DM Back Doors | Jack Raines

Jack: Hey, guys. I'm Jack Raines. Few things about me. I write a finance blog called Young Money. I edit a daily financial newsletter called exact sum that was started by a finance meme page called liquidity, which basically just means I live online.

I'm in Columbia Business School and I just started working on a new newsletter for Redpoint Ventures called the infrared letter. Quick show of hands. How many of you use LinkedIn? Is everybody on LinkedIn? Pretty much.

What do you think of LinkedIn? Anybody? Thumbs down. Is that the general consensus? People don't really like it.

Boy, it sucks. It does. So in August of 2022, I moved to New York City for business school. And as anybody who's been to New York knows, it's expensive. I moved from Tifton, Georgia, which is like pretty similar to Columbia, Missouri, and rent in South Georgia is like $500 a month.

New York City, I'm paying $25100 a month to share a shoebox with 2 roommates. But last year I was also posting satirical content on LinkedIn because like we said, LinkedIn sucks and specifically, LinkedIn is full of people posting, finance tips that are actually just lead generations for pyramid scheme. It's like Grant Grant Cardone and the Grant Cardones of LinkedIn are pretty terrible. So, I started posting content, making fun of this type of content. This particular post I was sharing with the world how I hadn't paid for any food in New York City in my first few months living there by going to all the hotels in Manhattan and walking in, signing off in different rooms, getting breakfast there, and then leaving.

Sometimes, I would go back, take girls on dates, the ones at that steak houses, begin sign off on room 724 and leave. I did not actually do this. I I may have at some I may have at some point or another gotten breakfast from a hotel for free, but I've never intentionally gone to the hotels. This particular post was a little bit too on brand, and an alumnus from Columbia Business School emailed my Dean of Students saying that this is ridiculous that Columbia is admitting students who are committing petty theft and then bragging about it on LinkedIn. So I was 2 months into business school, and I thought I was about to get kicked out of school.

My dad was gonna hate me, and I'd probably just end up homeless. So this is Dean Shapps. She's the Dean of Students at Columbia Business School. And she asked to meet with me about this ethical concern. I emailed back.

It took me a couple of hours to get over the initial panic attack. And then I emailed back saying, hey, Dean Shabst. I would love to meet. Just so you know, I have also, in the last 2 weeks on LinkedIn, claimed that, I got vaccinated a 1000 times in a 2 week period when mayor Adams was paying people to get vaccinated in New York. And, that I had called Joe Biden on a cell phone and said I actually wanted more student loan debt because it would make me grind harder when they started forgiving student loans.

So in the outcome of this, I did meet with her about a week later. And I've just thought she was gonna tell me, like, get out. Like, we don't want you here. But I walked in and I said, this has to be your most interesting student introduction. Right?

And she was like, well, after reading through all your stuff, you're definitely one of our more interesting students. And she said, so I went through your blog and I was like, I don't know if that's a good thing or not. She was like, so you are posting satirical content on LinkedIn, knowing you're gonna piss people off because it will get more eyeballs on your stuff. And then some of those people are gonna sign up for your blog. And I was like And then I sell ads on the blog and that's how I'm paying to live in New York City.

And she was like, it's kind of genius. I just wanted to make sure you weren't actually stealing food. So then she signed up for my blog and now we now I meet with her every semester. I think it's because we're friends. It might be because she wants to make sure I'm not actually committing petty theft.

So the moral of that story is, 1, LinkedIn is a terrible platform, but it's great if you don't care. But more importantly, it's to highlight the importance of just like being willing to post stuff on the internet. Because a month after this, Brent Beshore, who organized this entire event, messaged me on Twitter and just said, hey, I think your content's hysterical. I don't really know what your deal is or what you do, But I would love can we get this, got back on? There it goes.

But I would love to meet with you or like talk on the phone sometime. So, I was sitting in class when he messaged me and I texted him like, are you free to talk right now? And he said, yeah. So, I took a 30 minute stroll around campus and we just talked like, what's his story? What's my story?

And we kept in touch over the next 9 months And he was in New York, back in September, and we grabbed breakfast when he was in town. He was just asking, like, what I'm doing now, and I told him writing my blog, newsletter, a bunch of different projects online. And he was like, you need to come speak at this conference. And I was like, cool. About what?

And he said, social media stuff. And I was like, okay, I can probably do that. But more specifically, I wanted to talk about how you can leverage social media to accelerate your career. I think a lot of the speakers at this conference have a similar connection where they might have met Brett or some of the other speakers through Twitter or through LinkedIn. Or somebody's working on something cool and messaged somebody else.

