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

All right, thanks for having me.

I mean, basically, I think you saw one of my posts on LinkedIn and reached out. I was like, "Yeah, let's hang." I was causing a lot of trouble. It was great. 2022 and 2023 were a lot of fun.

I mean, basically that's very much the vibe I put off. I mean, the truth was I was working for a media startup called Liquidity, a finance meme page. I ran his newsletter, ad sales, all that. And then the whole posting and making noise on the internet was really just a top of funnel marketing strategy to get more people to sign up to my substack which then led to a book deal. So there were economic incentives beyond just annoying people on the internet. But the outward vibe was yeah I'm just trolling people while in business school for sure.

Yeah. No, it was, I mean, look, my Substack has about 61,000 subscribers now. I started writing it in 2021 and it was a mix of half finance blog, half travel blog. I was like backpacking Europe for a year before business school and it sort of consolidated into my long form thoughts on whatever was top of mind as a twenty-something. I used to grow really fast on Twitter. Then I realized LinkedIn has three times the active audience as Twitter and nobody posts on there because it's tied to your employment. So people are a lot less, there's a lot less personality and sauce on LinkedIn except the hustle culture sales bros, productivity gurus. And I realized there's a really interesting arbitrage here where if you satirically mock those guys on LinkedIn, it'll probably blow up and you'll get this mixture of some people think it's really funny, some people will unironically think it's advice and then some people will think that you're a douchebag and start telling you in the comments to kill yourself, which then helps grow the virality engine. And at the end, I put, "By the way, if you like this post, check out my newsletter." And every time something went viral, I would get like 400 new subscribers. So, it was basically a free audience acquisition tool that grew my following.

Well, the key is you have to go, if you're only half baiting people, it doesn't really work. You have to take, you have to hit this level of performative bait that's so deep. It takes people through this journey of this guy can't be serious. He committed to the bit so hard. Is he just completely tone deaf and serious? Back to he can't be serious. Like it's, I don't know, I was writing like 800-word short stories that were total fabrications but seemed to be giving really bad personal, it's like if you made a Black Mirror version of Dave Ramsey and gave him a LinkedIn account. That's effectively what I was going after. What's the inverse Dave Ramsey with social media?

So this was fall 2022. I had just started business school at Columbia, I think a month or two before that. And this was when I really started hitting the flywheel of LinkedIn post to newsletter subscriber. And this was the tail end of a trio of great hits, but this is the most well-known one. I believe I said...

Yeah, you just genius.

I did the math. There were however many hundreds of hotels in Manhattan, meaning that every day I could go to a different hotel, eat the continental breakfast, sign it off on room 421, and then you could go back for dinner, you can take a girl on dates to the bar there, just like charge everything to the room. And I said, "Follow me for more personal finance tips." And the comment section is just so incendiary. People were saying, somebody tagged the New York Police Department. People were saying this is petty theft. And I said, "I don't know what you're talking about." See, the best part of the bit was then re-engaging the comment section acting totally aloof. And anyway, multiple actually, Ari, was this you? Because multiple Columbia Business School alums sent a screenshot up into the dean of students at Columbia. I never found out who did that.

Well, I thought I was going to get kicked out of grad school because I get called into the dean of students office. I get this email from her saying some alums had emailed her about concerning content that Jack Raines is putting on LinkedIn. So I then screenshotted her email and put it on Twitter and said, "Yo, who snitch? I have to meet with the dean next week." So I go in and meet with her and I said, "This has to be one of your more interesting student meetings." She said, "Well, you seem to be one of our more interesting students." She said, "Are you going to post this on Twitter, too?" And I said, "I don't know. Maybe. I haven't decided yet." And anyway, she was like Samantha Shapsis, she's awesome. She said, "Okay, either this is a really good marketing start or you have just an insane set of hobbies because I see that in the last three weeks you claim to have been stealing hotel breakfast. You said you got vaccinated a thousand times as a side hustle when they were paying people $100 to get a shot. And you called Joe Biden on his cell phone and said, "You wanted more student loan debt and not less because you have that dog in you and it would make you grind harder." She said, "This is a newsletter growth hack, isn't it?" I said, "Yeah, you'd be shocked by how well it works." She thought it was hilarious.

