In the last two weeks, I've been ruminating on this post from @sama.
It's a simple observation, but one that cuts to the heart of entrepreneurship and venture capital.
While most of the world minimizes risk, every great enterprise exists because someone once chose to make a deliberate, calculated leap into uncertainty. At its core, venture capital is the business of taking intelligent risks alongside outlier founders. We back those who see possibilities where others see problems, and who lean into the unknown with enthusiasm and conviction.
We operate without perfect information. Our advantage lies in interpreting weak signals, forming hypotheses, making judgments, and acting before consensus. By the time data tells a compelling story, the early opportunity has often become obvious and, therefore, often unavailable. The business of venture is about identifying those rare asymmetric opportunities where the upside meaningfully outweighs the downside and having the courage to act before the world agrees.
The willingness to move early and with conviction is what differentiates great investors and attracts exceptional founders. Outlier founders seek partners who not only tolerate uncertainty but also share their optimism for what's possible and work to convert potential energy into progress and impact.
Company building is also an exercise in risk-taking. Every meaningful decision to start, hire, launch, or pivot carries uncertainty. Progress requires courage, and courage often looks like a series of small mistakes on the path to a few transformative wins.
The future belongs to those who see opportunity where others see obstacles, who imagine solutions when others see risk, and who dare to turn that imagination into reality. So what intelligent risks are you taking this week?
I keep coming back to this question:
Are you willing to sprint when the distance is unknown?
In 2021, Georgia Tech strength coach Lewis Caralla delivered this epic speech to the football team.
If it doesn’t light a fire under you, check your pulse…
He starts with a series of brutal truths:
• Winning isn’t loyal to you
• Winning doesn’t care about you
• Winning doesn’t care how sore you are
• Winning doesn’t care how hard you work
• Winning doesn’t care how much sleep you’ve had
But then comes the line that hit me:
Are you willing to sprint when the distance is unknown?
That mindset is rare.
It demands two things:
1. An unshakable belief in yourself
2. A deep conviction in the mission
If you have one without the other, you won’t last.
You need both.
From what I’ve seen, the greatest things in life are built by people willing to sprint when they can’t see the finish line:
The sprint to support loved ones when they need you most.
The sprint to create something meaningful.
The sprint to serve others and leave a lasting mark.
Your task: Identify those rare pursuits worth sprinting for when the finish line is hidden.
That, to me, is what winning really is.
"And why chase winning? Because the only thing that's guaranteed in life if you don't chase it is losing."
Making decisions when faced with incomplete information is what every Entrepreneur has to contend with on a daily basis. The same is true for Investors.
Curious what role Intuition plays? Curious how Intuition is misunderstood and misused? Read on: 🧵👇
1/ Why is “Buy Now, Pay Later” (BNPL) an early threat to trillions of dollars of market cap - Visa (almost $500B), MasterCard ($350B), card issuing banks, acquiring banks/services (Fiserv, FIS, Global Payments, etc)?
When everyone agrees with you when you make a decision, you get paid linearly. When everyone agrees with you after the fact, you get paid exponentially.
The confidence to say no to most things.
The patience to wait when there is nothing to do.
The discipline to do common things uncommonly well for a long period of time.
The decisiveness to act with speed and conviction when the time is right.
In my early 20s, having been mostly an entitled little shit but facing an existential crisis, I was trying to reform myself.
I made a little list to read each morning. Funny to stumble on that list almost 15 years later:
There are two forms of mental toughness: loud and quiet.
Loud = Grit in extreme moments, pushing through great challenges.
Quiet = Reliability in normal moments, showing up even when it’s easy to bail.
Loud gets the press. Quiet wins the trophies.