A Wall Street Genius's Final Investment Playbook-Chapter 36

"How about coming to my house?"

An invitation from Rachel arrived three days later. I soon realized why it had taken so long.

"I wanted to invite you, but I had to check with my family first…"

Apparently, permission was required. The important part? That this process had taken three whole days.

‘Could they have done a background check on me?’

If Rachel truly came from a prestigious family, that wasn’t entirely impossible.

If the investigation was complete, they must already know I’m a penniless orphan.

‘That’s a bit troubling… Wealthy people instinctively keep their distance from destitute orphans.’

Would I be able to gather the necessary information from someone who already sees me through a prejudiced lens? These concerns eased slightly with Rachel’s next words.

“There are a lot of our peers who can’t go home for the holidays this time. I thought we could all spend it together…”

So, it wasn’t just me—she was planning to bring a group.

“That’s a great idea. How many people are coming?”

“Well, including us, there’ll be eight…”

That wasn’t a bad number.

‘If I toss the right keywords, someone will eventually hit on a sensitive topic.’

While suspicion might fall on someone else, I could quietly extract the information I needed.

However, there was one thing that bothered me.

“Are they all peers?”

“Yes, for now…”

This wasn’t good.

“Would it be alright if I invited a few more people?”

“What?!”

Rachel’s eyes widened in surprise, but she quickly adjusted her expression, realizing her reaction was over the top.

“Oh, I’m sorry. It’s just that… this is the first time Sean has mentioned inviting others. But who do you have in mind?”

“Lenton mentioned he’d be spending the holidays alone. And I know a senior who doesn’t have any plans either.”

“That’s great! Feel free to invite them! The more, the merrier!”

Rachel clapped her hands, genuinely delighted. She looked like a kindergarten teacher feeling accomplished after helping a lonely child make friends.

‘I’m not exactly someone who lacks social skills… While it’s true I don’t have any close connections right now, that’s by choice. When you’re on borrowed time, there’s no room for friendship games.’

Still, there was no need to correct Rachel’s misunderstanding.

‘This could work to my advantage.’

The princess seemed determined to find me friends. If I was lucky, she might even introduce me to other members of the royal family.

“Invite as many as you’d like! Just let me know!”

“Sure. I’ll check with them and let you know.”

With that, the conversation concluded, but Rachel didn’t leave. Her lips twitched, as if there was something more she wanted to say.

However, she seemed hesitant to bring it up.

“Is there something else you’d like to say?”

“Well…”

Rachel fidgeted a little longer before finally making up her mind to speak.

“My brother will be there that day too.”

“Oh, I see. I’ve heard a lot about him. It’ll be nice to meet him in person.”

“It’s just that… his personality is kind of… similar to yours…”

That’s not a good sign.

It seemed she was concerned about potential conflict.

“I’ll try to be mindful.”

“It’s not that…”

Rachel hesitated again before finally continuing.

“I’m afraid… he might try to pick on you.”

"Me?"

"I mentioned you a few times when talking about work, but my brother doesn’t really like my friends… Sometimes he even sets up weird tests…"

As expected, Rachel is being cautious, likely worried about someone taking advantage of her.

"That makes sense. Older brothers tend to worry about their siblings."

"Still…"

Rachel hesitated for a moment before continuing.

"If he asks, could you just say we’re normal friends? Maybe just that we spend a bit more time together than I do with others. That way, he won’t do anything weird…"

She seems to be quite wary of me.

Not a good sign.

If she’s already talked about me, I might be on some kind of watch list.

I’ll need to present myself as nothing more than an ordinary coworker.

That would work in my favor anyway.

"I understand. Honestly, I’ll probably be focusing on the people I’ve invited that day. They might feel out of place among the others."

I assured her that I wouldn’t flaunt our acquaintance. Even so, Rachel’s worries didn’t seem to dissipate.

"It’s unlikely he’ll ask, but… could you avoid mentioning anything about the Castleman Foundation that day? It’s not a big deal if you do, but… as I mentioned before, my brother’s group decided to allocate their donations to David’s foundation instead. He’s very curious and might jump to conclusions…"

Right, she had said something like that before. Rachel had already declared her intention to donate to Castleman.

