A Wall Street Genius’s Final Investment Playbook Chapter 199

The ntion of Aaron Stark’s na itself wasn’t all that surprising.

He had also been a co-founder of Next AI in my previous life.

So, I had expected him to appear eventually…

‘But it’s too early for that now.’

Stark first ets Sander in the sumr of 2015.

That was still several months away.

‘By now… is it about ti he heads to the White House?’

I retraced Stark’s movents one by one in my mind.

Here’s what I rember.

Stark was always soone wary of the dangers of AI.

But in 2013, a conversation at his birthday party with a big tech CEO marked a turning point.

As usual, he expressed concern about things like ‘the possibility of AI replacing humanity’ and ‘the risk of digitizing human consciousness.’

But the CEO’s response was unexpected.

—Isn’t a digitized consciousness still an extension of humanity?

If we can transplant human consciousness into a computer, isn’t that progress? A kind of evolution?

Stark was shocked by this statent.

Soone who considered even the end of humanity to be a form of progress!

That conversation left him with a lasting sense of alarm.

Then in 2014.

News erged that this dangerous-thinking big tech company was trying to acquire a startup at the forefront of AI technology—BigMind.

BigMind possessed unrivaled capabilities in deep learning and reinforcent learning.

And now that technology was about to fall into the hands of a company with a dangerous philosophy!

Stark tried to block the acquisition but ultimately failed.

Feeling the urgency, he began searching for a like-minded partner who shared concerns about AI’s dangers.

He first went to the president to raise a warning, but although the president expressed understanding, he seed reluctant to get involved.

And in the process of looking for a new breakthrough, Stark t Alex Sander.

They agreed on the need to establish an organization to ensure AI safety.

And the discussion that began that sumr bore fruit in December with the founding of Next AI.

However, their partnership did not last long.

In 2018, Stark left Next AI.

The public reason given was that ‘Next AI’s goals conflicted with his other AI ventures’…

But that wasn’t the truth.

In reality, Stark had attempted to seize control of Next AI and failed—that was the real reason.

After Stark’s departure, and the loss of a major backer, Next AI began efforts to create a viable revenue model…

But that’s not what matters now.

As of 2015, Stark was just about to visit the president.

aning, the eting with Alex was still far in the future.

“Stark could beco a valuable collaborator, couldn’t he? We haven’t tried reaching out yet since the plan isn’t fully ford, but once Sean and I refine the concept…”

Due to the butterfly effect caused by , it was possible that Alex would now be the one to seek out Stark.

This had to be stopped here.

“I’m against it.”

“What? Why…?”

Alex couldn’t hide his confusion at my firm refusal.

But I had no choice but to oppose it.

‘Stark is too big of a variable.’

Aaron Stark.

He was a completely unpredictable individual.

His impulsiveness had already earned a reputation in my past life.

He declared Bitcoin would be accepted as paynt—then retracted the decision just months later.

He announced the acquisition of Twitter—then quietly backed out.

He even spread false information about turning his company private on social dia, leading to a fine from the SEC.

You think it’s okay because I know the future?

‘Not even close.’

Soone that impulsive isn’t likely to make the sa choices again.

And considering the butterfly effect of eting , his path would only beco more uncertain.

But that’s not all.

‘If Stark’s involved, we can’t even predict public opinion.’

Stark had a kind of cult-like charisma.

I’ve also built up considerable influence, but if the two of us clashed, who the public would side with was anyone’s guess.

An uncontrollable, unpredictable variable.

Soone like that should be kept at arm’s length.

‘We might run into each other soday…’

But even if we did, it should only be in passing—by coincidence.

Getting deeply involved with him was sothing I absolutely wanted to avoid.

That said, even if Alex didn’t go to Stark, Stark would definitely approach Alex in a few months.

So I had to make sure Alex would turn him down when that ti ca.

“He’s too extre. Surely you’re aware of what he said recently at MIT.”

A few months ago, Stark made headlines with this statent at a symposium held at MIT.

Developing artificial intelligence is like summoning the devil.

