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).

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.

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.

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.

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.

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.

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.

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

Always play the long game.

This encompasses many of the previous things we’ve touched on—like avoiding a grind so you can stay in the game and not burnout—but it is so important that it deserves its own section.

In a great blog post, Paul Millred perfectly described the differences between playing short-term vs. long-term games:

It’s so tempting to chase short-term growth, validation, rewards, etc. As your reach grows, there are more and more distractions and more ways to make money.

Ultimately, I’ve leaned into long-term partnerships that have compounded in value over the years.

I signed my first marketing agreement with Underdog in the summer of 2020 and just signed a new one the other day that will keep me partnered with the dog app through 2027.

That partnership has been successful because it has been so deeply integrated into everything I do. There’s no dine and dash element to it. When people see you are in something for the long haul, they know that they can trust you and aren’t just being used for another first time deposit bonus.

One side topic that is inextricably linked to playing long-term games is whether you should work for free or not. This topic pops up on a seemingly annual basis and lots of people have very strong opinions on it. Here’s my taek:

There’s a difference between working for “free” & being “unpaid.”

It’s up to you to determine whether an “unpaid” gig offers sufficient compensation in other forms than money. That could be a million different things—a platform, clout, resources, exposure, connections, upside, etc. All of those things might be as valuable as money to an individual, depending on their unique goals.

When I first started writing the Fantasy Life Newsletter for Matthew Berry in 2020, I did it for free the first year. Could I have asked Matthew for some nominal cash compensation while I proved myself? Sure, but I decided the long-term upside with a unique opportunity in getting to work for Berry was worth far more than locking in an hourly rate.

Matthew later rewarded that early work by offering me a dream job in an expanded role and an equity stake in the fast-growing company.

The content game has never been more saturated, and yet there has never been a better time to drill down, own a small niche, and find a community of people who love the same hyper-specific things that you do.

I once heard someone say that you want to be a content magnet, where you pull people to you as opposed to trying to appeal to everyone.

This approach has a couple of benefits. It allows you to focus on the stuff you are passionate about, which will attract like-minded people who feel similarly. It also makes the process of creating and staying in the game way more sustainable. Trying to game an algo or make content for everyone is an imperfect way to judge success and an easy way to burn out.

Of course, being a magnet requires much more patience. You won’t grow fast with this approach (or at least how I’ve executed it). It took me six years of making content on the side while working my corporate marketing gig before I felt comfortable going full-time.

This slow burn approach can lead you to comparing yourself to others who are growing faster and cause you to question if you should be doing things differently. I struggle with it a decent bit, but always come back to wanting to double and triple down on occupying this super small niche and delivering for my existing audience.

The 1000 True Fans concept is a great North Star for those willing to embrace the slow burn, niche life.

I’ve done thousands of hours of live streams since I first started regularly streaming in 2020. I love live streaming, it’s how I built my Youtube channel and found an audience…and yet, I’d be lying if I said it hasn’t made me lazy.

That’s because live streaming is easy. The barrier of entry is so low. Sites like Streamyard make it a piece of cake to produce a decent looking show. You simply show up, turn the cameras on, and let it rip.

Unfortunately, live streams are also completely un-evergreen by nature. They are meant to service the live viewers, the chat, and the diehards who make it appointment viewing. That’s a wonderful thing and a great way to serve a community, but I don’t want it to be the only thing.

When I look back on all of the content I’ve made this past decade, there are very few specific live streams I remember. What I remember is the stuff I put significant work into: the hardcopy Fantasy Football Comedy Hour draft guides, the Fantasyland audio documentary about Chris Wesseling, the Broathalons, my Deposit Kingdom videos, a Fantasy Feud game show, etc.

All of those projects required a significant amount of time and money to create and had a horrible return on investment, and yet they are the most rewarding things in retrospect.

Ultimately, I want to find a balance between short-form vs. long-form and live streaming vs. bigger projects.

If I spent all my time working on time-intensive, ambitious projects, I’d go broke. But if all I ever did was live stream, I’d feel unfilled. Finding that perfect balance is what I’m always after.

