodes. Yeah.

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It's just, it, it was so oversaturated and, and there was so much kinda glut in the market. And so I think the days of like, "Oh, I'm doing this one thing.

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I should obviously just launch a podcast," are, are ho-hopefully coming to an end 'cause it, it definitely makes discovery harder because there's just so many things out there. Yeah.

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Um, so I think, I think podcasts, not that they're... I mean, it's still one of my favorite channels, period, 'cause it's- Well, I can... Uh, let me, let me...

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I can speak to this a bit too from my perspective doing this, right? Like, it's hard.

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I, I mean, I don't know if I've ever said this, uh, in public on the, on the pod, but our numbers right now at this moment in time, it's, it's Wednesday, August 13th as we record this, 2025, we get, um, anywhere from 2,000 to 3,000 listens per week, right?

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And that's, that's miles better than what we were doing a year ago. Right. I'd never podcasted before a year and a half ago.

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Now I've been doing it for, for a year and a half, um, and I've gotten much better, and that puts us in the top 10% of worldwide- Mm... of podcasts worldwide. Right.

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Which is, you know, 2,000, 3,000 listens compared to the newsletter, which right now we're getting 140,000 plus unique opens every issue, right?

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Like, it's a pretty huge delta, um, and m-m-multiple levels of value here, right? Like, I spent a few hours researching you today. We spend an hour talking, um, and then we use that to then produce the newsletter.

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So we're getting value out of it multiple ways. Right. Um, but also, like, this was not a very good product when I started, right? It was kinda like, "I'm doing this anyways.

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Let's invest a little more time, a little more money, and we can put this out." Yeah. And now we put something out that I'm proud of, and, and it... I think it's gonna keep growing.

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But, like, it's gonna take us a while to keep getting there. Yeah. And we're never gonna be my first million, right?

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I think, I think, uh, uh, we'll get more into, like, kind of your time at The Hustle and the, the effects there a little later.

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But I think people saw what The Hustle did with newsletters and what Sam and Sean did with the podcast, and it's like, "Wow, I wanna do that," right?

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A, a lot of people I talked to when I first started doing this actually would bring them up as inspiration, um, which has been great for, for, for podcast, you know, for Riverside- Yeah...

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which I love Riverside, and I used it to record this, but a lot of those people don't really know what they're getting into. Um, so I think-A long way of saying I agree. I agree with you, it's really hard.

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Um, and it's like, it's not... It maybe was easy 10 years ago.

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You're, you're, you're two guys, you're a couple buddies, and you start talking into a mic, and you just keep doing it, and then, like, you know, suddenly 2020 hits, and you get all this attention. But it's...

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Those attention hours are so much harder to, to earn now. Yeah. I think the, the two biggest things that, that you said are, one is like, it really is a labor of love. Yeah.

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I mean, you have to be ready with a podcast to grind week after week after week after week. If you take a week or two off, where all of a sudden the feed goes dead- Yeah... like, you're kind of done.

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So it, it really is, it's a grind. You gotta do it for you. [laughs] Yeah, you... I mean, you really have to love doing it and assume nobody's gonna fucking listen. Yeah.

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And, like, maybe if they end up listening two years in, great. The other thing is it's just, like you said, the relationship is at... The, the commitment level is so much higher.

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For somebody to read your newsletter, all they have to do is take out their phone while they're fucking eating a turkey sandwich- Yeah... swipe, read quick, boom, done, delete.

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To take out my phone and listen to a podcast, I actually have to, I have to have a very high degree of confidence that I'm gonna enjoy it because it's a, it's a commitment. Mm. So it just feels...

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They're, they're such... Even though people think of them and say, "Look, oh, they're all different kinda marketing channels," they're so different. Yeah. But it's also why

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if, if it's successful, like Sam and, and Sean were at My First Million, you, you know how many different things that enables you to do afterwards because it is so intimate and, you know, gets you so much trust with your audience.

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Yeah. But yeah. Anyways, I, I interrupted you. There was one more. You had a third thing to put down after podcasts. Um, what did we talk about? Short form podcasts. Oh, I think [clears throat] I love newsletters. Yeah.

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Obviously I've been in the newsletter game for 20 years, but I do think that paid newsletters are- Mm... are going to probably decrease in their popularity. Um,

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I think it's really, really hard to charge people for just more of the same.

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I think when you, when you start reading someone's newsletter and you're like, "Oh, this is a great newsletter," and then you find out, like, oh, in order to get this, you know, it's 12 bucks a month, or in order to get two more emails, it's 20 bucks a month.

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I just think people aren't that excited anymore by just more. Yeah.

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It's also, I think it leads to a lot of burnout with creators because you, you end up spending a lot of time doing shit that you don't like doing, which is like, "Oh, I'm writing this piece of content.

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Should this be m- my free list or should this be for my paid list?" Like, "Oh, the people that are paying really need more. Now I've gotta do this live Q&A. Now I have to do this event." You know, it's...

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And I just don't think the economies are s- of scale are there as well. Yeah. And I also just think, I don't know, I, I, I just don't feel like people wanna continue paying for just a tiny bit more.

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Um, I think when it comes to certain spaces, like finance, investing, um, tech, business, people are more willing to pay- Yeah...

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for those things certainly, but I think in other spaces it's, it's gonna get more and more challenging. Yeah, I think there's two, there's...

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I mean, there's more than two categories for sure, but to really simplify it, I think there's the category where you pay because you just wanna support the person, and it's like, "I love your work.

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Put, put five bucks in the tip jar every month." Right. Right? And then there's one, like, uh, Oliver Darcy, Status Newsletter, um, big media reporter, right?

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Uh, he just celebrated a year of his newsletter status, um, go- going independent from CNN, and I was reading the one-year anniversary thing.

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You, uh, what you were just saying made me think of one point in there, which was that the free content does not convert to paid subscribers. Mm. But when they have a scoop, a scoop always spikes their paid subscribers.

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Right. Which again, is, is sort of a business thing.

