A Wall Street Genius's Final Investment Playbook-Chapter 306: The 100-Billion Race (2)

I headed straight for the CEO’s office. When I opened the door, Pierce snapped his head around from the sofa. He wore an easy smile, but his shoulders were rigid.

“You’re pursuing a hundred-billion-dollar capital raise?”

Pierce got right to the point.

“Good to see you.”

“Do you understand the market backdrop right now?”

I needed to raise a full $100 billion immediately, and at this scale an investment bank’s help was indispensable. But Pierce shook his head heavily.

“Rates are rising, and the whales are pulling out. This is the worst timing.”

“I’m aware.”

The hedge fund industry was facing the worst redemptions in a decade. The spark that set it off was none other than Buffett.

Back in 2007, Buffett made a million-dollar bet with a hedge fund manager. The topic was simple. “Over the next ten years, S&P 500 index versus hedge funds—who delivers the higher return?”

Buffett bet on the index fund, and he won in a landslide. While the S&P 500 delivered a 125% cumulative return, the hedge fund portfolio lagged far behind at just 36%. They took a 20% performance fee and still failed to beat the market average. Institutional investors read the writing on the wall and rushed to pull money from hedge funds.

And in this climate, start a brand-new mega-fund?

“Besides, the sheer size—one hundred billion—is a problem. You know raising capital gets harder the bigger you get, right?”

“Of course.”

“As assets under management grow, returns fall.”

That was industry gospel. The reason was straightforward.

“Strategy scalability.”

In investing, plenty of plays work with $100 million but break down at $100 billion. When a fund gets too big, each of your trades becomes a market-moving variable. If what you want is high returns, small and nimble wins. So insisting on running $100 billion… is accepting a low-return structure from the outset.

How many investors would willingly sign up for that?

“If you must reach a hundred billion, don’t try to raise it all at once. Start with three billion and scale gradually. That’s the practical route.”

He wasn’t wrong.

But—

“I intend to raise the full hundred billion in a single round.”

The reason was clear. That money needed to go straight into developing therapies. Drug development takes time. Even if we start now, it’ll be two to three years before anything is ready for clinical use. We didn’t have time to dawdle.

“Haah…” Pierce exhaled long and continued. “A step-up raise might actually get you to the goal faster. When a fund is too big, investors assume, ‘There’ll be room later anyway,’ and they don’t move. In cases like this, leveraging the scarcity principle works better.”

Again—not wrong. I just smiled it off.

“You don’t only need scarcity to move people. For example… there’s betting.”

“Betting?”

When I said the word “betting,” Pierce’s expression wavered hard. As his Adam’s apple bobbed, I went on.

“Yes. With bets, people put money down voluntarily—even without scarcity. So when do people bet?”

“…”

“One of the biggest examples is sports. A competitive arena where there’s a winner and a loser. In moments like that, the crowd doesn’t need instruction—they bet on their own.”

Silence stretched a beat. Then Pierce finally spoke.

“So you’re saying… you’ll go head-to-head with someone in public, and turn the whole world into a betting table?”

I shrugged. As if to say, what choice do we have? Honestly, who would invest in a low-return fund if I just sat still? So I planned to turn the raise itself into an event.

Like a sports match. Two fighters stepping into the ring for a decisive bout—to trigger the betting instinct.

“This time… who’s the opponent?”

I studied Pierce’s face. ‘He’s already guessed…’

His expression told me he knew whom I had in mind. He was just pretending not to—willfully looking away. I don’t see the point. It’s not like staying quiet would stop me from saying it.

“In sports, great matches happen between fighters of similar weight. And right now, when it comes to a hundred-billion-class fund… there’s only one.”

Pierce squeezed his eyes shut, then answered as if resigned.

“…Don’t tell me—the Visionary Fund?”

The Visionary Fund. A colossal, tech-focused vehicle raised by the Japan-based SoftFinance. It reshaped Silicon Valley’s landscape and rewrote the rules of the venture game.

That was the rival I’d chosen.

“You can’t mean… him. Not even you—” Pierce asked in disbelief.

That’s how legendary my chosen opponent was. He had a peculiar résumé. He once held the title of “richest person in the world,” then lost 99% of his fortune. Normally, that’s when you disappear into the footnotes of history. But he stood back up and climbed to the top again.

A gambler’s instinct and a genius investor— a man invariably listed among the world’s top five most famous investors.

“Yes. Masayoshi Son.”

***

Pierce was screaming inside.

‘Why did he move so fast…?’

He had never expected Ha Si-heon to cause another uproar this soon. The AI war had only just ended, so he thought they’d at least have a few months of peace.

‘Does this guy not understand the concept of a cooldown period?!’

Without giving anyone a chance to breathe, Ha Si-heon was already hinting at a new storm on the horizon.

‘Don’t tell me… he’s even removed cooldowns now?’