Though she hadn’t directly meddled with the trust, she was definitely treading on warning lines.

"Understood. I have no reason to bring it up anyway."

"Sorry for making such a strange request…"

With that, Rachel finally took her leave.

‘I really need to tread carefully… Looks like I’m already under suspicion. I’ll have to proceed as though that’s the case.’

But that’s a concern for later. For now, there’s work to be done.

After parting ways with Rachel, I immediately headed toward my next destination: the Natural Resources Department.

One of the people I planned to invite for Thanksgiving was here.

"Sean! What brings you here?"

"Don’t tell me… you’ve already started?"

As soon as I stepped in, a group of associates who recognized me swarmed around. Judging by their eagerness, they were all interested in the under-the-table fund I’d mentioned.

"What’s the minimum buy-in?"

"The amount doesn’t matter, but I want to keep it to a small group for better management."

"How many people?"

"Count me in!"

"The participant list isn’t finalized yet. Think it over and let me know when you’re sure. I need to inform the lawyer as well."

No verbal reservations.

If they wanted to join, they needed to commit with a signature.

With limited spots, they’d better act fast.

After leaving that warning for the potential investors, I moved on to my main target: Gonzalez.

He was one of the guys who’d participated in the salary wager I’d organized before.

As I’d suspected, he turned out to be from a wealthy South American mining family.

Third son or not, he was still a valuable connection.

"Half a million dollars."

Without even looking up from his screen, Gonzalez casually stated the amount he’d invest in the fund. Half a million dollars—roughly 500 million won.

A reasonable amount for a wealthy person’s side bet.

"If you need a signature, just let me know."

This wasn’t a negotiation—it was confirmation.

"Understood. I’ll take it into account."

Gonzalez nodded slightly, still not making eye contact. It seemed he assumed I was here because of the fund.

"Do you have any plans for Thanksgiving?"

Only after I revealed my real purpose did he slowly turn his gaze toward me. A flicker of curiosity lit up his otherwise languid eyes.

"Why?"

"I thought you might not be able to visit your family. A friend of mine invited me to their house…"

"Alright."

I paused briefly before confirming.

"Does that mean you'll attend?"

"Yeah."

This was unexpected.

I hadn’t imagined he’d agree so readily.

I had even prepared answers to deflect questions like, ‘Why invite me when we’re not particularly close?’ But there was no interrogation.

No point in overexplaining when he wasn’t even curious.

"Then I’ll consider you confirmed. Should I contact you via Bloomberg?"

"No, by phone."

Another surprise.

For someone from a mining tycoon family, I expected him to be more cautious, yet here he was giving me his personal contact information.

"Alright, I’ll reach out."

I nodded politely and walked away.

‘Should I try to build a closer connection?’

The reason I invited Gonzalez was simple: credibility. Being able to show Rachel’s parents that I have connections with a South American mining magnate would surely work in my favor.

That said, he seemed quite open to me. Perhaps it wouldn’t hurt to develop this into a proper relationship. But that’s something to think about later.

For now, I had more immediate matters to attend to.

Back in the M&A department, I headed straight for Dobby.

Tap, tap, tap!

Even when I stood right behind him, the guy didn’t bother turning around, focused entirely on his keyboard.

"Got plans for the holidays?"

"I told you, I’m going home."

Dobby’s family lived in Boston, so a day trip was feasible. I already knew this but asked anyway.

"Rachel invited me to her house…"

Dobby’s hands froze mid-typing.

"Too bad, maybe next time—"

"Wait, I can make it!"

Before I could even finish, Dobby spun around and grabbed my sleeve.

"What about your family?" freёweɓnovel.com

"It’s fine! They’ll understand if I say I’m busy with work."

This is why having sons is pointless.

Not that I’m one to talk.

"Alright, so it’s settled?"

"Of course!"

There’s a reason I decided to invite Dobby too. The guy has a loose tongue.

‘He might as well put that mouth to good use this time.’

I’ve achieved quite a bit during my time at Goldman: mediating between feuding MDs, maintaining an 80% success rate, being treated unusually well for an associate, and delivering stellar results in the teasers I’ve handled.

