A Wall Street Genius's Final Investment Playbook-Chapter 65

Sunday, 9:30 a.m.

I headed to North Cove Marina, the meeting place for the day.

This dock, not far from Wall Street, was today's rendezvous point.

Prescott had told me he sailed his private yacht all the way from Florida to New York.

And, for a change, he invited me aboard his yacht.

Looking around the docked yachts, I quickly spotted one named Serenity.

"A catamaran, huh."

A catamaran, known for its split-hull design, boasts a spacious deck and excellent stability at sea.

"Where would I be at a time like this…?"

Suddenly, I found myself missing my past life.

I used to own a yacht like this one, after all.

“Are you Sean?”

Looking up, I saw someone greeting me warmly from the deck.

A man in his mid-50s with silver hair and sun-kissed skin.

“Are you Mr. Prescott?”

“That’s right. Come aboard!”

Prescott gave me a once-over and burst out laughing.

“Ah, but you might have a hard time in that outfit…”

I was dressed in a crisp suit, contrasting sharply with his casual attire.

“Haha, you look so formal, it’s like you’re here for a yacht party.”

“Sorry, I wasn’t sure what to wear…”

I gave an awkward smile, which made Prescott pat my back and laugh heartily.

“No worries, don’t think too much about it.”

Alright, I won’t overthink it.

After all, as an employee of Goldman, I couldn’t show up to a first meeting with a client dressed casually.

Clearly, Prescott invited me onto his yacht to stage this exact situation.

“Well, no problem playing along.”

Pretending to be the "awkward newbie overwhelmed by a billionaire’s wealth" isn’t too difficult.

“Impressive yacht.”

“It’s my pride and joy. Haha, shall I give you a tour? Let’s start with the flybridge.”

“The flybridge?”

“Haha, the upper deck there—we call that the flybridge.”

Wow, he’s really falling for this act.

“Isn’t it amazing to enjoy the New York view from here?”

“It’s definitely a rare experience.”

While I was buttering him up, I noticed crew members bustling about, preparing for departure.

“Would you like to check out the wheelhouse too?”

Humming, Prescott led me to the wheelhouse.

Feigning ignorance, I wandered around, pretending to inspect things, while feeling his gaze on me.

Ah, this must be my cue to ask something.

“Don’t you take the wheel yourself?”

“Haha, that’s what amateurs think. The trick at departure is keeping the rudder neutral. With the wind like this, there’ll be plenty of thrust.”

Behind Prescott, a crew member nodded in agreement. I’d bet that person was the one who actually sailed this yacht from Florida to New York.

“Why don’t you rest in the cabin for a while? We’ll be setting off soon.” freeweɓnovel.cøm

“Is it alright for me to just relax alone…?”

“It’s fine, make yourself comfortable.”

Sure, he wouldn’t want to appear clumsy in front of me.

Following his suggestion, I headed to the cabin and sank into a plush sofa.

The interior was quite impressive, evoking the feel of a luxury resort.

At times like this, I couldn’t help but miss all the things I’d lost in my previous life.

Soon, the yacht gently left the harbor.

The cityscape gradually faded, and the salty sea breeze playfully brushed my face.

“I should’ve dressed more casually.”

This was my first time boarding a yacht in a suit.

Previously, as a yacht owner, I never had to bother with such inconvenient attire.

Though uncomfortable, I tried not to show it.

Prescott had just entered the cabin.

“How about a beer?”

He was holding a modest portable cooler, comically out of place on this luxurious yacht.

It seemed he was a man torn between flaunting his wealth and projecting a friendly, down-to-earth image.

“Thank you.”

I accepted the beer he handed me and took a refreshing sip.

Then, Prescott plopped down next to me and started a conversation.

"By the way, you're quite different from what I imagined—much younger and sharper-looking."

It seemed he had a stereotypical image of an Asian nerd in mind.

He probably envisioned someone wearing glasses, with a slight build and a timid demeanor.

"Are you really Sean?"

Ironically, Asians tend to gain trust when they match the "nerd" stereotype.

There's something about that look that exudes an air of being a math or science genius.

In that sense, my appearance might actually undermine my credibility. But it's fine.

I have my track record to back me up.

"And is it true you achieved a 630% return with the Genesis investment? I heard you went all-in! That's bold for someone like you!"

I barely managed to suppress a frown.

Here, "someone like you" clearly referred to Asians.

What he was expressing was astonishment that a supposedly "risk-averse" race would take such a gamble.

I'm used to this level of racial bias.

What actually concerned me was the part about going all-in on an investment.