Just the thought made Pierce’s spine turn cold. That meant even the few months of peace they’d occasionally enjoyed might now vanish completely. One catastrophe after another. Pierce feared he would spend the rest of his life cleaning up Ha Si-heon’s messes, never getting a chance to rest.

‘Well… there are rewards for it, at least.’

Pierce had already begun to build a reputation as the “Ha Si-heon problem solver.” Because of that, his name was now even being mentioned as a potential successor for Goldman’s CEO position. So, he didn’t mind cleaning up Ha Si-heon’s chaos—at least, not in principle.

But this time, things were different.

‘This one… isn’t to my advantage.’

Pierce’s ideal position was clear. He wanted to be the “insurance agent” who appeared whenever the Ha Si-heon typhoon hit— the kind who showed up at the disaster site saying, “Please stay calm, sir! This way to safety!” while minimizing the damage.

But what Ha Si-heon wanted now was different.

“If possible, I’d like all capital secured within this quarter.”

What he wanted was a capital raise—a massive fundraising round. That meant Pierce would have to personally introduce Ha Si-heon to investors and convince them to hand over billion dollars to him.

‘That’s… not good.’

In other words, he wasn’t being asked to be an “insurance agent.” He was being asked to be a salesman—someone running around telling clients, “Please, you must buy this!” while pitching Ha Si-heon himself.

He’d be the one personally delivering the typhoon into their living rooms. In short, a disaster express delivery service. And if that typhoon ended up destroying their houses, the one who’d take the blame would be Pierce.

‘No… calm down. It doesn’t have to end in disaster.’

After all, wasn’t Pierce himself living proof? No one ever lost money investing in Ha Si-heon. He always made a profit in the end. The problem was just that there was always that dark, terrifying period in between—when it felt like you’d lose everything before it all turned around.

But even that didn’t happen every time. In fact, Ha Si-heon’s healthcare investments had gone smoothly—quietly even—while achieving astonishingly high returns.

If this turned out to be one of those quiet ones again…

Pierce couldn’t even finish the thought. He simply couldn’t imagine a “quiet” Ha Si-heon. He had a bad feeling—like another catastrophe was about to erupt. And ominously enough, Pierce’s instincts had never been wrong before.

“Yes, it’s Son Jeong-ik... or should I say, Masayoshi Son.”

The moment he heard that name, Pierce instinctively shut his eyes.

‘Damn it. I was right.’

Masayoshi Son. A man hailed as a living legend in the world of investment.

He had started out distributing software but was one of the first to foresee the coming of the internet age—and bet big on it. Riding the wave of the internet and telecommunications boom, he rose meteorically. By the 2000s, he had become one of the richest men in the world.

But just as dramatic as his rise was his fall. When the dot-com bubble burst, the stock price of his company, SoftFinance, plummeted by 99% overnight. Masayoshi Son became a symbol of historic financial loss.

Yet what shocked people most was his attitude afterward.

> You know, the more wealth I had, the less happiness I felt. There was a time when even a little shopping made me happy, but once I reached the top, I could buy an entire department store and feel nothing.

> So I started wondering—what does all this even mean? And then, just like that, the problem solved itself! The very source of my worries simply disappeared, hahaha!

> Starting over feels good. I’ve even regained the old joys I’d forgotten.

Instead of collapsing in despair, he found new energy in ruin. And in 2014, he made a dramatic comeback—as if rising from the grave.

His return was marked by the IPO of China’s Alibaba. When the listing succeeded, another shocking revelation followed—Masayoshi Son already owned 30% of Alibaba’s shares. It was the result of one of his bold moves in the early 2000s. He had met Alibaba’s founder, and within five minutes, declared, “I can see it in his eyes,” and invested twenty million dollars on the spot.

That decision turned into an astonishing sixty billion dollars in profit. It was the single most profitable tech investment in history. At that point, the world had no choice but to acknowledge his uncanny foresight.

His entire life was a drama.

But unlike most big investors—who focused on minimizing loss and avoiding risk—Masayoshi Son embraced risk. If he believed in something, he bet on it harder than anyone else, even taking on massive leverage without hesitation.

His performance swung wildly between extremes. Sometimes he caught the wave of innovation and struck gold; other times, he miscalculated and took crushing losses. He had suffered humiliating public failures more than once.

But his true trademark was this—he never wavered. He never lost his nerve. Whenever he saw another opportunity, he jumped right back in.

His latest venture was the Visionary Fund. In October 2016, he announced plans to invest in the future of global infrastructure with a fund totaling a staggering one hundred billion dollars. No one in history had ever raised that much in one go.

But for Masayoshi Son, precedent didn’t matter. Wall Street was watching closely. Would he really succeed in building a hundred-billion-dollar fund? And if he did—where would all that money go? Even the movement of such capital could shake the entire global market.

Most of all…

Would this be another success—or another spectacular failure?