That's how I got here. That's how I met. Like, I knew Eric through Twitter before this, before we met in person just because we connected on there. And I think social media is the most insane leverage tool for accelerating your career, regardless of what you do. The way that I think about jobs in the labor market in general is there's 2 types of jobs.

There's traditional jobs, which you can find on LinkedIn posts, on job boards. They used to be the things you'd find in classifieds and newspapers. These are the jobs where a company's hiring a new class of analysts, or a CEO, or CFO leaves and they need to fill that spot. So they'll send out headhunters and recruiters looking to fill those roles. And these jobs rely on resumes, optics, maybe word-of-mouth, and you really have to beat out a lot of other applicants.

The other set of jobs are what I call opportunistic jobs and these jobs don't exist anywhere in the present moment because it's not an active role that needs to be filled. It's not like a company is going trying to hire for these. They're just a non existent thing until a serendipitous moments serendipitous moment happens where somebody with a specific need meets somebody who has a specific skill set and there's like a Eureka moment where they realize we should work together. Historically, these were pretty rare because the odds of the right person finding the right other person at the perfect time, where they could help each other, relied on people meeting in person at one moment in time. Bill Gates and Paul Allen going to school together, growing up together, and attending a high school that had access to a really advanced computer at that time, led to Microsoft being formed.

But there weren't that many opportunities for those many things to come together at the right time until now. The Internet has kind of changed all that because instead of having to meet one person in one place at one time, like meeting the right person at this conference, you can potentially meet 8,000,000,000 different people or a digital version of you can meet a digital version of 8,000,000,000 of them at any point. Anybody has access to your work and they could have a moment where they realize that they have, like, a need with a new project, or a new company, or a new startup, or hiring for a new role, and then they remember seeing something on Twitter, or LinkedIn, or Instagram, or TikTok, and they can reach out to that person. So how do you leverage the Internet to find those opportunities? I think of this, like, as a 5 step 5 step framework where first, you have to work on something interesting, and more importantly, tell the world about it.

Like, there's about 300,000,000 3 100,000,000 active users on Twitter and 800,000,000 on LinkedIn, but there's 8,000,000,000 people on the planet. So, that means one out of every 8 people is using it. And, even smaller percentage, maybe 5% of those people are posting regularly. So you have a few million people putting all the content on the internet. And then you have to keep iterating iterating and improving that thing until you're known for it.

And at that point, you'll attract an audience of other interesting people building their own thing. Like my Twitter network is riders, startup founders, investors, athletes, a lot of people doing unrelated stuff. They just like what each other's posting online. And sooner or later, somebody's gonna be working on a thing that could compliment your thing. And you shoot a message, see if you can grab coffee, hop on a zoom call, and just see if there's a way to collaborate.

I probably talk to 200 people on zoom, just through Twitter connections over the last year. 10 of those turn into a cool thing to work on part time or collaborate further, or just become a good connection to have for down the road. And I wanted to give a couple of case studies just on ways that this has worked out for me. So, is anybody here familiar with liquidity? The finance meme page.

Okay. So, like half the room. So, two and a half years ago, I was sitting by the pool drinking a Corona Light, and I needed a Spotify playlist because I had 10 friends over and I have a horrible taste in music. So I was the worst person to be DJ. And liquidity, the Spinets meme page, had made it a Spotify playlist called liquidity Hampton day sauce.

And I played it because I had no other leads on what music to put on by the pool, and I didn't want to look like a loser. And it was good. So I messaged him the next day and said, yo, Lit. Your Spotify playlist slap. Thanks for the good vibes.

And then we just kept chatting, and I sent him song recs back and forth for the next two and a half months. And then come August of 2021, I'd already gotten into business school at Columbia. I knew I was starting the following year and I'd made some money trading stocks during COVID. And unlike every other 23 year old dude who traded stocks during COVID, I kept most of the money that I made. So I was like, well, if I'm either gonna be sitting in my living room, working from my computer for another year, or I could go do anything other than that for another year, and I know I'm going to business school, the flight to Barcelona is $300.

So I just quit my job and took off to Europe, but I still wanted to make some money while I was doing that. I didn't want to just be draining everything that I've made. So I've been writing a few freelance articles for like Seeking Alpha and a few other sites and applied for jobs with Morning Brew and The Motley Fool and a few other publications. Nobody hired me. So I hadn't written enough to really get hired by one of them.