When we had April in December of 2022, I knew my time management habits had to change. I’ve always had a good work ethic, but I knew deep down that I wasted a ton of time. When there is nothing forcing you to be efficient, it’s hard not to be careless with your time.

I would go the gym for 2.5 hours and take my sweet ass time. I’d stay up until 2am editing a video while getting distracted on the internet. I’d spend an entire Saturday working on a writing project, taking an unnecessary amount of breaks throughout the day.

Becoming a Dad forced me into a decision quickly—either remove a ton of stuff from my plate or become extremely efficient.

I didn’t want to stop doing so many of the things I love doing, so I decided to become extremely efficient.

I time block my entire day, which removes the temptation of wasting time. I simply “show up” for everything on my calendar as if it were an important meeting. If something runs long or an unexpected thing pops up, I slide things around to another available time on my calendar.

It truly has been a game changer. Even with significantly less time, I’m getting more done now with a toddler than I did pre-kid.

As James Clear says, “You do not rise to the level of your goals. You fall to the level of your systems.”

As a related aside, I’ve also had to learn to delegate. I used to do everything myself, but now rely on talented people to edit my videos, make my thumbnails, track timestamps, brainstorm show ideas, etc. At first, that required some letting go, but now I fully appreciate it, as it affords me more time to make stuff, while also getting to collaborate with a great team.

Hopefully you found something in here that is helpful. At the very least it was a fun stroll down memory lane for me.

As I wrote this, I realized that there were so many other side tangents I wanted to explore. I think there are a lot of things I do that would not be “optimal” or realistic for others and those nuances would require a lot more time to unpack. I tried to keep these as actionable as possible.

I don’t have any grand aspirations for the next ten years or plans to change much of my approach. I just want to keep playing my own long game.

🤓 FANTASY LIFE: How To Attack Early BBM Drafts. Went through risers to target, falling knives to avoid, positional cliffs to be aware of, and a bunch more in this piece.

☕ BEST BALL BREAKFAST: The Rookies Soar In Early BBMVI Drafts. We kicked things off with a bang on Monday.

☣ LOLZ: A Proposal For Sports Betting Apps. Also, the Tom Dwan breakdown.

🚢 SHIP CHASING: The Gang Slaps It Up In A BBMVI Draft. A bear case for every player.

⏰ OFF & ON THE CLOCK: The Eliminator Is Built Different In 2025. Nez and I discuss strategy for the revamped Eliminator contest and rip a draft.

💪 THE SWOLECAST: A Shocking Turn For 2 Hosts. The one where Kitchen delivers the next great Best Ball-ism.

📈 ADP CHASING: Huge ADP Risers & Fallers On Underdog. The crew sifts through the ADP rubble after the NFL Draft.

🥃 DFS After Dark: Hot To Attack BBM w/ Sackreligious. We did a deep dive on the entire ADP landscape in the wake of the NFL Draft to get you prepped for drafts.

✍ Best Ballers Don’t Brawl: The Surprising Civility Of Fantasy’s Hottest Format. Fun piece by Jeff Edelstein that I was interviewed for.

DFS After Dark returns Saturday night (8:00pm et) with The Coachspeak Index. We’ll be discussing interesting nuggets from post-Draft press conferences and checking in on how his content empire has grown.

You can become a YT member for access or subscribe on Spotify for a private RSS feed (I post the video/audio there directly after the show).

🐊 Book #4 for May (25%): Gator Country: Deception, Danger, and Alligators in the Everglades by Rebecca Renner

Loving this. Will share my thoughts next week when I have more time.

🚂 Book #3 for April (FINISHED%): The Fish That Ate the Whale: The Life and Times of America’s Banana King by Rich Cohen
💉 Book #2 for March (FINISHED): Empire of Pain by Patrick Radden Keefe.
🐃 Book #1 for February (FINISHED): The Heart in Winter by Kevin Barry

Got a question for me? Reply to this e-mail and I’ll get back to you…