What’s up? If you’re new here, here’s my quick intro:

• Born in CLT, went to school in DC, lived in TX then NYC, now based in MIA
• Washed up college quarterback - now I play tennis, basketball, and golf
• Founded and scaled one of the largest venture media businesses
• Learned early-stage investing @ Mucker, learned operating @ Visible, learned allocation @ a single family office in NY
• Currently the GP @ Outlaw

Below is an ongoing list of things I have learned from people smarter than myself. This acts a de-facto operating system for how I work and think.

1. The future does not repeat the past, but it does rhyme with it. In order to understand the future, you have to study how we got here.
2. Identify what motivates people, and you’ll understand what actually drives companies. This will filter out opportunists from those that have conviction around the issue. This should be one of the first exercises you do when evaluating a company.
3. In order to be an investor, you have to share the mindset of an entrepreneur and know what it takes to walk that walk. Lacking empathy for the other side of the table equals no relatability.
4. Be as direct as possible even if it hurts. This is increasingly rare today.
5. Understand what drives economics for your fund. This is a different answer for different fund sizes. The more time you spend focusing on the drivers that matter, the better odds you outperform.
6. Develop a chip on your shoulder early in your career. Too many people reach an arbitrary title and coast. This leads to stagnation and later regret.
7. Thick skin is a superpower. You have to be willing to fail and test your emotions on things in order to move forward and improve.
8. Value intellectual curiosity over every other trait. The moment that you stop loving to learn is the moment that you plateau. The best entrepreneurs and investors are constantly looking for answers to their own questions.