Letters #51/52: Jackson Dahl (2021)
Letters #51/52: Jackson Dahl (2021)
Investment Partner at Paradigm | Reflections on Building 100 Thieves | The Big Wave
Hi everyone! Due to popular request (and a few persistent individuals), I’ll be restarting this newsletter, but with a few changes. Most notably, rather than sending “A Letter a Day”, I’ll be sharing a letter or transcript twice a week, once on Tuesday afternoon (2:22pm) and once on Saturday morning (6:06am). Second, I’m expanding the scope of the newsletter to include a broader range of subjects, but still focused on thought-provoking investors (across venture, hedge funds, and private equity), founders (not just tech), and operators (sales, marketing, product, etc.). Lastly, I’ll be limiting my commentary so it’s a smoother reading experience and you can read the work as is. (If you’d like to see my notes or trade thoughts, shoot me a DM on Twitter!)
Today’s letters are two essays from Paradigm Investment Partner Jackson Dahl. Prior to joining Paradigm, Jackson was an operator on the founding team of 100 Thieves and an investor at Lowercase Capital with Chris Sacca and Matt Mazzeo. He started his career at Universal Music Group. Throughout his career, he’s focused on helping creatives harness the power of the internet.
In the first essay, Jackson reflects on his journey, and ultimately, his decision to leave the organization he helped start and build up from scratch to a world-renowned brand and esports team. In the second, he walks us through his decision to return to the world of investing, what excites him, and his big bet on crypto. These two essays are a fascinating peek into the decision-making process of one of the superchargers of the creative world at one of the most pivotal moments of his career and life.
I hope you enjoy these essays as much as I did!
The Letter(s)
Letter 1: Reflections on Building 100 Thieves
Friday was my last day at 100 Thieves, a company I helped Matt ‘Nadeshot’ Haag start 4 years ago.
This was an incredibly hard decision, and I’ll share more on why and what’s next sometime soon.
But today, I simply want to take a bit of time to reflect and be grateful for this incredible ride.
The journey began when I met Matt through our friend Blake Robbins, who insisted that I meet this YouTuber who was trying to build a new esports team with Dan Gilbert. I was skeptical.
After weeks of follow-ups, we finally got dinner. As we wrapped up, Matt asked, “so, do you want to work with me…?” Neither of us really knew what we were doing. And he didn’t know it then, but I was sold.
I’ll be honest: I didn’t know much about Matt. Despite his wild success in the CoD world and on YouTube, I was concerned he would be all talk and little substance.
I was fortunate to work with two incredible early-stage investors early in my career at Lowercase Capital: Chris Sacca and Matt Mazzeo. One of the most important things I learned from them was to bet where the deck is stacked in your favor — where you have unfair advantages. And most importantly, when the founder has that little extra special quality that makes you want to run after them.
I’d been paying attention to the esports scene and it was clear there was an opportunity for a strong brand to emerge. Most teams built their audiences off of either winning, star players, or both. Anyone who has worked in or loved a sports team knows that both are fleeting.
Matt presented something unique: an incredible audience rallied behind him and his journey combined with a desire to actually build something bigger than himself.
This is tremendously hard for creators to do. The notion of giving up near-term selfish opportunities to try and build a brand is much harder than it looks. It takes a relentless commitment to the long term and a near-irrational ability to put the bigger dream above personal wins.
After meeting him, it was profoundly clear to me that this wasn’t a side hustle for Matt. This was it. He had a vision to bring his audience on a journey with him, return to the competition that formed him, and establish a brand that was actually more substantial than “Nadeshot.”
And that probably would have been enough, but Matt dreamed bigger: he thought a gaming brand could be a lot more than anybody considered back then, and that gaming was just as culturally important as music, sports, or anything else. We didn’t know exactly how we’d do it, but Matt’s early ideas about building an apparel brand and working with entertainers alongside competitors made me realize this could be something special.
And so we set off. When I joined 100 Thieves, I was not yet 24, the company didn’t exist, and it was just Matt, a logo (and a failed CoD team… shh), the founding investors, and an approved franchise application to Riot Games’ League of Legends league.
At the time, we had a loose idea of what could be possible and a big vision: to build the gaming brand Matt always wished he could be proud of.