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People who are in media read his newsletter to learn more about media, so when you have exclusive information that you're not gonna get anywhere else, or you're gonna have to wait for it to be waterfalled out because somebody's gonna read that and then write about it in their own thing- Right...

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people will pay for that when it's relevant to their jobs. Right. Right. It's also, that's harder to sustain, right- Yeah... for him.

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I mean, that means, like, I, I gotta have a scoop every three months or else I'm not gonna be able to sustain this. Yeah.

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And I also think about it in a similar way to, you know, the reason that we have all the streaming platforms that we have today is 'cause everyone got totally sick of cable, right?

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And you're like, "I over- I overspend on everything, and it doesn't have all the stuff I want."

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And so there was a great period where there was, like, Netflix and HBO, and you were like, "Cool, this is cheaper and the content's great." Mm.

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Now we're in the exact opposite, where I think people are looking and they're like, "I pay for Netflix, I pay for Amazon, I pay for Disney, Hulu."

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Like, there's nine different things you're paying for, and you're not even that happy anymore with the quality of the content. Yeah.

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So I think there's, like, a certain reversion back to the mean, and I feel like that could happen- The rebundling, as our, our friend Brian Morrissey likes to say. E- exactly. There's gonna...

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There, there could be that in the newsletter space. Like, right now people are like, "Oh, cool, I'll go, I'll go, um, you know, follow and pay for my favorite media reporter"- Mm...

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"or my favorite, you know, political reporter, or my favorite health person." I wonder how things are gonna look when they're paying, like, 12 different individual people for stuff that used to just be free.

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Hey, if you're enjoying this conversation, consider subscribing to the podcast. We release a new episode every Tuesday. All right, back to the show.

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But I've been thinking a lot about community engine optimization, which I don't... I think I may have just made that up, 'cause it's... I don't, I don't really think it's a thing.

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Um, but [clears throat] you know, I- You're at the forefront of it. You can make it a thing.

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[laughs] I, I mean, I'm sure my wife will make fun of me later for, for making some garbage up on the spot, but I do think it- That's what podcasts are about. Yeah, exactly.

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If, if you look at how many searches there are right now- Mm... you know, across Google, GPT, Snap, Amazon, Meta, it... right? In the hundreds and hundreds of billions per month. Mm-hmm.

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And as a member, and obviously prev- previous CEO of Hampton, um, I look at what, what goes on inside the digital community in Hamptons and Slack on a daily basis. Mm-hmm. It's so search driven.

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And it was just occurring to me the other day that, like, out of the billions and billions of searches that are happening per day, I know everyone's kind of saying like, "Oh, it's like, you know, SEO is like the...

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You know, GEO is the new SEO, and that's where we should focus," which of, of course.

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But I'm also just thinking about what impact will it have when some of the highest value, highest intent searches are all happening inside of communities? Yeah.

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'Cause if I look inside of Hampton on a regular basis, there's, like-Kind of low-level rudimentary searches going on, like, um, what's the best way to sell a domain? Mm-hmm.

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To more transactional things like how do I get unblocked from my AWS account, to much more sophisticated things, you know, like how do I set up this ERP in a way that does X, Y, and Z. Yeah. And there's...

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That's how, that's how these people, some of the most successful tech founders are... That's how they're finding solutions to their problem.

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They're not searching on Google, they're not looking in GPT, they're looking in their communities first because it has such high trust. And I've, I've just been thinking about that.

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I don't have like a, necessarily a takeaway yet, 'cause I don't know how, how it might be monetized in the future or what it means. Well, I think- But it's just something I've been thinking about. No.

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I- I think this is, this is sharp. Um, I mean, another word for this kind of thing is, like, dark social, right?

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Like, which is a term in social media that people use, uh, that social media managers will use for the stuff that you're not... you can't find on LinkedIn, you can't find...

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Maybe it's in the DMs or it's in the communities. Right.

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Um, but I think the way you monetized it, like, I don't know how the people who are producing the media monetize it, but the way that you monetized it was w- [laughs] was with Hampton, which is a high-ticket community model.

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Which, uh, yeah, let's talk about that for a little bit. So for anybody who doesn't know, the, like, most summarized to say what Hampton is, is it's a high-ticket exclusive community for people.

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I think the floor is, like, you need to be running a business making at least $3 million a year to get in. Maybe that's raised. Um, but, but Sam, previously founder of The Hustle, founded it. You were the CEO.

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That was your last job. You left, uh, six months ago or something as we record this.

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Um, it's kind of one of the big success stories of this new wave of paid communities, and we've been talking about communities a lot recently on the podcast. Mm-hmm.

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Um, I think one thing I've learned is there's kind of two non-negotiables that define a good community. Mm.

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Is one, it's people with shared values, shared interests, working towards shared goals, who have, have kind of a mutual accountability in both contributing to and taking from the community because they're all trying to work towards similar goals, so there's mutual exchange.

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And then number two is always, uh, the in-person aspect. That's kind of like, uh, uh, that's a... You can almost say that's more of a negotiable 'cause there are healthy communities that exist purely online. Mm.

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But it's always kind of, like, not real until it's real- Mm... is, is the thesis I've kind of been building more and more.

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So tell me, um, anything I missed about what Hampton is, and then I wanna hear your take on what are the non-negotiables for this kind of, you know, the, this buzzword that we now use- Right, right... community. Oh, man.

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There's so much to go into. Um, you're right about Hampton. Yeah, it's a, you know, private network for, for founders and CEOs. Um, yeah, you have to do at least 3 million in revenue. Um, there's other, you know- Yeah...

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um, criteria as well, but those are kinda the main ones. But [clears throat] I think the IRL piece depends, and it's funny, um, I think I...

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I can't remember if I told you or not, but I'm writing a report right now in, in collaboration- Yes, you did. Mm-hmm... with The Hustle and HubSpot. So I'm gonna go through all this when I release the report.

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But I think the IRL component really depends on what kind of community it is and how much you're charging. Mm. I think if you have a $200 a year community, you don't have to be doing IRL stuff.

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If you have a $1,000 a year community, the IRL can feel a lot different than when you're doing a $10,000 a year or $20,000 a year comm- So I think your p- your price point dictates a lot of the format. Mm.

