Early in my career, a mentor told me something that has stuck with me ever since:

“If you’re overthinking it, the answer is ‘no’”.

Since then, I’ve met with thousands of founders. Almost every time, I knew which ones I was interested in working with after the first call.

The best opportunities should smack you in the face.

Like everything in life, you get better with reps. The more companies I see and the more founders I meet with, the tighter the filter becomes , and harder it becomes to get to a “yes”.

Here’s how I think about picking and narrowing down opportunities to get to the “yeses”.

Picking starts with narrowing

The fund is centered around two core themes:

1. Growing revenue-per-employee
2. Recreating the modern investment firm

I narrowed down these themes after spending years watching and writing about the shifts in how software gets built, bought, and used - especially in lean, high-output teams and private market infrastructure. This applies a set of parameters for me and the fund to work within.

From there, I apply a focused set of filters to qualify:

• The submarkets within each theme where I see the most opportunity
• The companies building into those submarkets
• And the founders who’ve actually earned the right to build what they’re building

Conviction sometimes gets lost in a sea of optionality, and applying this set of rules for each new investment helps me create conviction into each new founder we back at Outlaw.

Writing gives poor thinking nowhere to hide

There is a reason that some of the best investors of all time started as writers first.