Yeah. I mean to your point like I don't really know if Corgi's a good business but we're talking about them right now. They know how to get attention. My take on all this stuff is all attention is good as long as you deliver, but the second that like the company does work, the whole world is waiting to dunk on you. Like there's this, you can keep playing this rage bait game as long as you deliver. Like Elon Musk is a total poster, but he keeps delivering so it doesn't really matter, right? I have no idea if Corgi is a good business or not. I am probably going to go to the Corgi Cafe launch party in New York this Friday. I don't know if you guys want to come. I RSVP'd. But yeah, Corgi was obviously one of the front runners of we're gonna piss everybody off on the internet for attention. I like Corgi as a product, it's just worse granola. It's an AI note taker that kind of sucks. I downloaded and tried it, but they get a lot of shots on goal to pivot and try other stuff because they've pissed everybody off and everybody knows who they are. Right. I think the highest enterprise value move would be clearly just disbanding and the top 10 employees at Corgi go run growth at different series B startups. Like I think that's the real play there. But yeah, there's this whole performative all attention is good attention. Piss people off. See what happens. And I think it's a good strategy as long as you deliver on the product because you can lower your CAC. But if your product sucks, everybody is just waiting for your downfall is kind of my, it's a high risk high reward.

I don't think so. I mean, I've pretty intentionally, I will make fun of the current thing, whatever the current thing is constantly. Like, and you know, I'll tell you a wave that's like been really annoying to me over the last couple years is the entire like tech sick of fancy toward Trump or whatever. It's like cool, everybody's act like the entire, oh, we are going to say now and pronouns are lamb and all this stuff. I made my pronouns we them boys on LinkedIn when like George Floyd was happening. Like I took a lot of real risk where I was counterculture back then. And now that it's not risky to be like conservative anymore, everybody's like, "Oh, woke is stupid." I don't think I crossed any lines, but I was willing to poke the bear when it was risky to do so. And now there's this whole wave of people acting like they're poking the bear when their take is actually the thing that's in vogue. It's way more fun to say the edgy thing that everybody's thinking but nobody wants to comment on than wait for it to be derided and say it. So, but I have stayed, like the things that are actually objectively bad like I don't know, like misogyny whatever, like I don't touch any of that cuz it's just stupid right?

Yeah. Yeah. Way lightly to lightly touch the stove and then pull your hand back. Right.

Yeah. I mean, basically trolling plus Substack turned into book deal and working for venture capital fund. So, the trolling is lead gen for the newsletter. The newsletter is quality content.

So, initially I started off with two newsletters. One was like a fun travel blog for a year and then one was going back five years. I tried to get a job writing for Morning Brew and some of these media startups covering markets and nobody would hire me so I just started my own newsletter to write about financial markets. What it's kind of evolved into is just me as I have thoughts I want to share on the internet about anything, markets, travel, random, young person life in New York, whatever. I just put it out there. And I kind of made this decision that I don't want to build a newsletter in a vertical where I'm then committed to writing about this vertical forever. I treat it more like newsletter is my ability to put Jack Raines' thoughts and personality on the internet as a signal or calling card which that itself is not very monetizable and my ability to sell ads against that versus a specific finance vertical is you can't, right, you can't charge much and I'm not going to...

I mean not directly. Like I used to paywall for a little bit, I used to run ads and it hit me that the amount of admin work versus the rate that I could realistically charge on ads my newsletter wasn't worth it. But the real upside is it's easier for me to sell books cuz I've just been writing long-form thoughts about stuff for a while. If you like that, you'll probably like the book. And it's also been a good calling card for the venture capital world. Like more people knew who I was than typical associate at VC firm. And when I joined slow, I get a lot of inbound from people starting companies because they like my stuff. So I treat it like direct monetization, no, but indirect, call it book deals, side consulting gigs, deal flow for venture capital. And there's a lot of stuff where make the content free and then opportunities from the content where the money comes in.