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So I think that's kinda the first thing. Um, I think one of the really, really big things is decentralization. Um, I think that's really, really critical, and that's also really hard.

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When you start a community, especially, you know, and I'll, I'll just kinda talk first person, but when I- Mm...

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started at Hampton and at, you know, let's say maybe we had 100-plus members at that time, um, you know, imagine how you would feel if you had 100-plus members, these very, very successful tech entrepreneurs, CEOs.

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You, you would want to ensure that the experience was A-plus, that everything was A-plus, and, and that can lead to you being very kinda controlling over the environment, which is a very centralized way of creating the community.

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But what ultimately happens, besides potentially burning out, is that the community then looks towards you and the company for direction. They don't create their own shared habits- Mm... their own traditions.

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They're not empowered to create value on their own. And the whole reason why communities can be so valuable is if they create excess value for, for members.

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So if they can get more value from being in the network, of course, you know, than they can on their own, then it has the opportunity of being an amazing experience.

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But if you make it all about the team, the CEO, the founder, you know, whatever, it's harder and harder to scale that. At a certain point, it just kinda breaks- Mm... and it doesn't really flourish.

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So that was a challenge for me in the beginning, um, of like how to kinda slowly release control of a lot of things and kinda build playbooks and, you know, build the right systems into the community so that members...

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so that it was more member-led than it was, like, company-led. I think that's- That's crucial... that's really important.

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And one other thing I'll say real quick is from the beginning, really, really, really defining your ICP, um, you know, your ideal customer profile, is super important, because you can go into things saying, "Oh, this is who our, you know, our, our kind of ICP is."

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But then just wait until you get people outside of your ICP who wanna hand you money. You're gonna be like, "Okay." Right? Like- I like money. Yes. Yeah. I, I enjoy money. That's why I started this.

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[laughs] Let's, let's do this. And but what can happen is you end up with a community with a lot of different kinda avatars of ICPs, and then you're trying to serve all of them. Mm.

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So, you know, kinda the, the most relatable example I can give is, you know, at a certain point in Hampton, we, we had, you know, bootstrap founders who were maybe doing 2 million in revenue

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sitting in a, in a room with a public company CEO or, you know, a venture-backed founder who just, you know, crossed 100 million in revenue. Like- Yeah... those three people have radically different problems.

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They have different expectations for what they want and they need. The solutions to their problems are totally different.

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And so if, if you're chasing kinda squirrels all over the place, that's, it's gonna lead to, like, feature bloat- Yeah... burnout... lot of customer support and just be kind of a real pain in the ass.

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So getting crystal clear about, like, who you're not gonna let in as much as who you are gonna let in, I think is, you know, really important. Yeah. No, that makes a lot of sense.

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Again, you need to make sure that, like, the goals and values are, are super aligned.

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One thing that just occurred to me, I, I hadn't really thought of before, is, like, the degree to which, you know, this is kind of a trend now and communities are this, this, this hot topic, but something like this, like, how different is it than one of these, like, traditional kind of communities like, uh, like the Elks or, like, the Masonic Lodges or whatever, like, you know, Harvard, um...

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There's, like, the, the, the clubs, the, the clubs there. I forget what they are. But, you know, the- all these, these classic elite communities- Mm...

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and then you get something like this, and I'm like, is there any substitu- subs- substantive difference, and is it just kinda like, you know, there's the classic joke about, like, oh, what if Uber released a product where it's like it can pick up multiple people at once and it stops on these lines and, and suddenly Uber's reinvented the bus, right?

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Mm. Um, so I guess, uh, uh, what I'm, I'm, I'm thinking through this, through this live, I've never thought about it before.

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Like, is this kind of just the startup version of one of those classic communities where, like, the, the axis upon which it, like, swings and where people gather- Mm...

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and what the commonality is, is this, like, new, like, startup founder, tech founder mindset? I don't know. I'm, I'm- Mm... I'm, I'm reaching at something and I'm not sure what it is. Yeah. Tell me if this is kinda...

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[clears throat] I'm not gonna, I'm not gonna go with the Masonic temple 'cause I, I- Yeah... even though my, my brother-in-law is in it, I don't know enough about it.

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I don't, I don't know, so to, to be clear, I don't know- Yeah... too much about any of these specific things. I just, I'm more, I'm just, like, throwing in examples of like- Yeah...

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these are old storied communities through which- Right... people come together, and, like, it's, it can be hard to get into them. Right. So let's use, like, YPO as, as a- Yeah... better kind of corollary, right?

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YPO has been a- around for kind of 100 years, and it serves a very similar purpose to Hampton. Mm-hmm. And, you know, I don't wa- wanna speak for Joe and Sam, the two current co-founders, but I would say that there's...

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The most revolutionary thing about Hampton as compared to YPO is just the people that we're serving. Yeah. Everything else is different around the edges. Like, they call them forums, we call them core groups.

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They do e- They're in chapters, we call... You know, it's like, but it's all, we're all trying to provide the same thing, which is, you know, member-led peer support. Yeah.

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Um, you know, founders helping each other out, making better decisions, going to events, improving their lives. The reason that they're so different is because of the people that we're serving.

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You know, so if you look at your, your quintessential Hampton founder versus your quintessential YPO founder, they, they, they look very different. Mm.

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Their businesses are very different, their age is different, po- potentially where they live is different, um, you know, whether or not they had generational wealth or the type of business model.

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All these different, these things are all just very different. But, but the product, the service... So if, if kinda part of your question is, like, are you re- you know, reinventing the wheel when it comes to community?

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Not at all. Yeah. Yeah. I mean- Well, I guess, you know, I, I- Or, sorry. W- w- where- No. You, you answered it correctly. I think I was just trying to figure out, like, what is, what is new about this?

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Like, that is, that is what I was wondering. 'Cause I'm a big believer that there's, you know, kinda no new ideas under the sun and it's just you recontextualize things for fresh eyes. Yeah.