You all know what happened to those who drew pentagrams and sprinkled holy water while claiming ‘we can control the demon,’ right? The ending is always failure.

I get what he was trying to say, but that was an excessively extre comnt.

When I pointed this out, Alex nodded.

“That was a bit much. But his influence could definitely help. Public awareness of this issue would change entirely.”

“I can generate public interest too.”

“Wouldn’t it be even better if both of you did it together?”

Suddenly cutting in was CTO Dross.

His gaze had a shadow of suspicion.

“Unless… is there so reason why it’d be a problem if Stark joined us?”

Just monts ago we were bonding like nerds, but now that it turned to operations, his Wall Street instincts were surfacing.

I responded with the most sincere expression I could muster.

“I want an environnt where everyone has an equal voice. Just like the discussion we just had.”

They liked horizontal cultures here.

So that was the angle to play.

“But if Stark gets involved, the atmosphere will completely change. He’s more of a ‘leader’ than a ‘collaborator.’ He’ll try to take control here too. Then instead of a ‘collaborative group,’ we’ll beco a structure of ‘leader and followers’… And I simply don’t want to be a follower in that kind of place.”

For a mont, silence fell.

No one could argue against what I said.

They too probably couldn’t imagine Stark sitting down for fair discussions with everyone.

However—

“But we’re in desperate need of funding right now. In that regard, he is…”

Alex cautiously began to speak.

It was clear he felt Stark was too valuable to dismiss entirely.

But I replied firmly.

This was non-negotiable.

“If it’s about funding, I can provide more than enough. And my assets are liquid. It’s true Stark is wealthy, but he likely doesn’t have much cash on hand.”

That was a fact.

Most of Stark’s wealth ca from equity in the companies he ran—especially privately held firms that weren’t easily converted to cash.

‘So that’s why he only made promises.’

Before the regression, Stark had promised to donate $1 billion to Next AI, but by the ti he left in 2018, he had only provided $100 million in actual funds.

As for ?

“I can provide $1 billion within the next month.”

In cash, ready to deploy imdiately.

"Of course, it’s not money without conditions. As I ntioned earlier, applicability to Castleman is important to . But if Stark gets involved, the story changes."

I looked straight at Alex and added, "This ti, I need to add one more condition. The leader of this organization must be Alex alone. Both I and Stark must be excluded."

"You're excluding yourself too?"

"Yes, I’m not interested in managent or operations. I just want decision-making power for joint research with Castleman, and leave everything else to Alex."

I ant it.

It's better to let soone capable handle the troubleso operations.

"Stark is certainly a great man, and in a way, I respect him.

However, if we collaborate with him, he’ll definitely demand a co-founder title."

That’s just his nature—he wouldn’t be able to resist.

"But an organization with two kings is bound to fall.

And I can't invest my money in such a place."

My words were essentially an ultimatum.

If Stark ends up as a leader, I was making it clear I would imdiately withdraw my investnt.

"I won’t force you. The choice is yours."

I firmly stated, looking Alex in the eye.

He had to make a choice.

Between Stark and .

Choosing both was not an option that should even be on the table.

That way, even if Stark approaches later, there would be no room left for negotiation.

After a brief silence, Alex opened his mouth.

"Could you give so ti to think? It’s all so sudden…"

"Of course. Take as much ti as you need."

I smiled gently as I replied.

However, as soone with limited ti, I couldn’t wait forever.

"I plan to stay in California for one more week. Please let know your decision within that period."

###

For the next few days, I went through the rest of my California schedule with COO Crane.

Mainly, we were scouting AI startups suitable for private equity investnt—and it was busier than expected.

"The effect is incredible. Ever since Sean’s donation announcent, we’ve been overwheld with eting requests."

Crane’s face was full of satisfaction.

Most promising AI startups were still in seed or Series A stages.

To engage with such early-stage companies, you had to access their internal networks…

And since we had just launched our private equity division, we lacked those connections, making even basic information gathering difficult.

But after my donation announcent at the summit, everything changed.

Invitations were pouring in from everywhere and doors were opening.

"We’re really benefiting from Sean’s presence…But is it okay? Ten billion dollars is no small amount."