Yeah. I mean, listen, there is no higher calling in life than allocating capital for institutional LPs. So...

Yeah, I mean to your point of nobody reads books, I've kind of had to do a bang-up job marketing because people don't look for books to read. You kind of need to shove it down their throat and say buy, buy, buy, buy, buy. True. No, I mean to turn back the clock a little bit. Like I said I've been writing a Substack for a while. It was basically 24 to now 29-year-old me yapping about like what's going on in life. And an editor at Portfolio, one of Penguin Random House's imprints, actually reached out to me, I guess 3 years ago now, going into my second year of business school, she said, "Hey, I really like your blog. Have you thought about writing a book?" Fun fact, talking about monetizing the LinkedIn posting, she found my Substack because of the LinkedIn post claiming that I got an internship at Goldman Sachs for winning a beer mile. So, which is, I mean that was my most viewed post. That one got four million impressions on LinkedIn. It was a, for anybody listening, Google Jack Raines Goldman Sachs beer mile and just read the post.

A beer mile is, so if you run a mile on a track, it's like four laps, 400 meters. A beer mile, you chug a beer, run a lap, and do that four times. Columbia, I don't know if they had this when you were at CBS, but Columbia Business School does do a beer mile, like a cluster competition beer mile at the end of the year at a track near campus, and I was nominated from my cluster to run the beer mile. I ran an eight minute and 48 second beer mile which is like pretty, I mean I can run a six minute mile, it's much harder doing the beer mile so I actually did this...

David Solomon, I was doing this whole DJ thing where he was DJing at Coachella that year and I put out this really long post on LinkedIn claiming that David Solomon had been hanging out with the Chain Smokers way too much and they gave him the idea of, he was asking for like novel ways to evaluate talent. They said do a beer mile because everybody, it both proves stamina and it proves your ability to consume alcohol which is very important in investment banking because it's a client services job. And I give this really long take about how every morning I would wake up at 6:00 a.m., shotgun three beers and then run half a mile on the Westside Highway to prepare for this. And I ended up winning the Goldman Sachs beer mile and I was excited to start my summer associate role in Goldman Sachs that summer. The comment section, and there was a picture of me. I actually did run the beer mile which made it somewhat believable. There's a picture of me with like beer cans in the background, somebody throwing up. I look exhausted. And the comment section is like, "Oh, was there a female beer mile? Because this needs to be inclusive." And I said, "Actually, there was cuz Goldman Sachs is an equal opportunity employer." And somebody said, "Well, what if you're in a wheelchair?" I said, "You think we didn't have a paralympic beer mile, too?" We did. And then the best comment was, "Well, this discriminates against people who don't drink." And I said, "If you don't drink, you're not allowed to be an investment banker in the first place." And it is just like, anyway, it's a fun read. So yeah, I got... Oh yeah, back to the book. So that post...

Lydia Yachty who was the editor who signed me at Portfolio, she found me through that, then found my substack, then she told me all this after I signed with them, but anyway she was like have you thought about writing a book and I was like well I mean yeah I think if you were going to write a blog consistently writing a book is like it gives you something permanent you can point to and I did want to write a book. I put together a proposal and the initial pitch was I think young, basically I think young people do a really bad job of both recognizing and maximizing the opportunity cost of young adulthood. There's a lot of stuff out there about how to get your career on track. I don't think there's as much material out there particularly written by young people about how finite your 20s and call it early adulthood pre-kids are and there's a whole subset of opportunities on the professional side. Yes, it's easier, you have high optionality in your career, you can take more interesting shots. But there's also just the ability to move to a new city, go abroad, like completely reset your career and try something new where I'm a big proponent of being highly experimental and risk on when you're young while you have the opportunity to do so, even if it isn't necessarily the income maximizing decision at all times. And that window of opportunity is really short. So, Young Money, the book is basically the first half is very much like a memoir of my early through mid-20s going into my psyche of hated my first job during COVID, corporate finance, boring, kind of had a throw caution to the wind, backpacked the world for a year, like $15 a day, staying in hostels. I had a blast. I would never do it again, but I'm glad I did it at 24. And then getting into, you know, the kind of reflections on why I did all the decisions I made. Like you only have a finite window of time to go after certain life experiences. And then I also get into, you know, business school, later 20s, refocusing on my career and then discussing how status games are such an issue for young people today and can be such a distraction. So it was basically a memoir slash reflection written for like early to mid-20-somethings on just thinking through how to get the most out of this part of life. The issue is most early to mid-20-something males don't read and that is a problem.

