Action as the Antidote to Fear: How Bold Steps, Big Bets, and a Growth Mindset Change Everything
#69
"Stress and worry tend to be higher before you act. Without action, all you can do is worry. Once you begin, fear shrinks as you start to influence the outcome." James Clear
🧠 Founder Psychology: The Conviction of Masayoshi Son
Before we dive in, a quick intro:
Masayoshi Son is the founder and CEO of SoftBank, a Japanese tech conglomerate and investment powerhouse. Born to Korean immigrant parents in Japan, Son built his fortune by spotting tech trends early and betting bigger than almost anyone else in the world. He’s the driving force behind the $100 billion Vision Fund, and his investments have shaped companies like Alibaba, ARM, and WeWork.
*I’m still reading Gambling Man (week 3 — I know), but each chapter makes me pause and rethink how founders and investors make big, wild, gut-driven decisions.
Masayoshi Son doesn’t just play the game — he redefines it by acting from obsessive conviction.
“Well, Masa, you are crazy.”
If you want to understand what true founder psychology looks like, you don’t have to look much further than Masayoshi Son.
From $20B to $100B—All In, Instantly
Son didn’t just raise a big tech fund—he reimagined what “big” meant. Originally, he planned a $20 billion fund. But then he asked himself: “Why think small?” In classic Masa fashion, he decided to raise $100 billion instead, creating the Vision Fund—the largest tech investment vehicle in history.
This wasn’t just a bet on capital. It was a bet on changing the very speed and scale of how startups grow. Most people thought it was reckless. Son didn’t care.
“If you’re going to do something, do something big.”
Behind the move:
This is a textbook example of “visionary bias”—the tendency of exceptional founders to see opportunities on a scale that others can’t even imagine. They aren’t just thinking bigger; they’re “operating” in a different mental universe. This kind of “positive delusion” is common among outlier entrepreneurs, fueling both their ambition and their resilience.
The ARM Deal—Conviction Under Pressure
When Son set his sights on ARM, the British chip designer, he didn’t hesitate. He immediately flew out, negotiated, and closed the $32 billion deal in just weeks—making it the largest-ever purchase of a European tech company at the time.
He called it a “once-in-a-lifetime opportunity.” For Son, if you feel it in your bones, you move—now, not later.
Behind the move:
This is a an example of trusting your gut in high-pressure situations. Successful founders often rely on quick instincts, especially when data is incomplete or time is tight. It’s about balancing logic with feeling.
“You’re Not Crazy Enough”—The WeWork Moment
One of the most legendary moments in startup history: Son meets Adam Neumann, co-founder of WeWork, and after a whirlwind tour, tells him,
“You’re not crazy enough.”
Within 28 minutes, Son commits $4.4 billion to WeWork. He wasn’t just investing in a company—he was betting on what he calls “founder madness,” the kind of wild vision that borders on delusion. Please check the WeCrashed series to learn more.
Behind the move:
Most investors seek safety in numbers, but Son looks for the outlier—the founder whose conviction is so strong it bends reality. This “contrarian conviction” is often what drives disruptive innovation.
The iPhone Gamble—Plotting with Steve Jobs
In 2005, Son flew to California and pitched Steve Jobs on a mobile-enabled iPod—before the iPhone even existed. Jobs called him crazy, but Son pressed for exclusive rights to sell Apple’s phone in Japan. On the strength of a handshake, Son bought Vodafone Japan for $17 billion, betting it all on a product he hadn’t even seen yet. When the iPhone finally launched, SoftBank brought it to Japan, upending the entire market
Behind the move:
Son’s willingness to bet big on unproven ideas shows a high tolerance for risk and ambiguity. Successful entrepreneurs often have a higher tolerance for ambiguity and loss, and are more likely to “double down” when they sense a once-in-a-lifetime opportunity.
What Drives Masa?
Confidence: Son is known for making billion-dollar decisions in under 30 minutes, driven by a belief that he’s right—even when the world doubts him.
Resilience: He once lost 99% of his wealth (about $70 billion) during the dot-com crash—and then rebuilt his empire from scratch.
Vision Over Details: He’s famous for focusing on the big picture, not sweating the small stuff, and demanding quick, decisive meetings from his teams.
Emotional Intensity: Son’s mood is intense, focused, and optimistic—even when facing setbacks. He thrives on pressure, using bold moves and visionary planning to cope with stress.
Cultural Fusion: Inspired by Japanese Bushido and Silicon Valley’s “move fast” ethos, Son blends discipline with daring in everything he does.
🧠 All-In Thinking
Masa’s story is about all-in, gut-driven decision-making. He doesn’t wait for consensus or perfect spreadsheets—he acts on timing, instinct, and his own conviction. That’s what makes him both “crazy” and brilliant.
If you’re building or investing, maybe the real question isn’t “Is this safe?” It’s: “Do I believe in this so much, I’d look crazy to everyone else?”
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💭 Reflections:
I was talking to a friend the other day, and she shared something her career coach suggested. He told her to break her life into five-year chunks and look at the moments she thought were failures. Then he asked: Were those really mistakes, or did they actually turn into something else?
That made me think. When you look back, a lot of what feels like a dead end in the moment is really just a twist in your story. Some things I once called “failures” actually opened up new opportunities, led to better choices, or helped me figure out what I really wanted.
We’re often too quick to judge ourselves for not getting things “right” the first time. But maybe the real trick is to face everything—good or bad—head-on, and see it all as part of the process. Sometimes life gives you lemons, and sometimes it gives you something you didn’t even know you needed.
So if you’re in a tough spot right now, try this: look back at your own five-year chapters. You might notice that what felt like a mistake at the time was actually life giving you a better plan.
📝 Quick Note:
You might notice a small format change — Sundays will now stay focused on founder psychology, tools, and personal reflections.
Midweek editions (for full subscribers) will dive into tactical content: funding rounds, report breakdowns, and tools/templates to help you raise smarter.
More on that soon!
Thanks for reading.
Stay bold,
Yana