But I saw that liquidity had a pretty big newsletter called exec sum that had like a 100,000 readers. We'd already been messaging and I'd started a finance blog about a month before this just to like kind of build out a portfolio of work. So I just DM'd him in like August and told him what I've been doing. Asked if he needed help with the newsletter. And we hop on a call a couple weeks later and he hires me to like run his newsletter.

I wasn't qualified at all to probably be an editor of a newsletter with a 100,000 readers, but he needed someone to help with it. We'd already been talking and it was easier to just get me because he knew that I knew how newsletters worked enough to send out my own blog, and we'd been exchanging songwriters for enough that he trusted me. So I've been doing that for like 2 years. But it came out of nowhere. This is not like a job posting.

He was like looking for somebody for I just threw my name out there. So going back to that framework, I'd been writing some freelance articles online, didn't get hired, realized I needed to get more reps, started my own blog, and was posting more and more on Twitter. I ended up leveraging that to work for him. And more recently, as of like 2 weeks ago, I started a new gig with Redpoint Ventures, helping them build out a newsletter for my data infrastructure and AI stuff. And this whole thing happened because I got back from a trip to Europe before my 2nd year of business school started and realized like all my friends have these return offers to go make a quarter $1,000,000 a year in banking.

And I'm writing a blog and writing a newsletter. What happens if I graduate from Columbia and I just don't have anything going on other than being the blog and newsletter guy? So I panicked and like touched on my resume for the first time since 2020, and then realized maybe I should at least look and see who's following me on Twitter that seems to be doing interesting stuff. A guy named Josh, who's a partner of Redpoint Ventures. I saw that we followed each other on Twitter.

And for those of you who are not familiar with Redpoint, they're pretty big on Instagram, TikTok, putting a lot of content out. So go on their site and see that they have, like, like 0. They have a few, like, some of their investors have put some written content, but it was pretty few and far between. So I just hit Josh up on Twitter. I realized that he was the one behind a lot of their content and stuff and just said, like, wanted to see if he wanted to grab coffee and tell her shop a little bit.

Told him I've been doing a lot of writing stuff. So he was behind a lot of their stuff and we grabbed lunch a week later and I thought I was just going to ask him how he went from running a career NASDAQ for 10 years to getting into venture capital. And the first thing he said was, dude, this is the perfect time to meet. I want to build a newsletter for Redpoint and talk about this stuff and to help put some of our investors thoughts on paper. I wanted to ask you about newsletter stuff.

And 30 minutes later, I just said, I mean, I could I could run this for you. Like, do you want me to just do it? And he was like, yeah. That would actually be way easier because we need to hire somebody for this. So I didn't know it was gonna turn into a job, but now it's like I started on this 2 weeks ago.

Spent 20 hours last weekend trying to figure out what an LLM was and how cloud storage worked because I majored in finance and Spanish and all the investors there were like PhDs from Stanford. But, I kind of just created another job out of Ben Air. So again, it's that same framework of I've been writing a blog for 2 years and build a newsletter. It's like a quarter 1000000 readers. And then I developed enough of a unique voice on Twitter and LinkedIn and through my newsletter that when I needed to go find an opportunity, it was just scrolling through who's following me on Twitter that might have an opening.

And I just reached out to grab coffee, and now it's the job. So I'm a rider. Obviously, for riding, it's the most obvious. If you put your content on Twitter and link to it, people are gonna see it. Or they have a need for a writer.

Okay. That's a pretty easy find, but it works for anything. Like, there's so many people on Twitter that are like in small business or accountants or startup founders. And instead of having to like pay a marketing firm or like a hiring agency, if you have a big enough following that you're attracting eyeballs, it's just so much easier to find talent for all these roles and you can kind of vet people. Because if I see that a lot of people I know follow Eric on Twitter and then he messages me, I automatically know that if he's in their network, it's probably someone I can trust more than just a random person on the street.

So it's really just a competitive advantage. The one, if you're looking for work, it's going to make it way easier to find it. If you've been putting content out that people can see. And then if you're not looking for work, it just leaves you like, it makes you so much more available to different opportunities. So that's it.

We have any questions. Hopefully, we have time for questions. That's my email, my Twitter. And, can somebody try this and see if it pulls on my blog? Because I think it will.

And, I wanna do this more, But let's check it out.

This transcript was generated with Transistor AI