But we also had a lot of work to do. In late November 2017, we had to figure out how to field a League of Legends team, find them a place to live and work, make content about them, and make an esports jersey that didn’t suck, all before the season started in January. Those were long days, but some of the most memorable.
We got through that, somehow, and even managed to make the finals of our very first split. Then, we made the World Championship in our first year! Little did we know how hard it would be to get back.
We made a documentary about that team called The Heist, led by the creative forces that are Gabriel Ruiz and Logan Dodson. 100T content started strong and didn’t slow down.
We convinced Jason Ton to leave the mothership that was Riot Games and join John and some kids to build something new. I still remember Jason’s first day, where our head of HR (yours truly) had to show him an excel sheet with everyone’s info and social security numbers. I texted Matt that I thought Jason was going to quit by the end of his first week. Fortunately, Jason believed in the vision and was able to forgive our early incompetencies.
We found a diamond in the rough in Julia Wu who has probably touched every single public-facing 100T output since early 2018. I think Julia might care more about this brand than Matt or I do.
We spent that spring trying to make a hoodie that we’d actually want to wear and that teased at the idea: “hey, maybe gaming can actually be cool!” Six months in, we sold out of our first “drop” in about 10 minutes.
We followed through on Matt’s entertainment vision, convincing established YouTube star NoahJ456 and a rising streamer named Valkyrae to take a risk on us before we were even a year in.
By that November, we’d built something real, and the esports and gaming worlds had started to take notice.
Since those early days, we’ve continued to build. We have about 100 employees, 20 creators, almost 50 players and coaches, multiple teams across various games, a half dozen trophies, all kinds of channels and content series, the best apparel brand in gaming, a laundry list of internet-breaking moments that are hard to believe happened, and most importantly, a community that trusts us to keep pushing forward.
We even managed to win that elusive LCS championship a few months ago, which felt fitting for me knowing that my departure was coming. We won a few other trophies along the way, too.
It’s hard to build a public brand on the internet. You live and die by the latest release or result, and little of what you make is remembered more than a few days later. At times, it can feel like a rat race of impermanence.
I always try to remember that all of these things we do and make aren’t actually what 100 Thieves is. They matter, of course, but they are the inputs of what we really are. At our core, 100 Thieves is an identity brand and community that says it’s ok to love video games. The permanent thing is that story and that sense of belonging, and when the content or the wins or the drop fades into memory, that is what stands.
I shared a note with our team on my last day, and the final section emphasized this point. I thought I’d share it here:
100 Thieves is the people
All of you, our team, our players, our creators, and our community. That’s all this thing really is. A logo doesn’t mean much without the people behind, around, and in front of it.
Brands around the world are trying to become more and more human. We have an amazing advantage here: our fans care so deeply about the humans that make up 100 Thieves. Their relationship with our brand will always be stronger when it’s connected to a favorite player or creator, or when they get to see inside the process of this amazing group of people behind the scenes building.
Nothing feels better than when we’re described as a family, whether that be the creator group or the entire company. A culture that is human led will take us very far. Treat each other with kindness and remember that you get to work with some of the most incredible people in this industry.
The “product” of 100 Thieves is this group of people, all running in one direction, making amazing experiences for a community that only wants more. It’s easy to get caught up on just the outcomes: the announcement video, the successful drop, the championship at long last. But the parts I remember most of this journey were the long days alongside many of you, pressing ahead, even when we didn’t know exactly where we were going or if it would work.
Stay the course, enjoy the journey, give a lot of yourself, and you’ll get amazing things back.
I’m really proud. Sure, it’s just entertainment, it’s just video games, it’s just a brand. But I also believe stuff like this matters. We all find joy in little things like TV shows, twitch streams, winning (or even losing) sports teams, friends to relax and play games with. And I think 100 Thieves fills that role for a lot of people. I think we’ve made a lot of people smile in the last four years, and hopefully even helped them meet new friends or make the days a little easier.
I’ll always love this brand. And better yet, I’ve never had more confidence in what we’re building and the team we have doing so.
There may be easier, more lucrative, or maybe even more fun jobs. But there is no more fulfilling work to me than running in one direction and trying to make something new with the right group of people. That’s what I’ve taken away from this experience, more than anything else.
