How I Cold DMed My Way Into Startups and Venture Capital

Living in NYC is means you’re asked "What do you do?" 17 times per week.

I have a solid rule of thumb to answer this question.

If the person is under 40, I simply respond, "I tweet" and then wait.

It usually makes people laugh in surprise.

In a world of finance bros, directors, and partners trying to one up each other, I'm the breath of fresh air of ridiculousness not trying to play the game.

When they then ask a follow-up question, I then explain I ghostwrite Twitters for founders and venture capitalists. Then they ask "How did you get there?"

In order to have a post I can share with them instead of explaining my story again and again, I've decided to devote today's post to sharing my full and complete story.

How I Cold DMed My Way into Startups and Venture Capital

In May 2021, I was a 24-year English major at Rutgers University.

A little old, I know, right?

I started out at the University of Michigan's Ross School of Business back in 2015 but left in 2016 to go smoke weed and run an e-commerce business that was making $2,000/month.

Unfortunately, I spent significantly more time smoking weed than running the business. The business failed, I went broke, and was doing a lot of drugs while living at my parents’ house.

April 2019: After a therapist sat me down and said “you’re going to die if you keep this up”, I quit getting high and slowly got my shit together. And that is how I found myself working at Home Depot for $12/hr and trying not to be upset about the state of my life. I went from Top 3 Business School in the country to being a very mediocre Home Depot employee. By mediocre, I mean extremely mediocre. I was in the bottom 10% of employees. I was a self-checkout cashier which means I stood next to the self-checkout machines and offered my help to people who clearly didn’t need my help otherwise they wouldn’t have chosen self-checkout. Fuck Home Depot.

At this point, I knew I needed to go back to college but I didn’t want to go to Michigan and have a repeat happen of the past. I was scared to get in with the same crowd and start screwing around. My stepmom teaches at Rutgers meaning I could go for free, so I figured why the fuck not. I started there in January 2020. I got into Rutgers Business School but chose the English major route because I thought I'd have more fun and didn’t enjoy Michigan’s business program (from the stoned memories I could pull up).

School goes surprisingly well. Even during the pandemic, I loved most of the creative writing classes—especially screenwriting. I got practice writing scripts, wrote for the local newspaper, finished the screenplay I started back in my druggie days, and even wrote a novel I hope to publish in the next few years.

January 2021: As I got closer and closer to graduation, I realized a very important thing: most English majors are broke and have trouble finding jobs, so I'll need to figure out a different way to make money until I could get big enough writing where I was making good money.

Around this time, I started helping out my parents’ kitchen remodeling business with Facebook Ads. I wrote the copy and orchestrated the campaigns. I hated it, but at least I was getting paid writing. I got on Twitter with hopes of finding more Facebook Ads clients.

And that’s when I stumbled across tech Twitter.

July 2021: On Twitter, I learned about something called a growth mindset. I knew I wanted to do something more fun and inspiring than running Facebook ads, but what? And that’s when I stumbled upon Lambda School on Twitter.

Lambda School is a coding bootcamp now known as BloomTech. I applied and then spoke with an admissions guy Tommy Collison (I wouldn’t realize he was the brother of Stripe founders Patrick and John Collison until after I got off the call 😂). But Tommy was super inspiring. He studied English and was a big book nerd, but learned how to code when he got the job at Lambda School. If he could do it, so could I, right?

Since I was a teenager, I thought I was too stupid to code. Well it turns out I was just high hahah. Without drugs clogging my brain, I learned to write Python and SQL. I loved the challenge of it. Even more so, I loved applying SQL skills to real datasets—especially health ones like my Oura Ring’s sleep data.

Around this time, I got a DM on Twitter from another bootcamp student named Justin Fineberg. We hopped on the phone and got along. He was writing a blog and told me to start a blog because it might help me refine my thinking (this would become Cyber Patterns). From July to September, I did the coding bootcamp, wrote online, and sent cold DMs and made internet friends inspired by my friendship with Justin. I had no idea you could just send a DM on Twitter and make a new friend until Justin sent me one. Mindblown.

September 2021: My junior year started back up at Rutgers. I was doing English classes and the coding bootcamp at the same time. Then I got recruited for a data engineering job at American Express. It was $90,000/year. I took it without hesitation. In the same week, I dropped out of both the coding bootcamp and college. I was getting a real fucking paycheck. It was game time.

October 2021: I saw a crypto company's marketing director tweet that she was looking for freelance writers. I'd been writing my blog for about 5 months at the time and didn't have more than 200 readers. I sent her a message, she liked my work, and paid me a couple hundred bucks per blog post.

After doing a few articles with her team and building up a portfolio, I started cold DMing founders of different startups and they started paying me to write for their companies. That’s how I met Greg Isenberg (founder of Late Checkout) and started working with him—from a cold DM. Greg and Justin from above will both be at my wedding. Insane.

I was doing the freelance writing thing at the same time I was doing the data engineering job at American Express. This was peak crypto market, so all the crypto companies were investing heavy in content. I quickly hit a point where I was making the same amount writing as from the coding job—so I quit the coding job. My parents and family was pissed off and confused. What they didn’t understand was I believed I could make more money writing than coding because I’m a much better writer. Coding was just a means to an end—paying rent until I could become a well-paid writer. Now it was game time.

April 2022: 3 days after I quit American Express, I was offered a full-time writing job as a Staff Reporter at crypto media company The Defiant. It was $80,000 with benefits. I took the job no questions asked.

I loved working there, I learned a shitload, and I went to a lot of crypto parties (they're cooler than they sound and usually have free food and stickers). Most importantly, being a reporter at tech news outlet meant 3 things:

1. I was forced to write 4+ hours/day for articles and press publish almost every day. It’s where I learned that publishing > perfection.

2. I spent a lot of time cold DMing founders asking them questions for articles I wrote in The Defiant’s newsletter of 90,000+ readers.

3. I had an endless supply of content to write about, so I grew my Twitter fast and hit 10,000+ followers in June 2022.

The combination of those 3 things—learning to press publish, growing my network by sending cold DMs, and building my reputation around my content—led there to be enough demand for my writing that I happily left The Defiant 6 months after starting.

September 2022: Within 2 months, I went from making $6k/month as a full-time reporter to making $25,000+/month on my own. I’ve been comfortably hovering around that mark for the last year.

A lot of people think I should start an agency and I do hire the occasional subcontractor, but I am much happier writing than managing people. I’ve hit the dream of being a well-paid writer.

Since September of 2022, I've been having the time of my fucking life. Every day, I’m grateful to be alive, happy, and doing what I get to do. Now is all about working my ass off to make sure I get to keep doing it!

I’m giving away $1,000

Sending cold DMs on Twitter changed my life.

That’s why today I launched The Cold DM Challenge.

I’m giving away $1,000 to whoever gets a DM back from the most famous person possible.

I hope the challenge will show people you can meet anyone and change your life with the power of the internet.

You can enter here and watch the launch video here.

Wait, wait, but how do you send the perfect DM?

Check out today’s video: The Art of The Cold DM

COOL SHIT CORNER

My friend Houck raised millions for his startup.

His new project made $100,000 last month.

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Thanks for reading nerds.

Create some cool shit this week.

Jason Levin

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