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Episode 187: Jack Raines Trolls LinkedIn and Ends Up with a Book Deal artwork

Episode 187: Jack Raines Trolls LinkedIn and Ends Up with a Book Deal

Marketecture: Get Smart. Fast.

August 21, 2026

Ari Paparo and guest co-host Paul Knegten sit down with Jack Raines, author of Young Money, to discuss how viral LinkedIn posts, humor, and attention-driven marketing helped him build a 61,000-subscriber newsletter, land a book deal, and create a personal brand.

Speakers Ari Paparo, Paul Knegten, Jack Raines

TopicsMarketingBusinessInvesting

Ari Paparo (0:00)

This episode is brought to you by Sojourn, the number one platform for travel and hospitality advertising. Travel data is unique. Someone searches for a flight, a hotel, and then a rental car. Those aren't three separate signals, that's a trip taking shape. With Sojourn, travel marketers get visibility into the entirety of the travel journey to target real travelers when they're in market. From impressions to insight to impact, Sojourn is the only travel data platform that closes the loop. Visit sojourn.com for more. That's sojern.com for more.

Welcome to the Marketecture Podcast. This is Ari Paparo. I have a special guest co-host. Eric is off for a couple of weeks. We have Paul Knegten, who is a fractional CMO, friend of ours, former BSWAC CMO. Paul, thanks for being here.

Paul Knegten (0:55)

Thanks for having me. It's always a pleasure. And I'm glad that Eric takes vacations.

Ari Paparo (1:01)

Yeah. He told us last week it was not a vacation. He's got important business to attend to, not a vacation. But so Eric, keep doing that important business. Paul, you're on everyone's podcast, but you're not a podcaster yourself, but you're in a studio.

You have a mic, you have a voice. What's the deal?

Paul Knegten (1:20)

Well, I'm very busy, Ari. As you know, I do work with a bunch of different ad tech companies.

Ari Paparo (1:26)

Is Sojourn one of them?

Paul Knegten (1:28)

Sojourn is one of them. It's a sponsor.

Jack Raines (1:29)

Is Sojourn a leader in travel?

Paul Knegten (1:31)

They are a leader in travel data. Yeah. Travel data is one of these things that, it's not like e-commerce data you know. You can actually, if someone searches for a flight and then gets a rental car and they're like, if you have one company that's managing all that data or has access to all that data, you can paint a really good picture of a journey and you can know if they didn't book at your hotel, they booked at a different one. Anyway, check it out. Don't want to plug them too much, but why don't I do more podcasts?

I like helping other people do podcasts. I mean, you were just on Matthew's podcast of VecMat. I think you have to have something to say and maybe I don't have something to say unless I'm your sidekick here. Maybe that's the conclusion.

Ari Paparo (2:09)

Maybe. We'll see how you do. People will let us know.

Also, this is not interesting, but it's interesting to me side note. This is the first pod that we're doing where we reverting and we're not doing proper ad serving. We're baking in all the ads. We've had a terrible experience, which is just absolutely ironic, where we're terrible at ad ops. Getting our podcast ads into our podcast is not something that Marketecture is good at.

We're experimenting this week and future weeks with baking our ads in, so it sounds nice and smooth and there's no potential of hearing a really weird ad from Hilton Hotels or something in the middle. I hope you enjoy the ad ops because I know I do.

One other, so our guest today, so we're doing something a little unusual. In addition to Eric being off on his adventures, we also have a non ad tech guest. So our guest today is a guy named Jack Raines, who some of you may know. He is an author. His new book out called Young Money. I've been a friend with him for several years. He's known for, I don't know what to call it, trolling, just getting attention online. He's really good at it. And I think there's some lessons here in what might be called like chaos marketing, troll marketing, just getting attention online, getting people involved with your brand. Now he's selling a book. And I think it's gonna be a really interesting conversation. Maybe there'll be some lessons or maybe there won't. Maybe we won't learn anything, but we'll still have an interesting conversation. Paul, what do you think about this whole topic?

Paul Knegten (3:36)

Shit marketing, I think is...

Ari Paparo (3:37)

I love it.

Paul Knegten (3:39)

I say that in the nicest possible way.

The zone is being flooded with shit. Make it good shit. And if you can get people angry, your valuation could rise.

Ari Paparo (3:51)

All right. You heard it here first. So let's jump in with Jack Raines, the author of Young Money.

All right. Welcome Jack Raines, the author of a brand new book called Young Money. Jack, thanks for being here.

Jack Raines (4:03)

All right. Thanks for having me.

Ari Paparo (4:05)

So you and I met a couple of years back when you were at Columbia Business School, where I'm an alum, and you were just causing all kinds of trouble. And I was like, hey, I got to meet this guy. What is going on here?

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