10 Lessons From 10 Years Making Content

In this week's P.O. Box:

It dawned on me the other day that I’ve now been making content on the internet for a decade.

I guess technically there is an embarrassing music blog floating around out there that I started from my college dorm room in 2007, but 2015 is when I first started making fantasy football content (s/o Fantasy Football Comedy Hour) that would directly lead to this bizarre, wonderful full-time career I have now.

I always enjoy when other creators put together these type of “lessons learned” posts, so I figured I’d take a stab at sharing some pearls of wisdom I’ve learned over the past ten years.

These “tips” aren’t necessarily one-size-fits-all, but simply represent what has worked for me (or has become clear in retrospect).

🛩️ 1) Build the plane while flying (just start)

If you want to start doing stuff, just start doing it. It’s easy to use perfection as a reason not to start.

I need the perfect idea, I need the perfect camera, I need the perfect co-host…then I can start.

The truth is that you are going to fail a ton before anyone seriously starts paying attention regardless of how prepared you feel at the start, so relish the fact that not many people are watching while you get your reps in.

I did thousands of hours of improv (I wish I was exaggerating) from 2010-2015 before I started the Fantasy Football Comedy Hour with three other improv friends. It took bombing on stage over and over again for small audiences in a black box theater to get both the skill set and the confidence to make content on the internet.

As you progress, there will be plenty of opportunities to improve your set-up and add to your tool kit, but just starting is far more important than whether you have a Yeti or Shur microphone.

🤟 2) Engage with the stuff you like

So much of the larger conversation surrounding content these days centers on virality and optimization. SEO, ChatGPT, and new AI tools are presented to us as skeleton keys for fast growth.

But I’d argue that the best way to grow and enjoy more opportunities is simply to engage with the stuff out there that you already like. Think of it like a less dirty and more honest version of “networking.”

When we were first starting out, we invited on all of our favorite fantasy personalities onto the Fantasy Football Comedy Hour, including Denny Carter, Matthew Freedman, and Scott Fish.

I think those early guests said yes because 1) they appreciated that we were doing something unique in the space, 2) because we had planned out interviews/bits/sketches that specifically played to their strengths and 3) because we demonstrated that we were fans who weren’t just trying to use them to signal boost our new show.

After his guest spot on FFCH, Freedman asked me to host the Fantasyland podcast that Rotoviz was launching, which is where I met Pat Kerrane and how Ship Chasing was ultimately launched…Fish offered to make us a website for free (!)… Denny and I would later make our own fantasy football comedy as Fantasy Mensa.

Along those same lines, I made a spoof “Swolecast Audition” tape in 2016 because it was my favorite DFS show. Three years later David Kitchen would ask me to join the show his tree as a regular cast member.

I have many examples like this. Not everything in content has to be a growth hack. By genuinely engaging and participating with stuff you enjoy, you will find your people and doors will open.

⚠️ 3) You don’t need permission to make stuff

In a similar vein to just starting, you don’t need permission to make stuff. We all not-so-secretly want validation from others that we are good at what we do and deserving of attention, but you can’t sit around waiting for it.

In 2016, I applied for an “on-air talent” job at DraftKings. It looked like a dream job to me at the time. Get in on the ground floor of a DFS company on the rise while broadcasting about fantasy sports? Yes plz.

I made it through multiple rounds of interviews, including a test recording. I fumbled my way through a teleprompter reading that I didn’t know was coming. I didn’t get the job. I wasn’t ready for it. Despite plenty of experience performing on stage, I had basically zero on camera experience. I was devastated. I had already accepted that job in my head hundreds of times. It was going to be my ticket out of cubicle town.

A month later I started making my first videos as The Manz. I knew if I actually wanted a job on camera…I needed to actually start doing things on camera.

That rejection from DraftKings was the exact push I needed to start making my own stuff. I didn’t need permission via a job to be on camera, I could do it myself. The Manz bit ultimately led me down a much more creative and fun path that I’m extremely grateful for.

And today, I would have absolutely zero interest in a corporate broadcasting job like that.

⚙️ 4) “Grinding” is bullshit

I hate the word grind when it comes to making content or participating in a hobby. Grinding infers that the work is unenjoyable.

There are plenty of things in life that are a grind, but doing something you love on the side (even if you have hopes to monetize it or turn it into a career) shouldn’t feel like a grind. It should feel like play. That’s the only way it will be sustainable.

If you devote your time to something that feels like a grind…and then get really good at that grind…the opportunities that come your way will involve you continuing to…grind?

Instead, collaborate with people you enjoy spending time with and work on stuff that you’d do for fun so that when opportunities do arise it doesn’t feel like work.

It’s kind of like that investment saying, “Time in the market beats timing the market.” In this case, “Enjoying the work beats working to find enjoyment.”

The biggest risk to anyone making a go at this is burning out. It will take awhile regardless, so you better enjoy the process.

🎭️ 5) Follow the funny

A phrase you’ll often hear in improv is “follow the funny.” When an audience laughs or reacts to something, that is a screaming indication that you just hit on something worth pursuing .

Whether you are doing comedic stuff or not, there is a lesson in that. Follow the things that captivate you, or the stuff that you’ve put out there that resonates with others.

When I started doing the Manz character, I envisioned it as a DFS bro parody bit. I randomly decided to do a Manz poker vlog on a trip with my buddies, which quickly became my most popular video at that time.

I decided to lean into the poker stuff, eventually getting to enjoy some really cool experiences—playing at the WSOP, hosting Poker Night In America’s heads up challenges, and playing on PokerGo with Jennifer Tilly.

Similarly, a one-off joke about playing a backup RB named Patrick Laird in DFS turned into a massive bit and a lasting friendship.

Sometimes, though, you’ll arrive at a dead end. The Top Shot boom was exciting and fun to participate in during the doldrums of quarantine lockdown, but eventually flamed out. I learned a lot from that experience.

Not every tangent you follow will yield exciting opportunities, but you’ll never know what possibilities exist if you don’t follow it in the first place.

🤝 6) Say “yes” a bunch early so you can say “no” later

Most people are familiar with the improv axiom, “Yes, and.” It’s a particularly valuable framework for beginner-level improvisers who need to be reminded not to neg their scene partner (say yes) and instead build on the reality that has already been established (then say and).

Adopting this mantra as a new content creator is similarly valuable. It’s important to try a bunch of things. Figure out what you are good at. Figure out who you like to work with. Experiment. Fail. Try again. Pivot to a new thing. Circle back to what works.

When Brian Hooper, cold dm’d me in early 2020 to start a DFS podcast, I initially hesitated, but ultimately said yes. We didn’t have a plan. Hell, we still don’t have a plan. But the show has now been running weekly for 5+ years and the knowledge I’ve gained from doing that show (and learning from Bric behind-the-scenes) have been immensely valuable and fun.

If anything, I’ve said yes to way too many things over the years. On the one hand, I have tons of different projects/shows/collaborators I enjoy, but I’ve also spread myself thin. It’s impossible for me to give any one thing 100% of my attention, which is an unfortunate sacrifice to being a variety-hound. This is an element of my path I would definitely not try to replicate, but I’ve found a way to make it work for me.

Over the past couple years I’ve gotten better at saying no to things that weren’t working, I wasn’t enjoying, or that I simply didn’t have time for, but that luxury only came from saying yes a lot at the beginning.

🕹️ 7) Play the long game

This might be the single most important lesson I’ve learned over the years.