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And I think, I think you did get it there. It's just, like, a specific group of people that wasn't being served maybe by some of these classic- Yeah... communities. Yeah. The- That makes sense...

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the audience is different. And then I, I also think the reason why it's just a thing right now and why, you know, communities are a buzzword is because you do have a certain amount of people that have gotten,

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you know, a, a large following in the last five, seven years. Yeah. And they're looking at, what else can I do? How else can I monetize this, right? That's spot on.

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It's like, and, you know, it used to be like, "Oh, I'll launch a software product." That was the obvious thing to do. Yeah. "I'm gonna build some sort of SaaS to live on top of this."

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And now it's just becoming like, "Oh, I can just launch a community." I mean, I can tell you, I'm, I'm sure we'll talk about it later, but I do, you know, advisory work.

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Almost every single week, I have a pro- a prospect call me, and th- their literal business is they have built a following on either Instagram, Twitter, or LinkedIn.

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They're now somewhere between one and two million in revenue just based off of, like, content and advertising- Yeah... and they're interested in building a community.

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[laughs] So it's just like, you know, it's just kind of the, the natural evolution of people reach a certain plateau in their own- Yeah... revenue kind of product journey, and now they're like, "Oh, SaaS, mass.

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Let me just- Yeah... launch a community." And I, and I think, I mean, a, a, a clear reason for this is likely, like, "Oh, we, I saw that, that Sam Parr did this, and now I wanna do it."

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I, I think, I mean, in the same way I, I've heard from so many people that they were inspired by The Hustle. Yeah. I, I think [laughs] that's probably a pretty direct reason, honestly.

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Um, okay, a question about community versus audience. We started this conversation with this. What are some of the most important differences in building...

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I also, after this, I, I, I wanna get into your, your Motley, your Motley Fool era, 'cause I think that's something that other podcasts that listen to you, it always kind of got pushed to the side and, and pe- I know...

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people forget to talk about it. It's my favorite too. And that's where I wanna go 'cause I think that's where a lot of your stuff about building an audience comes from.

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But before we get into there, uh, tell me a bit about, like, some of the core differences between audience building and community building as disciplines. Yeah, I mean, I think

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community building, like I kinda touched on in the very beginning, is you, you have to build the systems into place that allow for reciprocal communication. Mm-hmm.

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So if you're building, um, you know, an audience-based business, you're throwing up an Instagram account, a LinkedIn, a Twitter account, you're building a newsletter, whatever, and you're not as concerned about bringing people along for the ride.

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Um, you know, I think one of the things that's really helped in the last five years is, like, uh, the, the kind of build in public, um, you know, ethos that's become really popular.

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That has been great for community building, you know?

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And so people like, you know, Steph Smith, who's obviously a, you know, a friend and, and I worked with at The Hustle and Hubspot, like she's done an incredible job of building in public. Mm-hmm.

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And so, you know, Steph would be the kind of person if she wanted to go and launch a community in the future, it's such a natural extension because she's already been having these kind of bimodal sort of tren- you know, relationships with her audience for so long, versus someone that's been mostly head down, banging out newsletters, you know, for the last five years with no kind of two-way relationship.

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So I think, you know, building in publicGetting, um, feedback, you know, putting out prototypes, beta testing, you know.

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Not to, not to, you know, bring Sam up again, but I remember, um, when, when I was still at The Motley Fool and he... and Trends wasn't a thing yet.

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He hadn't built Trends, and he sent me a document through Facebook Messenger, because that was, like, S- Sam's preferred mode of comms. [laughs] And it was a, basically a Google Doc that was a beta version of Trends.

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Mm-hmm. And he was like, "Can you just tear this apart for me?" I mean, I had never even met Sam. Um, we had, like, texted twice or something. Yeah. And so I'm like, "Sure."

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[laughs] But I'm like, that's the kind of mentality that you have, and I, and I don't... At the time, it's not like Sam was thinking, "Oh, I'm gonna build a c- a, you know, a founder community- Yeah...

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10 years from now." But that's the kind of mentality. You have to wanna build in public. You have to wanna get people along for the journey.

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Uh, it's just a much different way of doing things than just building an audience.

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All the, all the people I've talked to in the past, let's say like four or five months who, who have been successfully building communities, they all are people who really are able to put themselves out there in that way where it's like we've exchanged two texts, but, like, I know that you're good at this one thing.

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Like, I have been able to suss that out. Like, it's very clear to me. Now here's this thing, like g- like can you help me out? And it's this very, like, creating intimacy really quick, um, i- in a relationship.

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I think, I think that's really core to the type of person who can build a successful one. Um, okay, Motley Fool, so, uh, you were there for 12 years.

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I'm gonna, I'm gonna read off what your [laughs] what was on your LinkedIn here. Okay.

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Started as a financial analyst, then you were managing editor, VP of audience development, VP of product, and then you were the chief growth officer for seven years. Long time.

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Um, and today, correct me if I've got any of this wrong, um, I think it's been around for 32 years, employs over 300 people, and I believe paid subscription product is still very core to the business. Is that all right?

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That all sounds accurate, yeah. Cool. Yeah. So a few questions here. Yep. One, um, why do you think this business has been able to survive over these m- wildly different eras of media in 32 years?

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Um, it's, it, it's thriving today as I understand still. Mm. Yeah. Is that, like, a leadership thing? Is it a strategy thing? Is it just, like, a product that delivers so much value that it's, like, unshakable?

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Why, how has this business survived for 32 years? Man, that's a great question. Um, maybe two things. Yeah. One is, um, so the, the co-founders are brothers David and Tom Gardner. Oh, interesting.

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Um, Tom Gardner was my boss. He was the CEO of the company for a long, long time. Both of them were incredible at adapting and, and pivoting. Mm-hmm.

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And so I, I believe they started the business in, let's call it '92, '93. Mm-hmm. And they literally began as a chat room in AOL. Like, they weren't even their own business.

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They were just like a by-product of a chat room inside of AOL. Yeah. Well, you could call that a proto-community. [laughs] Y- yeah, exactly.