But if I were to brag about these accomplishments myself, it would come off as tacky. My peers aren’t likely to bring it up either.

We’re all ordinary newcomers, so who would say something like: "Well, actually, Sean here isn’t like the rest of us…"

Why would they? The more they hype me up, the more inadequate they’d look by comparison. If Rachel brought it up, it would only raise more suspicion about me.

That’s where Dobby is perfect. He’s been involved in every project I’ve led, so if he wanted to highlight his own achievements, he’d have to mention me.

And to explain why our results were so impressive, he’d naturally have to talk about my success rate. It’d make for quite the compelling story.

‘This should cover all the key people I need.’

Now, the only potential issue left is Rachel’s brother’s wariness.

This calls for a contingency plan.

Thanksgiving approached swiftly. Rachel’s estate was located in Greenwich, Connecticut. It was about a 45-minute train ride from New York, but there was no need to take the train.

At precisely 1 p.m., a limousine glided to a stop in front of my residence. The door opened, and Dobby waved at me.

“Here!”

Beyond Dobby, Gonzalez was seated inside. Of course—he was the one providing the vehicle.

The limousine interior had long seats lining the sides. I chose to sit next to Dobby rather than beside Gonzalez. It was only proper to leave the provider of the car with more space.

“Thanks for including us…”

“I’m going there anyway,” Gonzalez replied curtly, closing his eyes.

It was clear he intended to nap during the ride—probably to avoid mundane conversations rather than due to lack of sleep.

“Where’s Rachel?”

I motioned for Dobby to be quiet, signaling not to disturb Gonzalez’s rest.

The limousine glided smoothly through the city.

Taking out my iPhone, I focused on the screen.

‘Still a long way to go.’

So far, 28 associates had expressed interest in my under-the-table fund. While the number wasn’t bad, the participants were mostly juniors, so the investment amounts were small—just a few thousand dollars each. Including Gonzalez’s contribution, the total stood at $2 million.

That was twice my initial seed money, but far short of my $5 million target.

‘Should I aim higher?’

I needed to attract VPs or MDs. But from their perspective, even if it was a promising unicorn, investing in a junior associate’s fund was a questionable move—it lacked prestige.

To entice them, I’d need to create an event or justification, something like the previous wager.

As I considered various strategies, I heard Dobby’s awestruck voice.

“Wow… This is like another world.”

Looking out the window, I saw the scenery had changed. The bustling city was replaced by rows of meticulously maintained mansions. Dobby gazed at each house with envy.

“When will I ever live in a place like this…”

Greenwich was a historic enclave for the wealthy, particularly renowned as a neighborhood for financial titans. It was practically a rite of passage for successful Wall Street players to buy a mansion here.

In my previous life as a relatively successful PM, I had also followed that tradition and purchased a house in Greenwich.

‘I miss it…’

If we went five minutes straight ahead, we’d reach the house I once owned.

For some reason, I felt an urge to see it again. But the limousine turned left instead.

After a while, the grand mansions disappeared, replaced by stone walls, meadows, and forests. The true wealthy lived in properties not visible from the road—mansions hidden within sprawling estates.

Rachel’s home was no exception. Beyond the massive gate, nothing was visible.

“This is Rachel Mosley’s guest.”

The gate opened, and even after driving further into the property, it took a while before the house came into view.

“Wow, I’m actually stepping into a place like this,” the driver whistled, impressed. No one responded.

“…”

Dobby was still in awe. It seemed he hadn’t fully realized Rachel’s status until now.

Gonzalez, on the other hand, glanced at me with mild surprise.

‘This adds to the credibility.’

It proved my connection to someone at this level.

“We’ve arrived.”

The limousine stopped at the entrance of the mansion, where a man stood waiting. Clearly, he wasn’t a servant. He exuded wealth and, most notably… was almost unfairly handsome.

“You must be Rachel’s friends. I came out to greet you instead of her—thought it might be less awkward for the other guests. Hope that’s okay?”

It was Rachel’s brother.

Smiling brightly, he extended his right hand.

“Gerard Mosley.”

Introductions began.

“Enrique Gonzalez.”

“Greg Lenton.”