And so, as I’m keen to recite, onwards! I’m enjoying the journey.
Finally, a few thanks:
To Blake Robbins: My guardian angel, to the extent you can have one of those in business. Thanks for being a confidant, encourager, and most importantly, for bringing me into this thing in the first place. Never doubt your conviction: you are usually right before the rest of us.
To John Robinson: As Matt is quick to share — I didn’t technically fully commit to this thing until I made sure that you were likely to be along for the ride. I was coming off a string of incredible career mentors, and I knew I needed that here. Thank you for being our rock, for making us better, and for relentlessly putting one foot in front of the next. I’m so glad our team has you at helm. The future is bright.
To Jason Ton, Gabriel Ruiz, Logan Dodson, Julia Wu, Eric Sanders, Ibrahim Eljeilat, Matty Lee, Jacob Toft-Andersen, Joseph Jang, and so many more of you who’ve made this journey worth it: Thank you for putting up with my chaotic energy, arguing back, and being damn great at what you do.
To Noah, Rae, Courage, and all of our incredible creators and players I’ve had the privilege to work with: Thanks for being the lifeblood of all that we do and making this brand come to life.
And finally to Matt: Thanks for being a brother, first and foremost. Thanks for inspiring me every day and for trusting me to build this thing you love so dearly alongside you. Thanks for making a lot of long days so damn fun. You’re on your way too, and you’re doing great. Slow down, you’re doing fine. Keep enjoying the journey, my friend. And don’t forget: when you are excited about something, there is no one more infectious in the world.
Letter 2: The Big Wave and My Next Adventure
Last week, I shared the news that I left 100 Thieves and wrote about the incredible four years I spent building the gaming brand and esports team. It was an emotional reflection and I’m deeply grateful for what has been the formative experience of my career. I think 100T is in a better place than ever, and I’m so excited to cheer from the sidelines.
My next adventure will be an exploration of crypto and how new technology will enable us to build a better internet.
Why Crypto?
For the past several years, I’ve looked the other way when it came to crypto. I was skeptical of its impact beyond financial infrastructure or speculation.
In early 2021, the pieces started to come together and I began to see the magic. The first big catalyst was a dinner with Fred Ehrsam—a long-time friend and crypto pioneer. Fred was asking about the challenges that creators face and what innovations were happening in the creator economy. We shortly realized that crypto unlocked many new ways to think about enabling creators and their communities. At one point, Fred remarked, “You’re making me so bullish on crypto.” You can imagine the irony I felt at that moment, but I think we were both fired up.
As a kid who grew up on the internet and has spent my career focused on how it’s changing everything, I finally started to pay real attention to crypto. I caught a glimpse of a white rabbit dropping down into a hole, to use the crypto world’s favorite metaphor.
This year, the tools and projects being built (primarily on Ethereum) and the new mental models they uncovered started to infect my brain. Big ideas, like decentralization, community ownership and organization, incentives for creators, curators, and fans, digital identity, scarce virtual goods, applying game design principles to social spaces, and composability of software -- to name a few.
All the while, I spent much of the spring and summer wondering if it was the right time for me to dive all the way in. This shift was obviously a big deal and was clearly *something* (but still probably nothing, of course). Crypto, like other paradigm shifts, has undeniable hype and expectations, but it will take a lot of experimentation to get to the most compelling developments.
The perfect timing to go all-in on major shifts like this one can be hard to nail down, and will always be debated. A dance between too early and too late and way too early.
The Big Wave
So — now is when I tell you that I’ve gotten the timing right and that this, right now — this is crypto’s big moment… right?
Well… not exactly. Candidly, I still think we’re really early. In some ways, it feels like it’s 1999 or 2007 and the web or mobile are becoming truly exciting. Of course, during the dot-com boom or the iPhone’s release, we had no understanding of the breadth of incredible innovation that was to come.
There is a metaphor that has been rattling around in my brain for a good chunk of the year that I’ve used to think about technology, the future, new opportunities, where to bet, and so forth:
Aside from the most essential and universal contributors to success (who you choose to work with, integrity, and persistence), there’s one other thing that I believe can have an outsized impact on your success and ability to get lucky: identifying big waves.