That was Masayoshi Son’s unique presence. A prophet of change. A gambler who could fall to ruin and still rise again.

In short—he was a madman. And that madman had just thrown down a hundred-billion-dollar gauntlet.

‘He’s planning to jump into that?’

Pierce felt dizzy. Ha Si-heon was just as crazy as Masayoshi Son—maybe even worse. Two madmen, and double the insane amount of money gathering around them.

This was pure madness. But Ha Si-heon simply smiled, calm and composed.

“Not a bad event, don’t you think? A true duel—let’s see who raises a hundred billion first.”

Pierce couldn’t respond. Honestly… it did sound interesting. If he weren’t directly involved, Pierce might’ve placed a private bet on it himself. No—he absolutely would have.

But now wasn’t the time to stand by as a spectator. His career was on the line.

‘This can’t happen.’

If he didn’t want to be branded as the “insurance broker who follows typhoons,” he had to stop Ha Si-heon. He had kept a “favor debt” from Ha Si-heon precisely for emergencies like this—but…

‘If I use that now, it’ll only make things worse.’

After the whole Swallow Repays a Favor incident, Pierce had erased that option from his list. Ha Si-heon was the kind of man you could never force into anything. He needed to be persuaded. Begged, even.

Pierce steadied his breathing and spoke carefully. 𝒇𝒓𝒆𝒆𝙬𝒆𝒃𝓷𝒐𝓿𝙚𝙡.𝒄𝓸𝒎

“A race, huh…”

“If it doesn’t appeal to you, I can always ask someone else,” Ha Si-heon replied.

That meant, *If you don’t help, I’ll just go to another investment bank.*

But Pierce couldn’t let that happen either. It was maddening, but losing Ha Si-heon would mean losing his exclusive reputation as the man who understood him best. Worse, rumors might spread—people whispering that there’d been a falling-out. His professional credibility would collapse.

“Not appeal to me? Between us? Never,” Pierce said with forced confidence. “I’ll help you, no matter what.”

He exhaled slowly and added, “It’s just… I’m worried your so-called race might not be fair. A proper competition means everyone starts at the same time, don’t you think? But you’re clearly the latecomer here.”

It was true. Masayoshi Son had already been moving for over a year. He’d raised sixty-five billion dollars from the Middle East alone.

“And rumor has it he’s already secured another ten billion from Anple,” Pierce continued.

That meant the rival had already gathered seventy-five billion out of the hundred. Surely that argument would convince him.

But Ha Si-heon didn’t even blink.

“That’s fine. The underdog’s victory always makes the race more exciting, don’t you think?”

There was genuine anticipation in his eyes. It was as if he believed being behind only made things better. Pierce’s throat went dry.

“You should at least consider the image risk. Son won’t fight you. He’s practically won already—there’s no reason for him to engage. But if you chase him down and pick a fight, what will people think?”

This was Pierce’s last hope. If Masayoshi Son refused to engage, maybe the entire contest would fizzle out. And that assumption had some weight behind it.

“In the past, maybe he would’ve been careless,” Pierce said, “but not now.”

All the big names Ha Si-heon had taken down before—every single one of them had underestimated him. They’d all thought the ‘rookie’ was harmless. And they’d all paid the price.

But now it was different. Ha Si-heon had already crushed White Shark, Ackman, and even a string of famous macro-funds. Masayoshi Son would not make the same mistake. He’d be cautious—especially now that he had already secured seventy billion dollars and was nearing his goal.

Would he really accept a direct challenge under those conditions?

Ha Si-heon merely smiled.

“That’s all right. Even if he doesn’t want to.”

“What do you mean?” Pierce asked, frowning.

Ha Si-heon paused, as if choosing his words.

“Think about it. Masayoshi Son’s Visionary Fund is like the Titanic,” he began. “Its sheer size alone amazed the world and captured everyone’s attention. Being the first of its kind made it even more iconic.”

He lifted one corner of his mouth.

“But imagine this—what if, a few months later, another company announces they’re building a second Titanic, exactly the same size?”

“Sure, the original might smile politely and say it’s not a competition, that both ships are simply taking different routes to greatness. But do you think the world would see it that way?”

Of course not. When two colossal projects shake the world at once, people will compare them. They’ll ask which is bigger, stronger, and lasts longer.

“And if both captains happen to be Asian—Korean immigrants, no less—don’t you think the world will find that story irresistible?”

In other words, no matter what Masayoshi Son said, he couldn’t escape the race.

Pierce felt goosebumps rise on his arms. ‘This guy’s terrifying…’

That was the true horror of Ha Si-heon. No matter how others tried to avoid him, they still ended up moving inside his calculations. Once he decided to set the stage, he always made his scenario a reality.

Masayoshi Son was destined to face him. Pierce almost felt sorry for the man.

Ha Si-heon gave one final smile.

“Be ready—in three days.”