I've not done that. It's pretty funny. I haven't done that, but I did record the audiobook because young people do listen to audiobooks, audiobook sales are way higher than print book sales for young people now because podcast, everybody listens to podcasts. So, but yeah, it's been like a ton of fun. I completely underestimated how hard writing a book is. I'm sure you feel similarly. But I'm glad...

I don't know how to say, I know what you mean.

So, I met Chris Gadec who's the CEO of Adqu, and then I ran into him at the Cannes Lions marketing festival, I guess a month, two months ago or whatever, and we were talking, you know, he was asking me how the book pre-sales were going. I said they're going pretty good. And he said, "Well, we can totally do a book launch stunt." And I was like, "Cool." And then I didn't really think about it that much up until launch week. And I was pretty nervous going into launch week. You know, we send out the early copies and this and that, but I was sitting there thinking, how do I really get people to care about and pay attention to this? And my entire launch campaign, which is basically flood the zone on Twitter, LinkedIn, Instagram, became just me texting everybody I knew that had any sort of platform where if I'd sent them an early book, it was like, "Hey, would love for you to, one, I hope you got the book. If you didn't, I'll make sure..."

I have not gotten.

No, it tells the world how much I wanted you as a guest that I continue regardless of my book status.

That was alluded to, but I'm explicitly speaking.

But I was just like flooding the zone with my own posts. Every time somebody posted a review about the book, I was sharing it. Like I was just going nuts on Twitter. And then the day after the launch, I texted Chris. I said, "Hey, totally last minute, but the book is kind of ripping now. I'd love to do some sort of out of home advertising thing. Like, do you have any inventory left?" And he said, "What city?" I said, "New York." And he said, "Fuck it. Do you want to just rip the NASDAQ?" And I was like, "I mean, yeah, why not?" and he gave me a little friends and family discount on it. And we were like, "All right, what should we make the creative be?" And we decided to make it the book cover with a tagline that said, "If you want to quit your job today, read this book." And we put it up there all day on Monday in Midtown when you know all the banking interns and the new hires were starting and you know they're probably coming back from, dreaded going in the office and it probably sold some books in person but it was actually more valuable I think having that as a social media thing to post which then went viral than the actual ad itself.

Exactly. Yeah. Yeah.

I know. I'm being called a world class smartass, the highest accolade I can get. I appreciate it, Paul. My biggest learning from this is everybody, like, I think mimetic desire drives everything, where if you can turn book promotion into a thing where obviously if the right people are recommending a book who have leverage, their followers want to buy it and read it, great. If you can turn the whole game of posting a picture of someone else's book into a fun thing you want to do, where the initial wave is obviously me trying to tell or encourage people I know to post about it, but then now there's this whole organic flywheel of random person from Wisconsin that I've never met is posting a picture of my book on Instagram and tagging me in it because the hard cover actually looks very good in person, and there's people posting with like mountains in the background or like they're in their office with their Bloomberg in the background, whatever.

Creating this mimetic flywheel of 'I also want to join this movement of people posting about this thing' just helps expand the reach so much, where you start creating ripple effects that compound. So you kind of want to create some sort of mimetic flywheel where it becomes a fun game for the reader to also post about the book and then ideally also tell their friends about it in person, whatever. But I don't know, there's probably three or four times as many people that I don't know who've now been posting pictures of it than people I do directly know, which means that my master plan of turn your book into a memeable object is working. I think that's kind of, especially in the world we live in today, you want to make yourself a meme. Like that's the meme's the most condensed form of information. So if you can create that, like that's the thing that'll drive more sales over time. So