A Wall Street Genius's Final Investment Playbook-Chapter 199

The mention of Aaron Stark’s name 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 meets Sander in the summer of 2015.

That was still several months away.

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

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

Here’s what I remember.

Stark was always someone 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 statement.

Someone 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 emerged 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 reinforcement 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 seemed reluctant to get involved.

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

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

And the discussion that began that summer 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.

Meaning, the meeting with Alex was still far in the future.

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

Due to the butterfly effect caused by me, 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 payment—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 media, leading to a fine from the SEC.

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

‘Not even close.’

Someone that impulsive isn’t likely to make the same choices again.

And considering the butterfly effect of meeting me, his path would only become 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. ƒree𝑤ebnσvel-com

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

‘We might run into each other someday…’

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

Getting deeply involved with him was something 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 time came.

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

A few months ago, Stark made headlines with this statement 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 extreme comment.

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 some reason why it’d be a problem if Stark joined us?”

Just moments 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 environment 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 become a structure of ‘leader and followers’… And I simply don’t want to be a follower in that kind of place.”

For a moment, 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 came 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 time he left in 2018, he had only provided $100 million in actual funds.

As for me?

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

In cash, ready to deploy immediately.

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

I looked straight at Alex and added, "This time, 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 management or operations. I just want decision-making power for joint research with Castleman, and leave everything else to Alex."

I meant it.

It's better to let someone capable handle the troublesome 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 immediately withdraw my investment.

"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 me.

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 me some time to think? It’s all so sudden…"

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

I smiled gently as I replied.

However, as someone with limited time, I couldn’t wait forever.

"I plan to stay in California for one more week. Please let me 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 investment—and it was busier than expected.

"The effect is incredible. Ever since Sean’s donation announcement, we’ve been overwhelmed with meeting 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 announcement 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 name 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 investments 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 means 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 investment 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 investment.

Meaning it all belongs to me.

‘Not to mention 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 investments 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 agreement.

"Usually people let that slide, but if the success is too visible, someone 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 investment. 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 moment 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 measure. If you’re that concerned, it’s best to announce it in our quarterly report. Even though this is a personal investment, 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 someone 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 moment I saw the caller ID, I couldn’t help but frown.

The name on the screen was someone completely unexpected.

<Gerrard Mosley>

Rachel’s older brother.

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

But his reason caught me even more off guard.

[Rachel told me 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 time. So instead, he was wasting time with pointless chit-chat.

‘I really hate this kind of thing.’

I don’t like wasting time 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 some time this evening. Would you like to grab dinner together?"

I was the one to suggest meeting first.

[Today? So suddenly?]

‘You little punk, huh?’

This is as far as my generosity goes.

"That’s a shame then."

Click.

I hung up without hesitation.

Then, a few seconds later—

Bzzz—

As expected, the phone rang again.

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

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

Suddenly, I found myself intrigued.

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