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I mean, that, that's what they were, and they kinda ran the stock market, you know, trend up through '99 and then had a spectacular fall with everybody else in, you know, late '99, 2000 and because they were mostly an ad-based business model.

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Mm. And I believe they had to th- I think they had over maybe 500 employees at that time, maybe more. They had to lay off- Wow... maybe 80, 80% of them at that time.

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Well, I mean, you have to do a lot of layoffs over the last three decades in media. You, you grow and you, and you contract. You, you grow and you contract and you adapt. And what they ended up doing...

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Again, I'll get all the dates wrong- Yeah... but, like, directionally accurate. Sometime in 2004, something like that, they shifted from an ad-based model to a subscription-based model. Mm.

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And I still probably think that was the number one greatest thing that they ever did. Um, they, they shifted their entire model. They also paid off all their VC debt that they had.

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They became pr- privately employee owned, and they put all their attention and energy into having the best investment picks, so doing that one thing really, really well and delivering that IP to, directly to subscribers.

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Mm-hmm. So they weren't reliant on other platforms. They weren't reliant on advertising. They were reliant on subscriptions. And so this was...

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You know, when I started there, which I think was 2008, 2007, 2008, um, subscription-based businesses, recurring, you know, revenue businesses weren't, you know, as, as popular as they are now. Yeah.

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But it was incredible what we were... You know, what they were able to do, what we were able to do at the business. I think the other thing is that they didn't get totally distracted by playing other people's games.

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So I would say that The Motley Fool, you know, and this is obviously a generalization, but did two things really, really, really, really well: investing and marketing. Mm.

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And those were the two things that I would say we fucking crushed it at.

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You know, if you came up through The Motley Fool as an investor, I have a very high degree of confidence that, that you are a, a really solid analyst. You understand that space well.

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And if you came up through The Motley Fool in the years that I was there, before me or right after me, you understand direct response marketing, you understand editorial, you know how to, you know...

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You just know the nuts and bolts of marketing really, really well.

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And a lot of companies are trying to do lots of different things, and I think, you know, it speaks to certainly the focus of, of leadership throughout the years to adapt but also just try to, try to be really good at the things that you're really good at and not kinda go outside the strike zone.

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Yeah. One immediate follow-up there is you said that the two things they're really good at, investing and marketing. Mm-hmm.

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Editorial wasn't in there, but it seems to me to be implied in that the editorial is a vehicle for delivering the investing- Yeah... and also, like, is kind of the same thing as the marketing, right? Yeah.

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I mean, it's... I, I knew when I said that that that was gonna be a natural follow-up because it is like- [laughs]... well, that's a separate thing. But at the time- Yeah...

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and it's not that they, they weren't separate teams. I mean, there was. I came up through the editorial team as a writer. Mm. Like, so I, my first job as an analyst was really to write about tech stocks.

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So I, I covered, like, tech stocks, media stocks. Um, so I was a writer, and then after that I was, you know, int- managing editor.

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So there was the editorial team and there was a marketing team, and they were different, but, but you also understood that both of the purposes was toDrive people through your funnel. Mm-hmm.

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You know, on the editorial team, it was to get people in the top of the funnel.

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I mean, that was our, our entire focus, at least while I was there, was, um, you know, we created content that was syndicated on Yahoo Finance, MSN, AOL, all, all those good stuff, and then also SEO.

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Um, so we were creating really great content that people would find, and then, you know, we were, we were using that content to move people throughout the funnel. Um- Yeah...

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so we just, we never really thought of it as being radically different. W- you know, we were focusing on different points in, like, a buyer journey, but... And we all loved investing.

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That was the other thing is, like, it didn't matter if you were a copywriter, or if you were a designer, or if you were like me, you were originally a writer, like, everyone loved investing, and that was one of the awesome parts of being at that company, is everybody shared this very geeky, like, background of, like, no matter if you had a weird liberal arts degree from someplace no one heard of, or you came from a, you know, a g- a government program, or you came out of an investment bank, like, you all loved investing.

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Mm. So that kinda made it like marketing wasn't... You know, sometimes marketing could be, like, a bad word. It's like, "Oh, you're in the marketing side of the business?" But everyone just loved investing. Yeah.

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So it just, it felt kinda like the same thing.

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One, one thing there is, like, o- one of my big theses of the creator economy is that it's just marketing all the way down, and, like, th- it's, you know, that can be a different thing than you can be a really good photographer, a writer, or whatever it is, and, like, participate in the creator economy and almost a little separate.

257
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But participation in the creator economy is all about marketing. Gaming, a short-form platform to get a lot of views and conversion, that's marketing.

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Uh, getting people to continue opening your newsletter, that's marketing. Mm.

259
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Maybe I'm taking a little license with the word, but I think, like, in the same way that up until a few years ago, the mantra a- at schools was like, "Learn to code, learn to code, learn to code," I think with kind of the AI vibe coding era, that kind of shifts to, "Learn to, learn to do marketing, learn to do marketing."

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[laughs] Rolls off the tongue a little less well. Yeah. Um, but, but that, that really lines up with what you're saying, and the fact that you didn't say editorial and you said marketing.

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I think that is kind of the nature of the creator economy, is, like, you can make a really...

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You can write a really beautiful piece with great ideas, whatever, but it's kind of like if a tree falls in the forest, nobody's around to hear it- Right... it doesn't make a sound, right?

263
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And I think that's why I say the creator economy is just marketing. Yeah. Yeah, I mean, sometimes we used to honestly just call marketing distribution, you know? Yeah.

264
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Because that, then that goes to your point of, like, if a tree falls. Um, it's like, cool, you can create the coolest shit ever, but if nobody finds it, nobody really cares. Yeah.

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Unless you're just doing it f- for the fun of it. But- [laughs]... if we're operating under the assumption that we're all trying to earn a living, then yeah, I mean, I, I think at the end of the day...

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You know, I wrote, I wrote a piece in my newsletter I think maybe a month ago that was called, um, like, "The Founder is, is the Funnel." Yeah. Um, and it kinda speaks to...