"Did you hear that from Attorney Mosley?"

If so, it was a clear mistake.

An all-in investment is a red flag for many investors, signaling excessive risk.

No matter how high the returns, it wouldn't be viewed favorably.

That kind of information needs to be shared cautiously and tactfully—something Raymond would never have done properly.

"No, I didn't hear it from Mosley. Do you know Jonathan Blake?"

"I'm not familiar."

"Ah, that makes sense. You're in different departments. He's the MD of the Retail Division. He's the one who spearheaded the acquisition of our chain a while back."

Prescott had worked with Goldman on an M&A in the past and apparently formed a connection with the Retail Division's MD.

The rumor about me had reached him through that MD.

When I heard this, a genuine smile spread across my face.

If it came from a Goldman MD, the story would have been delivered with vivid detail and credibility.

"Do you really have an algorithm with an 80% hit rate?"

"You seem well-informed."

"Sorry, but I can't say I fully believe it. However, Blake swore it was true. What's the principle behind it?"

This led to a brief explanation of my algorithm.

But midway through, Prescott abruptly cut in with a major declaration.

"The field that will dominate the investment world in the next ten years is healthcare."

He wasn’t wrong.

"In business, you come to realize one undeniable fact: the wealthiest consumer demographic is the Baby Boomers. And where will they spend the most money? Hospitals. That's why even at Heritage, we've been advised to allocate one-third of all assets to healthcare."

Prescott went on for quite some time, rattling off trends and forecasts in the healthcare sector.

Rather than seeking my opinion, he seemed more focused on flaunting his insights.

"To be honest, I only started investing in the stock market relatively recently. Before that, I was mostly into real estate. Our generation was taught that stocks were no different from gambling. If I had been born just a little later…"

He wasn’t wrong about this either.

A person’s investment tendencies are largely shaped by their environment.

In Korea, for instance, the generation that experienced the IMF crisis tends to prefer safe assets.

In contrast, younger people who witnessed the Bitcoin boom are more inclined toward crypto or stocks.

The Baby Boomers in the U.S. have lived through numerous economic upheavals that fostered a preference for safe assets—like the stagflation of the '70s and Black Monday in 1987.

Prescott, too, had built his wealth through real estate over many years.

But when returns started to plateau, he turned to stocks later in life.

He eventually found enough success to establish a family office.

"In biotech and pharmaceuticals, seed funding is everything. These days, major pharmaceutical companies outsource almost all of their early-stage R&D. So, if you have a good eye, success will follow. Look at my portfolio—my hit rate is remarkable. Even among startups, I have a 30% success rate. Isn't that incredible?"

"A 30% success rate is unheard of."

"Haha, maybe it's beginner's luck, but I once made a 2,400% return on a single stock!"

Ah, so that's what hooked him.

"It was sheer luck. I personally researched the company and just had a gut feeling the moment I saw it."

Prescott’s voice brimmed with pride.

While Prescott outwardly attributed his success to luck, what he really wanted to say was clear: ‘Don’t you think I have a natural talent for investing?’

This is a common misconception among beginners.

It's also a problem inherent in the nature of investing.

Investing is a game that offers overwhelming odds in favor of beginners.

Why? Stocks present only two options: buy or sell.

And the outcomes? The stock either goes up or down.

This means that even a complete novice theoretically has a 50% chance of success.

Compare this to other fields, like sports, music, or cooking.

In what field does a beginner have a 50% success rate?

Normally, you start at 0%, and it takes considerable time and effort to gradually improve.

But with stocks, even without any special knowledge, you can make money half the time.

As I said, the result is either up or down.

This leads beginners who get lucky with their first few hits to mistakenly believe they have talent.

But they overlook one crucial fact:

Even a monkey flipping a coin would achieve similar odds.

And that’s not the only problem.

They also fall into the dangerous illusion that their skills will steadily improve over time.

"If I start at 50%, wouldn’t studying and practicing push my success rate to 80% in 10 years?"

A ridiculous fantasy.

Even professional fund managers who make a living in this field hover around a 60% success rate.

True experts humbly accept that they’ll be wrong about half the time.

And within that reality, they focus on maximizing profits.

The key isn’t the success rate.

The real secret lies in this: identify which 60% of opportunities are winners and allocate the most capital there to maximize returns.

In other words, trying to hit more balls is meaningless.

No matter how hard you try, you'll only succeed about half the time.

Accept that from the start and focus on how far you can run when you hit a success.

That’s the professional mindset.

Beginners, on the other hand, are the opposite.

They swing at every pitch in sight, focusing solely on the ball without any concept of how far they need to run.

