“Big opportunities in life have to be seized.”
- Warren Buffett

Last week, I saw something that caught my attention.

Garry Tan, the CEO of YC, the incubator that helped birth household names like Dropbox, Airbnb, OpenAI, told a story about the most expensive decision of his life.

In 2004, he was 23 years old, making $70,000 a year at Microsoft. His fraternity brothers were starting a company with PayPal co-founder Peter Thiel, and they flew him down to dinner. Thiel offered him a founding role and wrote him a personal check for $70,000, a full year of salary, so quitting would cost him nothing.

Garry's answer: thanks, but "I might get promoted to level 60 this year."

The company was Palantir. Garry now calls it a $2 to $4 billion mistake. And the bill keeps growing. When he originally told this story on his own blog back in 2019, the price tag was $200 million.

That's a prime example of the Fear Tax. It’s the gap between what we could have, but don’t, due to fear. To be clear it’s just not financial. It shows up in every area of life. Fear surpasses our skills, agency and God-given gifts. Fear stops us from speaking up, leaving relationships we’ve outgrown, and from having uncomfortable conversations. We pay the tax both individually and collectively. Society doesn’t benefit when we play beneath our capacity and don’t fully use our gifts. And the worst thing about the Fear Tax is that i compounds, quietly, for decades. That’s why I’m on a mission to abolish the Fear Tax.

Anyway, Garry's story reminded me of an old talk Warren Buffett gave at the University of Georgia.

Buffett told students that his biggest mistakes never show up in any accounting, because they're mistakes of omission. He used an example of how he passed on an opportunity with Fannie Mae and reminded them: "Big opportunities in have to be seized." Going after them in a small way, he added, is almost as big a mistake as not going after them at all.

So the question isn't whether to swing big. It's how to know when.

Buffett borrowed his answer from hall of fame baseball player, Ted Williams. In The Science of Hitting, Williams carved the strike zone into 77 cells and learned his exact numbers. Swing only at his best cells: .400 hitter. Chase the worst ones: .230.

Buffett built Berkshire on this, writing in his 1997 letter that "waiting for the fat pitch would mean a trip to the Hall of Fame."

Before I left my corporate job, I created a financial model mapping out two futures. One column: what I'd earn over 20 more years if I stayed, weighted by certainty and baseline assumptions of salary increases and stock grants.

The other: what I could make as an entrepreneur, at what probabilities, and what it would take. The math said asymmetric bet. Then I added in what matters more than money: freedom of time, location, self-expression, who I worked with, and regret minimization.

Even with scar tissue from two failed businesses, when I saw the opportunity I had in front of me, I knew it was time to swing and swing big. The math was clear. I was able to pull the trigger with conviction, across my head, heart, and gut.

Garry’s problem was that he had no predefined criteria. So when the perfect pitch came across the plate, he completely missed it.

Psychologists call it loss aversion: losses feel roughly twice as heavy as equal gains. The $70,000 Garry could lose felt twice as real as billions he couldn't see. And for him, the weighting ran deeper. Raised in Fremont by immigrant parents who crossed continents and bet everything, he grew up watching his father struggle to keep a job. When you've watched a paycheck vanish, a salary isn't money. It's safety. He was operating from the survival paradigm. This is why success is 80% psychology and only 20% mechanics. Morgan Housel talks about this in The Psychology of Money and why Robert Kiyosaki says “the primary difference between a rich person and a poor person is how they handle fear.”

Fear can’t always be eliminated but it can be fact-checked and mitigated.

Let's go back in time and use The F.A.C.T.S. Framework to separate fact from fiction. It will help us see if we could’ve helped Garry in hindsight.

Find the fear. The surface fear says "the startup fails and I lose my paycheck." But under closer examination, that doesn't hold up. He was 23 with a Stanford engineering degree. No wife. No kids. No obligations. He was going to be fine, and some part of him knew it. The real fear lived deeper, in the ego. Ego is a self-defense mechanism, usually rooted in two things: a fear of inadequacy and a fear of losing control. So the fear he was most likely facing wasn't financial failure. It was psychological failure. What would his coworkers at Microsoft say when the weird startup died? What would his peers think of the guy who traded a prestigious badge for a flop? This is exactly why golden handcuffs work. They don't just pay you. They feed your status, your certainty, your sense of control. Fear dressed up as a career plan.

Assess the validity of possible outcomes. Fear presented exactly one outcome: Palantir dies and Garry is the guy who left Microsoft for nothing. That's how the brain works under threat mode. It goes short-term and single-track. The full list of outcomes was much longer. Palantir succeeds (it did). Or Palantir fails, and he still walks away having worked beside some of the smartest, most ambitious people of his generation, with startup experience on his resume, access to information and networks he'd never touch at Microsoft, and lessons he could pour into the next product. In Silicon Valley, even the failure branch pays. Our minds are like gardens, and in every garden, the weeds show up for free. Fears are the weeds in the garden of our minds. We don’t have to do anything for them to show up, but we do have to work to cultivate the fruits we want.

Calculate the probabilities of the possible outcomes. The odds Garry ends up permanently worse off than a level 59 Microsoft engineer? Near zero. Stanford grads with founding experience don't stay unemployed. And notice the trap: staying wasn't risk-less either. He might not have gotten the promotion. Nobody hands out certainty, not even Microsoft. The realistic downside of swinging was about one year. The upside was uncapped.

Take steps to de-risk. Here's the wild part. Peter Thiel had already done this step for him. The $70,000 check was a full year of salary, in hand, before day one. Fear rejected a bet that had already been de-risked. He was 23 years old, single, no kids, no wife. His floor was roommates and ramen. Literally. The downside wasn’t that bad.

Step back for perspective. This is where the miss really happened. Zoom out and look at the whole board. That's the exact season of life built for big swings. He should've been risk-on, and instead he played the position of a man with everything to lose. Nobody at 80 wishes they'd made level 60 a year sooner. The most common regret of the dying is not having the courage to live a life true to yourself, and Cornell research confirms our inactions haunt us far longer than our actions.

To be clear I am not advocating for recklessness. A strike zone is just as much about not swinging as it is swinging. Warren Buffett lets thousands of pitches pass, and most deserve it.

It's a case for deciding with ration and reason (e.g. the prefrontal cortex) instead of reaction (e.g. fight or flight in the amygdala) instead of in fear.

The moral of the story is your pitch is coming.
The only question is if you know when to have the courage to swing.

Here's your reflection for the week:

If the perfect pitch came to you this week, would you recognize it? Would you have the courage to swing big? How do you know? Do you have your predefined criteria clearly listed?

Here's your challenge for the week:

Create your Strike Zone criteria. Get super specific. What conditions do you need to swing big? Write them down. Are any of those conditions within your scope of influence? How can you start taking action towards influencing those outcomes?

With courage,

Jonathan