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I think if you look at, like, YC and other venture companies now, one of the biggest things they look at is the founder and whether or not, you know, they're able to- Bet on the jockey, not the horse, they say.

268
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Y- yeah, exactly. And I, and I think you see that more and more now. Um- Mm-hmm...

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I think it's, fortunately or not, just as important for founders sometimes to be able to, you know, build trust and be able to get eyeballs. To- Yeah...

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it doesn't have to be all the eyeballs, but the right eyeballs on their content, their product, whatever. So I agree with you.

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I think whereas it used to be code, code, code, and, you know, f- for a while engineers were, you know, kinda the rock stars at many places, which I still think, you know, they, they- Yeah...

272
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certainly can be, and I don't mean to diminish that. But I agree. The, the founder has to be able to wear a marketing hat pretty, pretty darn well.

273
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This, by the way, goes back to exactly what you were saying earlier where, you know, I think you said, like, if a, a friend was like, "If you started, like, a, a, a rug sales business or rug cleaning business tomorrow, like, I would back you to the hilt," right?

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It's the same thing. It's, it's, it's, it's just the ability to, to make things happen and whether that, you know, in marketing, that's distribution, whatever. Um, but yeah, I don't know, a good through line there.

275
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Uh, I w- I do wanna actually get into your newsletter, but one more thing about The Motley Fool. Yeah.

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Um, let's say you had still been working in media some, some, at some other company for those 12 years, but you were not working at The Motley Fool.

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What, what would you, what would be missing from how you approach your work today?

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What would you have missed out on by working at a media company or multiple media companies that were not The Motley Fool for those 12 years? Um, that is an awesome question. Give you some props on that.

279
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Um, I think the biggest thing was I, I probably understand database marketing and segmentation better than most people. Mm. I think at a traditional media company, you understand editorial.

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You might understand distribution, and a lot of times that might be where your, you know, knowledge kinda tends to drop off.

281
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But at The Motley Fool, I worked alongside such incredibly smart people who ran our BI teams, our database teams, um, you know, people that spent years at AOL and National Geographic. And, you know- Mm-hmm...

282
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I'm thinking of a particular gentleman that I learned a lot from who, you know, was the head of data intelligence for the, you know, Clinton campaign decades ago.

283
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I'm like, really, really, really incredibly smart people who, um, taught me so much, I think, about database marketing. Yeah. Hm, that's a great answer. Uh, okay, so your newsletter, it's Signal Noise.

284
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Um, to spell it out for, for anybody listening, it's signal//noise, so you can look it up. Uh, what is this newsletter to you? When did you start it? What is it to you? Yeah. Um, so you can go to jordandipietro.com.

285
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It's on there. I started it, I think, late March, early April, pretty much as soon as I stepped down from being a full-time CEO. I've, for years I've wanted to start doing, you know, pro- producing my own content again.

286
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Mm-hmm. Like I kind of alluded to in the beginning, I started my career as a writer, writing about tech stocks. I've always loved writing. That's always been the thing that brings me the most joy.

287
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So when I quit and I stepped down, I kind of started thinking... I wasn't even thinking really about building a business. I was just like, "What's, what's gonna get me up every day-" Yeah... "and make me happy?"

288
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And I was like, "Writing." So it started as I just wrote a couple blog posts. I threw something up on WordPress. I wrote a blog post or two. And then it was like, oh, people started asking...

289
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You know, it's just the classic kinda people said, "Hey, can you email me when you, when you write your next blog post?" You're like, "Ah, shit, I guess I should open up a Beehiiv account," blah, blah, blah.

290
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So-It just kind of started naturally and organically, which I think is the best way because it, you know, you can... When you read my newsletter- Mm...

291
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I hope that one of the things that you know and you feel is that there's a lot of care. Yeah. It's not AI, it's me. There's a lot of time and attention put into it, and it's a craft more than it is a business, um- Mm...

292
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for me. And you know what it's about, it's about being a CEO, it's about being a founder, um, it's about being a parent, a dad, um, it's about health and family.

293
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So I, you know, it's all of the things that I'm experiencing in my life as somebody who, you know, was a two-time CEO, spent 20 years in marketing and media, now has two amazing kids and is kinda living life.

294
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And I'm- Mm-hmm... I try to share as many stories and insights, uh, and helpful stuff as I can because it's, it's just really enjoyable to do, so. Yeah.

295
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I, I, I mean, it's a great newsletter and I think I, I would agree that your voice really comes across and the care. I was rereading, um, in my opinion, I, I read, I read all, I reread all of them [laughs] earlier today.

296
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Oh, wow. I was in the coffee shop. Ah. And your newsletter- Good to hear. Yeah... Up and to the Right, uh, is... I, I was gen- genuinely moving. I, I, I almost teared up in the coffee shop, honestly.

297
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That's a really, a really good essay. Um, I, I would recommend that people read it. Um- Thank you... one other thing I like from it that I think is really useful for people that, that I'll read out here.

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Um, you were talking about your process and, and the creative process, and kinda what you were just saying about, like, it's, "I care about the craft," et cetera. Um, you quote some writing advice that C.S.

299
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Lewis once gave out- Mm... so I'm gonna list it here. Cool.

300
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Uh, "Turn off the radio, read great books, avoid most magazines," which I think almost today you could maybe avoid the short form and, and read a magazine instead. [laughs] Yeah, yeah. [laughs] Same thing. Anyways.

301
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Good substitute. Yeah. Yeah, yeah. Uh, "Write with your ear, not your eye. Only write what genuinely interests you. Be ruthlessly clear. Don't throw away bad drafts, save them. Skip the typewriter, it kills rhythm.

302
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Uh, and know the meaning of every word you write." So I just thought that was great, uh, writing advice, and I wanted to- Thank you... share that. Thanks, man. Yeah. I appreciate it.

303
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It's, it's been, it's been a ton of fun. It's been a ton of fun. Yeah. I've gotten a couple messages from friends, um, other founders that are kinda... They'll read it one morning and then they'll send me a message.

304
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They're like, "This better not just take you an hour or I'm gonna be so pissed off 'cause this is so good," blah, blah, blah. And my answer is like, "Of course it doesn't take me an hour." Yeah.