"Just think of it as a marketing expense."

In truth, my donation was quite effective.

It instantly etched our na into the AI industry.

That kind of branding is priceless.

Still, Crane looked uneasy.

"If you're investing personal funds, wouldn’t the risk of failure fall entirely on you, Sean?"

Early investnts carry a high failure rate.

If we invested through a fund, the losses would be spread across investors, but with my personal money, all the risk was mine.

"Are you really okay with that?"

"Of course. Don’t worry about it."

The smile I gave was sincere.

‘I’m more than okay with it.’

Bearing the burden of failure also ans reaping all the rewards of success.

Take Tempest, for example.

That company would see explosive growth during the COVID era, reaching a valuation of $8 billion by 2020.

By then, my $200 million investnt would have grown to $2.4 billion.

If I had invested through a fund, I’d only get 20% of that return.

But this is a personal investnt.

aning it all belongs to .

‘Not to ntion Next AI.’

Who wouldn’t want to keep all that profit to themselves?

If anything, I was more concerned about the opposite situation.

"I can handle failure, but I also need to prepare for the opposite. If my investnts hit the jackpot, then we might have a real problem."

If a fund manager monopolizes promising opportunities, controversy could arise.

Investors might ask, "Why did you keep such a great opportunity to yourself?"

Crane nodded in agreent.

"Usually people let that slide, but if the success is too visible, soone might accuse you of breaching your fiduciary duty. But realistically, it won’t escalate that far."

"Are you sure?"

"In Tempest’s case, they originally refused private equity investnt. And all the projects Sean is investing in now are moonshots—too risky. It would be hard to argue you knew they’d succeed and acted alone."

I pondered Crane’s words for a mont before responding.

"So you’re saying, if a legal dispute arises, we can win?"

"Yes, exactly."

"But I’d rather avoid any disputes altogether. Is there a way to do that?"

At my question, Crane paused in thought, then replied.

"So you're looking for a preventative asure. If you’re that concerned, it’s best to announce it in our quarterly report. Even though this is a personal investnt, we can encourage investors to participate if they’re interested."

‘Not a bad idea.’

Disclosing everything from the start and saying, ‘You can invest in this moonshot too, if you want.’

Then if soone complains later, I can say, ‘I told you, but you ignored it.’

"Alright. Handle it that way."

As I spoke, Crane nodded while jotting it down in her notebook.

That’s when it happened.

Bzzz—

My phone rang.

And the mont I saw the caller ID, I couldn’t help but frown.

The na on the screen was soone completely unexpected.

Rachel’s older brother.

We weren’t even in regular contact, so why was he calling?

But his reason caught even more off guard.

[Rachel told you’re in San Francisco? Turns out I’m here on a business trip too…]

"I see."

I replied curtly.

So what?

Then—

[Which hotel are you staying at?]

"Rosewood Sand Hill."

[That’s a nice place. You on vacation, not work?]

He was making small talk he never usually did. I could instantly sense Gerrard’s intention.

‘He must need a favor.’

If that’s the case, he should just say so. But it seems like his pride wouldn't let him directly ask for my ti. So instead, he was wasting ti with pointless chit-chat.

‘I really hate this kind of thing.’

I don’t like wasting ti in general— And right now, I’m terminally ill.

Usually I’d just cut this off with, “I’m busy.”

But since he’s Rachel’s brother, I couldn’t be too rude.

Besides—

‘He might actually be useful.’

Gerrard was an heir candidate to the world’s largest private company.

Even if he was annoying, he was a valuable connection.

So I decided to make a generous offer.

"I have so ti this evening. Would you like to grab dinner together?"

I was the one to suggest eting first.

[Today? So suddenly?]

‘You little punk, huh?’

This is as far as my generosity goes.

"That’s a sha then."

Click.

I hung up without hesitation.

Then, a few seconds later—

Bzzz—

As expected, the phone rang again.

[Ah, no! My other appointnt just got canceled suddenly…Where should we et?]

‘He must be more desperate than I thought. What’s this about?’

Suddenly, I found myself intrigued.