Without calculating positions, they scatter small amounts of money all over, obsessed with meaningless batting averages.

And that’s how they go bankrupt.

Of course, I wouldn’t dare say this out loud.

Instead, I swallowed my wry smile and kept throwing out compliments.

"You have an incredible natural talent. At this rate, I might lose my job…"

“Haha, no need to flatter me that much.”

As the conversation flowed and reached a comfortable stage, I cautiously brought up the topic I’d been waiting for.

“By the way, I noticed one of your investments is in Theranos…”

At my question, Prescott’s eyes lit up.

“Ah, Theranos! That’s a stock I picked myself!”

As if.

It was almost certainly a recommendation from Raymond.

He probably tipped Prescott off about the rising star attracting the attention of prominent figures.

“Have you met Holmes in person?”

“No, not yet.”

“Haha, once you do, you’ll understand. Ah! You’ll see what charisma truly is. They say Steve Jobs had it too—the power to distort reality…”

Ah, the obligatory Jobs comparison.

Investors chasing "the next Steve Jobs" rarely succeed.

Jobs was an outlier.

By definition, outliers deviate from the norm and have unique traits.

The next outlier is more likely to have a completely opposite personality from Jobs.

But since this wasn’t worth voicing, I hid my thoughts and widened my eyes in feigned amazement, playing along.

Whatever fantasies Prescott entertained were none of my concern.

What mattered now was uncovering why investors were so captivated by Holmes.

“Great people truly stand out from the beginning. By the way, did you know Holmes’s mentor is Everett?”

“Everett? Surely not that Everett—the one from The Oracles?”

“Yes, that very same one!”

For once, my astonishment wasn’t feigned.

It was an appearance I hadn’t even imagined.

Everett—the founder of The Oracles.

A pioneer in database software and cloud computing.

A legendary figure who had reached the pinnacle of the global IT industry.

“Yes, that very Everett has been mentoring Holmes since the early days of her startup. They met every Sunday for advice, and he even participated as an early investor. He nurtured her during the most critical formative stages.”

I couldn’t believe it.

Everett was one of the silent victims all along.

This wasn’t just about support from respected elders.

It meant a towering IT expert had personally shaped Holmes’s development.

It was like Son Heung-min training a promising young soccer player every Sunday.

“On top of that, the Lambert family is also on the list of early investors.”

Once again, my jaw dropped.

The Lambert family is a legendary name in Silicon Valley venture capital.

Over three generations, they had discovered companies like HartMail, SkypeZ, Teslan, and Bawidu.

For such sharp-eyed investors to recognize Holmes’s talent and invest in her? That was monumental.

“Not only that, but Holmes interned under Professor Carrington during her time at Stanford.”

Professor Carrington of Stanford was a superstar in the field of chemistry.

He had served as an expert witness in major lawsuits, leading to groundbreaking victories.

For example, in a lawsuit over the side effects of IUD contraceptives, his testimony secured $2.4 billion in damages.

The manufacturer couldn’t bear the payout and eventually went bankrupt.

In another case against a tobacco company, he helped secure $6.6 billion, the largest settlement at the time.

And now, according to Prescott, this superstar professor had recognized Holmes instantly.

“Apparently, Holmes worked as a summer intern in Asia during the SARS outbreak. Watching the influx of patients, she made a decision: ‘In this age of advanced technology, diagnosing with swabs and syringes is unacceptable.’ She then came up with the idea to revolutionize diagnostics by integrating nanotechnology, microfluidics, medicine, and chemistry. The moment Carrington heard it, he immediately knew: ‘This kid is the next Bill Gates or Steve Jobs.’ In fact, it was Carrington himself who encouraged her to start her company.”

Listening to all this made my head spin.

It was becoming clear why investors were so enamored with her.

Titans from IT, venture capital, and academia were all singing her praises in unison.

She wasn’t just a rising star endorsed by Son Heung-min—she had the backing of Messi and Ronaldo as well.

Well, I had gathered enough background information by now.

It was time to focus on something else.

“Incredible… It’s amazing that such prominent figures recognized her talent so early…”

“Exactly. The truth is, the public often lacks the discernment to spot a genius. They discover them in their teens and think that’s remarkable. But those with real vision? They can identify talent in its infancy. That’s when you need to invest to maximize returns.”

“You’re absolutely right. However…”

I trailed off deliberately, avoiding his gaze, as if hesitant to bring something up.

“What’s the matter? You seem to have something to say.”

As expected, Prescott took the bait.

I carefully planted the next hook.

“Well, the thing is… my algorithm…”