Carpe DM

The art of the direct message (not the 3 AM Saturday type tho)

Jack Raines
September 13, 2021

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“Sliding in the DMs”, the rally cry of a generation. Maybe a girl that you’re interested in posts something fire on Instagram, and you make sure to let her know that you noticed. Maybe you get back home from a late night out and start firing messages left and right. Then you delete everything the next morning (one of my friends is notorious for this, you know who you are 🤝).

On the other side of the spectrum, we use DMs as the number one way to exchange memes. Everyone has group messages set up to send memes of Kanye West, Vin Diesel, Jake Paul, and whatever else is popping off in the world today.

I’m here to tell you about a new, better way to use direct messages. If used correctly, direct messages provide a 0 risk, high reward opportunity to build connections, expand your network, and maybe even find a new job.

Carpe DM.

The Evolution of Networking


For most of modern history, three variables drove your chances to connect with movers and shakers.

  • Ability
  • Luck
  • Nepotism

Talent alone wouldn’t be enough, but it was a prerequisite to get your foot in the door. Say you were really good at your craft. Then luck and nepotism come into play. Maybe you have a chance encounter with an investment banking director at a cocktail party. Maybe your rich uncle plays golf with the editor of that publication that you want to write for. If you had a certain baseline talent level AND a lucky streak or powerful family member, you had a decent chance of landing the gig that you were pursuing. Otherwise? Good luck, Charlie.


There was this cool new technology that really caught fire in the 1990s: the Internet. And this “internet” evolved quickly. As the internet grew from a research mainframe to a communication platform for the world, new venues for connecting emerged. Friends and family could link up on Facebook. You can follow your favorite celebrities on Instagram. You can connect with coworkers on Linkedin. You can create your own personal “internet world” on Twitter. As the internet became a social organism, individuals that were previously unreachable became quite available. Elon Musk shitposts about other billionaires on Twitter to the delight of millions.

Investors communicate stock ideas on Discord, Reddit, and Twitter.

Business leaders chat back and forth with regular folks in Twitter threads.

Most importantly, many important figures have their direct messages open, inviting anyone and everyone to reach out.

Expanding Your Network

As you know, I traded stocks a lot last year. What you don’t know is that I made hundreds of connections in the investing sphere through social media. I cofounded a Reddit page for SPACs that now boasts 176k followers. From this page, I joined a tighter-knit community of investors via a Discord server. We exchanged countless hours of information, and a lot of people made a ton of money through this network.

Through Twitter and Seeking Alpha, I met dozens of other investors who were interested in the same stocks as me. A year later, I have dozens of strong relationships with people that I’ve never met thanks to these internet circles.

There are online communities for everything. If you take the time to look for them, you can find a group of like-minded individuals who pursue the same interests as you. Maybe these connections will turn into financial opportunities. Maybe they will give you a chance to share your thoughts with others who are in the same boat. Regardless, you can build a powerful network online if you put in the work.

Local communities have always been defined by geographies. Online communities are defined by similar interests. Local communities are largely formed by chance. Online communities are actively built. Whatever your interests, don’t neglect the world’s greatest community builder: the internet.

Pursuing New Opportunities

Beyond building networks, the opportunity to find and pursue new opportunities online cannot be overstated. Twitter has quickly become the casual alternative to Linkedin. Company founders, thought leaders, and the top 1% across countless industries all hang out on the site with their direct messages open. If you are a writer, you can chat with employees and executives at companies like Morning Brew and The Hustle. You like investing? You can reach out to hedge fund managers that you come across online. Trying to play a college sport? Twitter DMs are the easiest way to contact coaches. The list goes on and on, but you get the point.

A couple of months ago, there was a certain account with about 600k followers that I reached out to:

I didn’t really expect a response, but that message turned into a series of phone calls. We now have some projects in the works that I am very excited for. Now I’ve messaged dozens of popular people/accounts for various reasons, and maybe 1/3 of them respond. 1/3 may not sound great, but those odds are fantastic when you look at the risk/return.

Zero Risk, Unlimited Rewards

In the investing world, we look for low risk, high return opportunities. Risking a 100% loss for a 100% gain is a terrible trade off, as you could lose all of your capital. Meanwhile, risking 2% for a 100% gain is a fantastic opportunity. Online networking is the epitome of a low risk, high reward play. What are you “risking” when you message someone that you are interested in working with? Maybe 30 minutes of your time, max. What is the potential reward? Job opportunities. New additions to your network. A chance to learn from a winner in your field. If you show a sincere interest and some talent, many people are willing to at least hear you out. Getting your foot in the door has always been the hardest part, but it’s now easier than ever.

Closing Thoughts

  • Networking used to be a game of luck, but the dynamics have shifted.
  • The Internet introduced a variety of ways to expand your circle.
  • Many movers and shakers are accessible through Twitter and other platforms, don’t be afraid to shoot your shot.
  • When your maximum risk is a few minutes of your time, and the upside is unlimited, you take that bet every time. That’s the opportunity presented when you message someone that you want to work with.

Carpe DM indeed.

That’s all today. Have a great week, and I’ll catch you guys Thursday!


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