Every once in a while a shift in technology can change everything. Sometimes, catching these waves at all can be a lot more important than exact timing or even precisely what you’re working on. Persistence on the big wave can be the most vital thing to get right.
Crypto and the future internet that it enables is the proverbial big one for the prime of my career.
Something clicked for me along the way. I realized that if you really believe the big wave is coming, timing is less important than you think. Every surfer knows that the obvious answer is that you just have to start paddling as hard as you damn well can.
And I’m ready to paddle hard. There are all kinds of questions and uncertainty and ideas and excitement and everything in between.
What’s Next?
I’m joining a group I believe to be at the edge of this new frontier: the aptly-named Paradigm. Paradigm is a crypto/web3 investment firm founded by Fred and Matt Huang, two of the most thoughtful and intelligent investors I’ve been fortunate enough to spend time with. They have built an outstanding team of investors, researchers, and hackers, and I’m so excited to learn from them.
At Paradigm, I’ll be an entrepreneur-in-residence (EIR). My goal is to stand under the Paradigm umbrella and use their resources, guidance, and expertise to determine where specifically it makes sense for me to go deep and build. In addition to my personal crypto vision quest, I’ll be supporting Paradigm’s incredible portfolio of companies and helping them think through new opportunities that overlap with my scope of experiences and interests.
I’d love to meet people pulling on the same loose threads that I am. I’m eager to explore how crypto will impact the future of my obsessions with the internet, attention, creative people, communities, culture, games, and art. I’ll share more of my explorations as I go. Put simply, I’m focused on Web3, or the internet that crypto enables.
If you’re spending time on the following, please don’t be a stranger:
Creators, Communities, and Investing in People
the evolution of people driven-brands (DAOs) and the convergence of people and brands
how creators and curators of art and media capture value
economies built around fandom
how crypto and the internet enable niche at scale
Digital Identity & Pseudonymity
The shift away from a “real name” internet to a more robust identity system
medium is the message -> context is the identity
tools for individuals to use multiple identities and identities to be made up of multiple individuals
“influencers” of the future
Games & Social Software
third spaces on the web and the rules that govern them
digital objects, fashion, and status
applying game-like incentives to other social spaces
achievement-based NFTs and tokens
games that allow players to capture value they create
The future is bright. I don’t know what the next year or decade will hold, but I’m confident in the following:
The internet can make the world better, more equitable, and more fun.
Digital spaces and tools can connect us, entertain us, inspire us, and empower us. They should also fade into the background when needed, and don’t always do that today.
A digital-native incentive structure and value system are imperative to build the internet we want.
Users should own their own data and have ownership in the value they create.
A decentralized, individually sovereign digital future is far better than the opposite.
The internet should enable niche at scale, rather than trending towards homogeny and mass attention.
Artists should be able to find their audience and make a living because of it.
Brilliance and creativity can come from anywhere and that opportunity should be distributed as such.
The internet should be composable and interoperable.
We’re better when we cooperate and play positive-sum games rather than zero-sum games.
We, collectively, should own the internet.
We can build the digital future we want to live in.
And so, I’m ready to get to work. Onwards!
Wrap-up
If you’ve got any thoughts, questions, or feedback, please drop me a line - I would love to chat! You can find me on twitter at @kevg1412 or my email at kevin@12mv2.com.
If you're a fan of business or technology in general, please check out some of my other projects!
Speedwell Research — Comprehensive research on great public companies including Constellation Software, Floor & Decor, Meta (Facebook) and interesting new frameworks like the Consumer’s Hierarchy of Preferences.
Cloud Valley — Beautifully written, in-depth biographies that explore the defining moments, investments, and life decisions of investing, business, and tech legends like Dan Loeb, Bob Iger, Steve Jurvetson, and Cyan Banister.
DJY Research — Comprehensive research on publicly-traded Asian companies like Alibaba, Tencent, Nintendo, Sea Limited (FREE SAMPLE), Coupang (FREE SAMPLE), and more.
Compilations — “An international treasure”
Memos — A selection of some of my favorite investor memos
Bookshelves — Collection of recommended booklists.