305
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Like, I literally set aside Monday and Tuesday just to read. Yeah. Like, tho- those are my two days where I literally just, I read and I write, and I read and I write.

306
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Um, so I am, I'm putting a lot of time and energy and effort into it, and you know, there's also a part of me, I feel so grateful and so lucky to have had such an amazing career and to- Yeah...

307
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have had so many opportunities. I mean, so many opportunities when I didn't deserve most of them. So [clears throat] it also feels a little bit like it's just enjoyable to be able to share, help people.

308
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You know, so many people respond to, to the actual newsletter every week asking me for advice. Um, so it's just, it's also a lot of fun. Yeah. No, I love to hear that.

309
00:45:45.304 --> 00:45:57.904
Um, one, one more thing I wanna touch on before we move on is, uh, the, you have another one, actually I think it is Up and to the Right, where you talk about sort of the emotional, logical battle, uh, when you were deciding to leave Hampton and go out on your own.

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And I think people should go read that. I don't need to sum it all up here.

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But I was really thinking about it because I, I think it was right, right around the time that we first spoke, um, this episode's out now, it came out a few weeks ago as we speak.

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I interviewed this guy named Landon Huseby, who, uh, has a local media business in Wichita, Kansas. Um, he, he said it made around 120K last year. He's been doing it for about eight years.

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He's been an engineer professionally for the past decade or so. Last year switched to being, to working in philanthropy. Um, but he's got a young family, I think he has- Mm... two kids.

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And I was thinking about this 'cause he told me how he's been considering going all in on this for a few years, and he's very confident he can get this up to being a 500,000 a year business pretty quickly.

315
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Um, but he's, he just can't bring himself to do it. And, and- Mm... you know, I think for you, you're at least 10 years further in your career than him.

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You've, I, I, you know, I don't know your finances, but you've been an executive for a while, so I'm sure you've got pretty healthy finances. The risk is a bit different for- Yeah...

317
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a guy like him, young family, bought a house a year or two ago, I think.

318
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Um, but anyways, long preamble for, I'm curious, like, what kind of advice you would give somebody like that who's a bit earlier in, in their career, and maybe they're building something that seems viable, um, and they're not sure yet if they should leave their stable job for what could be their dream thing.

319
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But it's- Yeah, yeah... it's, it's, it's a lot of risk, and I'm wondering what you would give advi- what advice you would give to someone like Landon. I guess there's two things. Um, the first is that,

320
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you know, nothing is without sacrifice.

321
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And, you know, there's, there's so much talk about, like, having the best work-life balance, and we should all be, you know, super happy and fulfill every single one of our parts of dreams, et cetera.

322
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But like you said, I mean, the only reason I've been able to do what I do is 'cause I worked my ass off for 20 years. I've been super lucky. Yeah. And I think it's hard for people to... Like, people naturally wanna have

323
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it all. Mm. And I, I just think you have to ask yourself very candidly, like, "What, what are the trade-offs I'm willing to make?"

324
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The process that I went through in the last six to eight months before I left was I was increasingly seeing, 'cause it was hitting me in the face, all the trade-offs. Yeah.

325
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And it was, you know, for the most part, it was time with my kids. I've, you know, a seven and 10-year-old, and it's incredible time. They're awesome. I love being with them.

326
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And it was like, man, more and more and more... Physically I wasn't with them, but then even when I was with them, like, mentally I was just thinking about being a CEO all the time.

327
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So it was getting more and more obvious the trade-offs I was making, and it's easy to kinda push those aside and just kinda keep focused. Mm. But I, I just forced myself to really look at those and say,

328
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"All right, well, how are you gonna feel about this, you know, in 10 years?" Like- Yeah...

329
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what if you have a huge exit and you have a, a bank full of cash, but you missed, like, the five years before, you know, teenagers when your kids really wanted to hang with you? Yeah. Is that gonna be a win?

330
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'Cause that's kinda what I was going towards, you know? I'm like-Oh, seems fucking lame to me, you know?

331
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[laughs] Um, so part of it is just really asking yourself about the trade-offs you're willing to make and you're not willing to make. And then the other piece of advice I would give is, like, I, I really got caught,

332
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like I think a lot of people do, assuming that the way that I was doing something w- was the way to do it. Mm-hmm.

333
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So for me, because I, I'm actually not a natural entrepreneur, I tend to be a little bit more risk-averse, and, you know, having grown up working at companies, it, it wasn't natural for me to go and do my own thing.

334
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And so in my mind, you know, it's like 13 years at The Motley Fool. Cool. Then my next job is CEO.

335
00:49:30.024 --> 00:49:42.254
Okay, then my next job was CEO, and it was like, in my mind, what I was gearing towards was a hopeful big exit, public recognition, you know, making it rain in my bank account, and then we all live happily ever after.

336
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And that was kind of how I had structured my life, my dreams, my hopes, my aspirations, my family, all these different things.

337
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And it, it was hard to stop and say, "Is there actually a different way that optimizes for some different stuff here?" Yeah. What if I'm not optimizing for a big exit? What if I'm not optimizing...

338
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You know, ironically, you and I are on a podcast right now, but a big part of me was thinking, "Well, it's fine if I optimize for nobody know who the fuck I am." Yeah. You know?

339
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And it's fine if I just disappear after Hampton. That'll be okay with me.

340
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So I just started playing a different game and optimizing for different stuff in my life, and ironically, it's all, it's all working out wonderfully.

341
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So I also think there's a little bit of, like, when you have a passion and a love for something, it's also worth it to take a risk, you know? Yeah.

342
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Uh, there's a bit of, I mean, that classic piece of advice, if you love something, let it go in there, right? And it sounds like, you know, the, the things you love of this come back to you.

343
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Like, uh, on the podcast [laughs] side, it strikes me... It, it's funny.

344
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It strikes me that there's sort of a Hustle mafia, a la the PayPal mafia, you know, where all these people were involved in it, and it became very rich and, and famous, et cetera. But I'm just thinking, I've had... I...

