If you’re going to back a fund, you should know a lot about the person running it.
Here are some bullet points about my life that have shaped how I have gotten here and how I think about investing …
Born in Charlotte, NC. Lived upper-middle class lifestyle in the suburbs from the time I was born until I left for college. Dad was an entrepreneur, mom stayed at home to raise us. Could not have asked for a better environment to grow up.
I'm a Christian. I went to Christian school from kindergarten until 5th grade and went to church most Sundays. I think it’s important to understand the code every person follows, and my belief system is rooted from the Bible.
Middle of three brothers. Having brothers gives you so many advantages in life, and constant competition gives you an edge that you do not appreciate until you get older. I am still close to both my brothers, and I talk to them at least once a week.
Sports was my path. Both of my parents played college sports, and both of my brothers and I were exposed to different sports growing up. I was most interested in basketball, then baseball, then finally football. I realized early on that sports were my best bet to get into an elite college, and I figured that football gave me the best odds to do that.
High school purgatory. I knew I wanted to be a college quarterback ever since I was 13, and high school was the only thing standing in the way. I did not understand the idea of optionality back then, and I put all of my eggs into the football basket; if I did not get a scholarship, I honestly do not know where I would be now. My high school football career was not smooth (went through three coaching changes, missed my sophomore year with a broken back, played my entire senior year with a torn labrum in my throwing shoulder), but I finally got my break after my season ended senior year. Georgetown offered a scholarship, and even though I originally had no plans of leaving the South, I took it.
Quarterback. Nothing humbles you like being the quarterback on a losing team. I got my teeth kicked in for two years as the starter in college, had my body in constant pain, and dealt with real failure at a young age. So much time, sacrifice, and effort had gone into the ultimate goal of playing college football; I felt like my college career was mostly a failure when I got there. For those unfamiliar with football, quarterback gets all of the credit when a team wins, but it also gets all of the blame when a team loses. We lost a lot of games, which meant I carried the weight of that loss throughout the week. I don't expect many people to grasp what this feels like, but I can promise you that the weight is a lot heavier than what most other 21-year old college kids deal with. Ultimately this sucked, I hated this period of my life, but I'm glad I went through it. Good judgement comes from suffering, and I learned a lot from in a short time from this experience.
Georgetown business school. Georgetown is a top 10 undergrad business school, and I double majored in finance and management, and I minored in economics. I juggled all of this while competing academically against some of the smartest undergrad kids in the world along with a 40+ hour commitment per week to football. I learned a lot about time efficiency, operating on a sleep deficit, and humility through this period of my life. Since graduating and working for the past several years, I have learned that a lot of venture people do not have any sort of formal finance experience and financial literacy is comically low for this asset class. Although I agree that knowing how to build a DCF model is not useful in early-stage venture, my finance degree has given me fluency with later-stage investors who start to value businesses based on metrics more than narrative.
Stumbling into venture. All of my friends from school went to go work in investment banking and consulting, and I had no interest in doing the same. I didn’t have the grades even if I was interested. Startups seemed cool, I knew I wanted to start a company one day, so I figured working around startups would be an ideal setup to learn. I interned for an accelerator for two summers, they needed a full-time analyst by the time I graduated, and I said yes.
COVID. After around ~a year of working full-time, COVID hit. The accelerator ran on sponsorship dollars, and when COVID hit, those sponsor dollars disappeared. I got laid off. This sucked, but it taught me a lot about personal agency, creating your own luck, and many of the downsides of traditional W-2 employment. This was a forcing function for me to spend more time building which ultimately unlocked more opportunities than I could have imagined.
Started building. Being exposed to builders made me want to build something for myself, and so I got started doing that. I built one of the largest private communities for private investors out of necessity when I started working for my first job in Charlotte. In case you're unaware, Charlotte is not a venture town, and I had to be creative in terms of how I was learning and seeing interesting companies. Building this community was my way to do that, and fast forward to today and there are:
Started writing. The newsletter business originally started as a way for me to share what I was learning and solidify how I was thinking about different things. This started acting as an opportunity multiplier as the media business and community gave me access to interesting people I otherwise wouldn’t have a chance to meet. It also taught me how to actually operate and grow a business - something that makes it easier for me to connect with and help founders. Good things take time, and today the newsletter has ~20k subscribers with zero full-time employees (primarily GPs, partners, LPs, and venture-backed founders are readers). If you want to get a sense of how I think, you can read a few of the pieces here:
Being a nomad. After the accelerator experience ended, I didn’t really have a reason to be in Charlotte anymore. By that point, I knew I wanted to play in the venture game, and I didn’t see Charlotte as the best place to do that. But I also didn’t want to move to SF. I figured there was a middle ground somewhere, so my goal was to find that by staying in different places I could see myself in for ~a month. I spent time in Nashville, Austin, LA, NY, DC, Charleston, Miami, Naples, Lisbon, and Costa Rica. After around two years of living out of a suitcase, I was done, and I picked Austin to settle down (at least that’s what I thought).
Different doors opened. From the accelerator, I worked at Mucker where I learned more about how much work goes in behind-the-scenes to truly support pre-revenue companies. I then worked GTM at Visible where I learned how a great company operates hyper-efficiently. I then worked at a large family office in New York where I learned how hundreds of other fund managers told their story and tried to differentiate in a world of commoditized capital.
The NY experiment. When I chose Austin, I planned to live there for a while. It had what I was looking for, it was a good quality of life, I found a gym, a church, and friends. But when I started working for the family office, I was being asked to come up to NY more and more. I moved their full-time (something I told myself I would never do), but I was planning my exit before I even moved into my new apartment.
Walking away from a dream gig and taking a bet on myself. After a few years of working with the family office, I wanted out. Most people assume you’re crazy if you leave a family office job. You get paid well, the work-life balance is there, and it’s high-status. All of those things were true, but I realized I didn’t care. The only thing that I wanted was the ability to freely make decisions and live with the consequences of those decisions. I realized that was not going to be possible unless I started my own fund, and that is the genesis for Outlaw.
Each experience from my life has acted a stepping stone towards the ultimate goal which was running my own fund, owning the GP, and betting on myself.