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Updated: 3/29/2023 | Originally posted: 4/24/2022
When I was 16, I had an idea for a food truck that serves s’mores with different types of chocolate rather than just Hershey’s milk chocolate.
My parents told me to write a business plan (which I did), but I then immediately got intimidated by the scope of the project and backed off.
I still think the idea is brilliant — imagine white chocolate s’mores — , but I have no interest in running a food business.
Regardless, what I wish I could have told my younger self though was “go work for a food truck and learn how it’s done.”
I would’ve spent the summer working on a food truck and partying at music festivals instead of going to Planet Fitness and screwing around with friends.
2 years later, I fell for a similar trap.
I started an online music magazine called Monday Mourning after never having written for a magazine. For me being a freshman in college, I think it was pretty successful. We interviewed Bad Suns, Matt Costa, and a few other big indie musicians.
But, on the business side of things, I had absolutely no clue what I was doing. I was pouring money into Facebook ads with no idea how I was going to make any money. Eventually, I quit the project because I saw no future ROI.
Maybe it would’ve been smart to write for a magazine or even just write some articles for my college friend who was putting on shows and publishing album reviews. But I was a cocky 18-year-old and thought I could do it myself.
While I think it's great for teenagers to build businesses online, for 99% of people, you can only get so far by yourself. You need a guide to take you to the next level.
When I started Cyber Patterns, I had never written professionally besides the local paper. I had no clue how the newsletter biz worked, growth hacks, what to charge for ads, whatever. On top of that, I also didn't know anyone who did know how this shit worked!
As I grew my Twitter and made more online friends, I became a digital apprentice to internet masters who taught me everything I know about the content biz.
Enter Digital Apprenticeships
Let’s jump from my stubborn teenage years to age 24 in March 2022.
I’m working in corporate and trying to get the writing thing going on the side. I was writing my blog and leveraged that into a gig writing for a small crypto company.
I sent a cold DM to Twitter legend Greg Isenberg and leveraged that work into writing for his team at Late Checkout. The highlights were live jam sessions with the team and Greg’s comments on my Google Docs.
I’d write a decent piece and then he’d hop in, drop a killer hook, and boom. It’d go viral.
When I worked with Greg, I felt like an apprentice learning my craft.
It had been my goal to be a professional writer since I was a kid, but I didn't know any.
I had no idea how to make a living writing online so I tried a dozen things and failed. Then I became an apprentice and everything changed. I needed to meet some writers like Greg, work under them, and to build up my skills.
What's so cool about digital apprenticeships is that unlike applying for jobs on LinkedIn, you don’t need to apply for an apprenticeship. You can just find someone on Twitter who is further along your career path and send them a cold DM (how-to do that here).
“Because apprenticeships are jobs with clear career trajectories, they’re the only pathway to socioeconomic mobility that truly level the playing field”
After working with Greg and the Late Checkout team, I leveraged my portfolio into a full-time job as a Staff Reporter for The Defiant. I was officially writing for a living!
There, I worked under ex-Bloomberg journalist Camila Russo, who is the author of The Infinite Machine, a book about Ethereum that is getting turned into a movie. Working under Cami, I learned how to write and publish on a daily basis.
While I was an employee, I saw myself as a digital apprentice. I tried to learn as much as humanly possible. Within 6 months, I left The Defiant because there were so many freelance opportunities. Since then, I've built up a massive portfolio of content writing gigs and learned under a dozen incredible founders.
What's crazy is it's not just me doing digital apprenticeships.
My friend Billy Oppenheimer cold DMed his way into an apprentice working for best-selling author and internet master Ryan Holiday. Because Ryan Holiday was apprentice to author Robert Greene 20 years prior, Billy has actually been working for them both. Now whenever Billy posts, they both retweet his work to their collective 1.5M followers. Needless to say, he's been blowing up this year. He couldn't have done this without them.
Trung Phan and Steph Smith both worked at The Hustle under Sam Parr. Trung has surpassed the master, growing his Twitter to 500,000+ and becoming the unofficial king of shitposting. Steph has killed it as well. She sold a book about content and now runs podcasts for venture capital firm Andreessen Horowitz.
Digital apprenticeships are the ultimate pattern to growth online. What's cool is they are like a cycle. Let me explain.
From Student to Teacher
When I originally posted this article in April 2022, I didn't expect people to hit me up and ask me to become my apprentice, but that's exactly what they did.
The student has become the teacher
— GREG ISENBERG (@gregisenberg)
May 24, 2022
A few weeks after posting the article, a young writer named Steve Flanders hit me up and told me he read it and wanted to apprentice under me.
I was initially against it because I felt like I didn't deserve an apprentice yet. But Steve offered to work for free so I took him on. And then when I had the budget to pay him, I hired him to work with me on all my projects.
Steve and I have been working together on projects since then. He's a full-time freelance writer hiring apprentices of his own.
A few months after posting the blog, a college hustler named Luke Clancy hit me up, told me he read the piece, and wanted to grab lunch.
Luke bought me a Chipotle burrito, we chatted all things content and growth, and stayed in touch on Twitter. Luke was interning for startups so when I was looking for a growth guy for Cyber Patterns, I went to him first. He's been a killer.
As Henrik Karlsson says, "A blog post is a very long and complex search query to find fascinating people and make them route interesting stuff to your inbox."
I never expected people to reach out after this initial blog post. But unknowingly, this post has put serious money in my pocket.
Become a digital apprentice!
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