345
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You're on the podcast right now. I've had Matt McGarry on, uh, Adam Ryan. Um, all these people have worked at The Hustle in some capacity. Yeah. I almost had Brad Wolverton on. He introduced us. Yeah.

346
00:51:02.224 --> 00:51:10.794
But when I was trying to get him on, he was starting a new job, and he didn't need attention on him. Right. Um, just, uh, a couple weeks before this comes out, Jonathan Hunt will have been on the podcast.

347
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I think he kind of took the job you had at HubSpot after you left. Similar-ish. Right. I don't know if it's exactly the same. Yep. Um, so that... He, he's a little bit separate from that.

348
00:51:19.104 --> 00:51:23.124
But, uh, all of this to say, it seems like so many...

349
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I mean, obviously there's more people involved in the, in The Hustle than just the people I listed, but so many people, I've wanted to talk to them, obviously, and you yourself included because you've, you have this great experience that is relevant to the audience.

350
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Mm-hmm. But I think all of you are also good speakers who, um, are game to appear on podcasts- Mm... and, and seem to enjoy this kind of work. So I don't know.

351
00:51:42.604 --> 00:51:50.304
I, [laughs] I, I d- I didn't really think about that until, until today. Yeah. But, uh- It was a lot... I was curious if you have any thoughts on this Hustle mafia. Yeah.

352
00:51:50.344 --> 00:51:58.934
I mean, there, there's a lot of people that went through that, um, through the team, and I think really, really talented young, young group of folks who have all gone on to do loads of awesome stuff.

353
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And, um, I mean, I could continue listing people, and I, I keep in touch with almost all of them. Yeah. I'll say one of the things that I

354
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am most excited about in my 20-year career is kind of this, like, family tree of sor- sorts- Mm... of all the different, you know, people that I've reported to and learned from.

355
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Like, when I was at The Motley Fool, I reported to Tom Gardner, my CEO. On our board of directors was John Mackey, founder of Whole Foods, Kip Tindell, founder of the, um, Container Store.

356
00:52:26.224 --> 00:52:36.644
Um, I mean, we, we had VPs of Google. Like, we had such an incredible cast of, of characters on our board. And then at The Motley Fool, I mean, those people have all gone on to do amazing things.

357
00:52:36.724 --> 00:52:42.824
Obviously, you mentioned a lot of The Hustle, um, folks. The people at HubSpot are incredible. Now the people at Hampton.

358
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So when I think about, like, building out this family tree of all the people, not just that have reported to me- Mm... but that I've worked with, it's just incredible, and it's like I'm so grateful for it.

359
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I love keeping in touch with everyone. A- um, you know, a- anytime I get a text from someone that's worked for me that's like, "Hey, can you help me think about taking this new job?"

360
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Or, you know, "Should I negotiate this salary?" Yeah. It's like, it, it's just so much fun, man. It's like, it's just about building relationship with people. And life's short.

361
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You gotta have fun, gotta treat people well, and, and enjoy the ride, you know? I'm a big believer that every business is a relationships business, and I think that's...

362
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I, I've been trying to say more and more on the podcast to harp on that, like, solo creators, wh- whether it's a newsletter, YouTube, whatever, it's like I think it's det- it's detrimental to anybody's career and life, honestly, more than career, to long term just try to be solo and not work with other people.

363
00:53:32.764 --> 00:53:44.404
Maybe, you know, it, it might take more work or you take a smaller share of whatever revenue you're bringing in, but I think that's something that's kind of lost in this, like, internet entrepreneur, solopreneur world.

364
00:53:44.914 --> 00:53:54.524
Yeah. Um- Totally agree. Yeah. I think that's really important. I was just emailing yesterday or the day before. I won't say his name, but he's a reader of my newsletter, and he also runs his own business.

365
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He's in LATAM doing exceptionally well, young guy, and he was like, "I'm remote. My team's remote." And he seems lonely as fuck. Yeah. And I'm like, "Dude, go, go find your team. Go hang out with people."

366
00:54:07.984 --> 00:54:17.424
Like, you gotta get out from behind the screen, and it, it's hard. I mean, that, that was honestly one of the reasons... I didn't really mention this, but another reason I left Hampton- Mm...

367
00:54:17.464 --> 00:54:23.344
was the team was remote, and that was obviously my, my doing. I could... You know, if I could go back and do it differently, I probably would.

368
00:54:24.064 --> 00:54:30.904
But spending 40 hours a week on Zoom just, like, doesn't really feel like a way to live your life. Yeah.

369
00:54:30.914 --> 00:54:39.114
Um, and since I grew up at The Motley Fool where everybody was in an office, you know, and I know the whole office wars is, is a big generational kinda gap and, and argument.

370
00:54:39.454 --> 00:54:46.284
And I love remote work for lots of reasons, but when I was the CEO, I'd always pictured running a company where everybody would be in the office.

371
00:54:46.354 --> 00:54:58.364
And so the, the long hours and the hard work would be offset by the relationships- Yeah... and the camaraderie and the fun, and man, you can't get that shit on Zoom. Yeah. Amen. Um, I, I think we'll stop it there.

372
00:54:58.444 --> 00:54:59.064
There's... Uh, there...

373
00:54:59.124 --> 00:55:11.884
I had a lot of other questions about your time at The Hustle and HubSpot and the transition there, but I think for anybody listening who, uh, really was hoping to get some of that, I think your podcast on Brian Morrissey's The Rebooting show from a couple years ago- Mm...

374
00:55:11.904 --> 00:55:17.944
has a lot of that. Um, you also got into some of this with Matt McGarry on his podcast. Um, maybe we'll have to do a round two at some point.

375
00:55:18.044 --> 00:55:26.004
But, uh, I, I, I, I wanted to get to a lo- a lot of this other stuff that you don't always get the chance to talk about. But this was really good. Thanks. Thank you for coming on. Thank you, brother.

376
00:55:26.064 --> 00:55:29.904
I appreciate it, man. Of course. Uh, listener, we'll see you next week.

377
00:55:36.044 --> 00:55:48.624
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