Good morning 👋
Working in venture my entire career has forced me to understand, think through, and prioritize asymmetric opportunities. Without asymmetric returns, our asset class does not work.
I used to only apply this thinking to business, but I’ve realized that asymmetric opportunities are all around us, and nobody has captured this better than Graham Weaver (Alpine Investors) in this piece.
Here are the principles he uses to create asymmetry in his own life …
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living asymmetrically
I cannot take credit for the ideas presented here, and all credit goes to Graham Weaver from Alpine Investors. He has built a career on finding asymmetric opportunities both in business and in life.
Here are the principles that he uses to create asymmetry in his own life:
Principle 1: Do Hard Things

The graph above depicts growth and change in our lives. We typically hit a plateau at some point, shown by the red circle. Once we reach a plateau, things are going to have to get worse before they get better. This is true for nearly all growth and improvement. For example, if you need to have a difficult conversation with your partner, your life will get worse first. But once you have the discussion, you will work through the issue and become closer. If you need to leave a difficult relationship, you might have a painful breakup, be lonely for a while, and then experience the anxiety or nervousness of dating again. Your life will get worse before it gets better. This is true for changing jobs, starting a new career path, learning a new skill, or starting a new habit.
Everything you want is on the other side of “worse first.” But when you can get comfortable being uncomfortable, you can have nearly anything you want in this life.
Principle 2: Do Your Thing
The first principle of Buddhism is Dukkah, which translates to “suffering.” Life has suffering. As I learned during this phase in my career — and Buddha learned 2,800 years before me — there is no “easy” or “safe” path. No matter what path you take, life will present suffering.
Life is suffering. So figure out something worth suffering for.
When faced with choices about what we want to do, most of us miss one important piece of the equation. We factor in all the risks and tradeoffs, but we completely discount how differently we will show up when we’re truly energized about something. When our whole being is fully invested, we tap into a superpower, and we can sustain that for a long time. You won’t tap into this power as long as you’re living someone else’s dream.
Principle 3: Do it for decades
Vince Lombardi, the legendary coach of the Green Bay Packers, once said, “The Green Bay Packers never lost a football game, but on a few occasions, we ran out of time.”
The equation for returns is X = (1+R)^N, where N is quadratic. Consider this equation where X represents your competence in any given role. The R represents everything you’re doing to improve yourself: coaching, reading, learning, writing out your goals, using your imagination, etc. The most powerful part of the equation is the N, the number of years you are in your role. If you love what you do, you will do it for a long time, and your N will be large. And if you improve at a reasonable rate over a long period, you can become the best in the world at what you do.
There is almost no obstacle that won’t yield to you at full power for a decade.
Principal 4: Write your story.
No matter where you are in your life right now, you can write a new story.
Fear
One of the biggest things that will hold you back in life is fear. Fear is a master manipulator. It will disguise itself as helping you, as being practical, as keeping you safe. And ultimately, fear will disguise itself as “not me” and “not now.” It might already be creeping in as you read this.
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- Clay
(Founder @ Confluence.VC | GP @ Outlaw)

