“Speak softly and carry a big stick; you will go far.” 

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At first reading this statement feels aggressive but it relates to today’s entrepreneurs, founders, and even creators because it’s all about confidence in your expertise. 

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Teddy Roosevelt’s foreign policy embraced this idea and he framed it slightly more pragmatically when he described his foreign policy as “the exercise of intelligent forethought and of decisive action sufficiently far in advance of any likely crisis.”

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If you look closely at that quote it sounds exactly like building expertise and strategic planning.

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Let me take you back to fall of 2011.

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I was a first year law student at SMU. I ended up at law school for three main reasons.

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First, I had majored in history so I needed a graduate degree.

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Second, I wanted to know and understand the rules of society.

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Third, I loved the West Wing and thought this might be the starting point for the political journey I envisioned.

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If you think I’m joking about the West Wing thing...I’m not. I imagine that show influenced a lot of people just like me. The other day I even had a conversation with a friend who worked on capital hill and he told me how people would model themselves after characters in the show. 

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Art becomes reality.

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But back to law school. I was surrounded by brilliant people. The goal for every law student is to make it into the top 10% in order to get one of the coveted big law jobs. The ones that start at $160,000 back then. Before the crash of 2008, SMU put about 40% in big law but this was a new age. 

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Sure I could compete with every other student and hope to be in the top 10% but law school is a subjective sport. Professors judge on a curve with no clear rubric. We jokingly referred to the grading system as throwing the exams down the stairs because that’s how it seemed professors graded exams. Not really a system I wanted to trust. 

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So I did what any history major would do and that’s to start hunting for other opportunities. I looked at the data to find a route to success. What skill set did I possess? What skill set did others in my class not possess? Where is there a niche being underserved? How can I stand out?

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I came up with a wild idea. 

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Become a trial lawyer and reach 100 jury trials. 

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This was my game plan. This is how I could build expertise and play the long game. Strategize a way to stand out and own a skill set that would be seen as highly valuable. 

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I knew trial lawyers were highly regarded. All I needed to do was sit in class and see how professors talked about the great trial lawyers. I could see it when guest speakers came onto campus. The trial lawyers knew how to work a room. They knew how to pull people into their orbit. 

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They made law exciting, intriguing, and most of all, a way to excel in the future.

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Seven years later I achieved my goal. 100 jury trials. I went into two more just to test my skills on the other side of the law. When I won both of those, I said 102 is enough. 

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Time to leverage. 

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The point of that story is for you to ask yourself what expertise do you have or what can you build? 

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What will be your big stick that you use to get where you want to go?

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Roosevelt’s foreign policy came down to five main components.

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1. Possess serious military capability that forces close attention
2. Act justly to others
3. Never bluff
4. Strike only when ready to strike hard
5. Allow the opponent to save face in defeat

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Many of these components apply to individuals when it comes down to expertise and how they carry themselves. 

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All of these components apply to business. 

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What becomes clear is that the opening statement isn’t about aggression, it’s about restraint. Building such expertise that you don’t need to try and scare someone but always being ready to move when needed. It’s a focus on personal victory but without obliterating the other person. 

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I think more people need to carry a big stick. 

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Founders will want to work with investors that bring real expertise. It could be design like Jack Butcher, writing like David Perell, or even speaking with me. 

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The expertise opens opportunities. Expertise is leverage. 

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Not only that but it opens up greater distribution channels by becoming a true expert in a field. Look at Pomp with bitcoin. He recently led the funding round for Synthesis school and with his announcement on twitter, the company had millions of new eyes watching what they are about. 

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These types of opportunities only exist if you build out your expertise. 

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Start building now because while you might be behind, you aren’t too late. I started my journey building this expertise around strategy, persuasion, storytelling, game theory, and speaking back in 2011. That’s 10 years. But you need time to do it right. 

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You’ll want that time to strategize. You’ll want that time to plan. 

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You’ll want that time to grow into this mindset.